Swfloridafinehomes.com Search Results

$5,685,000

Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm textures and elegant proportions create an atmosphere that is refined and welcoming. Just over a mile from the world-renowned sands of Siesta Key Beach, this is a home that celebrates the best of Sarasota’s lifestyle, a water connection, a celebration of indoor-outdoor living and architectural details that convey quiet luxury. Set on more than half an acre with 135 feet of water frontage, the residence opens with a stunning walnut-domed foyer, where soaring ceilings and floor-to-ceiling windows flood the space with light. Rich finishes—including Birdseye maple, tongue-and-groove cypress tray ceilings, and handcrafted millwork—are woven throughout the home, delivering a consistent sense of quality and character. The kitchen is a dream for chefs and entertainers alike, appointed with quartz countertops, a large center island, professional-grade appliances, a built-in espresso machine, and a walk-in butler’s pantry that seamlessly connects to formal and casual living areas. The owner’s suite is a private retreat, complete with a sitting room, dual walk-in closets, a spa-style bath with steam shower and a peaceful balcony overlooking the water. Each of the four guest suites offers its own en-suite bathroom and generous closet space, with three featuring walk-in closets and one boasting a built-in wall closet, ensuring privacy and comfort. Whether you need a quiet office, a vibrant game room or a cozy retreat, the bonus room, game room and loft offer the flexibility to suit your lifestyle. True to its coastal character, the home opens fully to expansive covered terraces designed for year-round enjoyment. Retractable screens, a wood-paneled ceiling, integrated fans, and ambient lighting create an outdoor living room atmosphere, complete with a fireplace and a full summer kitchen with built-in grill and bar seating. Beyond, the resort-style pool and raised spa are surrounded by tropical landscaping and natural stone decking, with multiple lounge areas designed for sun and shade. A custom fire pit anchors the space, offering a cozy, elegant setting for evening gatherings with water views. Water enthusiasts will appreciate the boat dock, built to accommodate a large vessel, complete with a boat lift. With quick access to the Intracoastal Waterway, the location is as functional as it is beautiful. Below, the expansive under-building garage offers room for more than 10 vehicles across five bays, plus a workshop, EV charging station and golf cart storage. A brand new whole-house generator was installed in June of 2025, creating peace of mind. Set on a quiet cul-de-sac just minutes from Sarasota’s best beaches, shopping, dining and cultural destinations, this rare offering is a seamless blend of timeless design, superior craftsmanship and the relaxed elegance of coastal Florida living.

5 Beds ⋅ 7 Baths ⋅ Hidden Harbor SubDv. ⋅ 34242 Zip Code

Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm textures and elegant proportions create an atmosphere that is refined and welcoming. Just over a mile from the world-renowned sands of Siesta Key Beach, this is a home that celebrates the best of Sarasota’s lifestyle, a water connection, a celebration of indoor-outdoor living and architectural details that convey quiet luxury. Set on more than half an acre with 135 feet of water frontage, the residence opens with a stunning walnut-domed foyer, where soaring ceilings and floor-to-ceiling windows flood the space with light. Rich finishes—including Birdseye maple, tongue-and-groove cypress tray ceilings, and handcrafted millwork—are woven throughout the home, delivering a consistent sense of quality and character. The kitchen is a dream for chefs and entertainers alike, appointed with quartz countertops, a large center island, professional-grade appliances, a built-in espresso machine, and a walk-in butler’s pantry that seamlessly connects to formal and casual living areas. The owner’s suite is a private retreat, complete with a sitting room, dual walk-in closets, a spa-style bath with steam shower and a peaceful balcony overlooking the water. Each of the four guest suites offers its own en-suite bathroom and generous closet space, with three featuring walk-in closets and one boasting a built-in wall closet, ensuring privacy and comfort. Whether you need a quiet office, a vibrant game room or a cozy retreat, the bonus room, game room and loft offer the flexibility to suit your lifestyle. True to its coastal character, the home opens fully to expansive covered terraces designed for year-round enjoyment. Retractable screens, a wood-paneled ceiling, integrated fans, and ambient lighting create an outdoor living room atmosphere, complete with a fireplace and a full summer kitchen with built-in grill and bar seating. Beyond, the resort-style pool and raised spa are surrounded by tropical landscaping and natural stone decking, with multiple lounge areas designed for sun and shade. A custom fire pit anchors the space, offering a cozy, elegant setting for evening gatherings with water views. Water enthusiasts will appreciate the boat dock, built to accommodate a large vessel, complete with a boat lift. With quick access to the Intracoastal Waterway, the location is as functional as it is beautiful. Below, the expansive under-building garage offers room for more than 10 vehicles across five bays, plus a workshop, EV charging station and golf cart storage. A brand new whole-house generator was installed in June of 2025, creating peace of mind. Set on a quiet cul-de-sac just minutes from Sarasota’s best beaches, shopping, dining and cultural destinations, this rare offering is a seamless blend of timeless design, superior craftsmanship and the relaxed elegance of coastal Florida living.

5132 Jungle Plum Road, Sarasota

$735,000

Virtually staged to showcase the full potential of this beautiful Siesta Key condo! Just steps from the powdery sands of Siesta Key Beach, this turnkey 2-bedroom, 2-bath unit offers the perfect blend of comfort, style, and value. The unit features vaulted ceilings that create a spacious feel, along with a covered parking space and private storage area. New hurricane-impact windows and doors have already been purchased and are scheduled for installation, providing added peace of mind for future owners. A new roof is also coming soon. This unit has no history of flood damage during current ownership and delivered strong rental income in 2023, generating $62,000 net in just 9 months as the owners reserved 3 months for personal use. Residents and guests enjoy access to resort-style amenities including a clubhouse, sparkling pool, tennis courts, and 24-hour security. Owners also benefit from maximum rental flexibility with the option of short-term rentals through Airbnb, VRBO, or the on-site rental office. Plus, you are just moments from Siesta Key’s top restaurants, bars, and boutique shops. Whether you are seeking a stress-free getaway or a high-performing property, this condo checks every box: location, lifestyle, and long-term value.

2 Beds ⋅ 2 Baths ⋅ Siesta Dunes Beach SubDv. ⋅ 34242 Zip Code

Virtually staged to showcase the full potential of this beautiful Siesta Key condo! Just steps from the powdery sands of Siesta Key Beach, this turnkey 2-bedroom, 2-bath unit offers the perfect blend of comfort, style, and value. The unit features vaulted ceilings that create a spacious feel, along with a covered parking space and private storage area. New hurricane-impact windows and doors have already been purchased and are scheduled for installation, providing added peace of mind for future owners. A new roof is also coming soon. This unit has no history of flood damage during current ownership and delivered strong rental income in 2023, generating $62,000 net in just 9 months as the owners reserved 3 months for personal use. Residents and guests enjoy access to resort-style amenities including a clubhouse, sparkling pool, tennis courts, and 24-hour security. Owners also benefit from maximum rental flexibility with the option of short-term rentals through Airbnb, VRBO, or the on-site rental office. Plus, you are just moments from Siesta Key’s top restaurants, bars, and boutique shops. Whether you are seeking a stress-free getaway or a high-performing property, this condo checks every box: location, lifestyle, and long-term value.

6204 Midnight Pass Road Unit 201, Sarasota

$680,000

Professionally Redesigned, Renovated & Updated in 2021, this lake-front Contemporary Coastal Chic townhouse is sure to delight! Located just steps away from the cool quartz sand on Siesta Key Beach this open, light & bright townhouse lives large with high ceilings & 4 sets of glass sliders. This 2-bedroom, 2-full bathroom home has a 1-car garage under the unit with extra storage space for the equipment to enjoy sand, pool & tennis/pickleball activities. Start your day with coffee & sunrise on the Eastern balcony & wind down on the 21 ft. covered porch with long-lake views & sunsets over the Gulf! The remodeled kitchen with soft-close hardwood cabinets, Quartz Countertops, & detailed tile backsplash is well equipped for efficiency to serve the adjacent dining table or kitchen dinette. The Primary Ensuite has a long-lake view from the King bed & large screen TV. The spa-like Ensuite has a solid-wood double vanity w/ Quartz top, detailed porcelain flooring, a walk-in shower w/ Frameless Glass Enclosure & 2 large closets. Bedroom #2 is separated on the 2nd floor, has 2 twin beds & enjoys the morning Sunrise over the balcony. The 2nd full bathroom, also on the 2nd floor has an enlarged tub, dual showerheads, folding glass shower curtain & solid wood single vanity w/Quartz top. The solid-surface floors throughout & the full-sized in-house washer & dryer provide easy maintenance. Onsite amenities include tennis, a resort-style pool, BBQ & picnic area. Across the street, the Siesta Key Public Beach offers Pickleball, Tennis, a Kid’s Playground, Lifeguards, wheelchair access & Sand Volleyball on the beach. A FREE Trolley runs up & down the Key to a variety of restaurants, bars, small boutiques & shops. Being sold turn key, this is a wonderful opportunity for a new owner and/or also a great investment property. The owners currently have the home in an Airbnb and there is also an onsite, short-term Rental Company with a waiting list for 2026 reservations. Siesta Key Beach was Ranked in 2025 by Tripadvisor #1 beach in the U.S. & #4 in the world. The Townhomes at Our House on The Beach do not last long on the market, so don’t miss your opportunity!

2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code

Professionally Redesigned, Renovated & Updated in 2021, this lake-front Contemporary Coastal Chic townhouse is sure to delight! Located just steps away from the cool quartz sand on Siesta Key Beach this open, light & bright townhouse lives large with high ceilings & 4 sets of glass sliders. This 2-bedroom, 2-full bathroom home has a 1-car garage under the unit with extra storage space for the equipment to enjoy sand, pool & tennis/pickleball activities. Start your day with coffee & sunrise on the Eastern balcony & wind down on the 21 ft. covered porch with long-lake views & sunsets over the Gulf! The remodeled kitchen with soft-close hardwood cabinets, Quartz Countertops, & detailed tile backsplash is well equipped for efficiency to serve the adjacent dining table or kitchen dinette. The Primary Ensuite has a long-lake view from the King bed & large screen TV. The spa-like Ensuite has a solid-wood double vanity w/ Quartz top, detailed porcelain flooring, a walk-in shower w/ Frameless Glass Enclosure & 2 large closets. Bedroom #2 is separated on the 2nd floor, has 2 twin beds & enjoys the morning Sunrise over the balcony. The 2nd full bathroom, also on the 2nd floor has an enlarged tub, dual showerheads, folding glass shower curtain & solid wood single vanity w/Quartz top. The solid-surface floors throughout & the full-sized in-house washer & dryer provide easy maintenance. Onsite amenities include tennis, a resort-style pool, BBQ & picnic area. Across the street, the Siesta Key Public Beach offers Pickleball, Tennis, a Kid’s Playground, Lifeguards, wheelchair access & Sand Volleyball on the beach. A FREE Trolley runs up & down the Key to a variety of restaurants, bars, small boutiques & shops. Being sold turn key, this is a wonderful opportunity for a new owner and/or also a great investment property. The owners currently have the home in an Airbnb and there is also an onsite, short-term Rental Company with a waiting list for 2026 reservations. Siesta Key Beach was Ranked in 2025 by Tripadvisor #1 beach in the U.S. & #4 in the world. The Townhomes at Our House on The Beach do not last long on the market, so don’t miss your opportunity!

1155 Lake House Circle Unit C119, Sarasota

$1,500,000

Siesta Key Canal Front Home with 175’ of sea wall on the Grand Canal in the desirable and quaint neighborhood of Siesta Isles. Ride your bike to the Village or the world-famous Siesta Key Beach rated #1 in USA. This beautifully well-kept 3 bedroom, 2 bath Rutenberg built home is located on a quiet cul-de-sac that is a perennial favorite with lush tropical landscaping and great privacy. The home sits high up on almost a 1/3 of an acre. This home was not affected by hurricane damage. Enter thru the charming Spanish style courtyard with its new landscaping, double front doors and wide foyer. Boasting a flowing floor plan with tile floors and crown molding, the living room & dining room open to the custom gourmet kitchen, featuring handsome wood cabinets, granite counters, & tumbled stone backsplash, perfect for entertaining while overlooking the Grand Canal from any window. The master bedroom ensuite with private sitting area is nice to enjoy. A new lanai cage installed July 2025. The lanai area faces southeast . There is a paver sundeck & outdoor dining area along with a covered lanai with rectangular pool, boat lift, dock, and cement seawall. Relax while you enjoy the serene water views and fabulous Florida wildlife, manatee, native birds and many types of fish. You may also enjoy fishing or kayaking from your backyard! Tropical mature foliage in park-like yard. Minutes to the open bay by boat and near Siesta Key Village where you can enjoy shops and restaurants. This truly is Paradise! Isn't this the lifestyle you've been planning? Selling Turn Key! Great Rental Income!

