Siesta Key FL Real Estate, Homes for Sale With Stone Counters - Ed Grabowski

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

An exceptionally rare opportunity on the coveted north end of Siesta Key, 3740 Bayou Louise Lane is set in a remarkable waterfront location at the tip of a protected peninsula, surrounded by the beauty of the Gulf and Bay. Enjoy extraordinary water views, spectacular sunsets, and exceptional boating access to the Gulf and Intracoastal Waterway all from one of Sarasota's most desirable and distinctive settings. Built in 1995, this three-bedroom residence offers approximately 2,330 square feet of living area, three full baths, and a powder room. Inside, a gourmet kitchen with high-end appliances is complemented by custom wood flooring, extensive crown molding, and refined architectural millwork. The home's special location offers easy access to the mainland, downtown Sarasota, and Siesta Key's beaches.

3740 Bayou Louise Lane, Sarasota

$3,100,000

3 Beds ⋅ 5 Baths ⋅ Sanderling Club SubDv. ⋅ 34242 Zip Code

Discover coastal living at 7200 Melaleuca Way, a custom waterfront home in the private Sanderling Club on Siesta Key, Florida. Built in 2018 on approximately three-quarters of an acre, this residence combines coastal architecture, detailed craftsmanship, and access to the natural beauty of Heron Lagoon. Offering approximately 3,587 square feet of living space, the home includes three bedrooms, four full bathrooms, and one half bath. Soaring ceilings, custom millwork, and generously proportioned rooms define the interiors. Concrete block construction and impact-rated windows and doors complement the home’s design with practical features that distinguish it within Siesta Key’s housing market. Designed for entertaining and everyday comfort, the living spaces connect to an outdoor retreat with a swimming pool, spa, and grounds that provide room to relax in privacy. A private dock on Heron Lagoon offers a setting for kayaking, paddleboarding, and observing island wildlife. The three-car garage accommodates vehicles, recreational equipment, and storage. Residents of Sanderling Club enjoy a private Gulf-front beach, clubhouse, and tennis facilities, along with access to community boat slips for owners, subject to availability and a waitlist. Nearby, Siesta Key Village offers restaurants, boutiques, and live music that complement the island lifestyle. Spend the day paddleboarding on Heron Lagoon, strolling Siesta Key’s celebrated white-sand beaches, or gathering with friends for dinner in the Village. At 7200 Melaleuca Way, architectural craftsmanship and a private waterfront setting come together in one of Siesta Key, Florida’s most distinctive coastal communities.

7200 Melaleuca Way, Sarasota

$1,359,000

2 Beds ⋅ 2 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code

Virtually Staged - Perfectly positioned to capture the ever-changing beauty of the Gulf, this northwest-facing residence offers a front-row seat to nature’s daily masterpiece. From the lush green lawn and swaying palm fronds to the Gulf’s ever-changing shades of turquoise, blue, and emerald, the views unfold in layers of coastal color. As the day draws to a close, the western sky ignites in brilliant sunset hues, transforming the landscape into a breathtaking panorama that never looks quite the same twice. Here, the view isn’t just something you see—it’s an experience to savor. Welcome to Windward Passage, where the beauty of Siesta Key meets the comfort of an exceptionally spacious coastal retreat. Offering 1,626 square feet of living space, this two-bedroom, two-bath residence blends timeless Gulf views with thoughtful modern updates. Renovated kitchen and bathrooms, luxury vinyl plank flooring throughout, impact-resistant windows on the waterfront facing side, and a newer air-conditioner provide the perfect balance of style, comfort, and peace of mind. Situated on the third floor, the home enjoys an ideal elevation—high enough to embrace sweeping coastal scenery while maintaining a wonderful connection to the tropical landscape below. An oversized private garage adds a level of convenience and storage rarely found in condominium living. Beyond the residence, the best of Siesta Key is practically at your doorstep. Just a leisurely 10-minute stroll brings you to the heart of Siesta Key Village, where lively tiki bars, exceptional dining, boutique shops, and live music create an atmosphere that’s distinctly island. And when the beach calls, the nearest public beach access lies just beyond "The Village" or an even easier 5-minute bike ride away. Whether you’re seeking a full-time residence or a cherished coastal getaway, this is a place to slow down, settle in, and appreciate the extraordinary beauty of everyday life on Siesta Key. Some properties are defined by their features. Others are remembered for how they make you feel. This one offers both.

4712 Ocean Boulevard Unit W5, Sarasota

$1,650,000

3 Beds ⋅ 3 Baths ⋅ Sara Sands SubDv. ⋅ 34242 Zip Code

An exceptional opportunity for waterfront living. Discover a private waterfront retreat where boating, tropical gardens, and relaxed island living come together in one of Siesta Key's desirable residential neighborhoods. Set behind a gated entrance and surrounded by lush landscaping, this beautifully refreshed three-bedroom, two-and-a-half-bath residence offers an inviting blend of coastal comfort, privacy, and exceptional outdoor living. Designed to embrace the Florida lifestyle, the spacious, open living and dining areas feature easy-care tile flooring, abundant natural light, and effortless connections to the outdoors. The updated kitchen offers granite countertops, white cabinetry, stainless steel appliances, and a welcoming dining area overlooking the pool and gardens. The comfortable primary suite and two additional bedrooms provide flexibility for family, guests, or a home office. A distinctive Bali-inspired bath with an indoor-outdoor shower adds an unexpected touch of tropical character. The heart of this property is its extraordinary screened outdoor living area. An expansive swimming pool and elevated spa are surrounded by generous paver decking, multiple lounging and dining spaces, and a covered lanai, creating a wonderful setting for entertaining or simply enjoying the island breezes. Beyond the pool, a beautifully landscaped backyard unfolds toward the waterfront, offering a peaceful garden setting with mature palms, tropical foliage, and room to relax. For boating enthusiasts, the private dock and 7,000 lb. boat lift provide convenient access to Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond. Spend the morning cruising the waterways, enjoy an afternoon on the water, or launch a kayak or paddleboard right from your backyard. A welcoming covered entry, gated paver driveway, and attached two-car garage with additional storage complete this distinctive island property. Just minutes from Siesta Beach's renowned quartz-white sands, Siesta Village's restaurants and boutiques, and the cultural attractions of downtown Sarasota, this residence delivers the best of coastal living in a wonderfully private setting. Whether entertaining around the pool, exploring Sarasota's waterways, or simply enjoying the tranquility of your own tropical gardens, this is an opportunity to embrace the Siesta Key lifestyle

5140 Windward Avenue, Sarasota

$7,450,000

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

This private waterfront estate on Siesta Key combines modern Mediterranean architecture, beautifully updated interiors, and sweeping views of Little Sarasota Bay to create an exceptional coastal retreat. Set on over an acre of lush property behind a gated entrance and winding pavered driveway, this custom residence offers more than 100 feet of direct bay frontage, exceptional privacy, and unobstructed boating access to Sarasota Bay and the Intracoastal Waterway. Built in 2012 and extensively refreshed, the home encompasses more than 6,000 square feet of living space, four en-suite bedrooms, a four-car split garage, and an impressive collection of indoor and outdoor entertaining spaces. Offered fully furnished with contemporary pieces throughout, this remarkable home is ready for immediate enjoyment. A dramatic entry introduces soaring cathedral ceilings, a neutral color palette, and walls of floor-to-ceiling glass framing the waterfront. The grand living room features a fireplace and spectacular two-story windows, while the adjoining formal dining room provides an elegant setting for entertaining. Tile flooring complements the main living level, with beautiful hardwood flooring upstairs. The light-filled gourmet kitchen features quartz countertops, custom cabinetry, all-white appliances, gold fixtures, oversized center island, separate breakfast bar, dual built-in ovens, six-burner gas cooktop, and concealed 6-by-10-foot walk-in pantry. The adjoining informal dining area and spacious family room create an inviting gathering space overlooking the bay. Walls of pocketing glass sliders open completely to the covered outdoor cabana and fully equipped summer kitchen, seamlessly connecting indoor and outdoor living. Privately positioned on the main level, the beautiful primary suite features peaceful water views, an oversized dual walk-in closet, and a luxurious marble-appointed bathroom. A nearby office/den offers a quiet retreat, while private access to the pool deck enhances the suite's connection to the outdoors. A secluded second en-suite bedroom with its own exterior entrance provides an ideal arrangement for guests or extended family. The first-floor laundry room offers generous built-in storage. Upstairs, two spacious bedroom suites feature hardwood flooring, walk-in closets, updated en-suite bathrooms, and private balconies overlooking Little Sarasota Bay. An additional bonus room with dual closets and a wet bar overlooks the dramatic living room below and offers flexibility as a fifth bedroom, media room, or additional office. Outside, lush tropical landscaping surrounds an expansive pavered pool deck with a heated swimming pool, raised spa, and covered outdoor living area. A waterfront firepit, private basketball court, and extended dock with a 20,000-lbs. lift complete this exceptional setting. Boaters will appreciate the property's 103 feet of shoreline and direct access to the open waters of Sarasota Bay. Recent improvements include a new roof in 2025, three updated bathrooms, and HVAC replacements in 2024 and 2022. Ideally situated on Siesta Key, this private bayfront estate offers convenient access to Siesta Key Beach, Turtle Beach, Siesta Key Village, and the island's waterfront restaurants and recreational opportunities, just minutes away. Nearby mainland destinations include Downtown Sarasota, Marina Jack, Selby Botanical Gardens, renowned theaters, galleries, and cultural attractions.

8569 Midnight Pass Road, Sarasota

5830 Midnight Pass Road Unit 38, Sarasota

$540,000

1 Beds ⋅ 1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code

Beautifully renovated in 2025, turnkey furnished, and a short distance from the powder-white sands of Siesta Key Beach! Discover an exceptional opportunity to own a virtually new coastal retreat in Jamaica Royale, a highly desirable beachfront community on world-renowned Siesta Key. Completely rebuilt from the studs up in 2025, this beautifully transformed one-bedroom, one-bath, ground-floor residence combines contemporary coastal elegance, thoughtful design, and effortless island living with the added appeal of an established vacation rental history. Enter inside to discover a bright, inviting, open-concept interior showcasing a fresh coastal-inspired design and quality finishes throughout. Beautiful Cali longboard luxury vinyl plank flooring creates a seamless flow between living spaces, while the completely renovated kitchen features crisp white Shaker-style soft-close cabinetry, gleaming granite countertops, a ceramic tile backsplash, and new stainless-steel appliances. The beautifully remodeled bath is equally impressive, featuring a spacious walk-in shower with ceramic tile surround, a new white Shaker-style vanity, and updated fixtures. Additional enhancements include a hurricane-rated sliding glass door and front entry door, along with the everyday convenience of an interior laundry room equipped with a stacked washer and dryer. Extend your living space outdoors to the generously sized patio, an inviting setting for morning coffee, afternoon relaxation, or evening cocktails amid lush tropical surroundings. Overlooking one of the community's sparkling swimming pools just a short distance away, this outdoor retreat enhances the relaxed, resort-style atmosphere. Best of all, the Gulf's turquoise waters and Siesta Key's legendary powder-soft quartz sand are only a short stroll from your doorstep! Jamaica Royale is a beautifully maintained beachfront community offering approximately 300 feet of private deeded beach frontage and an impressive collection of resort-style amenities. Residents and guests enjoy three heated swimming pools, including a beachfront pool, lush tropical landscaping, shuffleboard courts, community grilling areas, and newly renovated beachside restrooms and changing facilities. One assigned parking space adds convenience, while nearby public tennis courts offer additional recreational opportunities. Pet owners will appreciate that pets are permitted for condominium owners, subject to community restrictions, while tenants are not permitted to have pets. Spend sun-filled days on the beach, enjoy spectacular Gulf sunsets, and embrace the laid-back elegance of Siesta Key living. Exploring the island is effortless, with a complimentary shuttle stop directly in front of the community providing convenient access to Siesta Key Village's acclaimed restaurants, charming boutiques, entertainment, and vibrant nightlife. Turnkey furnished and move-in or rental ready! This exceptional residence offers immediate enjoyment and attractive income potential, with an established rental history, existing future bookings, and participation in the TSA Prime rental program. Whether you're seeking a personal beachfront escape, a seasonal winter retreat, or an income-producing vacation rental, this extensively renovated condominium delivers an outstanding combination of location, lifestyle, and investment appeal. Experience the best of Siesta Key, where every day feels like a vacation!