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Siesta Key Canal Front Home with 175’ of sea wall on the Grand Canal in the desirable and quaint neighborhood of Siesta Isles. Ride your bike to the Village or the world-famous Siesta Key Beach rated #1 in USA. This beautifully well-kept 3 bedroom, 2 bath Rutenberg built home is located on a quiet cul-de-sac that is a perennial favorite with lush tropical landscaping and great privacy. The home sits high up on almost a 1/3 of an acre. This home was not affected by hurricane damage. Enter thru the charming Spanish style courtyard with its new landscaping, double front doors and wide foyer. Boasting a flowing floor plan with tile floors and crown molding, the living room & dining room open to the custom gourmet kitchen, featuring handsome wood cabinets, granite counters, & tumbled stone backsplash, perfect for entertaining while overlooking the Grand Canal from any window. The master bedroom ensuite with private sitting area is nice to enjoy. A new lanai cage installed July 2025. The lanai area faces southeast . There is a paver sundeck & outdoor dining area along with a covered lanai with rectangular pool, boat lift, dock, and cement seawall. Relax while you enjoy the serene water views and fabulous Florida wildlife, manatee, native birds and many types of fish. You may also enjoy fishing or kayaking from your backyard! Tropical mature foliage in park-like yard. Minutes to the open bay by boat and near Siesta Key Village where you can enjoy shops and restaurants. This truly is Paradise! Isn't this the lifestyle you've been planning? Selling Turn Key! Great Rental Income!

1038 Contento Street, Sarasota

$440,000

Say Hello to a Good Buy! Best value -1BD/1BA condo with Open Balcony plus private Florida Room offers fabulous views of the pool area and Intercoastal. Enjoy peace of mind, HVAC, and a new dishwasher in 2024, a new water heater, and a new main electrical panel in 2023. The remodeled condo offers stunning travertine stone floors, granite countertops, stainless steel appliances, and a beautifully remodeled bathroom. You'll be surprised by the number of closets and storage space. You may enjoy the condo and Harbor Tower amenities for personal use and/or take advantage of the 2-week rental policy for income. FYI. 2025, the owner has appreciated just under 17000 rental income. Why Harbor Towers Yacht & Racquet Club? It is loaded with amenities. Here's 10 reasons why 1.) In 2024, the complex was refitted entirely to meet and exceed current hurricane storm codes. 2.) Located on the Bayside of Siesta Key, it is less than 1100 yards from Siesta Key Public Beach. Take the Trolley, or you can easily walk to the Beach entrance, which is easier than finding a parking place. 3. Two heated pools, adjacent outdoor grilling patio, state-of-the-art Fitness Center; treadmills, elliptical trainers, free weights, plus a dry sauna 4. Best of the Best Har-Tru Tennis Courts are maintained daily with a rebound net for additional practice time. 5.) Seawall stroll and an Island Gazabo for relaxing in the shade along the intercoastal or cast a fishing line. You might catch dinner! 6.) Marina with 40 boat slips available on a first-come, first-served basis, and Kayak dry dock storage. 7.) Boaters - Red Right Returning - Marker 70 8.) Bicycle Storage Building 9.) Siesta Key Trolley Stop at Harbor Towers 10.) Kayak Storage and Direct Kayak Launch to Intercoastal Waterway. The owner says I have enjoyed the best of both worlds: personal use and leasing it to seasonal vacationers. My personal and business life have become increasingly busy; it's time to let go of this condo for someone else to own and enjoy. I'm ready to make a deal. Let's talk.

1 Beds ⋅ 1 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code

Say Hello to a Good Buy! Best value -1BD/1BA condo with Open Balcony plus private Florida Room offers fabulous views of the pool area and Intercoastal. Enjoy peace of mind, HVAC, and a new dishwasher in 2024, a new water heater, and a new main electrical panel in 2023. The remodeled condo offers stunning travertine stone floors, granite countertops, stainless steel appliances, and a beautifully remodeled bathroom. You'll be surprised by the number of closets and storage space. You may enjoy the condo and Harbor Tower amenities for personal use and/or take advantage of the 2-week rental policy for income. FYI. 2025, the owner has appreciated just under 17000 rental income. Why Harbor Towers Yacht & Racquet Club? It is loaded with amenities. Here's 10 reasons why 1.) In 2024, the complex was refitted entirely to meet and exceed current hurricane storm codes. 2.) Located on the Bayside of Siesta Key, it is less than 1100 yards from Siesta Key Public Beach. Take the Trolley, or you can easily walk to the Beach entrance, which is easier than finding a parking place. 3. Two heated pools, adjacent outdoor grilling patio, state-of-the-art Fitness Center; treadmills, elliptical trainers, free weights, plus a dry sauna 4. Best of the Best Har-Tru Tennis Courts are maintained daily with a rebound net for additional practice time. 5.) Seawall stroll and an Island Gazabo for relaxing in the shade along the intercoastal or cast a fishing line. You might catch dinner! 6.) Marina with 40 boat slips available on a first-come, first-served basis, and Kayak dry dock storage. 7.) Boaters - Red Right Returning - Marker 70 8.) Bicycle Storage Building 9.) Siesta Key Trolley Stop at Harbor Towers 10.) Kayak Storage and Direct Kayak Launch to Intercoastal Waterway. The owner says I have enjoyed the best of both worlds: personal use and leasing it to seasonal vacationers. My personal and business life have become increasingly busy; it's time to let go of this condo for someone else to own and enjoy. I'm ready to make a deal. Let's talk.

5855 Midnight Pass Road Unit 201, Sarasota

$3,000,000

Repositioned to the market - $500,000 Price Adjustment. Exquisite custom estate in one of Siesta Key’s exclusive neighborhoods. Positioned just across from Gulf-front homes in a private enclave on Siesta Key, this exceptional residence offers the ultimate in island luxury. Masterfully built by Perrone Construction and designed by acclaimed architect Rick Oswald, this custom home is a testament to craftsmanship, quality, and elegant coastal living. Sited on a nearly 22,000-square-foot homesite, the home makes a striking first impression with its stately paver driveway and welcoming entry. Inside, wide-plank engineered hardwood floors and rich architectural detailing define the refined interiors, while soaring beam-and-plank ceilings elevate the spacious great room. The heart of the home is the gourmet kitchen, featuring a Thermador six-burner gas range, custom cabinetry, stone countertops, a generous island and breakfast bar, and an adjacent grilling deck for entertaining. The dining room opens seamlessly to the expansive covered lanai, where you’ll enjoy views of the lushly landscaped backyard oasis. A luxurious main-floor primary suite offers a private retreat with exquisite finishes and spa-style comforts, designed for relaxation and ease. Two upper-level guest suites provide privacy for family or visitors and are easily accessed by either the elegant staircase or a private elevator serving all levels. On the main level, a versatile game room doubles as a fourth bedroom with an adjacent half bath, ideal for guests, hobbies or additional living space. Designed with luxury and peace of mind, this home is built with solid concrete-and-steel frame construction and includes a generator, impact-rated doors and windows, lightning protection, Lutron lighting on the main level, tankless water heaters, central vacuum, and a refreshing outdoor shower. The showstopper? One of the largest residential pools on Siesta Key—nearly 44 feet long—designed for swimmers and hydrophiles alike. You'll find multiple places to relax in the sun or shade, surrounded by lush, tropical foliage and an expansive, fenced yard. Car enthusiasts will appreciate the dual two-car twin garages, while the lower-level non-conforming space offers flexibility for an exercise room, pool cabana or additional recreation space. Though built in 2014, this home rivals new construction in design and condition, with a freshly painted exterior and timeless appeal. Just moments from the world-renowned sands of Siesta Beach and Turtle Beach, with easy access to Turtle Beach Marina, island dining, boutique shopping and downtown Sarasota’s vibrant cultural scene, this residence offers a rare opportunity to own a home that blends location, luxury and lifestyle.

4 Beds ⋅ 4 Baths ⋅ White Beach Fruit Companys Su SubDv. ⋅ 34242 Zip Code

Repositioned to the market - $500,000 Price Adjustment. Exquisite custom estate in one of Siesta Key’s exclusive neighborhoods. Positioned just across from Gulf-front homes in a private enclave on Siesta Key, this exceptional residence offers the ultimate in island luxury. Masterfully built by Perrone Construction and designed by acclaimed architect Rick Oswald, this custom home is a testament to craftsmanship, quality, and elegant coastal living. Sited on a nearly 22,000-square-foot homesite, the home makes a striking first impression with its stately paver driveway and welcoming entry. Inside, wide-plank engineered hardwood floors and rich architectural detailing define the refined interiors, while soaring beam-and-plank ceilings elevate the spacious great room. The heart of the home is the gourmet kitchen, featuring a Thermador six-burner gas range, custom cabinetry, stone countertops, a generous island and breakfast bar, and an adjacent grilling deck for entertaining. The dining room opens seamlessly to the expansive covered lanai, where you’ll enjoy views of the lushly landscaped backyard oasis. A luxurious main-floor primary suite offers a private retreat with exquisite finishes and spa-style comforts, designed for relaxation and ease. Two upper-level guest suites provide privacy for family or visitors and are easily accessed by either the elegant staircase or a private elevator serving all levels. On the main level, a versatile game room doubles as a fourth bedroom with an adjacent half bath, ideal for guests, hobbies or additional living space. Designed with luxury and peace of mind, this home is built with solid concrete-and-steel frame construction and includes a generator, impact-rated doors and windows, lightning protection, Lutron lighting on the main level, tankless water heaters, central vacuum, and a refreshing outdoor shower. The showstopper? One of the largest residential pools on Siesta Key—nearly 44 feet long—designed for swimmers and hydrophiles alike. You'll find multiple places to relax in the sun or shade, surrounded by lush, tropical foliage and an expansive, fenced yard. Car enthusiasts will appreciate the dual two-car twin garages, while the lower-level non-conforming space offers flexibility for an exercise room, pool cabana or additional recreation space. Though built in 2014, this home rivals new construction in design and condition, with a freshly painted exterior and timeless appeal. Just moments from the world-renowned sands of Siesta Beach and Turtle Beach, with easy access to Turtle Beach Marina, island dining, boutique shopping and downtown Sarasota’s vibrant cultural scene, this residence offers a rare opportunity to own a home that blends location, luxury and lifestyle.

7333 Point Of Rocks Road, Sarasota

$475,000

Welcome to paradise on Siesta Key! This delightful elevated first-floor one-bedroom, one-bath unit in the highly sought-after Gulf and Bay Club Bayside combines comfort, style, and unbeatable convenience—with no flood or storm damage. Enjoy direct deeded beach access just across the street to world-famous Siesta Key Beach, and embrace true resort-style living with incredible amenities at your fingertips. Step inside to an open-concept floor plan with a spacious living/dining area, a large eat-in kitchen, and a fabulous glassed and screened lanai overlooking lush tropical landscaping. The comfortable bedroom includes an updated bath, and the unit is complete with a private one-car garage, in-unit washer and dryer, and turn-key furnishings—ready for you or your guests. This is one of the largest one bedroom available on Siesta Key! Important upgrades include a new electrical panel, AC, and water heater—all replaced in 2022, offering peace of mind and modern efficiency. Gulf and Bay Club Bayside features: Two resort-style pools Tennis and pickleball courts Newly renovated fishing dock Walking paths, boat loading zones, and four BBQ areas Clubhouse for private events Freshly painted buildings with new metal roofs This weekly-rental-friendly community also offers onsite management, making it an exceptional income opportunity for investors or those seeking a flexible-use property. Location couldn’t be more attractive—cross the road for beach access, or hop on the free trolley to explore Siesta Key Village or South Siesta. Park your car and instantly feel like you're on vacation! Live the island lifestyle at Gulf and Bay Club Bayside—where coastal charm meets modern convenience.

1 Beds ⋅ 1 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code

Welcome to paradise on Siesta Key! This delightful elevated first-floor one-bedroom, one-bath unit in the highly sought-after Gulf and Bay Club Bayside combines comfort, style, and unbeatable convenience—with no flood or storm damage. Enjoy direct deeded beach access just across the street to world-famous Siesta Key Beach, and embrace true resort-style living with incredible amenities at your fingertips. Step inside to an open-concept floor plan with a spacious living/dining area, a large eat-in kitchen, and a fabulous glassed and screened lanai overlooking lush tropical landscaping. The comfortable bedroom includes an updated bath, and the unit is complete with a private one-car garage, in-unit washer and dryer, and turn-key furnishings—ready for you or your guests. This is one of the largest one bedroom available on Siesta Key! Important upgrades include a new electrical panel, AC, and water heater—all replaced in 2022, offering peace of mind and modern efficiency. Gulf and Bay Club Bayside features: Two resort-style pools Tennis and pickleball courts Newly renovated fishing dock Walking paths, boat loading zones, and four BBQ areas Clubhouse for private events Freshly painted buildings with new metal roofs This weekly-rental-friendly community also offers onsite management, making it an exceptional income opportunity for investors or those seeking a flexible-use property. Location couldn’t be more attractive—cross the road for beach access, or hop on the free trolley to explore Siesta Key Village or South Siesta. Park your car and instantly feel like you're on vacation! Live the island lifestyle at Gulf and Bay Club Bayside—where coastal charm meets modern convenience.

1223 Siesta Bayside Drive Unit 1223, Sarasota

$550,000

THE ANCHORAGE - PARADISE AWAITS: A UNIQUE CORNER CONDO WITH DEEDED ACCESS TO SIESTA KEY BEACH ....Experience coastal paradise at this stunning 2-bedroom, 2-bathroom corner condo offering three private balconies and coveted deeded access to TripAdvisor's #1 Rated Beach in the USA. This fully furnished retreat captures Florida's natural beauty through its unique double-aspect design, flooding the space with abundant sunlight and panoramic views. The thoughtfully designed open floor plan features two spacious master suites, an updated kitchen with modern appliances, convenient breakfast nook, and VIEWS —creating an expansive, luxurious feel throughout. Start each day with breathtaking sunrises, unwind on your private balcony during tranquil afternoons, and toast to spectacular Gulf sunsets each evening. Ideally situated at the gateway to Siesta Key, enjoy the convenient proximity to shopping, diverse dining options, and effortless access to the complimentary Siesta Key Village Trolley. The Anchorage, a meticulously maintained and low-density complex, enhances your lifestyle with resort-style amenities, park like grounds and offers an optional on-site rental program allowing weekly stays, making this versatile property ideal as your private Florida retreat, personal sanctuary away from the everyday, or a lucrative rental income generator with impressive return potential! Don't miss this opportunity to own your special piece of Florida paradise!

2 Beds ⋅ 2 Baths ⋅ Anchorage SubDv. ⋅ 34242 Zip Code

THE ANCHORAGE - PARADISE AWAITS: A UNIQUE CORNER CONDO WITH DEEDED ACCESS TO SIESTA KEY BEACH ....Experience coastal paradise at this stunning 2-bedroom, 2-bathroom corner condo offering three private balconies and coveted deeded access to TripAdvisor's #1 Rated Beach in the USA. This fully furnished retreat captures Florida's natural beauty through its unique double-aspect design, flooding the space with abundant sunlight and panoramic views. The thoughtfully designed open floor plan features two spacious master suites, an updated kitchen with modern appliances, convenient breakfast nook, and VIEWS —creating an expansive, luxurious feel throughout. Start each day with breathtaking sunrises, unwind on your private balcony during tranquil afternoons, and toast to spectacular Gulf sunsets each evening. Ideally situated at the gateway to Siesta Key, enjoy the convenient proximity to shopping, diverse dining options, and effortless access to the complimentary Siesta Key Village Trolley. The Anchorage, a meticulously maintained and low-density complex, enhances your lifestyle with resort-style amenities, park like grounds and offers an optional on-site rental program allowing weekly stays, making this versatile property ideal as your private Florida retreat, personal sanctuary away from the everyday, or a lucrative rental income generator with impressive return potential! Don't miss this opportunity to own your special piece of Florida paradise!

6415 Midnight Pass Rd Unit 204, Sarasota

$585,000

Embrace waterfront living in this end-unit residence in Sunrise Cove, an updated, turnkey-furnished 2-bed/2-bath condo offering 1,228 sq ft of coastal style, just one shared wall, tile flooring and crown molding throughout, abundant closets, and a coveted in-unit washer-dryer. The granite kitchen features high-end stainless appliances, two pantries, and generous cabinetry, while impact-rated windows, plantation-shuttered in both bedrooms, capture spectacular sunrise panoramas over Little Sarasota Bay from the living area and screened lanai and serene sunset Gulf views from the kitchen and guest suite. Extra end-unit windows flood the primary suite and guest room with light; newer systems include an HVAC (2022) and water heater (2021). Community highlights: two heated pools (one Olympic length), lighted tennis/pickleball courts, a freshly renovated clubhouse, fitness and game rooms, barbecue area, kayak launch and optional boat docks, all tended by an on-site crew Monday, Friday, with a funded assessment for new roofs, carports, and dock upgrades under way. On-site management supports 30-day rentals for effortless income potential, while Turtle Beach, three restaurants, and the free Siesta Key Breeze trolley are just steps from your door, delivering the complete island lifestyle and an investment opportunity in one.

2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code

Embrace waterfront living in this end-unit residence in Sunrise Cove, an updated, turnkey-furnished 2-bed/2-bath condo offering 1,228 sq ft of coastal style, just one shared wall, tile flooring and crown molding throughout, abundant closets, and a coveted in-unit washer-dryer. The granite kitchen features high-end stainless appliances, two pantries, and generous cabinetry, while impact-rated windows, plantation-shuttered in both bedrooms, capture spectacular sunrise panoramas over Little Sarasota Bay from the living area and screened lanai and serene sunset Gulf views from the kitchen and guest suite. Extra end-unit windows flood the primary suite and guest room with light; newer systems include an HVAC (2022) and water heater (2021). Community highlights: two heated pools (one Olympic length), lighted tennis/pickleball courts, a freshly renovated clubhouse, fitness and game rooms, barbecue area, kayak launch and optional boat docks, all tended by an on-site crew Monday, Friday, with a funded assessment for new roofs, carports, and dock upgrades under way. On-site management supports 30-day rentals for effortless income potential, while Turtle Beach, three restaurants, and the free Siesta Key Breeze trolley are just steps from your door, delivering the complete island lifestyle and an investment opportunity in one.

8911 Midnight Pass Road Unit 308, Sarasota

$1,527,000

TWO BUILDABLE LOTS! Motivated Seller! Incredible opportunity to build your dream home—or two—on Siesta Key’s iconic Grand Canal. This exceptional waterfront property is located on picturesque Oxford Street, a charming canopy road with direct boating access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico. Features include an updated seawall cap, a rare covered boat slip and lush, tropical vegetation. A storm-damaged home remains on-site; boundary survey, topographical survey, demolition estimate are on attachment. Ideally situated just minutes from the powdery white sands of world-renowned Siesta Key Beach and the energetic Siesta Key Village, where you can stroll through charming boutiques, restaurants that offer fresh seafood, sip cocktails at lively beach bars, and soak up the island’s carefree, tropical spirit. Nestled amid lush tropical vegetation, this waterfront property invites you to embrace a luxurious island lifestyle. Enjoy boating, kayaking, paddleboarding, and fishing right from your backyard, surrounded by the natural beauty of one of Florida’s most sought-after coastal communities. While offering peaceful island serenity, the property is also just moments from downtown Sarasota, where world-class cultural attractions, gourmet dining, and vibrant entertainment await. It’s the ideal blend of relaxed coastal living and city convenience.

3 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

TWO BUILDABLE LOTS! Motivated Seller! Incredible opportunity to build your dream home—or two—on Siesta Key’s iconic Grand Canal. This exceptional waterfront property is located on picturesque Oxford Street, a charming canopy road with direct boating access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico. Features include an updated seawall cap, a rare covered boat slip and lush, tropical vegetation. A storm-damaged home remains on-site; boundary survey, topographical survey, demolition estimate are on attachment. Ideally situated just minutes from the powdery white sands of world-renowned Siesta Key Beach and the energetic Siesta Key Village, where you can stroll through charming boutiques, restaurants that offer fresh seafood, sip cocktails at lively beach bars, and soak up the island’s carefree, tropical spirit. Nestled amid lush tropical vegetation, this waterfront property invites you to embrace a luxurious island lifestyle. Enjoy boating, kayaking, paddleboarding, and fishing right from your backyard, surrounded by the natural beauty of one of Florida’s most sought-after coastal communities. While offering peaceful island serenity, the property is also just moments from downtown Sarasota, where world-class cultural attractions, gourmet dining, and vibrant entertainment await. It’s the ideal blend of relaxed coastal living and city convenience.

5033 Oxford Drive, Sarasota

$4,325,000

One or more photo(s) has been virtually staged. *Located on the north end of Siesta Key, this custom-built luxury waterfront home sits on a very private lot, surrounded by lush tropical landscaping and mature coconut palms. Perfectly positioned on a coastal playground just off Big Pass, it offers deep-water access, boating convenience, and serene natural beauty. The flexible layout includes 5 en-suite bedrooms, an elevator to all three levels, and a spacious main-level suite ideal for guests or multigenerational living. An engineer-approved option to remove a non-load-bearing wall allows for easy creation of a great room concept—a virtual rendering is included in the photo gallery to illustrate the potential. The chef’s kitchen features GE Monogram and Fisher & Paykel appliances, a butler’s pantry, beverage station, and pocketing glass doors opening to a full summer kitchen, PebbleTec saltwater pool and spa, and lush outdoor spaces. Hurricane-rated windows and doors, elevated construction, and a full-home generator protected the interior during recent storms—no water intrusion or damage occurred, with water reaching only the garage level. Extras include a 13,000 lb. lift, composite dock, 3-car garage with EV charger, whole-house water filtration, security system, and ample storage. A rare opportunity to own a private, resilient, and reimagined Siesta Key waterfront retreat.

5 Beds ⋅ 6 Baths ⋅ Gulfmead Estates SubDv. ⋅ 34242 Zip Code

One or more photo(s) has been virtually staged. *Located on the north end of Siesta Key, this custom-built luxury waterfront home sits on a very private lot, surrounded by lush tropical landscaping and mature coconut palms. Perfectly positioned on a coastal playground just off Big Pass, it offers deep-water access, boating convenience, and serene natural beauty. The flexible layout includes 5 en-suite bedrooms, an elevator to all three levels, and a spacious main-level suite ideal for guests or multigenerational living. An engineer-approved option to remove a non-load-bearing wall allows for easy creation of a great room concept—a virtual rendering is included in the photo gallery to illustrate the potential. The chef’s kitchen features GE Monogram and Fisher & Paykel appliances, a butler’s pantry, beverage station, and pocketing glass doors opening to a full summer kitchen, PebbleTec saltwater pool and spa, and lush outdoor spaces. Hurricane-rated windows and doors, elevated construction, and a full-home generator protected the interior during recent storms—no water intrusion or damage occurred, with water reaching only the garage level. Extras include a 13,000 lb. lift, composite dock, 3-car garage with EV charger, whole-house water filtration, security system, and ample storage. A rare opportunity to own a private, resilient, and reimagined Siesta Key waterfront retreat.