5830 Midnight Pass Road Unit 38, Sarasota

120 Whispering Sands Drive Unit V20, Sarasota

$725,000

3 Beds ⋅ 3 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

RARELY AVAILABLE & EXQUISITELY REMODELED! Discover an exceptional 3 bedroom/3 bath freestanding villa with 2-car garage in Whispering Sands, Siesta Key’s coveted resort style GULF FRONT community on 800’ of private beach! Completely gutted and reimagined in 2016, this remarkable residence showcases creative design, quality finishes, and meticulous attention to detail throughout. An impressive 1,640 square feet of interior living space unfolds beneath soaring vaulted ceilings, with an open concept layout designed for effortless living and entertaining. The expansive 16' x 22' living room is delightfully complemented by sophisticated indirect LED illumination. Beautiful ceramic plank flooring flows throughout. The spacious entertainer’s kitchen combines style and function with granite countertops, a generous breakfast bar, soft close cabinetry & pullout drawers, LG and Bosch stainless appliances, and recessed and pendant lighting. The spacious primary suite offers two closets – a custom walk-in and a separate built-in. The third bedroom could also easily function as a home office, featuring a built-in desk, shelving, and custom closet. All three beautifully remodeled bathrooms feature granite counters, soft close cabinetry, tiled glass-enclosed walk-in showers, recessed lighting, and/or skylights. Two out of three bathrooms are ensuite — a rare advantage. All 2016 hurricane impact windows and sliders. Extend your entertaining outdoors into the private fenced brick paver patio, complete with a gas grill, with propane tank and gas hookup. The epoxy finished 2-car garage includes a full size LG washer and dryer, utility sink, workbench and shelving – and plenty of space for your bikes and beach essentials. Enjoy the Whispering Sands lifestyle. Just around the corner from famous Siesta Key Village, this 55+ Gulf front community includes 800’ of private quartz sand beach, two heated pools, clubhouse (currently undergoing complete remodeling), beachside Tiki Hut, shuffleboard, and canoe/kayak storage. Don’t miss this distinctive villa offering exceptional space, privacy, and effortless coastal living!

120 Whispering Sands Drive Unit V20, Sarasota

6310 Midnight Pass Road Unit 403N, Sarasota

$749,000

2 Beds ⋅ 2 Baths ⋅ Crescent Arms SubDv. ⋅ 34242 Zip Code

Dont Miss this one' beachfront Unit at Crescent Arms on beautiful Siesta Key. Wake up to the sound of gentle waves and step directly onto the powdery white sands of world-renowned Siesta Key Beach from this beautifully fourth floor unit. Perfectly positioned for effortless coastal living, this 2-bedroom, 2-bath unit offers Gulf views and a short walk-out to the beach. The open-concept layout is bathed in natural light, featuring a spacious living area that flows seamlessly to the screened lanai, you can enjoy sunsets over the Gulf . This unit was updated several years ago with solid-surface countertops, tiled floors through out and ample storage making it ideal for both full-time living and vacation stays. The primary suite boasts ample room for a king bed which will boost rental income and a private ensuite bath, while the guest bedroom and bath provides comfort and privacy for family or visitors. Crescent Arms offers resort-style amenities, including a heated beachside pool, private beach lounges, grilling area, and gated access for security and peace of mind. Located on Siesta Key, this community is within minutes of Siesta Key Village, shops, restaurants, and island nightlife. Whether you’re seeking a serene retreat, an investment property with excellent rental potential, or your forever beach home, this beachfront gem delivers the ultimate Siesta Key lifestyle. Recent upgrades include new AC system. This unit has a Strong rental history.

6310 Midnight Pass Road Unit 403N, Sarasota

$9,500,000

5 Beds ⋅ 6 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code

Virtually Staged. A Private Waterfront Paradise on Siesta Key Nearly one acre. Extraordinary tropical gardens. Private beach access. Bridge-free boating. An architectural masterpiece. Some properties are simply impossible to replicate. Hidden behind private gates along the peaceful waters of Coconut Bayou, this extraordinary Siesta Key estate is a world of its own. The grounds are nothing short of spectacular! a lush botanical paradise filled with flowering tropical plants, mature trees, vibrant colors, and winding garden scenery that creates a sense of complete seclusion. With nearly an acre of land, this is a rare opportunity to enjoy the beauty, privacy, and space of a true waterfront sanctuary, with room to envision a pickleball court or additional resort-style amenities. Designed by acclaimed architect Mark Sultana and built by Voigt Construction, the four-bedroom residence is a striking celebration of contemporary architecture. Soaring ceilings, dramatic walls of glass, and a sculptural floating staircase create light-filled interiors that flow effortlessly into the surrounding landscape. Above it all, a spectacular 2,500-square-foot rooftop terrace offers sweeping panoramic views of Siesta Key, Coconut Bayou, the Sarasota skyline, and surrounding waterways. Accessible by private elevator, this extraordinary rooftop retreat is made for sunset cocktails, unforgettable entertaining, and evenings beneath the stars. And then there is the water. Enjoy direct, bridge-free boating access to the Intracoastal Waterway and Gulf of Mexico, with an existing boat lift, kayak and paddleboard launch. Even more special, the property enjoys private access to the secluded Cocoanut Bayou beach, an intimate stretch of shoreline reserved for neighborhood residents, a hidden gem offering a peaceful escape just moments from home. Inside, refined luxury meets effortless entertaining. The chef's kitchen features custom Italian cabinetry, premium appliances, a generous service pantry, and a temperature-controlled wine cellar. A dedicated theater room, expansive terraces, and beautifully connected indoor-outdoor living spaces offer endless opportunities to gather and unwind. The primary suite is a private retreat with two custom walk-in closets, a waterfront balcony, a versatile loft ideal for an office or fitness space, and a luxurious Champagne Jacuzzi infinity tub. Outdoors, the saltwater pool, dramatic fire bowls, and fully equipped summer kitchen are surrounded by the property's magnificent flowering gardens, creating an atmosphere reminiscent of an exclusive tropical resort. A fully detached guest house offers privacy for family and visitors, while garage parking for five vehicles provides exceptional convenience. Thoughtfully elevated above Coconut Bayou, the residence and pool area remained free from flooding during last storms, an important distinction in waterfront living. Just minutes from Siesta Key Village, world-famous Siesta Beach, and The Out-of-Door Academy, this one-of-a-kind estate offers a remarkable combination of architectural beauty, boating freedom, private beach access, and breathtaking natural surroundings. A tropical sanctuary. An architectural statement. An extraordinary way of life.

4317 Midnight Pass Road, Sarasota

$1,150,000

2 Beds ⋅ 2 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code

Discover the relaxed elegance of waterfront living at Dolphin Bay, one of Siesta Key’s desirable gated condominium communities. Enjoy beautiful views of Sarasota Bay from this spacious two-bedroom, two-bath residence offering 1,915 square feet of thoughtfully designed living space, complemented by multiple outdoor areas that invite you to embrace the coastal lifestyle. Bright, welcoming interiors feature an expansive living and dining area, a separate family room, and a beautifully refreshed kitchen with white quartz countertops, freshly painted cabinetry and an inviting breakfast bar. A unique and thoughtful feature is the remote-controlled privacy screen that separates the family room from the kitchen, creating a comfortable, temporary guest retreat when needed. This versatile space offers added flexibility for visiting family and friends while preserving the home's open, inviting design. Hard-surface flooring flows throughout, while the split-bedroom floor plan provides privacy and comfort, with both bedrooms featuring en-suite baths. The generous covered rear lanai extends the living space outdoors, offering peaceful views of the tropical grounds and sparkling bay beyond. A covered front terrace and additional sunning deck provide even more opportunities to enjoy Siesta Key's beautiful weather. Additional highlights include a private one-car garage beneath the building, ample guest parking, and a new HVAC system and water heater installed in 2024. Dolphin Bay offers an exceptional combination of waterfront beauty and resort-style amenities, including a clubhouse, swimming pool, spa, tennis courts, fitness center and day dock. This gated, pet-friendly community enjoys a convenient location near Siesta Key's celebrated beaches, with the island trolley just outside the entrance connecting you to the restaurants, shopping and entertainment of Siesta Village. Whether enjoying a quiet morning overlooking the water, entertaining friends or spending the afternoon at the beach, this inviting residence captures the comfort, versatility and effortless enjoyment of the Siesta Key lifestyle.

1260 Dolphin Bay Way Unit 203, Sarasota

$2,495,000

4 Beds ⋅ 4 Baths ⋅ Beach Villas At The Oasis SubDv. ⋅ 34242 Zip Code

Experience exceptional Siesta Key living in this distinctive two-level penthouse, crowned by an expansive private rooftop terrace with Gulf glimpses, spectacular sunsets and refreshing coastal breezes. Ideally situated in the heart of Siesta Village, just a short stroll from the world-renowned sands of Siesta Beach, this turnkey furnished residence offers 3,236 square feet of beautifully appointed living space, four bedrooms, four baths and multiple private outdoor terraces. The rooftop terrace is a true highlight, creating an extraordinary setting for sunset gatherings, entertaining under the stars or simply relaxing above the vibrant Village atmosphere. Inside, spacious open-concept living areas are designed for comfort and entertaining, complemented by a well-appointed kitchen with a generous center island, breakfast bar and seamless access to outdoor terraces. A separate entertainment room features a wet bar and expansive terrace, providing additional space for family and guests. The inviting primary suite offers a private terrace and spacious bath with soaking tub and walk-in shower, while a second en-suite bedroom and two additional guest bedrooms provide comfortable accommodations. A private elevator connects the oversized attached two-car garage to the living levels, offering convenience and ample storage for beach and recreational gear. Within an intimate, gated community of just 12 residences in three four-unit buildings, each building enjoys its heated pool and spa. Offered turnkey furnished for immediate enjoyment, this exceptional penthouse places the boutiques, restaurants and lively atmosphere of Siesta Village nearby, with Siesta Beach an easy distance from home. Whether enjoyed as a full-time residence, luxurious island retreat or vacation property with rental potential, subject to community restrictions, this remarkable offering combines generous living spaces, exceptional outdoor retreats and one of Siesta Key's desirable locations.