3465 Gulfmead Drive, Sarasota

$7,454,237

Welcome to one of the most impeccably reimagined residences at 8155 Midnight Pass on the quiet southern end of Siesta Key — a breathtaking bayside coastal estate that artfully blends modern innovation with timeless design. Set on nearly an acre of prime waterfront with 154 feet of shoreline, this gated property offers just under 7,500 square feet of luxurious living area with more than 9,200 total square feet of combined living and entertaining space, recently transformed through a full-scale two-year architectural renovation by Braidenview Architects and Christner Brothers — winners of the 2024 Aurora Grand Award for Best Renovated Home. From the moment you arrive at the gated motor court, you’ll be struck by the serenity of the grand live oaks, artistically designed landscaping, and elegant curb appeal. Inside, the home, with classical proportions, opens to soaring ceilings, DuChateau European oak flooring, and thoughtful details at every turn — from custom cabinetry and designer lighting to Euro-Wall sliders and state-of-the-art automation by Coastal Smart Homes. The heart of the home features multiple expansive living areas, all with views of Little Sarasota Bay and the Intracoastal Waterway from nearly every room, a show-stopping kitchen outfitted with Wolf and Sub-Zero appliances, double islands, and a butler’s pantry make for effortless entertaining. With four bedrooms, 2 of which offer additional sleeping areas in the suites, six baths, a private gym, a large office with two separate workspaces, a sewing/project room, and bespoke closets throughout — every space is both beautiful and functional. Step outside to enjoy a reimagined resort-style pool and new spa, Brazilian IPE decking, and multiple areas to savor sunsets over the Intracoastal Waterway. For boating enthusiasts, there is an impressive 200-foot dock with lift to accommodate a 25’ vessel plus an additional mooring area. Whether hosting a family celebration or simply savoring the coastal breeze, this property is designed for making lasting memories. Plus you are minutes from Siesta Key beach when you want to take a walk and put your toes in the famed quartz-sand as you watch the sun disappear into the horizon. With Sarasota’s vibrant cultural offerings, shopping and dining just moments away, you are all set to enjoy every imaginable amenity for an impressive lifestyle.

4 Beds ⋅ 6 Baths ⋅ Mira Mar Sub SubDv. ⋅ 34242 Zip Code

Welcome to one of the most impeccably reimagined residences at 8155 Midnight Pass on the quiet southern end of Siesta Key — a breathtaking bayside coastal estate that artfully blends modern innovation with timeless design. Set on nearly an acre of prime waterfront with 154 feet of shoreline, this gated property offers just under 7,500 square feet of luxurious living area with more than 9,200 total square feet of combined living and entertaining space, recently transformed through a full-scale two-year architectural renovation by Braidenview Architects and Christner Brothers — winners of the 2024 Aurora Grand Award for Best Renovated Home. From the moment you arrive at the gated motor court, you’ll be struck by the serenity of the grand live oaks, artistically designed landscaping, and elegant curb appeal. Inside, the home, with classical proportions, opens to soaring ceilings, DuChateau European oak flooring, and thoughtful details at every turn — from custom cabinetry and designer lighting to Euro-Wall sliders and state-of-the-art automation by Coastal Smart Homes. The heart of the home features multiple expansive living areas, all with views of Little Sarasota Bay and the Intracoastal Waterway from nearly every room, a show-stopping kitchen outfitted with Wolf and Sub-Zero appliances, double islands, and a butler’s pantry make for effortless entertaining. With four bedrooms, 2 of which offer additional sleeping areas in the suites, six baths, a private gym, a large office with two separate workspaces, a sewing/project room, and bespoke closets throughout — every space is both beautiful and functional. Step outside to enjoy a reimagined resort-style pool and new spa, Brazilian IPE decking, and multiple areas to savor sunsets over the Intracoastal Waterway. For boating enthusiasts, there is an impressive 200-foot dock with lift to accommodate a 25’ vessel plus an additional mooring area. Whether hosting a family celebration or simply savoring the coastal breeze, this property is designed for making lasting memories. Plus you are minutes from Siesta Key beach when you want to take a walk and put your toes in the famed quartz-sand as you watch the sun disappear into the horizon. With Sarasota’s vibrant cultural offerings, shopping and dining just moments away, you are all set to enjoy every imaginable amenity for an impressive lifestyle.

8155 Midnight Pass Road, Sarasota

$655,000

Coastal living at it's best at Harbor Towers Yacht & Racquet Club. You will fall in love from the moment you enter this gated premier waterfront paradise on Siesta Key which recently completed a $13 million, four-year hurricane hardening and structural upgrade program in 2024, meeting all new safety standards for hurricane/wind protection. WOW this beautifully furnished 2-Bedroom, 2-Bathroom condo INCLUDES IT'S OWN CARPORT (A RARE COMMODITY!!) and two balconies with unobstructed views of the intracoastal, marina, and pool. This unit has been tastefully renovated, plantation shutters and freshly painted through out including all new 6 panel interior doors, new furnishings 11/24, new A/C 2023, new water heater 2022, and 20" tile flooring on the diagonal through out. The amenity rich Harbor Towers is in a class of its own, offering boating, fishing, kayaking, bayfront gazebo, two heated pools, large BBQ area, kitchen prep area, state of the art fitness center, an active three Har-Tru tennis courts, a sauna, a clubhouse, high-speed WIFI, a fabulous marina with new docks, pilings, electrical pedestals and water. If interested, the association has slips available on a first come first serve basis at $3 a foot. The property is conveniently located moments from Siesta Key Village with an abundance of shopping, dining, and nightlife options. Enjoy getting around Siesta Key on the free trolley that stops right outside the community or you can walk to the World-Famous Siesta Key Beach! If you are not planning on living here full time or just want an investment, this unit can be rented for a two-week minimum rental period plus you can utilize the on-site rental program or manage rentals yourself.

2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code

Coastal living at it's best at Harbor Towers Yacht & Racquet Club. You will fall in love from the moment you enter this gated premier waterfront paradise on Siesta Key which recently completed a $13 million, four-year hurricane hardening and structural upgrade program in 2024, meeting all new safety standards for hurricane/wind protection. WOW this beautifully furnished 2-Bedroom, 2-Bathroom condo INCLUDES IT'S OWN CARPORT (A RARE COMMODITY!!) and two balconies with unobstructed views of the intracoastal, marina, and pool. This unit has been tastefully renovated, plantation shutters and freshly painted through out including all new 6 panel interior doors, new furnishings 11/24, new A/C 2023, new water heater 2022, and 20" tile flooring on the diagonal through out. The amenity rich Harbor Towers is in a class of its own, offering boating, fishing, kayaking, bayfront gazebo, two heated pools, large BBQ area, kitchen prep area, state of the art fitness center, an active three Har-Tru tennis courts, a sauna, a clubhouse, high-speed WIFI, a fabulous marina with new docks, pilings, electrical pedestals and water. If interested, the association has slips available on a first come first serve basis at $3 a foot. The property is conveniently located moments from Siesta Key Village with an abundance of shopping, dining, and nightlife options. Enjoy getting around Siesta Key on the free trolley that stops right outside the community or you can walk to the World-Famous Siesta Key Beach! If you are not planning on living here full time or just want an investment, this unit can be rented for a two-week minimum rental period plus you can utilize the on-site rental program or manage rentals yourself.

5855 Midnight Pass Road Unit 204, Sarasota

$1,900,000

Sold Data purposes only.

4 Beds ⋅ 5 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

Sold Data purposes only.

5143 Oxford Drive, Sarasota

$2,800,000

Price improvement! Discover your coastal retreat in the heart of Siesta Key, where lush gardens create a relaxing oasis near the Gulf. This stunning four-bedroom, three-and-a-half-bath coastal contemporary home offers a blend of luxury and convenience, perfect for full-time living or as your ideal vacation residence. Just .2 miles from the pristine, powdery white sands of Siesta Beach and only a half mile from the charming shops and restaurants of Siesta Village, this home offers an unbeatable location. With everything you need nearby, you can park your car and unwind in paradise. The moment you step inside, you are greeted by a color palette inspired by the sea and nature, creating a bright and welcoming atmosphere. The open-concept floor plan features a great room with built-in cabinetry and fireplace, a dining area, and a chef’s kitchen and breakfast bar, which boasts custom cabinetry, quartz countertops and a suite of GE Café appliances, including a smart 5-in-1 oven, wall convection oven and a five-burner range with a pot filler. New pendant lighting and dining chandelier add to the inviting feel. The new, custom-designed bar room is the perfect place to gather and enjoy a cup of coffee in the morning with the new Miele coffee system, as well as watch sporting events with family and friends. Entertaining will be a pleasure with the two Uline wine refrigerators and freezer drawer. A private balcony overlooks the pool, with direct access to the expansive backyard via a curved staircase. A bedroom on the main floor doubles as a second primary suite, offering a luxurious en-suite bath, complete with stone countertops, custom cabinetry, glass subway tiles, and river stone floors—a convenient half bath rounds out the main level. Upstairs, the home offers even more space with a bonus room equipped with a mini kitchen and a west-facing balcony for those unforgettable, mango and fuchsia Siesta Key sunsets. The primary suite includes a private balcony overlooking the pool, while two additional guest bedrooms and a shared bath complete the upper level. Throughout the home, you'll find high-quality touches, including crown molding, transom windows, tray ceilings, and wide-plank wood and bamboo flooring. Go outside and discover the gem of this home, the professionally landscaped gardens. Tropical and lush, the private oasis offers ample space to sunbathe, swim in the large freeform saltwater pool, or relax under covered areas designed for entertaining, dining, and lounging. After a day at the beach, the outdoor shower will quickly become a favorite. In the evenings, gather around the fire pit to stargaze or unwind with family and friends. This home also boasts numerous upgraded amenities, including a new three-floor elevator from the garage, metal roof (2023), Lennox five-ton HVAC (2024), fresh exterior paint, wood balcony ceilings, garage doors (2022), newly renovated great room and bar room with custom built-ins, a whole-house gas generator, irrigation well and eco-friendly faux turf. With Hardie board siding, a paver driveway, and extensive landscape lighting, this home is both functional and beautiful. Ideally located on Siesta Key, close to Out-of-Door Academy and only 15 minutes from downtown Sarasota’s vibrant shopping, dining, and cultural attractions, this home is move-in ready. Don’t miss out on the opportunity to own a piece of paradise; your dream home awaits!

4 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Price improvement! Discover your coastal retreat in the heart of Siesta Key, where lush gardens create a relaxing oasis near the Gulf. This stunning four-bedroom, three-and-a-half-bath coastal contemporary home offers a blend of luxury and convenience, perfect for full-time living or as your ideal vacation residence. Just .2 miles from the pristine, powdery white sands of Siesta Beach and only a half mile from the charming shops and restaurants of Siesta Village, this home offers an unbeatable location. With everything you need nearby, you can park your car and unwind in paradise. The moment you step inside, you are greeted by a color palette inspired by the sea and nature, creating a bright and welcoming atmosphere. The open-concept floor plan features a great room with built-in cabinetry and fireplace, a dining area, and a chef’s kitchen and breakfast bar, which boasts custom cabinetry, quartz countertops and a suite of GE Café appliances, including a smart 5-in-1 oven, wall convection oven and a five-burner range with a pot filler. New pendant lighting and dining chandelier add to the inviting feel. The new, custom-designed bar room is the perfect place to gather and enjoy a cup of coffee in the morning with the new Miele coffee system, as well as watch sporting events with family and friends. Entertaining will be a pleasure with the two Uline wine refrigerators and freezer drawer. A private balcony overlooks the pool, with direct access to the expansive backyard via a curved staircase. A bedroom on the main floor doubles as a second primary suite, offering a luxurious en-suite bath, complete with stone countertops, custom cabinetry, glass subway tiles, and river stone floors—a convenient half bath rounds out the main level. Upstairs, the home offers even more space with a bonus room equipped with a mini kitchen and a west-facing balcony for those unforgettable, mango and fuchsia Siesta Key sunsets. The primary suite includes a private balcony overlooking the pool, while two additional guest bedrooms and a shared bath complete the upper level. Throughout the home, you'll find high-quality touches, including crown molding, transom windows, tray ceilings, and wide-plank wood and bamboo flooring. Go outside and discover the gem of this home, the professionally landscaped gardens. Tropical and lush, the private oasis offers ample space to sunbathe, swim in the large freeform saltwater pool, or relax under covered areas designed for entertaining, dining, and lounging. After a day at the beach, the outdoor shower will quickly become a favorite. In the evenings, gather around the fire pit to stargaze or unwind with family and friends. This home also boasts numerous upgraded amenities, including a new three-floor elevator from the garage, metal roof (2023), Lennox five-ton HVAC (2024), fresh exterior paint, wood balcony ceilings, garage doors (2022), newly renovated great room and bar room with custom built-ins, a whole-house gas generator, irrigation well and eco-friendly faux turf. With Hardie board siding, a paver driveway, and extensive landscape lighting, this home is both functional and beautiful. Ideally located on Siesta Key, close to Out-of-Door Academy and only 15 minutes from downtown Sarasota’s vibrant shopping, dining, and cultural attractions, this home is move-in ready. Don’t miss out on the opportunity to own a piece of paradise; your dream home awaits!