304 Calle Miramar Unit 304S, Sarasota

$2,400,000

5 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Some homes on Siesta Key are about the beach. Others are about boating. This one lets you have both. Set along a protected canal with direct boating access to Sarasota Bay through the Grand Canal, and from there to the Intracoastal Waterway and the Gulf, this Siesta Key waterfront home is made for the way life is meant to be lived. Take the boat out for the morning, launch a kayak or paddleboard from your own waterfront, spend some time at Siesta Key Beach, then come home to your private saltwater pool, outdoor kitchen and quiet canal view. The important updates are already here too: a 2021 reroof, impact windows and sliders installed in 2022, plus new first floor flooring, fresh interior paint, a luxury renovation of the first floor primary bath, an outdoor kitchen and waterfront pavers, all completed in 2026. Plantation shutters finish every window and slider. At the center of the home, a fully screened courtyard lanai with a tabletop fire pit extends the living space. Seven impact sliders connect several rooms directly to the courtyard, filling the home with natural light and creating an easy indoor outdoor flow toward the pool and waterfront. Additional sliders from the flex room open toward the pool. The home and pool sustained no storm damage during the 2024 storms. If you haven’t dropped anchor yet, wait until you see the two amazing primary suites. The first floor primary offers courtyard access, two walk in closets and a beautifully renovated 2026 ensuite bath with upscale finishes. Upstairs, the entire second level becomes a private retreat with canal views, a spacious bath, two more walk in closets and its own waterfront balcony. One closet is so large you may wonder if it could qualify as a New York City apartment. When it is time for a little quiet, open the sliders and take in sunset over the canal, or start your morning with fresh air and coffee on the balcony. A redesigned media and flex area now includes an additional bedroom while preserving an approximately 424 square foot flex room for a media room, gym, game room or lounge. Another bedroom includes a Murphy bed and built in desk, making it an easy guest room, home office or both. Outside is where this home really earns its Siesta Key address. The private saltwater pool is surrounded by tropical landscaping and spaces for relaxing, dining and entertaining. The seawall, bulkhead and davits were replaced in 2021, with the waterfront setup planned around a 45 foot Sea Ray. This is a home for boaters who want to use the water, not simply look at it. Set in the heart of Siesta Key, the home is just minutes from Siesta Key Beach, named the No. 1 in the U.S. for 2026 and recognized among the nation’s best many times over. Known for its powdery quartz sand and Gulf waters, it is one of the reasons living here is so special. Siesta Key Village is close by for restaurants, bars, live music and boutiques. Sarasota is just beyond the North Bridge, with downtown waterfront dining, shopping, galleries, theaters, performing arts and cultural attractions close at hand. Whether you are looking for a full time Siesta Key waterfront home or a second home for family and friends, 5376 Shadow Lawn Drive offers true boating access, a private saltwater pool, substantial updates, flexible living space and an exceptional island location. This is the kind of home where every day can include the beach, the boat and dinner by the pool. That is a pretty wonderful way to live.

5376 Shadow Lawn Drive, Sarasota

$1,750,000

3 Beds ⋅ 3 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code

Experience refined waterfront living at Dolphin Bay, an intimate, pet-friendly community of just 50 residences on Siesta Key. Beautifully redesigned with a sophisticated coastal aesthetic, this exceptional three-bedroom, three-bath condominium offers nearly 2,500 square feet of beautifully appointed living space and captivating views of the Intracoastal Waterway. Bright, open interiors create an effortless sense of space, with 9-foot ceilings, elegant plank tile flooring, custom built-ins and beautifully updated baths. At the heart of the residence, an impressive chef's kitchen makes a striking statement with expansive countertops, generous gathering spaces, custom cabinetry and premium Sub-Zero, Monogram and Viking appliances. A dramatic six-foot, built-in double-door wine cellar adds a distinctive touch for entertaining. The spacious living and dining areas flow beautifully toward the waterfront, where walls of glass frame the Intracoastal views. An expansive, air-conditioned enclosed lanai extends the living space, creating an inviting year-round retreat for relaxing, entertaining or simply watching the boats pass by. Thoughtful details include custom cabinetry, recessed lighting and integrated theater speakers. The generously sized bedrooms and spa-inspired baths offer comfort and privacy for family and guests. Recent improvements include impact-resistant windows and sliding doors installed in 2025, along with custom motorized light-filtering and room-darkening shades. Additional updates include the HVAC system (2020) and water heater (2021). A private one-car garage beneath the building adds convenience and additional storage. Residents of Dolphin Bay enjoy an inviting coastal lifestyle with a beautifully updated clubhouse, fitness center, Har-Tru tennis courts, heated pool and spa, and a day dock for boating and fishing. Siesta Key's world-renowned white-sand beaches and the restaurants, boutiques, and entertainment of Siesta Village are just minutes away, with convenient trolley access. Combining beautifully curated interiors, remarkable waterfront views and easy elegance of island living, this is an exceptional opportunity to enjoy Siesta Key at its finest.

1260 Dolphin Bay Way Unit 301, Sarasota

5950 Midnight Pass Road Unit 101, Sarasota

$485,999

1 Beds ⋅ 1 Baths ⋅ Siesta Beach House SubDv. ⋅ 34242 Zip Code

An exceptional opportunity to own a beautifully updated and turn-key beach condominium in the heart of Siesta Key, offering the flexibility of a strong rental investment, seasonal getaway, or your own private coastal retreat. Built a solid foundation of bookings into February and March bookings. Repeat Guests and higher demand! Located within Siesta Beach House this residence places you just a short walk to both Siesta Beach and Crescent Beach, while also offering the rare advantage of private beach access exclusively for residents and guests. Inside, the condo has been thoughtfully upgraded and meticulously maintained, creating a bright and modern coastal atmosphere. The kitchen features quartz countertops, ceramic tile backsplash, under-cabinet lighting, stainless steel appliances, and solid wood cabinetry, all opening seamlessly into the main living space. Porcelain ceramic tile flooring runs throughout, enhancing the clean, beach-inspired feel of the home. Additional improvements provide peace of mind and long-term value, including a new elevated A/C system installed in 2024 and a brand-new electrical panel completed in 2025. Beautiful upgraded baseboards in the living room, extra hallway storage, and tasteful finishes throughout further separate this condo from many others currently available on the island. The spacious bedroom includes a walk-in closet, while the open-concept floor plan maximizes functionality and comfort within the space. Being sold fully furnished and turnkey, this property is truly ready for immediate enjoyment or rental use. The Siesta Beach House community offers a community pool and direct private beach access, all within a highly desirable location. With a flexible minimum lease period of just 3 days, this property also presents excellent income-producing potential for investors seeking short-term rental opportunities. Whether you are searching for a beachside investment property, a lock-and-leave vacation home, or a cozy private condominium steps from world-renowned beaches, this Siesta Key opportunity delivers exceptional lifestyle and value in one of Sarasota’s most sought-after coastal destinations. Schedule your private showing today and experience the island lifestyle firsthand.

5950 Midnight Pass Road Unit 101, Sarasota

6157 Midnight Pass Road Unit E53, Sarasota

$449,000

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

Experience the best of island living in this inviting third-floor condo located in the sought-after Bay Oaks community on Siesta Key. Spanning 1,101 square feet, this two-bedroom, two-bathroom residence offers a seamless blend of comfort and convenience, with elevator access making every arrival effortless. The interior is bright and welcoming, designed with both relaxation and functionality in mind. The kitchen has stone counter tops with tile backsplash. Ceramic tile covers the floor throughout. The primary bedroom serves as a private retreat, featuring an en-suite bathroom with a spacious walk-in shower and large walk-in closet. The second bedroom is equally well-appointed, with easy access to the second bathroom which boasts a large whirlpool tub and shower—perfect for unwinding after a day in the sun. Throughout the condo, you’ll find plenty of storage options, ensuring a tidy and organized living space. Large living room and dining area add to this comfort as well as the screened in balcony overlooking the pool. Besides the large, heated community pool, Bay Oaks also provides, tennis courts, a community room with pool table & a waterfront park like setting with a BBQ area. Nature enthusiasts will appreciate the private fishing pier situated right on the Intracoastal Waterway at the rear of the complex—a perfect spot to watch the morning light dance on the water. It’s the lifestyle outside your door that truly shines. When you're ready for the sand, the world-famous beach of Siesta Key is easily accessible nearby. A free island trolley is accessible at street side in front of the condominium that will take you to one end of the Island to the other to enjoy, Turtle Beach, South Village Amenities, the public beach with lifeguards and the famous Siesta Village. This property isn't just a beautiful retreat; it’s a proven performer with a strong rental track record. For an investor or a savvy buyer, the transition could not be simpler. The condo is being sold fully turnkey furnished, meaning it comes with everything needed to hit the ground running. It is completely ready for immediate renters the moment you close. The timing couldn't be better—the unit is already booked for January, February, and March. If you close by the end of the year, you’ll step into immediate ownership with three months of rental income already booked. Whether you are looking for a lucrative investment or a seasonal getaway or your new home, this condo places you in the heart of everything that makes Siesta Key a premier destination. Come see why life is better when you’re surrounded by the beauty of the Bay and the Gulf.

6157 Midnight Pass Road Unit E53, Sarasota

$950,000

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

Tucked within a charming Gulf-side community of just 27 residences, this unique and rarely available townhouse on Siesta Key is in model condition and offers private access to one of the most celebrated beaches in the country. With 1,760 square feet of living space, the home features soaring two-story ceilings and abundant natural light throughout the main living areas. Head upstairs on the grand staircase to an additional bedroom plus a versatile loft space—currently used as a TV room and office—which could easily function as a third bedroom. The primary suite is conveniently located on the first floor and opens to a private enclosed sitting area. An updated kitchen with wood and glass cabinetry, natural stone countertops, stainless steel appliances, a spacious island flows into a casual dining area and living space, all finished with engineered hardwood floors, crown molding, and a neutral color palette. Two updated full bathrooms serve both levels, and laundry is located inside on the main floor. Additional features include built-in beverage refrigeration, hurricane shutters, and dedicated closets. Enjoy the private entry and an unheard of oversized garage with space for three vehicles adding loads of additional storage and convenience. The amount of storage is like living in a single family home. The community is primarily owner-occupied, with limited rentals, and welcomes large pets. Recent association improvements include new garage doors, exterior paint, landscaping, privacy fencing and more making this community feel like new. Steps from the white sands of Siesta Key, community pool, and close to shopping and dining. This move-in ready home invites you to settle into the ease of coastal living.

1163 Coquille Street Unit 207, Sarasota

6005 Midnight Pass Road Unit S6, Sarasota

$839,000

2 Beds ⋅ 2 Baths ⋅ Provintial Gardens SubDv. ⋅ 34242 Zip Code

Escape the winter blues with this turnkey furnished free-standing villa ready for IMMEDIATE occupancy with DEEDED SIESTA KEY BEACH and BAY access steps away in a non age restricted community. No logistical headaches having to furnish a property in order to occupy or rent it. This beautifully decorated and extensively updated, maintenance-free, open floor plan, villa can be your very own piece of paradise. Offering two spacious bedrooms and bathrooms, a flex (den) space, a full size washer/dryer, and your very own lush private patio oasis, all designed with comfort and style in mind. Added peace of mind comes from no flooding or storm damage sustained from recent storms. Some of the many updates include an extensive renovation to replace the old 1960s cast iron drain lines under the property’s slab with all-new PVC lines. Once completed, designer selected wood look tile flooring was added throughout the majority of the home. This intrusive, time-consuming, and costly project has already been completed, putting a new owner at ease regarding future concerns and major costs. The roof and A/C are new as of 2025, exterior painting will be completed by December. The primary bathroom has been completely updated, along with new hardscaping and landscaping. Handpicked light fixtures and ceiling fans have been installed, along with brand new solid core doors throughout the home to reduce noise from room to room. New coastal colors and tones have been added to the interior, along with all new appliances within the past two years. For accessibility 36 inch doorways and grab bars are present, as well as smart home features such as keyless electronic front door entry, nest thermostat, and ring door bell. The residence invites plenty of natural light into the home, with multiple windows and sliding glass doors enhancing the appeal of the split floor plan. The primary and expansive guest suite are located on opposite sides of the villa, providing ample space and privacy for all. The kitchen features an abundance of soft close cabinets, granite countertops, a large pantry, water filter system, and stainless steel appliances. Throughout the villa, you will find plenty of built-in storage closets, crown molding, as well as both a walk-in shower (primary) and a soaking tub (guest). Open your three sliding glass doors to create a seamless extension of your living space into your private tropical sanctuary, complete with an outdoor shower. The guest suite includes its own private outdoor space with a water fountain. When you are ready to venture out and enjoy your surroundings, there is an endless list of options to keep you busy. Enjoy your morning coffee while watching the sunrise/wildlife at the community’s bay front park with a new seawall. Here, you will find a kayak launch with two storage racks specifically for your use. Head out on the water kayaking/paddle boarding among dolphins and manatees. The community’s bay front park includes a day dock for residents’ use. Choose between relaxing on the beach with the sand between your toes or reading a book by the pool, with deeded access to the beach and one of the largest heated pools on Siesta Key via Aloha Kai across the street. Catch the free trolley to enjoy a casual lunch or a fine dining dinner. Owners can rent their property on a monthly basis with three weekly rentals permitted a year (outside of Jan-March) and can have one pet. The monthly HOA fee is $1,113. Come enjoy winter on Siesta Key!

6005 Midnight Pass Road Unit S6, Sarasota

$2,695,000

4 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Enjoy the best of Siesta Key living from this Key West-style waterfront home on sought-after Palm Island, ideally located just a short walk from the powder-white sands of Siesta Key Beach and the shops, restaurants and entertainment of Siesta Key Village. Set along a quiet canal, this 4-bedroom, 2.5-bath residence offers a wonderful opportunity to enjoy the island lifestyle today while adding your own personal touches over time. The home features a functional, comfortable layout with generous living spaces and abundant natural light. Significant recent improvements include a brand-new roof along with impact-resistant windows and sliding glass doors throughout. The property has also remained high and dry with no history of flood damage. Outdoors, a pool overlooks the canal, creating an inviting setting for relaxing and entertaining. Boaters will appreciate the private dock and 8,000-lb boat lift, making it easy to take advantage of Siesta Key’s surrounding waterways. An adjacent county-owned vacant parcel provides additional separation and a welcome sense of privacy. With its combination of waterfront access, boating amenities, pool, privacy and proximity to both Siesta Key Beach and the Village, 182 Island Circle presents a compelling opportunity to create your own island retreat in one of Siesta Key’s most desirable residential neighborhoods.

182 Island Circle, Sarasota

$6,400,500

Sarasota Beach SubDv. ⋅ 34242 Zip Code

Steps from Siesta Beach. A brief stroll to the Village. A lifetime away from your tenants worries and cares. Prime Siesta Key investment opportunity at a 7 cap or dream family compound just steps from the world-famous Siesta Key Public Beach! This exceptional multi-family property features two beautifully updated duplexes (totaling 8 bedrooms and 8.5 baths across 5,331 sq ft) on combined large lots, offering flexible zoning for short-term rentals (1-7 days), long-term income, or a luxurious private residence. Enjoy breathtaking Gulf sunrises and sunsets, a heated exotic lagoon-style pool with waterfall, Rocky Mountain quartz deck, professional tropical landscaping (updated 2024/2025), Miami-Dade impact windows/doors, newer roofs/insulation, and meticulous maintenance throughout. One building designed by renowned Lee Wetherington. Wake up to morning coffee overlooking the quartz sands, with Siesta Key Village shops and dining 0.5 miles away. Turnkey, versatile, and perfectly positioned for endless possibilities—your beachfront lifestyle awaits!

662 Calle Del Otono, Sarasota

$1,995,000

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

Experience luxury coastal living in this bespoke, move-in-ready residence built in 2017 by award-winning custom builder MGB. Perfectly situated on prestigious North Siesta Key, this home pairs sophisticated architecture with lock-and-leave convenience. With partial water views and deeded beach access just steps away, this is an opportunity to embrace the ultimate Florida dream. Crafted for low-maintenance luxury, the residence features solid concrete construction, a standing-seam metal roof, impact glass throughout, and spray foam insulation—yielding minimal upkeep, low utility costs, and no HOA restrictions. An elevator provides effortless access across all four levels. The ground floor welcomes you with an oversized single-car garage, an entry foyer, and a versatile storage room that opens directly to a private, sunlit patio for intimate outdoor entertaining. The second level serves as a guest sanctuary complete with three bedrooms, two designer full baths, and a dedicated secondary lounge. On the third floor, the core gathering space centers around a chef-inspired gourmet kitchen equipped with custom cabinetry, premium quartz countertops, stainless steel appliances, and a grand center island. Adjacent luminous living and dining areas flow seamlessly to a covered patio with water views. The top floor serves as an exclusive primary suite—featuring a dedicated executive home office space and a secluded balcony overlooking the water. Complete with natural gas, tankless water heating, and high-end eco-conscious finishes throughout, this exceptional residence presents a turnkey opportunity for luxurious personal living or a high-yielding luxury rental investment.

116 Garden Lane, Sarasota

6285 Midnight Pass Road Unit 406, Sarasota

$749,000

2 Beds ⋅ 3 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code

Welcome to this beautiful Penthouse end unit at the highly desirable Excelsior Beach to Bay community. Perfectly positioned on the Bay side, this 2 bedroom, 2.5 bath condo offers an open, airy layout enhanced by vaulted ceilings, abundant natural light, and impact windows throughout for peace of mind and energy efficiency. The living and dining areas flow seamlessly together, creating an ideal setting for entertaining or relaxing. The dining area features a mirrored accent wall, a built-in cabinet under the stairs, and another built-in at the end of the room for elegant storage and display. A wood staircase leads to the loft, a rare feature in this complex. The spacious loft includes a half bath, and 2 generous closets, offering flexibility as a guest retreat, office, or media room. The loft expands your living options beautifully. The kitchen is both functional and stylish, featuring wood cabinetry, Cambria quartz countertops, marble floors, a tray ceiling and a built-in eat-in area/desk. A window over the sink provides a charming peek of the Bay. The Primary Bedroom impresses with soaring vaulted ceilings, custom built-in furniture, and a bright, open feel, while the Primary Bath offers two separate sink areas with granite counters, built-in cabinetry, and a wall of closets-providing abundant storage and space. Pella sliding glass doors lead to the Florida room/lanai, enclosed in glass and framed by vaulted ceilings invites you to relax and enjoy tranquil views year-round. Residents of Excelsior enjoy private beach access, along with two heated pools, fitness center, tennis and pickleball courts, and clubhouse. Whether you’re seeking a full-time residence, vacation getaway, or investment opportunity, this Penthouse condo offers a rare blend of comfort, style, and location.

6285 Midnight Pass Road Unit 406, Sarasota

$625,000

2 Beds ⋅ 2 Baths ⋅ Polynesian Gardens SubDv. ⋅ 34242 Zip Code

TURNKEY FURNISHED, FREE-STANDING VILLA ON SIESTA KEY! TAKE YOUR GOLF CART TO PUBLIC BEACH! Ideally located in the highly desirable Polynesian Gardens along the Intracoastal Waterway, this charming 2-bedroom, 2-bath villa offers the privacy and feel of a single-family home with the convenience of low-maintenance, lock-and-leave living. TWO DOGS ALLOWED! LOW HOA FEES. An excellent choice for a personal island retreat. One of only ten villas overlooking the expansive community pool, this home features a private entrance, covered carport, screened lanai, and inviting outdoor living spaces surrounded by lush tropical landscaping. Relax around the LP gas fire pit or enjoy the Florida sunshine just steps from the community pool. The villa is also positioned at one of the higher elevations within the community. Major updates include a NEW ROOF (2023), HVAC SYSTEM (2023), WATER HEATER (2025), NEW GUTTERS (2025), programmable Nest thermostat, remote-entry touch keypad lock, and remote camera system. (OVER $100,000 OF RENOVATIONS HAVE BEEN DONE.) Enjoy everything the Siesta Key lifestyle has to offer! Spend your days fishing or watching dolphins and manatees from the community dock and fishing pier overlooking the Intracoastal Waterway. Walk or take your GOLF CART to nearby dining, shopping, coffee shops, nightlife, grocery stores, marina access, and local favorites including Captain Curt’s. World-famous Siesta Key Beach, known for its powdery white quartz sand, is just across the street. Hop aboard the free trolley to Siesta Key Village for even more dining, shopping, and entertainment. Rental history is available in the attachments. Whether you’re looking for your own island getaway, a seasonal rental, or an easy-care Florida retreat, this villa offers an exceptional opportunity to enjoy the ultimate Siesta Key lifestyle. MOVE IN, RENT OUT, OR SIMPLY RELAX!

1229 Moonmist Circle Unit P6, Sarasota

1250 N Portofino Drive Unit 304, Sarasota

$394,000

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

Under contract-accepting backup offers. Looking for a home for your boat, a beach lifestyle, or an investment? Enjoy sunrises over the marina, afternoons on Siesta Key Beach, and evenings on your enclosed balcony overlooking the boats and colorful skies. This furnished 1BR/2BA condo in Siesta Harbor is beautifully updated with an open floor plan, luxury vinyl flooring, remodeled kitchen (2022) with white shaker cabinetry, granite counters, glass backsplash, peninsula seating, and stainless appliances. Bathrooms feature quartz vanities and tiled showers; guest bath includes a soaking tub. Impact windows, same-floor laundry, and private storage add convenience. Siesta Harbor, a 55+ community, offers private beach access, heated pool/spa, lush landscaping, fishing pier, and a full calendar of social activities. Dock leases may be available for boats up to 30’. Additional amenities include covered parking, on-site manager, and a new roof (2025). Ideally located off the South Bridge near dining, shops, and the free Siesta Key trolley, this turnkey condo is perfect as a vacation retreat, full-time residence, or investment.

1250 N Portofino Drive Unit 304, Sarasota

1300 N Portofino Drive Unit 105, Sarasota

$399,900

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

YOU DESERVE PARADISE! MOVE RIGHT IN TO THIS PRISTINE DOLLHOUSE! BEACH ACCESS! BOATING! PERECT ONE BEDROOM WITH 2 FULL BATHS! GRANITE COUNTERTOPS, TOP OF THE LINE SHOWER ENCLOSURE, IMPACT/HURRICANE WINDOWS!! THIS HAS IT ALL!, WALK RIGHT OUT FROM YOUR LANAI TO YOUR BOAT DOCK, HEATING SWIMMING POOL, HOT TUB, SAUNA, SHUFFLEBOARD, DOCK ON THE INTRACOASTAL FOR MEETING WITH YOUR FRIENDS, FISHING OR JUST RELAXING! SIESTA HARBOR IS IN A PRIME LOCATION ON THE KEY, WALKING DISTANCE TO SHOPS, RESTAURANTS, CATCH THE TROLLEY RIGHT OUTSIDE YOUR DOOR, BEACH ACCESS RIGHT ACROSS THE STREET TO BEAUTIFUL SIESTA KEY BEACH WITH QUARTZ CRYSTAL SAND! THIS UNIT IS HOME OR A RENTAL, UP TO YOU! MOVE RIGHT IN, NEW HVAC, TILE FLOORS, CROWN MOLDING, PLANTATION SHUTTERS, FULL GLASS ENCLOSURE ON THE LANAI THAT BRINGS IN THE SUNSHINE, WATCH THE DOLPHINS, BOATING.. EVERYTHING UPGRADED WITH THOUGHT, NO POPCORN ON THE CEILINGS, ALL REDONE! ALL UNDER $400,000! YOU DESERVE PARADISE!