497 Island Circle, Sarasota

$635,000

You have the best of both worlds with this unit, a View to the East overlooking over the Intracoastal waterway and the Private Beach to the West. As you walk into the dining/living room you will become enchanted with the mesmerizing view. Whether its a daytime view of the intracoastal boats of many sizes and shapes-yachts-sailboats, and dont forget its birds, sea faring animals; or when nighttime falls you will see the twinkle of the city lights under your watchful eye. Going Turnkey Furnished! Not much to do in this unit; impact windows on lanai, bathrooms and kitchen updated. Where else can you get a supersized utility room, parking under the building two heated pools, tennis and pickle ball courts, fishing pier, clubhouses and of course beach access. Management on site.

2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code

You have the best of both worlds with this unit, a View to the East overlooking over the Intracoastal waterway and the Private Beach to the West. As you walk into the dining/living room you will become enchanted with the mesmerizing view. Whether its a daytime view of the intracoastal boats of many sizes and shapes-yachts-sailboats, and dont forget its birds, sea faring animals; or when nighttime falls you will see the twinkle of the city lights under your watchful eye. Going Turnkey Furnished! Not much to do in this unit; impact windows on lanai, bathrooms and kitchen updated. Where else can you get a supersized utility room, parking under the building two heated pools, tennis and pickle ball courts, fishing pier, clubhouses and of course beach access. Management on site.

1255 E Peppertree Drive Unit 506, Sarasota

$1,100,000

Step into this beautifully refreshed 2-bedroom, 2-bathroom condo offering 1,285 sq ft of upscale comfort with breathtaking views of the Gulf of Mexico. Nearly every feature is under three years old—including stylish furnishings, bedroom carpet, fresh interior paint, a modern master shower, washer and dryer, refrigerator, and a brand-new AC installed in April 2025. Located on the desirable Siesta Key, this unit combines comfort, style, and breathtaking beauty. The bright, open layout features neutral tile floors throughout the main living areas, with plush carpeting in the bedrooms. The spacious living room opens to a private patio, perfect for enjoying the panoramic Gulf views. The well-equipped kitchen boasts ample wood cabinetry, a peninsula island with an eat-in breakfast bar, and appliances, including a full-size refrigerator, range, microwave, and dishwasher. The master suite is a peaceful retreat with sliding doors leading to the patio and Gulf views. It includes a king-sized bed, lounging chair, and two walk-in closets. The ensuite bathroom offers double sinks and a large shower. The guest bedroom, with two twin beds, provides a cozy space with easy access to the second full bath featuring a tub/shower combination. Additional conveniences include an in-unit washer and dryer, along with window treatments and a dedicated entryway. Fully turnkey furnished, this condo is ready for you to move in or rent out. Siesta Breakers offers an exceptional array of amenities for its owners and tenants. The property features a private, gated beach access, so you can step out from your unit directly to the soft, powdery sands of Siesta Key’s world-famous beach. The heated community pool is perfect for relaxing or swimming laps, with plenty of outdoor seating and a private air-conditioned clubhouse that includes a small library, tables for socializing or playing games, and a comfortable atmosphere for gathering with neighbors. For those who enjoy a more active lifestyle, the community offers on-site tennis and pickleball courts, and the HOA maintains the grounds to ensure they are always beautiful. Parking is a breeze with a dedicated, covered carport space, as well as guest parking available for your visitors. An on-site manager makes it easy to rent out your unit for additional income, with a minimum one-week rental policy, allowing you to capitalize on the popularity of Siesta Key as a vacation destination. Whether you use the on-site management or choose to self-manage the rentals, this property is an excellent income-producing opportunity. In 2024, it generated over $84,000 in rental income, and solid bookings are already in place well into 2026, making it a great investment. Just steps from the beach, Siesta Breakers is also within walking distance to shopping, dining, and local markets, offering the best of island living. With easy access to Sarasota-Bradenton International Airport, travel is a breeze. Whether you’re looking for a second home, vacation rental, or full-time residence, this condo offers the ultimate Siesta Key lifestyle with income potential, luxury, and unbeatable Gulf views.

2 Beds ⋅ 2 Baths ⋅ Siesta Breakers SubDv. ⋅ 34242 Zip Code

Step into this beautifully refreshed 2-bedroom, 2-bathroom condo offering 1,285 sq ft of upscale comfort with breathtaking views of the Gulf of Mexico. Nearly every feature is under three years old—including stylish furnishings, bedroom carpet, fresh interior paint, a modern master shower, washer and dryer, refrigerator, and a brand-new AC installed in April 2025. Located on the desirable Siesta Key, this unit combines comfort, style, and breathtaking beauty. The bright, open layout features neutral tile floors throughout the main living areas, with plush carpeting in the bedrooms. The spacious living room opens to a private patio, perfect for enjoying the panoramic Gulf views. The well-equipped kitchen boasts ample wood cabinetry, a peninsula island with an eat-in breakfast bar, and appliances, including a full-size refrigerator, range, microwave, and dishwasher. The master suite is a peaceful retreat with sliding doors leading to the patio and Gulf views. It includes a king-sized bed, lounging chair, and two walk-in closets. The ensuite bathroom offers double sinks and a large shower. The guest bedroom, with two twin beds, provides a cozy space with easy access to the second full bath featuring a tub/shower combination. Additional conveniences include an in-unit washer and dryer, along with window treatments and a dedicated entryway. Fully turnkey furnished, this condo is ready for you to move in or rent out. Siesta Breakers offers an exceptional array of amenities for its owners and tenants. The property features a private, gated beach access, so you can step out from your unit directly to the soft, powdery sands of Siesta Key’s world-famous beach. The heated community pool is perfect for relaxing or swimming laps, with plenty of outdoor seating and a private air-conditioned clubhouse that includes a small library, tables for socializing or playing games, and a comfortable atmosphere for gathering with neighbors. For those who enjoy a more active lifestyle, the community offers on-site tennis and pickleball courts, and the HOA maintains the grounds to ensure they are always beautiful. Parking is a breeze with a dedicated, covered carport space, as well as guest parking available for your visitors. An on-site manager makes it easy to rent out your unit for additional income, with a minimum one-week rental policy, allowing you to capitalize on the popularity of Siesta Key as a vacation destination. Whether you use the on-site management or choose to self-manage the rentals, this property is an excellent income-producing opportunity. In 2024, it generated over $84,000 in rental income, and solid bookings are already in place well into 2026, making it a great investment. Just steps from the beach, Siesta Breakers is also within walking distance to shopping, dining, and local markets, offering the best of island living. With easy access to Sarasota-Bradenton International Airport, travel is a breeze. Whether you’re looking for a second home, vacation rental, or full-time residence, this condo offers the ultimate Siesta Key lifestyle with income potential, luxury, and unbeatable Gulf views.

6480 Midnight Pass Road Unit 315, Sarasota

$670,000

Rarely available, this recently fully-renovated lake-front townhome is steps away from the crystal sands of Siesta Key Beach! Beautifully updated with a Coastal Chic interior, this end unit townhouse lives large. Light & bright with high ceilings, an open floor plan & four sets of glass sliders inviting the Gulf breezes inside makes each new day a delight. This 2-bedroom, 2-full bathroom home has a 1-car enlarged garage with ample storage for the water & sunshine toys, a covered balcony for coffee at sunrise & a 21’ long covered porch to celebrate evening sunsets! The kitchen with soft-close, hard-wood cupboards, granite counters & bar top is well equipped for efficiency to serve the adjacent dining table, bar seating or rattan cozy coffee table for two! The Primary Ensuite has a lake-view from the King bed, walk-in shower, dual vanities and 3 separate closets. Bedroom 2 is separated on the 2nd floor and enjoys the morning sunrise & adjacent 2nd full bath. The solid-surface floors & the full-sized inhouse washer & dryer provide easy maintenance & electric power shades on all windows provide closure at the end of the day. This unit was totally remodeled with high-end furnishings & interior finishes several years ago & has been lightly used, reserved for only Family & Friends. Onsite amenities include tennis, a resort-style pool, BBQ & picnic area. Across the street, the Siesta Key Public Beach offers Pickleball, Tennis, a Kid’s Playground, Lifeguards, wheelchair access & Sand Volleyball on the beach! A FREE Trolly runs up & down the Key to a plethora of restaurants, bars, small boutiques & shops. Being sold turn-key, this is a great opportunity for a new owner and/or is also a great investment property. There is an on-site, short-term Rental Company with a waiting list for 2026 reservations. Siesta Key Beach was Ranked in 2025 by Tripadvisor #1 in the U.S. & #4 in the World. Don’t miss this opportunity for a fabulous townhome across the street at Our House at The Beach!

2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code

Rarely available, this recently fully-renovated lake-front townhome is steps away from the crystal sands of Siesta Key Beach! Beautifully updated with a Coastal Chic interior, this end unit townhouse lives large. Light & bright with high ceilings, an open floor plan & four sets of glass sliders inviting the Gulf breezes inside makes each new day a delight. This 2-bedroom, 2-full bathroom home has a 1-car enlarged garage with ample storage for the water & sunshine toys, a covered balcony for coffee at sunrise & a 21’ long covered porch to celebrate evening sunsets! The kitchen with soft-close, hard-wood cupboards, granite counters & bar top is well equipped for efficiency to serve the adjacent dining table, bar seating or rattan cozy coffee table for two! The Primary Ensuite has a lake-view from the King bed, walk-in shower, dual vanities and 3 separate closets. Bedroom 2 is separated on the 2nd floor and enjoys the morning sunrise & adjacent 2nd full bath. The solid-surface floors & the full-sized inhouse washer & dryer provide easy maintenance & electric power shades on all windows provide closure at the end of the day. This unit was totally remodeled with high-end furnishings & interior finishes several years ago & has been lightly used, reserved for only Family & Friends. Onsite amenities include tennis, a resort-style pool, BBQ & picnic area. Across the street, the Siesta Key Public Beach offers Pickleball, Tennis, a Kid’s Playground, Lifeguards, wheelchair access & Sand Volleyball on the beach! A FREE Trolly runs up & down the Key to a plethora of restaurants, bars, small boutiques & shops. Being sold turn-key, this is a great opportunity for a new owner and/or is also a great investment property. There is an on-site, short-term Rental Company with a waiting list for 2026 reservations. Siesta Key Beach was Ranked in 2025 by Tripadvisor #1 in the U.S. & #4 in the World. Don’t miss this opportunity for a fabulous townhome across the street at Our House at The Beach!

1113 Lake House Circle Unit C110, Sarasota

$370,000

PRICED TO MOVE and a Super Fantastic Buy! Siesta Harbor is the BEST kept Secret on Siesta Key! This Lovely Turnkey Furnished 2BR/ 2 Bath - 3rd Floor - Unit Features: Gulf to Bay Access with Inter-coastal Canal Water Views, Located across the Street from the Famous Siesta Key Beaches w/Deeded Beach Access through Crescent Arms, Semi-Updated Kitchen w/2024 Refrigerator, Tastefully Furnished, New Interior Paint, Tile Flooring throughout, 2019 AC, Brand New Hurricane Impact Windows Installed in 3/2025, Lanai Sliders also include Hurricane Impact Glass, Elevator Access, Unit has a Storage Locker for Beach Chairs or Bicycles, Carport Parking Space #314, NO FLOOD or STORM DAMAGE TO UNIT, Annual Boat Dock Leases Available w/Average Boat Size Cost at about $1000 per Year, New 2024 Fully Funded Condo Roof, Condo Car Wash Station, Fabulous Community Pool w/Clubhouse & Gym, Well Managed and Maintained Complex w/On-Site Management, All Milestone & Structural Integrity Reports are Done. 55+ Age Restricted Community, 12 Rentals allowed per a year w/30 Day Minimum. Unit is Vacant and Easy to Show.