1300 N Portofino Drive Unit 105, Sarasota

1350 Siesta Bayside Drive Unit 1350B, Sarasota

$899,000

3 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code

Experience turnkey island living in this second-floor, three-bedroom townhome residence at Gulf & Bay Club Bayside on Siesta Key. Offered fully furnished and operating as an active rental with strong income history, this two-story getaway presents an outstanding opportunity for personal enjoyment and investment potential in one of Sarasota’s most desirable beach communities. Spanning nearly 1,500 square feet, the light-filled layout features tile flooring throughout the main living areas, high ceilings, and an open living/dining design ideal for gathering and entertaining. The updated granite kitchen is equipped with stainless-steel appliances, custom cabinetry, breakfast bar seating, built-in planning desk, and a sunny dining nook with additional storage. French doors open to the screened terrace, where added windows transform this space into a true year-round Florida room—an upgrade not commonly found in many Bayside residences. This enhancement expands the usable living area and allows you to enjoy the outdoor setting in every season, whether hosting guests or relaxing after a day at the beach. The primary suite is conveniently positioned on the main level and offers a walk-in closet, granite-appointed en-suite bath, and direct access to the enclosed terrace. Upstairs, a versatile loft provides flexible living space, while two guest bedrooms share a full bath—creating an ideal layout for visiting family or rental guests. This residence includes a deeded garage space and benefits from weekly rental flexibility, further enhancing its income-producing appeal. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in nearby Building 1328 on the first floor. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multigenerational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year. Gulf & Bay Club Bayside is known for its coastal architecture and resort-style amenities. Residents enjoy heated swimming pool, tennis and pickleball courts, fitness center, clubhouse, grilling stations, and a fishing dock on the Intracoastal Waterway. Deeded beach access directly across the street places Siesta Beach’s renowned quartz sands and Gulf waters just moments away. Located in the heart of Siesta Key, this residence offers convenient access to Siesta Village’s restaurants, boutiques, and live music. Boating, paddleboarding, and waterfront dining are close by, while downtown Sarasota—home to the Sarasota Opera House, Selby Gardens, The Bay Park, and St. Armands Circle—is just a short drive away. Whether seeking a beach retreat, a rental investment, or the flexibility of dual-unit ownership on Siesta Key, this Gulf & Bay Club Bayside residence delivers location, versatility, and exceptional lifestyle value.

1350 Siesta Bayside Drive Unit 1350B, Sarasota

1328 Siesta Bayside Drive Unit 1328C, Sarasota

$699,000

2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code

Welcome to Gulf & Bay Club Bayside, one of Siesta Key’s most desirable resort-style communities. This turnkey-furnished residence offers the perfect blend of coastal comfort, modern updates, and access to Siesta Key’s world-famous beaches. Designed with a bright, open layout and porcelain tile flooring throughout, the interior feels fresh and inviting from the moment you step inside. Oversized windows and glass sliders fill the home with natural light and extend the living space to the screen-protected lanai, creating an ideal spot to relax after a day at the beach. The updated kitchen features stone countertops, contemporary cabinetry, quality appliances, and generous storage. The dining and living spaces connect effortlessly, giving the residence a comfortable flow for both everyday living and seasonal enjoyment. Both bedrooms provide privacy for owners and guests, and the primary suite features a walk-in closet, en-suite bath, and direct access to the lanai. A second bedroom serves well as a guest room, home office, or multi-use space. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in the same building on the second floor, a townhome layout. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multi-generational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year Gulf & Bay Club Bayside is known for its beautiful coastal architecture and outstanding amenities. Residents enjoy two heated swimming pools, tennis courts, pickleball, a well-equipped fitness center, grilling stations, a fishing dock on the Intracoastal Waterway, and a stylish clubhouse. The community’s deeded walking beach access—located directly across the street—places you moments from Siesta Beach’s unique shores and turquoise water, making it effortless to enjoy sunrise or sunset strolls, and spontaneous beach days. Situated in the heart of Siesta Key, the location offers quick access to the island’s best attractions. Explore nearby Siesta Village, known for its open-air restaurants, boutique shops, live music, and laid-back coastal atmosphere. Boaters will appreciate the proximity to the Intracoastal Waterway, marinas, and local rental options. For even more dining, arts, and entertainment, vibrant downtown Sarasota is just a short drive away—home to the Sarasota Opera House, Van Wezel Performing Arts Hall, Selby Gardens, the Ringling Museum, St. Armands Circle, and an ever-growing culinary scene. Whether you’re seeking a full-time residence, a seasonal getaway, or an investment opportunity with weekly rentals permitted, this Gulf & Bay Club Bayside property delivers the ideal combination of location, lifestyle, and value on Siesta Key.

1328 Siesta Bayside Drive Unit 1328C, Sarasota

9397 Midnight Pass Road Unit 506, Sarasota

$665,000

2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code

LIVE WHERE THE GULF MEETS THE BAY. Discover an extraordinary island lifestyle at The Pointe on Midnight Pass, a private, gated, waterfront community at the southernmost tip of Siesta Key, uniquely positioned at the convergence of The Gulf of America, Little Sarasota Bay, and Blind Pass Lagoon. This beautifully renovated 2-bedroom, 2-bath residence captures the rare magic of both sides of the island—wake to spectacular sunrises over Little Sarasota Bay and the Jim Neville Nature Preserve, then watch the sky transform at sunset over The Gulf. Thoughtfully updated, the residence features elegant tray ceilings and recessed lighting, solid-wood cabinetry, granite countertops, stainless-steel appliances, breakfast bar and pantry, contemporary baths with floor-to-ceiling tile, ceramic tile flooring throughout, sleek white interior doors, and sun-control shades on the lanai. A spacious lanai extends the living space outdoors, creating the perfect setting for morning coffee, sunset cocktails, or watching dolphins, manatees, seabirds and boats move through the surrounding waters. A private utility room houses the washer and dryer, while ground-level storage provides coveted space for beach, boating and golf gear. And then there is The Pointe—more than five acres of waterfront living, surrounded by water on three sides and embraced by an extensive seawall, with pathways winding throughout lush, mature tropical vegetation. Enjoy a heated pool and spa, lighted tennis and pickleball courts, fitness center, sauna, clubhouse, private island pavilion with grills, kayak and canoe storage and launches, fishing areas, boat docks, and on-site management—with a vibrant social calendar during season that brings neighbors together and makes it easy to connect, participate, or simply enjoy the island lifestyle at your own pace. The newly reopened Midnight Pass adds another extraordinary dimension, reconnecting the Gulf and Intracoastal waters and enhancing the boating, fishing and wildlife experience right outside your door. Walk or bike to Turtle Beach, enjoy nearby restaurants, or take the trolley to explore more of Siesta Key. This is not simply a condominium—it is the rare opportunity to own a front-row seat to the natural beauty, wildlife and ever-changing waters of southern Siesta Key.

9397 Midnight Pass Road Unit 506, Sarasota

$2,199,000

3 Beds ⋅ 3 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code

Expansive floor-to-ceiling sliders open wide to welcome refreshing Gulf breezes and showcase unobstructed, panoramic water views, turning your open-floorplan living space into an indoor/outdoor oasis. With over 2,300 square feet, this light-filled condominium lives like a private home suspended above shimmering waters. The gourmet kitchen is both elegant and functional, featuring quartz countertops, custom wood cabinetry, and premium appliances, including a Thermador refrigerator and freezer, Wolf double ovens, Wolf microwave, and a Thermador induction cooktop. Panel-ready finishes, a built-in beverage cooler, and exceptional storage make this space ideal for both everyday living and entertaining. Rich acacia engineered wood flooring adds warmth and sophistication throughout the main living areas. The spacious primary suite captures sweeping Gulf views and offers a serene escape, complete with a beautifully renovated spa-inspired bath featuring split vanities and a large walk-in shower. Two additional bedrooms and stylishly updated baths are thoughtfully positioned on the opposite side of the residence for added privacy. Impact-rated windows and sliders provide peace of mind, eliminating the need for hurricane shutters. A private two-car garage with ample storage adds to the home’s convenience. Windward Passage features a Gulf-side pool, lushly landscaped grounds, and a pet-friendly setting. Perfectly positioned on the sought-after north end of the key, you’re just a short walk to the Village for charming boutiques, dining, and live entertainment.

4708 Ocean Boulevard Unit E4, Sarasota

$3,400,000

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

Set along the coveted waterways of Siesta Key, this exceptional newer-construction home is a refined coastal sanctuary where sophisticated design, effortless boating, & the relaxed beauty of island living come together. Thoughtfully designed for everyday enjoyment, the home offers a rare opportunity to embrace the Siesta Key lifestyle from a private waterfront setting, complete with a boat lift & kayak launch. The home reveals an elevated level of craftsmanship & thoughtful design. Soaring ceilings, engineered hardwood floors, plantation shutters, crown molding, and carefully considered architectural details create an atmosphere of understated elegance & comfort. An elevator provides access to all levels while expansive sliders open the main living spaces to the balcony, pool & tropical surrounds. The beautifully appointed kitchen combines sophisticated finishes w/exceptional functionality. Luxurious quartz countertops, oversized island w/seating, custom soft-close cabinetry, tile backsplash, farmhouse sink, KitchenAid appliances, Vitafresh refrigeration & under-cabinet lighting create an inviting culinary environment suited to quiet mornings & memorable gatherings. The dining area elevates with a beautifully appointed wet bar, wine/beverage fridge, dedicated wine storage & distinctive hammered sink. The family room offers an inviting gathering space centered around a Dimplex electric fireplace w/marble surround, illuminated custom cabinetry & electric sunshades. Pocket sliders open to the covered balcony, where tongue-and-groove wood cypress ceiling & ceiling fans create a warm & sophisticated setting for enjoying the tropical surroundings. The primary suite is designed as a private retreat w/engineered hardwood flooring, plantation shutters, crown molding & direct balcony access. The spa-inspired primary bath features elegant quartz & marble detailing, statement pendant lighting, a glass marble shower & luxurious soaking tub. A walk-in closet with custom built-ins completes this serene sanctuary. Upstairs, beautifully appointed guest accommodation provides privacy for family & visitors. A charming music/reading nook framed by a stained-glass window adds a unique sense of character, while an expansive bonus room with built-in desk, wine fridge & dramatic open-to-below design offers an extraordinary space for an office, lounge, or additional entertaining. The outdoor spaces transform the property into a private retreat. A fully enclosed, 2 story caged pool & lanai are surrounded by lush tropical landscape and thoughtfully designed gathering spaces. The outdoor living area features a tongue-and-groove cypress ceiling, ceiling fans, minimalist stone landscaping, and a crystal fire pit, creating an inviting setting for long afternoons by the pool. The private boat lift provides effortless access to the surrounding waterways, while the kayak launch invites leisurely exploration of Siesta Key beach coastal landscape only .3 miles away. An oversized garage w/epoxy non-slip flooring, hanging storage & convenient elevator access provides exceptional functionality of the home's elevated lifestyle. Mornings can begin on the waters of Siesta Key, afternoons can unfold along the powder-soft sands of world-renowned Siesta Key Beach & evenings can be spent wandering through Siesta Village where charming boutiques, restaurants & cafés capture the spirit of island living.

70 Island Circle, Sarasota

$1,599,000

3 Beds ⋅ 4 Baths ⋅ Tiffany Sands SubDv. ⋅ 34242 Zip Code

Exceptional opportunity to own a slice of heaven on Siesta Key Beach. The sparkling turquoise water and quartz sand beach await you. This sought after renovated townhouse has lovely Gulf Views and fabulous deeded Beach front access for everyday enjoyment. TURNKEY furnished & spacious with 3-bedrooms and 3.5 baths. Open floor plans to capture great light and an airy feeling created by coastal living. Enjoy the magnificent decks off the Primary Suite and Living Room to capture beautiful sunsets and Gulf breezes. Also, it is a great place just to relax on a lounge chair in the Florida Sunshine. The Gourmet Kitchen has a lovely wood painted cabinetry, granite counters cook-top island, Breakfast Bar with counter seating and all Stainless Appliances. The main level offers a bonus room that is very versatile with a full bath & separate entrance. Perfect for guests, home office or media room. The Primary Suite has Views of the Gulf from Sliders that opens to a great deck. The Master Bath has dual marble vanities and a large frameless glass shower & separate water closet. The other two bedrooms share a Full Bath. Laminate flooring and Plantation Shutters throughout. So close to Siesta Key Villate for boutique shopping, fabulous restaurants & island entertainment. Ready for the next buyer to own this spectacular beach retreat. Motivated Seller.