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

PRICED TO MOVE and a Super Fantastic Buy! Siesta Harbor is the BEST kept Secret on Siesta Key! This Lovely Turnkey Furnished 2BR/ 2 Bath - 3rd Floor - Unit Features: Gulf to Bay Access with Inter-coastal Canal Water Views, Located across the Street from the Famous Siesta Key Beaches w/Deeded Beach Access through Crescent Arms, Semi-Updated Kitchen w/2024 Refrigerator, Tastefully Furnished, New Interior Paint, Tile Flooring throughout, 2019 AC, Brand New Hurricane Impact Windows Installed in 3/2025, Lanai Sliders also include Hurricane Impact Glass, Elevator Access, Unit has a Storage Locker for Beach Chairs or Bicycles, Carport Parking Space #314, NO FLOOD or STORM DAMAGE TO UNIT, Annual Boat Dock Leases Available w/Average Boat Size Cost at about $1000 per Year, New 2024 Fully Funded Condo Roof, Condo Car Wash Station, Fabulous Community Pool w/Clubhouse & Gym, Well Managed and Maintained Complex w/On-Site Management, All Milestone & Structural Integrity Reports are Done. 55+ Age Restricted Community, 12 Rentals allowed per a year w/30 Day Minimum. Unit is Vacant and Easy to Show.

1250 N Portofino Drive Unit 303, Sarasota

$850,000

INCREDIBLE Views!....INCREDIBLE Privacy!....INCREDIBLE Siesta Key Neighborhood!....Only (2) Owners have Enjoyed this Peaceful Island Oasis along the Edward C. Wright Nature Preserve & Bird Sanctuary---just a short Bike Ride to the Powdery Quartz Sands of TOP-RATED Siesta Key Beach!....Conveniently Located, with easy access to the North Bridge, in the "park-like" Bayside Club community along a tree-lined street on an Oversized High Elevation WATERFRONT Lot ---this home incurred No Flooding****Generously Sized Living Spaces & Gracious Floor Plan**** are ready for New Owner to "make their own"....You will savor your morning coffee while being Indulged by the "Post-Card" Sunrises across the "never-ending" Waterfront Preserve Horizon. PRIVATE PIER and DOCK for launching Kayaks and Paddle-boards to Navigate the Sights & Sounds of the Lagoon as well as continue your journey into the Intracoastal Waterway.****Many Special Outdoor Spaces**** that are Perfect for Entertaining...Catching up on your Favorite Podcast...or Relaxing with some Binoculars and the Quiet Enjoyment of Identifying the Variety of Birds & Plant Species....IDYLLIC as Year-round; Vacation or Seasonal Residence.

3 Beds ⋅ 2 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

INCREDIBLE Views!....INCREDIBLE Privacy!....INCREDIBLE Siesta Key Neighborhood!....Only (2) Owners have Enjoyed this Peaceful Island Oasis along the Edward C. Wright Nature Preserve & Bird Sanctuary---just a short Bike Ride to the Powdery Quartz Sands of TOP-RATED Siesta Key Beach!....Conveniently Located, with easy access to the North Bridge, in the "park-like" Bayside Club community along a tree-lined street on an Oversized High Elevation WATERFRONT Lot ---this home incurred No Flooding****Generously Sized Living Spaces & Gracious Floor Plan**** are ready for New Owner to "make their own"....You will savor your morning coffee while being Indulged by the "Post-Card" Sunrises across the "never-ending" Waterfront Preserve Horizon. PRIVATE PIER and DOCK for launching Kayaks and Paddle-boards to Navigate the Sights & Sounds of the Lagoon as well as continue your journey into the Intracoastal Waterway.****Many Special Outdoor Spaces**** that are Perfect for Entertaining...Catching up on your Favorite Podcast...or Relaxing with some Binoculars and the Quiet Enjoyment of Identifying the Variety of Birds & Plant Species....IDYLLIC as Year-round; Vacation or Seasonal Residence.

700 Tropical Circle, Sarasota

$1,550,000

SUBSTANTIAL PRICE DECREASE! Welcome to Hidden Harbor, the premier yachting community located on Siesta Key. The canopy lined, brick paver streets are as lush and tropical as it gets, offering an unparalleled old Florida look and feel. Location, Location, Location... Just minutes away from award winning Siesta Key Beach, Siesta Key Village, and world class shopping, dinning and entertainment in downtown Sarasota. Opportunity of a lifetime to build your NEW DREAM HOME on protected Sailboat Water, with no fixed bridges to the Gulf and only three minutes sail to the open waters of Sarasota Bay. PRICED BELOW LOT VALUE!

3 Beds ⋅ 2 Baths ⋅ Hidden Harbor SubDv. ⋅ 34242 Zip Code

SUBSTANTIAL PRICE DECREASE! Welcome to Hidden Harbor, the premier yachting community located on Siesta Key. The canopy lined, brick paver streets are as lush and tropical as it gets, offering an unparalleled old Florida look and feel. Location, Location, Location... Just minutes away from award winning Siesta Key Beach, Siesta Key Village, and world class shopping, dinning and entertainment in downtown Sarasota. Opportunity of a lifetime to build your NEW DREAM HOME on protected Sailboat Water, with no fixed bridges to the Gulf and only three minutes sail to the open waters of Sarasota Bay. PRICED BELOW LOT VALUE!

5179 Hidden Harbor Road, Sarasota

$2,250,000

Welcome to 1241 Big Oak Lane, a stunning waterfront property on one of Siesta Key’s most private and desirable streets. Boasting nearly 200 feet of frontage directly on the bay-front of Sarasota and a Deep water Canal, this home is a boater’s dream, offering breathtaking water views and endless possibilities. Located in a rare RMF-zoned area, the property allows for completely legal short-term rentals of less than seven days, making it a high-income-producing opportunity. While the home offers incredible potential and did NOT flood, it does require renovations, making it an excellent investment for those looking to customize their dream waterfront retreat. The property already features a great existing pool and a mother-in-law-style kitchenette, making it well-suited for rental income with some updates. Alternatively, with its generous lot size and zoning flexibility, this site is prime for redevelopment, offering the opportunity to build a luxury waterfront estate that maximizes its direct Intracoastal setting. A trolley and bus stop just steps away provide easy access to Siesta Key Village and the beach, eliminating parking and traffic concerns. Whether you're looking to renovate, rent, or redevelop, this is a rare opportunity in an unbeatable location. Schedule your private showing today—no trespassing allowed!

2 Beds ⋅ 2 Baths ⋅ Secluded Harbour SubDv. ⋅ 34242 Zip Code

Welcome to 1241 Big Oak Lane, a stunning waterfront property on one of Siesta Key’s most private and desirable streets. Boasting nearly 200 feet of frontage directly on the bay-front of Sarasota and a Deep water Canal, this home is a boater’s dream, offering breathtaking water views and endless possibilities. Located in a rare RMF-zoned area, the property allows for completely legal short-term rentals of less than seven days, making it a high-income-producing opportunity. While the home offers incredible potential and did NOT flood, it does require renovations, making it an excellent investment for those looking to customize their dream waterfront retreat. The property already features a great existing pool and a mother-in-law-style kitchenette, making it well-suited for rental income with some updates. Alternatively, with its generous lot size and zoning flexibility, this site is prime for redevelopment, offering the opportunity to build a luxury waterfront estate that maximizes its direct Intracoastal setting. A trolley and bus stop just steps away provide easy access to Siesta Key Village and the beach, eliminating parking and traffic concerns. Whether you're looking to renovate, rent, or redevelop, this is a rare opportunity in an unbeatable location. Schedule your private showing today—no trespassing allowed!

1241 Big Oak Lane, Sarasota

$3,500,000

Welcome to 1364 Point Crisp, a breathtaking waterfront home on one of the most private and interesting streets on Siesta Key. With only seven homes on this secluded section of road, you’ll enjoy peace, quiet, and incredible views of Little Sarasota Bay and the Intracoastal Waterway. Watch sailboats glide by or fishermen return from a great day out in the Gulf. This home is a boater’s dream, featuring a 16,000# boat lift and a 10,000# personal watercraft lift not to mention a separate day dock and kayak Launch in the back yard. The heated saltwater pool was custom built and features a spacious deck, and plenty of room to entertain family and friends. Relax on one of the two large second-floor balconies with an outdoor grill area and roll-down screens—perfect for enjoying a glass of wine while watching the sunset. Other features include: a 100KW Kohler commercial backup generator powered by natural gas, Impact-rated doors and windows, well water for irrigation and city water access at multiple points, including the dock. Six climate-controlled garage spaces plus tons of extra storage on the first level, with easy access to the backyard and pool. Inside, with an elevator serving all levels of the home, you’ll find 4 spacious bedrooms, 5 full bathrooms, and a modern kitchen with a Sub-Zero refrigerator, Thermador induction cooktop, and GE Monogram appliances. The wet bar includes a beverage fridge and extra storage—perfect for entertaining. This home has been meticulously maintained and offers countless hidden conveniences that make life easier. Don’t miss your chance to own this incredible waterfront retreat!

4 Beds ⋅ 5 Baths ⋅ Point Crisp SubDv. ⋅ 34242 Zip Code

Welcome to 1364 Point Crisp, a breathtaking waterfront home on one of the most private and interesting streets on Siesta Key. With only seven homes on this secluded section of road, you’ll enjoy peace, quiet, and incredible views of Little Sarasota Bay and the Intracoastal Waterway. Watch sailboats glide by or fishermen return from a great day out in the Gulf. This home is a boater’s dream, featuring a 16,000# boat lift and a 10,000# personal watercraft lift not to mention a separate day dock and kayak Launch in the back yard. The heated saltwater pool was custom built and features a spacious deck, and plenty of room to entertain family and friends. Relax on one of the two large second-floor balconies with an outdoor grill area and roll-down screens—perfect for enjoying a glass of wine while watching the sunset. Other features include: a 100KW Kohler commercial backup generator powered by natural gas, Impact-rated doors and windows, well water for irrigation and city water access at multiple points, including the dock. Six climate-controlled garage spaces plus tons of extra storage on the first level, with easy access to the backyard and pool. Inside, with an elevator serving all levels of the home, you’ll find 4 spacious bedrooms, 5 full bathrooms, and a modern kitchen with a Sub-Zero refrigerator, Thermador induction cooktop, and GE Monogram appliances. The wet bar includes a beverage fridge and extra storage—perfect for entertaining. This home has been meticulously maintained and offers countless hidden conveniences that make life easier. Don’t miss your chance to own this incredible waterfront retreat!

1364 Point Crisp Road, Sarasota

$1,100,000

Nestled in the highly sought-after Siesta Cove neighborhood of Sarasota, 5239 Siesta Cove Drive is a stunning property offering an exceptional blend of luxury, tranquility, and prime location. This beautifully updated 4-bedroom, 4-bathroom residence spans 2,333 square feet of living space and is set on a lush 0.31-acre lot, making it the perfect retreat for those who appreciate both privacy and convenience. The home also boasts a NEW roof and NEW hurricane rated windows and doors, providing peace of mind and enhanced durability for years to come. As you enter the home, you are welcomed by a spacious open floor plan that combines modern design with timeless elegance. The living areas feature large windows that flood the home with natural light, creating an airy and inviting atmosphere. The gourmet kitchen is a chef’s dream, with high-end stainless steel appliances, custom cabinetry, quartz countertops, and a large center island perfect for meal prep or casual dining. The open concept seamlessly connects the kitchen, dining, and living areas, creating an ideal space for entertaining guests or enjoying quiet family time. The master suite serves as a luxurious sanctuary, with expansive windows allowing plenty of natural light, a generous walk-in closet, and a spa-like en suite bathroom that includes a soaking tub, and a separate walk-in shower. The additional bedrooms are equally spacious, offering comfort and flexibility for family, guests, or a home office. A convenient mother-in-law suite is located downstairs, providing privacy and comfort for extended family. The outdoor living space is designed for relaxation and entertainment. Step outside to a large private terrace, perfect for enjoying a morning coffee or peaceful evenings outdoors. The expansive second floor deck features a beautiful pool, offering the perfect place to cool off on warm Florida days or host poolside gatherings. With ample space, the backyard provides a tranquil environment for unwinding and enjoying the beautiful Florida weather. Siesta Cove is one of Sarasota’s most desirable communities, known for its serene atmosphere and close proximity to Siesta Key’s world-renowned beaches. Whether you prefer relaxing on the powdery white sands of Siesta Key Beach or taking advantage of the many water activities available, this location offers the best of both worlds. In addition to beach access, you’ll find a variety of dining, shopping, and cultural attractions just a short drive away in Sarasota’s vibrant downtown. For those who enjoy an active lifestyle, Siesta Cove offers the perfect balance of outdoor adventure and relaxation. Don’t miss the opportunity to own this incredible piece of paradise in one of Florida’s most desirable neighborhoods!

4 Beds ⋅ 4 Baths ⋅ Siesta Cove Sub SubDv. ⋅ 34242 Zip Code

Nestled in the highly sought-after Siesta Cove neighborhood of Sarasota, 5239 Siesta Cove Drive is a stunning property offering an exceptional blend of luxury, tranquility, and prime location. This beautifully updated 4-bedroom, 4-bathroom residence spans 2,333 square feet of living space and is set on a lush 0.31-acre lot, making it the perfect retreat for those who appreciate both privacy and convenience. The home also boasts a NEW roof and NEW hurricane rated windows and doors, providing peace of mind and enhanced durability for years to come. As you enter the home, you are welcomed by a spacious open floor plan that combines modern design with timeless elegance. The living areas feature large windows that flood the home with natural light, creating an airy and inviting atmosphere. The gourmet kitchen is a chef’s dream, with high-end stainless steel appliances, custom cabinetry, quartz countertops, and a large center island perfect for meal prep or casual dining. The open concept seamlessly connects the kitchen, dining, and living areas, creating an ideal space for entertaining guests or enjoying quiet family time. The master suite serves as a luxurious sanctuary, with expansive windows allowing plenty of natural light, a generous walk-in closet, and a spa-like en suite bathroom that includes a soaking tub, and a separate walk-in shower. The additional bedrooms are equally spacious, offering comfort and flexibility for family, guests, or a home office. A convenient mother-in-law suite is located downstairs, providing privacy and comfort for extended family. The outdoor living space is designed for relaxation and entertainment. Step outside to a large private terrace, perfect for enjoying a morning coffee or peaceful evenings outdoors. The expansive second floor deck features a beautiful pool, offering the perfect place to cool off on warm Florida days or host poolside gatherings. With ample space, the backyard provides a tranquil environment for unwinding and enjoying the beautiful Florida weather. Siesta Cove is one of Sarasota’s most desirable communities, known for its serene atmosphere and close proximity to Siesta Key’s world-renowned beaches. Whether you prefer relaxing on the powdery white sands of Siesta Key Beach or taking advantage of the many water activities available, this location offers the best of both worlds. In addition to beach access, you’ll find a variety of dining, shopping, and cultural attractions just a short drive away in Sarasota’s vibrant downtown. For those who enjoy an active lifestyle, Siesta Cove offers the perfect balance of outdoor adventure and relaxation. Don’t miss the opportunity to own this incredible piece of paradise in one of Florida’s most desirable neighborhoods!

5239 Siesta Cove Drive, Sarasota

$3,250,000

Under Construction. A rare opportunity to own a beautifully crafted custom home on Siesta Key by Nutter Custom Construction. This stunning custom residence is now nearing completion, with anticipated delivery in September 2026. Every detail has been thoughtfully curated to deliver an exceptional luxury living experience. This Coastal Contemporary residence offers 3,200 sq. ft. of interior living space and over 5,500 sq. ft. of total indoor/outdoor living, thoughtfully designed to maximize both luxury and comfort. Enjoy three spacious balconies, an outdoor kitchen, and a generous covered lanai that seamlessly blends indoor and outdoor living. Inside, the open floor plan is filled with natural light and features a stunning chef’s kitchen equipped with luxury appliances, custom cabinetry, and a walk-in pantry. The kitchen flows effortlessly into the dining area and great room, creating the perfect space for entertaining or relaxing with family. The home includes 4 bedrooms and 4 full bathrooms, providing ample space for family and guests. The expansive primary suite offers dual walk-in closets, a private balcony, and a serene retreat for homeowners. Upstairs, a versatile loft with access to a private balcony makes an ideal office or second living area. Additional highlights include an oversized 2.5-car garage, elevator access to all levels, and a full utility room for added convenience. The private backyard oasis features a beautiful pool and lush surroundings for year-round enjoyment. Located just minutes from Siesta Key’s world-famous beaches, as well as the vibrant shopping and dining options in The Village, this is a unique opportunity to personalize your dream home during this phase of construction. Don’t miss your chance to own a custom-built home in one of Sarasota’s most sought-after coastal communities. Please note: Some photos have been virtually staged for illustration purposes.

4 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

Under Construction. A rare opportunity to own a beautifully crafted custom home on Siesta Key by Nutter Custom Construction. This stunning custom residence is now nearing completion, with anticipated delivery in September 2026. Every detail has been thoughtfully curated to deliver an exceptional luxury living experience. This Coastal Contemporary residence offers 3,200 sq. ft. of interior living space and over 5,500 sq. ft. of total indoor/outdoor living, thoughtfully designed to maximize both luxury and comfort. Enjoy three spacious balconies, an outdoor kitchen, and a generous covered lanai that seamlessly blends indoor and outdoor living. Inside, the open floor plan is filled with natural light and features a stunning chef’s kitchen equipped with luxury appliances, custom cabinetry, and a walk-in pantry. The kitchen flows effortlessly into the dining area and great room, creating the perfect space for entertaining or relaxing with family. The home includes 4 bedrooms and 4 full bathrooms, providing ample space for family and guests. The expansive primary suite offers dual walk-in closets, a private balcony, and a serene retreat for homeowners. Upstairs, a versatile loft with access to a private balcony makes an ideal office or second living area. Additional highlights include an oversized 2.5-car garage, elevator access to all levels, and a full utility room for added convenience. The private backyard oasis features a beautiful pool and lush surroundings for year-round enjoyment. Located just minutes from Siesta Key’s world-famous beaches, as well as the vibrant shopping and dining options in The Village, this is a unique opportunity to personalize your dream home during this phase of construction. Don’t miss your chance to own a custom-built home in one of Sarasota’s most sought-after coastal communities. Please note: Some photos have been virtually staged for illustration purposes.

4903 Commonwealth Drive, Sarasota

$475,000

GREAT GULF FRONT OPPORTUNITY! This incredibly well priced 2 bed/2 bath villa represents an exceptional opportunity to start fresh with almost new construction in the idyllic GULF FRONT property of Whispering Sands on Siesta Key. This lovely unit experienced flooding last fall and is now being sold post remediation and pre rebuild – providing the next owner with the wonderful opportunity to customize it to their own individual style. It has undergone professional remediation, mold, asbestos, and lead inspections, drywall removal and installation, and has been newly painted. New baseboards, interior doors, trim, and remaining flooring have yet to be added back to the villa. This unit features a wonderful galley kitchen with small breakfast bar. The lower kitchen cabinets, appliances, and bathroom vanities & fixtures have been removed. The kitchen and bathroom countertops were able to be saved, are in great shape, and are stored in the villa. The interior includes gleaming crown molding, recessed lighting, and newer ceiling fans. Two sets of beautiful French doors with privacy mini blinds open from the living space. One set opens into a gorgeous sunroom with high windows, vaulted ceiling, sliding windows with screens, and its own A/C system, and the other into a private patio. The primary and guest bedroom windows are covered with plantation shutters. This will also features a one car garage, with a W/D hook up. A NEW 2025 CONCRETE TILE ROOF IS BEING PUT ON THE VILLA - PAID BY THE SELLER. The garage was reroofed in 2020.

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

GREAT GULF FRONT OPPORTUNITY! This incredibly well priced 2 bed/2 bath villa represents an exceptional opportunity to start fresh with almost new construction in the idyllic GULF FRONT property of Whispering Sands on Siesta Key. This lovely unit experienced flooding last fall and is now being sold post remediation and pre rebuild – providing the next owner with the wonderful opportunity to customize it to their own individual style. It has undergone professional remediation, mold, asbestos, and lead inspections, drywall removal and installation, and has been newly painted. New baseboards, interior doors, trim, and remaining flooring have yet to be added back to the villa. This unit features a wonderful galley kitchen with small breakfast bar. The lower kitchen cabinets, appliances, and bathroom vanities & fixtures have been removed. The kitchen and bathroom countertops were able to be saved, are in great shape, and are stored in the villa. The interior includes gleaming crown molding, recessed lighting, and newer ceiling fans. Two sets of beautiful French doors with privacy mini blinds open from the living space. One set opens into a gorgeous sunroom with high windows, vaulted ceiling, sliding windows with screens, and its own A/C system, and the other into a private patio. The primary and guest bedroom windows are covered with plantation shutters. This will also features a one car garage, with a W/D hook up. A NEW 2025 CONCRETE TILE ROOF IS BEING PUT ON THE VILLA - PAID BY THE SELLER. The garage was reroofed in 2020.

147 Whispering Sands Drive Unit V29, Sarasota

$6,600,000

* Pending. Accepting backup offers.* Nestled along the pristine northern shores of Siesta Key, this magnificent three-story waterfront retreat redefines coastal luxury and exclusivity. The home features 10,600 sq ft under roof with approximately 5,500sq ft under air. This exceptional home is crafted for grand entertaining and effortless relaxation. While Siesta Beach and Village are just minutes away by golf cart, the gated personal estate ensures total privacy, creating a secluded paradise where the rhythm of the waves and the beauty of the Gulf serve as the ultimate backdrop. As you approach, a sprawling driveway and state-of-the-art security gates provide both exclusivity and convenience, granting access to a four-car garage, perfect for luxury vehicles, watercraft, or additional storage. Stepping inside, you’re greeted by a grand entrance with a 34-foot-high foyer. Up the stairs you will find walls of glass showcasing unobstructed Gulf panoramas. Expansive retractable glass doors erase the line between indoors and out, immersing you in the stunning coastal setting from the moment you arrive. Descending to the main living level, a chef’s dream kitchen awaits, masterfully designed with thick quartz countertops, a spacious center island, and a custom eight-seat breakfast bar. Flowing seamlessly into sun-drenched living and dining areas, this space is enhanced by towering 12-foot ceilings, creating an atmosphere of grandeur and warmth. A hidden bonus room unveils a fully equipped outdoor kitchen and entertainment lounge, offering a seamless transition to alfresco dining and unforgettable gatherings under the stars. The upper levels of the home are dedicated to rest and rejuvenation, with four private bedroom suites, each offering breathtaking Gulf views, intimate balconies, and spa-inspired en-suite baths. The primary suite, a haven of tranquility, boasts 270-degree water views, expansive lounging terraces, and a marble-clad spa bath, designed to capture the essence of relaxation and indulgence. Beyond the home’s elegant interiors lies a spectacular tropical oasis. Designed by the renowned Lucas Lagoons, the lagoon-style pool and spa feature a cascading waterfall, offering the ultimate retreat for relaxation. A meandering stone pathway winds through the gorgeous landscape, passing a serene saltwater tidal pond, leading to a two-story Tiki retreat, an idyllic setting for sunset cocktails and ocean breezes. At the edge of the property, a Gulf-front fire pit, nestled into the immaculate white sands, invites you to unwind as the sky transforms into a breathtaking masterpiece of colors. Whether envisioned as a luxurious primary residence or an exceptional coastal retreat, this one-of-a-kind Gulf-front estate offers an unparalleled blend of seclusion, sophistication, and effortless luxury. With unrivaled beach frontage and panoramic water views, this property is more than just a home—it is a rare opportunity to own a true piece of paradise on one of the most coveted stretches of Siesta Key. This listing does not include the lot at 0 Solymar Dr. MLS number (A4642147). Creative Seller Financing Available!