548 Beach Road Unit A, Sarasota

5855 Midnight Pass Road Unit 605, Sarasota

$719,000

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

Harbor Towers 605 represents a unique opportunity to live on a high floor in the building with the coveted south-facing views looking over the pool. Welcome to Harbor Towers, your home at the beach- this perennial favorite building is now better than ever after undergoing massive exterior renovations which include strengthening and impact glass windows and sliding doors for all units! The unique and large grounds of Harbor Towers provide a spectacular setting with lots of space to enjoy the coastal lifestyle. You are not just buying a home, you're buying into a Yacht and Tennis Club, with har-tru tennis courts, a recently revamped marina with inexpensive boat mooring prices, a heated community pool, fitness center, meeting area, community kayak area and much much more. This unit has been renovated and lovingly cared for over the years. Besides the impeccable view down the Intracoastal Waterway, this unit offers well maintained luxury featuring tile floors throughout, kitchen update in 2021, in unit washer/dryer combo, full furniture package included- just to name a few. This unit must be seen to be appreciated. It is currently positioned in the rental program, but can be removed if desired. Pick your desired lifestyle- keep it all to yourself or earn some income to help pay for your investment. Harbor Towers is well taken care of and well managed. Onsite management, security and well funded reserves make this complex a true winner. This unit also has a covered carport spot that is included in the purchase. Don't wait on this opportunity- these types of units don't come to market very often. Schedule your private showing today!

5855 Midnight Pass Road Unit 605, Sarasota

$2,900,000

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

Welcome home to the coveted community of Bay Island, on the north end of Siesta Key where island living meets timeless design just 800 feet from Beach Access 1 on Shell Road. Evening sunsets sandy morning strolls are practically at your doorstep. This 2020 built elevated contemporary residence offers thoughtful craftsmanship plus hurricane-rated doors and windows, a 5V metal crimp roof with open-cell spray foam insulation for lasting energy efficiency, and a striking circular driveway framed by stained tongue-and-groove soffits at both entryways a first impression that sets the tone for everything inside. Step through the door to an open, light-filled floorplan where high ceilings, recessed lighting, and wood-look tile flooring carry you through generous living and dining spaces. The kitchen anchors it all with stone countertops and backsplash, a waterfall-edge island with breakfast bar, sleek cabinetry, and stainless steel appliances built for everyday living and effortless entertaining alike. Glass sliders open to a screened lanai, where an outdoor kitchen makes alfresco dining a daily possibility, and a sparkling pool and spa invite you to unwind amid lush, tropical surroundings. The primary suite, thoughtfully situated on the first level, offers a private escape with sliders opening directly to the lanai, a spa-like bath with dual vanities, a soaking tub, oversized shower, and a walk-in closet with custom built-ins. Three additional bedrooms, each with its own en-suite bath, ensure plenty of space for family and friends alike true four-bedroom retreat built for gatherings. A three-car garage (one sectioned off and air conditioned) on the lower level rounds out the home's thoughtful design. Just moments from world-renowned Siesta Key Beach, scenic waterways, and the shops, restaurants of Siesta Key Village AND downtown Sarasota, this Bay Isles residence is a rare opportunity to own a true island sanctuary.

3913 Roberts Point Road, Sarasota

$1,650,000

4 Beds ⋅ 3 Baths ⋅ Siesta Woods SubDv. ⋅ 34242 Zip Code

Experience the best of Siesta Key living at 5188 Siesta Woods Drive, a spacious four-bedroom home offering exceptional privacy, expansive indoor and outdoor living and a resort-style pool setting just one mile from Siesta Key Beach. Surrounded by extensive tropical landscaping and enclosed by a privacy wall and gated entrance, the property feels wonderfully secluded while remaining close to everything that makes island living so desirable. Additional pool privacy screens and thoughtfully designed landscaping further enhance the sense of seclusion. The elevated main living level is bright and open, with vaulted ceilings, tile and hardwood floors and an easy flow between the living, dining and kitchen areas. The remodeled kitchen features granite countertops, custom wood cabinetry, stainless steel appliances, abundant workspace, breakfast bar seating and a Culligan reverse osmosis water system. Three new refrigerators, located in the kitchen, garage and bar area, provide added convenience. French doors with impact glass open to a spacious covered balcony overlooking the pool and tropical surroundings, with plenty of room for dining, entertaining or relaxing. A split bedroom plan provides privacy, with a spacious primary suite featuring two thoughtfully redesigned walk-in closets. Two additional bedrooms, a full bath and laundry room complete the main level. The lower level adds tremendous flexibility with a large family room, office, oversized fourth bedroom, bonus area and half bath, creating wonderful options for guests, recreation or working from home. French doors lead directly to the expansive screened lanai and heated, free-form saltwater pool, one of the home’s standout features. A generous paver deck offers both sunny and shaded areas for lounging, dining and entertaining, complemented by multiple covered areas, privacy screens, lush landscaping and an outdoor shower. A new pool pump and chlorinator were added in 2024. Impact windows and doors provide additional peace of mind, complemented by a metal roof, three-zone air conditioning, composite decking and stairs and an oversized two-car garage with additional storage. Recent 2025 improvements include a new washer and dryer, a resurfaced and sealed garage floor and newly resurfaced pavers surrounding the pool and along the driveway. Meticulously maintained and in excellent condition, with a pre-listing inspection completed, this home offers an uncommon combination of privacy, space and exceptional outdoor living. An extensive collection of furnishings is also available for purchase separately, offering buyers the opportunity for a turnkey, move-in-ready island home. Ideally situated approximately one mile from Siesta Key Beach and convenient to Siesta Key Village, with downtown Sarasota’s dining, shopping, arts and cultural attractions just a short drive away. (Garage refrigerator, TVs and Sono system are not included)

5188 Siesta Woods Drive, Sarasota

$895,500

2 Beds ⋅ 2 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

Under contract-accepting backup offers. Best Value Near Siesta Key Beach — Just 100 Yards Away | VERY MOTIVATED SELLERS | Now $895,500 This is your opportunity to secure a prime coastal property at a newly reduced price—just steps (100 yards) from the world-renowned white sands of Siesta Key Beach. Whether you’re looking for a personal beach retreat, a high-performing investment, or both, this property delivers exceptional value in one of Florida’s most sought-after locations. With projected short-term rental income between $62,900 and $81,770 annually, this fully renovated 2-bedroom residence offers immediate income potential while still allowing you to enjoy it as your own private getaway. Inside, the home features a bright, open-concept design with upscale coastal finishes throughout. The updated kitchen is equipped with quartz countertops, a large island, and premium stainless-steel appliances—ideal for entertaining or hosting guests. The primary suite provides a relaxing, spa-like experience, while the second bedroom offers a private exterior entrance, creating flexibility for rentals or visiting guests. Step outside to a private tropical setting complete with lush landscaping, a patio for outdoor living, and an outdoor shower—perfect after a day at the beach. With no HOA restrictions, recent renovations, and highly motivated sellers, this is one of the most compelling values currently available this close to Siesta Key Beach. Opportunities like this—price, location, and income potential—are rare. Schedule your private showing today.

643 Calle Del Otono, Sarasota

8701 Midnight Pass Road Unit 304A, Sarasota

$649,000

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

Experience the ultimate Bayfront lifestyle on Siesta Key in this turnkey furnished 2BR/2BA residence at Turtle Bay. Tucked away on the serene south end of the island, this spacious condo blends modern coastal luxury with vibrant island living. Wake up to spectacular sunrises over the Intracoastal from your private, enclosed lanai, and wind down with sunsets via deeded beach access directly across the street. The generous primary suite features a walk-in closet, and a private entrance to the lanai. An in-unit laundry room includes a full-size washer/dryer and extra storage—a rare luxury on the Key! Additional upgrades include hurricane-impact windows to perfectly frame the water views. One of the most valuable features is the private, oversized 1-car garage providing secure parking and ample gear storage. Pet-friendly Turtle Bay offers premium amenities: brand-new boat docks/slips (just $300/year and you can add your own hoist), an updated fishing pier, kayak launch/storage, heated pool/spa, lighted tennis/pickleball courts, shuffleboard, clubhouse, and grilling area. Enjoy maintenance-free ease with on-site management, secure entry, and elevators. Leave your car behind and take the free trolley to nearby Siesta Village, South Village, or Point of Rocks snorkeling. Just minutes to Stickney Point Bridge and 20 minutes to downtown Sarasota. Perfect as a full-time residence, seasonal escape, or a great investment income opportunity.

8701 Midnight Pass Road Unit 304A, Sarasota

$1,349,000

3 Beds ⋅ 3 Baths ⋅ Siesta Key Beach Residences Ii SubDv. ⋅ 34242 Zip Code

Location, location, location! Set directly on the world-famous white sands of Siesta Key Beach, this beautifully appointed 3-bedroom, 3-bath residence at Hyatt Residence Club Siesta Key Beach offers a rare opportunity to enjoy a true beachfront resort lifestyle with the service and amenities of the Hyatt brand at an exceptional value. Located on the third floor, the residence is conveniently situated on the same level as the fitness center and concierge, putting some of the property’s most-used amenities just steps from your door. Inside, a bright, open-concept layout offers generous living and dining spaces, a private lanai, and three well-appointed bedrooms with three full baths, providing plenty of room for family and friends. Step outside and everything that makes the Hyatt Residence Club special is at your fingertips: direct access to Siesta Key’s famous sugar-white sand, beach service with lounge chairs and towels, a resort-style pool and waterfall Jacuzzi, Tiki Bar, fitness center, concierge and valet services, on-site parking, complimentary breakfast, and professional management. It’s an effortless way to enjoy beachfront living without the upkeep of a traditional beach home. The location also makes exploring Siesta Key easy. Walk to the restaurants and shops of South Bridge Village, take a quick drive to Siesta Key Village, or enjoy convenient access on and off the Key via the South Bridge. For buyers who prioritize beachfront location, resort amenities, convenience, and value, this residence presents a compelling opportunity to experience one of Siesta Key’s premier beachfront properties. Come for the beach, stay for the sunsets, and enjoy the ease of the Hyatt resort lifestyle.

915 Seaside Drive Unit 310, Sarasota

116 Vista Hermosa Circle Unit 108C, Sarasota

$400,000

2 Beds ⋅ 2 Baths ⋅ Vista Hermosa SubDv. ⋅ 34242 Zip Code

Your Siesta Key Lifestyle Awaits — The Time to Own Is Now! Welcome to one of Sarasota’s most sought-after coastal destinations, where the beauty of Siesta Key is right outside your door. This completely updated ground-floor residence captures the true essence of coastal living with a soft, neutral palette and a relaxed, welcoming atmosphere. This property sets itself apart from all the others—it makes you feel right at home at the beach the minute you arrive. The spacious bedrooms provide plenty of room for family and guests, with the oversized guest bedroom large enough to accommodate two full-size beds, comfortably sleeping four. The beautifully refreshed kitchen features new appliances, quartz countertops, updated cabinetry, and a new tile backsplash that perfectly complements the home’s coastal-inspired design. Extend your enjoyment outdoors in the enclosed lanai, offering privacy and a comfortable space to enjoy year-round. There is also the possibility of adding a paver extension to the lanai, creating even more outdoor living space for relaxing and entertaining. A convenient in-unit laundry closet with washer and dryer adds to the ease of everyday living, while storm windows and doors provide added peace of mind. And then there’s the lifestyle! Spend your days enjoying the world-famous sands of Siesta Key Beach, explore the beauty of Selby Gardens, shop and dine at St. Armands Circle, or head into downtown Sarasota for its incredible restaurants, arts, culture, and waterfront attractions. And don’t miss one of the area’s most anticipated fall events—the Siesta Key Crystal Classic Sand Sculpting Festival. Come be part of the fun, experience the incredible artistry, and enjoy yet another reason why life on Siesta Key is so special. The time is now to make this coastal retreat your own and be ready for the 2027 season. Whether you’re looking for a full-time residence, a beach escape, or your own piece of the Siesta Key lifestyle, this beautifully updated home offers something truly special. Come see for yourself why this one feels different. Your beach lifestyle begins the minute you arrive.

116 Vista Hermosa Circle Unit 108C, Sarasota

6140 Midnight Pass Road Unit 101, Sarasota

$875,000

1 Beds ⋅ 1 Baths ⋅ Horizons West SubDv. ⋅ 34242 Zip Code

Experience the ultimate Siesta Key beach get-away in your TURNKEY FURNISHED, west-facing condo at Horizons West and just steps from your private beach with plenty of beach chairs and five sun cabanas. Enjoy the crystal sands of Crescent Beach where the sand is always cool and you’ll never miss a sunset. This spacious 1-bedroom retreat boasts over 1,000 sq. ft. and has tiered ceilings up to 9 ½ feet. The west facing wall has oversized 6-foot-high impact windows that frame breathtaking panoramic Gulf, beach, resort pool and sunsets sunset views, including dolphin sightings. Perched above the lobby and mezzanine, use the elevator to enter this bright and cheerful end-unit with west and south facing windows in the living room. Enjoy an open, airy floor plan with a designer kitchen featuring stone countertops, stainless appliances, and a breakfast bar. The generously sized bedroom has south and east facing windows and an en-suite bathroom with a beautifully tiled walk-in shower. Resort-style amenities abound: 300 ft. of private beach, two pools, spa, cabanas, grills, and a bayside park with day dock. This unit comes with private carport storage for all your beach toys. Hop on the free Siesta Key trolley for world-class dining and shopping. Come see why Siesta Key is ranked the #1 Beach in the USA and #4 in the world—your piece of paradise awaits!

6140 Midnight Pass Road Unit 101, Sarasota

6480 Midnight Pass Road Unit 612, Sarasota

$1,325,000

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

Welcome to the ultimate Siesta Key getaway at Unit 612 in Siesta Breakers! This beautifully updated penthouse is completely move-in ready and offered TURNKEY FURNISHED—just bring your sunglasses, swimsuit, and sense of adventure! Light, bright, and stylish, this fabulous residence offers gorgeous beach and pool views from the living room and screened-in patio. Spacious rooms, two oversized walk-in closets, and the convenience of an interior washer and dryer add to the great layout. The open kitchen and well-designed floor plan create the perfect setting for entertaining family and friends or relaxing after a sun-filled day at the beach. And when you’re ready to let the property work for you, Siesta Breakers permits weekly rentals and features an on-site management and rental office to help maximize rental opportunities. This gated, beautifully landscaped beachfront community sits directly on world-famous Crescent Beach and offers a fabulous lineup of amenities, including a sparkling pool, lighted pickleball and tennis courts, updated clubhouse, and DEEDED BEACH ACCESS. Just across the street, enjoy dining, shopping, and a full-service marina with boat rentals. Popular Siesta Key South Village is only steps away with local favorites such as Captain Curt’s Crab & Oyster Bar and a full-service grocery store. Need to stay connected? The updated clubhouse provides a convenient space for an uninterrupted Zoom meeting or conference call. Current building renovations are enhancing the community and offering peace of mind. The free Siesta Key trolley provides easy access to everything the island has to offer and you may find yourself happily ditching the car altogether. This is coastal Florida living at its most carefree, convenient, and fun—come experience your own slice of paradise on Siesta Key!

6480 Midnight Pass Road Unit 612, Sarasota

$3,995,000

4 Beds ⋅ 3 Baths ⋅ Ten35 Seaside SubDv. ⋅ 34242 Zip Code

Welcome to Ten35 Seaside Drive, a newer mid-rise community at the south end of world-renowned Siesta Key Beach, where turquoise Gulf waters meet pristine quartz sand. Ten35 Seaside elevates island living with luxurious residences designed to highlight the area’s natural beauty. Gulf-view residence 502 offers four bedrooms, three baths and 2,385 square feet of thoughtfully designed living space. Floor-to-ceiling glass, an open-concept interior, and expansive terraces frame sweeping views of the sea, sand and sky. Refined finishes include porcelain tile floors, premium cabinetry, top-of-the-line appliances and a spacious primary suite with a spa-inspired bath. The main terrace is ideal for enjoying spectacular sunsets, while a second terrace off the en-suite guest bedroom captures beautiful sunrises. The kitchen features solid-wood cabinetry, Wolf and Sub-Zero appliances, a gas cooktop and a wine refrigerator. Additional highlights include solid-core entry and interior doors, floor-to-ceiling, hurricane-resistant balcony doors with laminated solar-tinted glass, sound-reducing laminated windows with solar-tinted glass, a recirculating hot-water system, high-efficiency heating and air conditioning, stained tongue-and-groove cypress terrace ceilings, tiled terrace floors and two covered parking spaces. Ten35 Seaside offers amenities that complement its beachfront setting, including a swimming pool and spa, fire pit, beach lounge chairs and umbrellas, kayaks, paddleboards, concierge-arranged water activities, fitness center and Gulf-front barbecue area. Daily beach chairs and umbrellas are also available. Residence 502 presents a rare opportunity to own a fully operational, potential income-producing property on Siesta Key’s Crescent Beach, one of Florida’s desirable vacation rental destinations. The residence is enrolled in the community’s on-site professional rental management program, providing immediate revenue while eliminating the setup time and day-to-day demands of vacation-rental ownership. Marketing, guest services, housekeeping and operations are managed on-site, allowing owners to potentially earn income while reserving time for personal use. Rental terms permit one-week minimum stays during the off-season and two-week minimum stays during peak season, balancing revenue potential with property preservation. Just moments from the dining and shopping of Siesta Key’s South Village, the property consistently attracts repeat visitors, supporting strong occupancy. Whether you are expanding an investment portfolio, completing a 1031 exchange or seeking a vacation home that can offset ownership costs, Residence 502 offers a rare combination of a Gulf-front location, professional management and potential rental income from day one. A must-see opportunity.

1035 Seaside Drive Unit 502, Sarasota

1130 W Peppertree Lane Unit 118, Sarasota

$670,000

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

Live the Siesta Key lifestyle! This beautifully maintained 2-bedroom, 2-bath condo offers the perfect combination of island living, rental potential, and resort-style amenities. Ideally situated in the desirable Gulf-side community of Peppertree, this second-floor residence is just a short stroll from the tennis and pickleball courts, heated pools, and Siesta Key’s private-access beach. From the moment you arrive, you’ll appreciate the peaceful setting and tranquil views overlooking one of Peppertree’s picturesque ponds. The condo has been thoughtfully updated with all new impact windows, renovated kitchen and bathrooms, and updated flooring, creating a comfortable and inviting beach retreat. The spacious primary bedroom easily accommodates a king-size bed and features a walk-in closet. The home is offered turnkey furnished, making it ready to enjoy immediately or continue as a seasonal rental. It has consistently generated rental income during peak season, while also providing the flexibility to enjoy it personally during the off-season. Additional features include a full-size washer and dryer, newer A/C installed in 2019, a private storage unit conveniently located just outside the back patio, and a dedicated parking space. Peppertree is truly a destination within Siesta Key, offering direct Gulf-to-Bay access, a private fishing pier, tennis and pickleball courts, two heated pools, two clubhouses, BBQ grills throughout the community, beach chairs, car wash areas, and on-site management with a rental program. High and dry with no storm damage, this exceptional condo offers the opportunity to own your own piece of paradise on world-famous Siesta Key. Whether you’re looking for a personal beach getaway, an investment property, or the best of both, this inviting Peppertree residence is ready to welcome you home.

1130 W Peppertree Lane Unit 118, Sarasota

6265 Midnight Pass Road Unit 102, Sarasota

$675,000

2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code

Virtually Staged. Experience the world renowned beaches of Siesta Key in this rarely available first floor luxury condominium steps away from your private deeded beach access. Conveniently located to Siesta Key’s south bridge, accessing the mainland, shopping in the village and access to nearby restaurants and stores is a breeze. Take the free public transport available to Siesta Village or head to Turtle Beach. Arrive home to a tastefully decorated unit with peaceful courtyard lake views. Entertaining and sharing a meal is an event with this updated chef’s kitchen. The enclosed lanai invites you for a cup of coffee, a book or contemplation. The primary suite features wood flooring, a true retreat like en-suite bath and upscale built-ins for the closet. Have peace of mind with impact windows and a new HVAC system installed 2025. There is plenty to do without going to the beach. Two heated pools, hot tubs, pickleball, tennis, fitness, fishing dock, library, beachside restrooms and more.

6265 Midnight Pass Road Unit 102, Sarasota

5880 Midnight Pass Road Unit 307, Sarasota

$1,400,000

3 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code

A TRUE 3-bedroom condo residence in desirable Casarina, a premier building positioned directly on the quartz white sands of #1 Siesta Key beach and the Gulf of Mexico. Step into this beautiful spacious residence and experience the flow of this 2,165-square foot open floor plan conducive to daily living, entertaining and accommodating family and friends. Sold turnkey furnished, this residence boasts impact windows & sliders providing security and protection, large ceramic floor tile throughout perfect for beach living and rich new carpet in the primary bedroom. The updated kitchen is stunning boasting neutral cabinetry, quartz countertops, stainless Jenn-Air appliances, Fisher & Paykel double dishwasher, quartzite island & breakfast bar, instant hot water faucet & 3 spacious pantries. The primary bathroom was updated in 2026 with quartzite countertops and upgraded dual vanities. Custom wood closet organizers are featured in all the bedrooms and an electric fireplace in the living room. The A/C was replaced in 2025 and tankless water heater in 2023. Casarina is a secure building which has just undergone a complete building renovation & infrastructure. It offers an onsite manager and is fully funded with a 10-year capital plan and no special assessments. Besides the powder-white sand beach, experience tropical living on 7 acres of refreshed lush Florida landscaping, large refurbished heated pool and spa, cabana with outdoor kitchen & dining area, new poolside pergola with seating, 2 grilling areas, sunset decks, gas firepit with Adirondack chairs, resurfaced & lighted tennis court, 2 pickle ball courts, basketball hoop, fitness center, and social room/library. This condo offers secure under-building garage parking with an adjacent storage closet #5. The building renovation & infrastructure within the past two years includes a new reengineered resilient roof, new electrical and fire alarm systems elevated to the 2nd floor, new raised backup generator, new secured A/C units, multiple custom flood-prevention panels/dams, new ground water pump infrastructure, relined plumbing pipes, and refurbished elevators. Minutes to Siesta Village, shopping, restaurants and the culture of downtown Sarasota! So come on down and enjoy Florida living!