4 Beds ⋅ 5 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code

* Pending. Accepting backup offers.* Nestled along the pristine northern shores of Siesta Key, this magnificent three-story waterfront retreat redefines coastal luxury and exclusivity. The home features 10,600 sq ft under roof with approximately 5,500sq ft under air. This exceptional home is crafted for grand entertaining and effortless relaxation. While Siesta Beach and Village are just minutes away by golf cart, the gated personal estate ensures total privacy, creating a secluded paradise where the rhythm of the waves and the beauty of the Gulf serve as the ultimate backdrop. As you approach, a sprawling driveway and state-of-the-art security gates provide both exclusivity and convenience, granting access to a four-car garage, perfect for luxury vehicles, watercraft, or additional storage. Stepping inside, you’re greeted by a grand entrance with a 34-foot-high foyer. Up the stairs you will find walls of glass showcasing unobstructed Gulf panoramas. Expansive retractable glass doors erase the line between indoors and out, immersing you in the stunning coastal setting from the moment you arrive. Descending to the main living level, a chef’s dream kitchen awaits, masterfully designed with thick quartz countertops, a spacious center island, and a custom eight-seat breakfast bar. Flowing seamlessly into sun-drenched living and dining areas, this space is enhanced by towering 12-foot ceilings, creating an atmosphere of grandeur and warmth. A hidden bonus room unveils a fully equipped outdoor kitchen and entertainment lounge, offering a seamless transition to alfresco dining and unforgettable gatherings under the stars. The upper levels of the home are dedicated to rest and rejuvenation, with four private bedroom suites, each offering breathtaking Gulf views, intimate balconies, and spa-inspired en-suite baths. The primary suite, a haven of tranquility, boasts 270-degree water views, expansive lounging terraces, and a marble-clad spa bath, designed to capture the essence of relaxation and indulgence. Beyond the home’s elegant interiors lies a spectacular tropical oasis. Designed by the renowned Lucas Lagoons, the lagoon-style pool and spa feature a cascading waterfall, offering the ultimate retreat for relaxation. A meandering stone pathway winds through the gorgeous landscape, passing a serene saltwater tidal pond, leading to a two-story Tiki retreat, an idyllic setting for sunset cocktails and ocean breezes. At the edge of the property, a Gulf-front fire pit, nestled into the immaculate white sands, invites you to unwind as the sky transforms into a breathtaking masterpiece of colors. Whether envisioned as a luxurious primary residence or an exceptional coastal retreat, this one-of-a-kind Gulf-front estate offers an unparalleled blend of seclusion, sophistication, and effortless luxury. With unrivaled beach frontage and panoramic water views, this property is more than just a home—it is a rare opportunity to own a true piece of paradise on one of the most coveted stretches of Siesta Key. This listing does not include the lot at 0 Solymar Dr. MLS number (A4642147). Creative Seller Financing Available!

3935 N Shell Road, Sarasota

$1,060,000

Build your dream estate on this private, one-acre lot on a spectacular stretch of magical Heron Lagoon, and become a member of the Sanderling Club, one of Sarasota’s most desirable gulf-front coastal communities. For boating enthusiasts, the community marina offers sailing and powerboat access directly to Sarasota Bay, the Intracoastal Waterway and the Gulf via the recently reopened Midnight Pass, and a limited number of slips are available to rent. This spectacular property is outside of the main gate, yet part of the club where residents enjoy a serene lifestyle with access to social events and a private community beach where, each evening, colorful sunsets paint the sky over the Gulf, creating a picture-perfect backdrop for relaxation. This property is more than just a piece of land, it’s an invitation to embrace the beauty, luxury and convenience of coastal living. Conveniently close to Siesta Key’s world-renowned crystal quartz sands, Turtle Beach, and the vibrant dining and shopping scene of Siesta Village and the South Village. Just a short drive away, downtown Sarasota offers a wealth of cultural attractions, including theaters, ballet, opera, museums and art galleries.

2 Beds ⋅ 2 Baths ⋅ Sanderling Club SubDv. ⋅ 34242 Zip Code

Build your dream estate on this private, one-acre lot on a spectacular stretch of magical Heron Lagoon, and become a member of the Sanderling Club, one of Sarasota’s most desirable gulf-front coastal communities. For boating enthusiasts, the community marina offers sailing and powerboat access directly to Sarasota Bay, the Intracoastal Waterway and the Gulf via the recently reopened Midnight Pass, and a limited number of slips are available to rent. This spectacular property is outside of the main gate, yet part of the club where residents enjoy a serene lifestyle with access to social events and a private community beach where, each evening, colorful sunsets paint the sky over the Gulf, creating a picture-perfect backdrop for relaxation. This property is more than just a piece of land, it’s an invitation to embrace the beauty, luxury and convenience of coastal living. Conveniently close to Siesta Key’s world-renowned crystal quartz sands, Turtle Beach, and the vibrant dining and shopping scene of Siesta Village and the South Village. Just a short drive away, downtown Sarasota offers a wealth of cultural attractions, including theaters, ballet, opera, museums and art galleries.

7510 Midnight Pass Road, Sarasota

$2,995,000

Rare and extraordinary waterfront offering on the coveted North end of Siesta Key, this premier Bay Island estate parcel presents the ultimate canvas for creating a world-class coastal retreat. Set on nearly half an acre, the property commands sweeping waterway views and offers 90 feet of protected sailboat-water frontage, complete with an existing 73-foot composite and tile dock—an exceptional amenity for the discerning boating enthusiast. To seamlessly bring your vision to life, fully customizable luxury home plans, as well as projected expenditure framework are available for review from Salt Wave Construction thus significantly expediting the design-build process. The seller has also committed to demolition of the existing structure, allowing for a smooth and efficient transition to new construction. The proposed residence spans approximately 6,366 square feet, including over 4,000 square feet of refined, air-conditioned living space, thoughtfully designed to maximize waterfront exposure and elevate indoor-outdoor living. Multiple entertaining spaces, expansive terraces, and view-oriented decks create the perfect setting for both grand gatherings and intimate moments, all framed by captivating water vistas. Ideally located for effortless access on and off Siesta Key and just minutes from the culture, dining, and sophistication of Downtown Sarasota, this exceptional property offers the rare combination of privacy, prestige, and proximity. An unparalleled opportunity to craft a legacy waterfront estate in one of Sarasota’s most sought-after enclaves.

3 Beds ⋅ 5 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code

Rare and extraordinary waterfront offering on the coveted North end of Siesta Key, this premier Bay Island estate parcel presents the ultimate canvas for creating a world-class coastal retreat. Set on nearly half an acre, the property commands sweeping waterway views and offers 90 feet of protected sailboat-water frontage, complete with an existing 73-foot composite and tile dock—an exceptional amenity for the discerning boating enthusiast. To seamlessly bring your vision to life, fully customizable luxury home plans, as well as projected expenditure framework are available for review from Salt Wave Construction thus significantly expediting the design-build process. The seller has also committed to demolition of the existing structure, allowing for a smooth and efficient transition to new construction. The proposed residence spans approximately 6,366 square feet, including over 4,000 square feet of refined, air-conditioned living space, thoughtfully designed to maximize waterfront exposure and elevate indoor-outdoor living. Multiple entertaining spaces, expansive terraces, and view-oriented decks create the perfect setting for both grand gatherings and intimate moments, all framed by captivating water vistas. Ideally located for effortless access on and off Siesta Key and just minutes from the culture, dining, and sophistication of Downtown Sarasota, this exceptional property offers the rare combination of privacy, prestige, and proximity. An unparalleled opportunity to craft a legacy waterfront estate in one of Sarasota’s most sought-after enclaves.

732 Siesta Drive, Sarasota

$2,950,000

New price! Experience the epitome of Siesta Key living in this exquisitely crafted residence near Siesta Village and renowned pristine beaches, with every conceivable amenity nearby. On a generous one-third-acre lot, this 2019 custom masterpiece by award-winning John Cannon Homes epitomizes luxury and sophistication. Boasting four spacious bedrooms, an office, and five baths, this home is an entertainer's dream, designed to host large gatherings with ease and elegance. Built with an unwavering commitment to quality and luxury, every detail has been thoughtfully considered to offer unparalleled comfort and convenience. Innovative technology is seamlessly integrated throughout the home, allowing for remote control from your smartphone, a cutting-edge media system for immersive sound and visual experiences, a Lutron lighting and blind system, and a reliable backup generator, ensuring uninterrupted enjoyment. The open-concept floor plan offers soaring ceilings illuminated by natural light. The great room flows seamlessly to the dining area and the fabulous chef’s kitchen, which features sleek custom cabinetry, an expansive island with seating, and quartz counters. Top-of-the-line Thermador appliances include a six-burner natural gas range and a built-in Miele coffee system, ensuring culinary excellence. The primary suite is a sanctuary of relaxation, welcoming its occupants after a day filled with sun and fun. Guests are pampered with their own en-suite baths and access to bespoke entertainment options, ensuring privacy and luxury for everyone. The heart of this magnificent property is the expansive outdoor lanai, featuring a stunning pool set against the backdrop of silver travertine tile, a rejuvenating spa, and a fully equipped kitchen and bar area, living room and fireplace, promising unforgettable moments under the sun or stars. As the sun sets, the outdoor living space becomes a central gathering spot, where music, laughter, and culinary delights blend to create the perfect evening. An automated irrigation system maintains lush greenery. A high-ceiling garage with a two-car lift provides ample space for your luxury vehicles, while a comprehensive camera system, impact doors, windows, and garage door, and a natural gas-powered generator ensure security and peace of mind. The high-quality construction offers an added benefit with reasonable insurance rates. This home promises a life of exquisite luxury and unmatched convenience, where the car keys are forgotten. Enjoy the convenience of being near the vibrant Village, as well as the white quartz sands and azure waters of Siesta Beach. Welcome to your paradise on Siesta Key, where every day there is a testament to the beauty of island living.

4 Beds ⋅ 5 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code

New price! Experience the epitome of Siesta Key living in this exquisitely crafted residence near Siesta Village and renowned pristine beaches, with every conceivable amenity nearby. On a generous one-third-acre lot, this 2019 custom masterpiece by award-winning John Cannon Homes epitomizes luxury and sophistication. Boasting four spacious bedrooms, an office, and five baths, this home is an entertainer's dream, designed to host large gatherings with ease and elegance. Built with an unwavering commitment to quality and luxury, every detail has been thoughtfully considered to offer unparalleled comfort and convenience. Innovative technology is seamlessly integrated throughout the home, allowing for remote control from your smartphone, a cutting-edge media system for immersive sound and visual experiences, a Lutron lighting and blind system, and a reliable backup generator, ensuring uninterrupted enjoyment. The open-concept floor plan offers soaring ceilings illuminated by natural light. The great room flows seamlessly to the dining area and the fabulous chef’s kitchen, which features sleek custom cabinetry, an expansive island with seating, and quartz counters. Top-of-the-line Thermador appliances include a six-burner natural gas range and a built-in Miele coffee system, ensuring culinary excellence. The primary suite is a sanctuary of relaxation, welcoming its occupants after a day filled with sun and fun. Guests are pampered with their own en-suite baths and access to bespoke entertainment options, ensuring privacy and luxury for everyone. The heart of this magnificent property is the expansive outdoor lanai, featuring a stunning pool set against the backdrop of silver travertine tile, a rejuvenating spa, and a fully equipped kitchen and bar area, living room and fireplace, promising unforgettable moments under the sun or stars. As the sun sets, the outdoor living space becomes a central gathering spot, where music, laughter, and culinary delights blend to create the perfect evening. An automated irrigation system maintains lush greenery. A high-ceiling garage with a two-car lift provides ample space for your luxury vehicles, while a comprehensive camera system, impact doors, windows, and garage door, and a natural gas-powered generator ensure security and peace of mind. The high-quality construction offers an added benefit with reasonable insurance rates. This home promises a life of exquisite luxury and unmatched convenience, where the car keys are forgotten. Enjoy the convenience of being near the vibrant Village, as well as the white quartz sands and azure waters of Siesta Beach. Welcome to your paradise on Siesta Key, where every day there is a testament to the beauty of island living.

4940 Peaceable Way, Sarasota