5880 Midnight Pass Road Unit 307, Sarasota

9226 Midnight Pass Road Unit 3B, Sarasota

$650,000

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

It's time to SIMPLIFY! Sun. Sand. Surf. Fantastic Opportunity and sure to impress! The last unit in this community sold for 800,000. Welcome to this completely renovated residence at Castaway Cove, a boutique waterfront condominium community tucked away on the quiet south end of Siesta Key, just a short walk to Turtle Beach. This second-floor unit offers a rare coastal vantage point with sweeping views of Blind Pass Lagoon, the Intracoastal Waterway, and the Gulf of Mexico, delivering a rarely found three-water perspective. Morning light reflects across the lagoon, afternoons might feature manatees or dolphins, and evenings are reserved for unforgettable sunsets over the Gulf. Dock space is potentially available for boating enthusiasts, and the calm lagoon waters provide ideal conditions for kayaking and paddleboarding from Castaway’s private launch toward the newly-opened Midnight Pass. The residence has been remodeled wall to wall and floor to ceiling since 2020, with thoughtful attention to both design and infrastructure. The open floor plan blends the kitchen, dining, and living areas seamlessly, allowing water views to take center stage from nearly every angle. Porcelain tile flooring runs throughout the entire unit, creating a clean, cohesive look that complements the seaside setting. The kitchen features shaker-style Providence White cabinetry with glass-front display cabinets and interior lighting, a pantry with pull-out shelving, Pompeii Quartz countertops, a Glazzio tile backsplash, and updated appliances including refrigerator, range, dishwasher, built-in microwave, washer, dryer, and HVAC system. The primary suite, perched above Blind Pass, is a serene retreat with crown molding, solid core doors, and custom closet systems with mirrored panels. The ensuite bath offers dual vanities topped with Pompeii Quartz, a walk-in shower with glass enclosure, tiled bench, multiple body jets, subway tile walls, and subtle motion-sensor lighting. The guest suite, with views of the ICW, features a barn door entry and a bath with cast-iron tub and quartz-topped vanity. A screened lanai extends the living space outdoors with porcelain tile flooring, a tongue-and-groove ceiling, new screens and railings, and tranquil water views that invite morning coffee or evening relaxation. Additional features include recessed lighting throughout, ceiling fans, a woven dining area chandelier, sheer and room-darkening solar shades, Schlage door lock, Ring doorbell, and Nest thermostat. Castaway Cove is a low-density community of just eight residences offering ample parking, professional management, and exceptionally low association fees. Recent community improvements include a new seawall, refreshed landscaping, updated exterior lighting and irrigation system, and a freshly painted building. The two-story structure is NOT subject to a Milestone Inspection.

9226 Midnight Pass Road Unit 3B, Sarasota

$1,695,000

2 Beds ⋅ 2 Baths ⋅ Siesta Gulf View SubDv. ⋅ 34242 Zip Code

Sold data. Fully renovated in 2021, direct beach front, turnkey furnished.

420 Beach Road Unit 502, Sarasota

1300 N Portofino Drive Unit 103, Sarasota

$449,500

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

Welcome to your own piece of paradise on world renowned Siesta Key! This beautifully updated and freshly painted 2 bedroom, 2 bathroom residence in the highly desirable Siesta Harbor 55+ community is clean, bright, inviting, and ready for its next owner. Just steps from the soft, powdery sands of Siesta Beach, this is the perfect opportunity to enjoy the laid back island lifestyle you've been dreaming about. From the moment you walk in, you'll appreciate the fresh coastal feel and thoughtful updates throughout. The residence features beautiful luxury vinyl flooring, a renovated kitchen, updated bathrooms, a brand-new vanity in the guest bath, and new and newer appliances. The open and comfortable floor plan is filled with natural light and designed for easy everyday living. Adding even more peace of mind, a brand new air conditioning system was installed in October 2026, so the next owner can enjoy the comfort of a brand-new system from day one. One of the true highlights is the spacious all season's lanai, where you can sit back, relax, and take in the fantastic waterfront views. Watch boats cruise along the shimmering saltwater canal as you enjoy your morning coffee or unwind with a glass of wine in the evening. The canal leads directly to the Intracoastal Waterway and Gulf of Mexico, creating a beautiful backdrop and a constant reminder that you are living on Siesta Key. Siesta Harbor is an active and welcoming 55+ community with an incredible selection of amenities and activities. Enjoy the heated pool and spa, fitness center, sauna, clubhouse, shuffleboard courts, private Intracoastal pier, and a wonderful social calendar filled with community events and activities. Fishing enthusiasts will love the private waterfront pier, while boaters have the opportunity to lease dock space on a first come, first served basis. Residents also enjoy deeded beach access through Crescent Arms, beautifully maintained tropical grounds, on site management, private storage, and same floor laundry. With the free trolley stop conveniently located just outside the community, Siesta Key Village, local shops, restaurants, and entertainment are all easily accessible. The South Bridge provides convenient access to mainland Sarasota, downtown, and the area's many cultural attractions. Whether you're looking for a full-time home, a seasonal escape, or your own island retreat, this residence offers an incredible combination of location, thoughtful updates, waterfront views, amenities, and lifestyle. With the brand-new air-conditioning system, freshly painted interior, updated kitchen and baths, and beautiful waterfront setting, so much has already been taken care of for you. Just move in, relax and enjoy everything Siesta Key has to offer. Come see why life is better on the Key!

1300 N Portofino Drive Unit 103, Sarasota

$580,000

2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ii SubDv. ⋅ 34242 Zip Code

Welcome to your Siesta Key getaway at Midnight Cove II! This desirable first-floor condominium offers a wonderful combination of coastal living, resort-style amenities, and investment potential. Conveniently located close to the heated community pool, the unit enjoys a peaceful canal view and easy access to all that this popular Siesta Key community has to offer. Midnight Cove II is a sought-after bayside community with weekly rentals allowed, making this an attractive opportunity for those seeking a vacation home, investment property, or both. The community offers on-site management and a rental office, providing convenience for owners who want professional support while maximizing their time enjoying the island. Residents and guests can take advantage of an impressive array of amenities, including a heated swimming pool, fitness center, tennis courts, and pickleball courts. The community also provides easy access to the beautiful beaches of Siesta Key, where you can enjoy the area's famous white quartz sand and spectacular Gulf sunsets. Whether you're looking for a place to escape to, a property to generate rental income, or your own piece of paradise on Siesta Key, this first-floor condo at Midnight Cove II is an opportunity worth seeing. Property Highlights First-floor location Beautiful canal view Conveniently located near the heated pool Weekly rentals allowed On-site management On-site rental office Heated community pool Fitness center Tennis courts Pickleball courts Desirable Siesta Key location Excellent vacation-home or investment opportunity Live the Siesta Key lifestyle and enjoy the flexibility of owning a property where you can relax, play, and potentially generate rental income.

1600 Cove Ii Place Unit 412, Sarasota

$3,400,000

5 Beds ⋅ 6 Baths ⋅ Roberts Point SubDv. ⋅ 34242 Zip Code

Under Construction. Brought to you by Noah Thomas Builders - Best in Luxury Coastal. A masterclass in luxury homebuilding, this Noah Thomas Builders contemporary coastal home offers an exceptional blend of modern aesthetics and is built to FEMA's latest standards. Step inside this 3240 sqft home offering five bedrooms, six bathrooms, an open-concept floor plan with high ceilings and premium finishes throughout. It features all hurricane-rated windows and doors and is constructed to be as hurricane and flood-proof as possible-giving you peace of mind while living steps from the water. The kitchen boasts quartz countertops, top-tier appliances, and a spacious island perfect for entertaining. Retreat to the luxurious master suite with spa-inspired bath and expansive walk-in closets. Endless sunshine, gentle breezes, and your own private pool and spa — relax, unwind, and entertain in your personal outdoor oasis. Additional highlights include a private elevator, gas generator and wine room. The rooftop deck, however, defines this residence. This elevated sanctuary invites you to experience Siesta Key from a completely new perspective. Your private escape above it all — a space built for sunsets, sea breezes, and unforgettable gatherings. Situated on the quiet north end of Siesta Key, Roberts Point is prized for its natural beauty, privacy, and proximity to Siesta Beach, Siesta Village, and downtown Sarasota. All images, renderings, and descriptions illustrate the intended design and style by Noah Thomas Builders. Finishes, materials, and specifications may change during the build process. Pricing, availability, and final details subject to adjustment prior to completion.

4183 Roberts Point Circle, Sarasota

$1,350,000

3 Beds ⋅ 3 Baths ⋅ Shells On Siesta Key SubDv. ⋅ 34242 Zip Code

EXCEPTIONAL WEEKLY RENTAL TOWNHOME JUST STEPS FROM SIESTA KEY VILLAGE! An exceptional opportunity to enjoy a turnkey-furnished, three-bedroom townhome in a highly desirable location on the beach side of the road, just steps from the vibrant atmosphere of Siesta Key Village. With weekly rentals, pet-friendly accommodations, a two-car garage, and gated access to world-renowned Siesta Key Beach, this property offers the perfect combination of personal enjoyment and rental potential. Renters consistently give this residence five-star reviews, praising its convenience, cleanliness, and comfortable accommodations. Summer 2026 rentals have been exceptionally strong, further highlighting the appeal and income potential of this sought after location. The home has been thoughtfully updated, including a newer roof (2020), whole-home re-pipe (2023), hurricane-impact windows (2019), renovated kitchen and baths (2018– 2019), and updated systems and major appliances (2018–2019). Just a couple of blocks away, Siesta Key Village offers an irresistible mix of casual and fine dining, live entertainment, shopping, and the fun-filled island lifestyle that makes Siesta Key so special. Imagine enjoying your own piece of paradise where white crystal-sand beaches, rolling waves, spectacular sunsets, and the energy of the Village are all part of everyday life. Whether you're looking for a vacation retreat, an income-producing investment, or both, this exceptional Siesta Key townhome is truly a dream come true.

306 Beach Road Unit 306, Sarasota

$649,900

2 Beds ⋅ 2 Baths ⋅ Sea Village SubDv. ⋅ 34242 Zip Code

Views, views, and more views. Stunning FULL GULF views, dolphin views, manatee views, pelican views, eagle views, pool views and spectacular sunset views that will take your breath away! If a picture is worth a thousand words, this turnkey furnished Sea Village Ocean Blvd beauty will write a book with it's truly one of a kind ocean views! Experience the top finishes, including plantation shutters, this built for entertaining oasis has to showcase. This ground floor, end unit has in-unit washer/dryer, designated covered parking right in front of the unit, and is conveniently located right beside the mail room which also houses the units very own storage locker. Once inside you'll notice low maintenance, durable travertine tile throughout and beautiful crown molding. The kitchen is a dream for the chef in the family with KitchenAide appliances, and an abundance of space on high-end "titanium" granite countertops & backsplash, and a nice sized pantry. While standing at the kitchen sink, soak up the sea views, while grabbing instant hot water for a cup of tea or filling your water bottle with filtered water at the touch of a finger. The under cabinet lighting gives the ambiance of inviting warmth that says "home"! The family room has two matching sofas, one is a sleeper sofa. You can sit in the family room or at the dining room table and be in awe of the sunsets! Both the primary bedroom and second bedroom have two closets. The second bedroom is equipped with a "guest chest" which is a storage cabinet that doubles as a bed. Enjoy the 2 nicely equipped bathrooms, featuring dual sinks in the primary bath and a tub/shower to soak your cares away or a walk in shower in the hall bath, each with Kohler fixtures. Step out through the newly installed hurricane impact sliding doors onto your travertine tiled lanai. A few more steps to enjoy one of two newly updated pools, and a few more steps and you are standing on the newly installed fishing pier, where you can watch wild life for hours... dolphins, manatee, eagles, osprey, pelicans, and much more! Cap off your day with the storybook sunset! Sea Village on Ocean Blvd is on the north side of Siesta Key, only 1 mile from The Village shopping, restaurants, and nightlife, and is unlike any other place! New water heater '24, all new kitchen appliances '25, instant hot water & filtered water '25, HVAC & Hurricane Impact Sliding doors '26

4660 Ocean Boulevard Unit F1, Sarasota

Browse All Properties for Sale with Stone Counters

Siesta Key Real Estate & Homes With Stone Counters

How much is your home worth?

How much is your home worth?