Siesta Key FL Real Estate, Homes for Sale With Split Bedroom - Ed Grabowski

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

YOUR FURNISHED SIESTA KEY ESCAPE—BEAUTIFULLY REIMAGINED This extensively and tastefully renovated 3 bedroom, 3 and 1 half bath with quality finishes throughout has been meticulously maintained and is being offered furnished. This 2300 square feet under air, a 2 car garage and large pool with panoramic screened cage residence welcomes you with tropical landscaping, a circular paver driveway, and an inviting island style. Renovated in 2017–2018 this home offers a relaxed living space that with substantial improvements throughout. Each bedroom features its own private en suite bathroom, complemented by a separate guest half bath. All bathrooms were completely redone during the renovation. Improvements included a new metal roof, PGT WinGuard Aluminum 700 Series impact windows throughout, all new doors, plumbing, electrical, air-conditioning and ducts, drywall, lighting, and tile flooring. The kitchen features white cabinetry, a contrasting island with seating, and an impressive appliance selection: a Thermador gas stove and oven/microwave combination, Bosch dishwasher, and Café refrigerator. A 250-gallon propane tank supplies the gas stove and tankless water heater. Open living and dining spaces provide a welcoming setting for entertaining, with warm-toned tile flooring and views of the surrounding greenery. Outside, the pool, paver deck, and lanai invite relaxed outdoor living. A Panoramic View pool enclosure enhances the outlook, creating a beautiful setting for morning coffee, poolside dining, and quiet afternoons. Additional conveniences include central vacuum throughout the home, wiring for ceiling fans in every room, and an oversized two-car garage. Thoughtfully updated with quality finishes throughout, this welcoming Siesta Key retreat is ready for your next chapter of island living.

Sarasota

$3,195,000

3 Beds ⋅ 4 Baths ⋅ Spice Bay SubDv. ⋅ 34242 Zip Code

LIVE THE SIESTA KEY LIFESTYLE IN SPICE BAY—an intimate, gated enclave of just 14 estate-sized homesites in one of Siesta Key’s most distinctive Intracoastal communities. Custom built by award-winning builder Ryan Perrone of Nautilus Homes, this sophisticated residence offers approximately 3,235 square feet of beautifully designed SINGLE-LEVEL LIVING with exceptional craftsmanship, privacy, and effortless indoor-outdoor entertaining. Offered FURNISHED, this exceptional home is ready for you to immediately begin enjoying the Siesta Key lifestyle. From the moment you enter through the impressive mahogany front door, a dramatic wall of glass sliders draws your eye to the lush tropical surroundings and expansive outdoor living areas beyond. Filled with NATURAL LIGHT, the home blends refined finishes with relaxed “barefoot elegance,” creating a coastal retreat that feels both luxurious and inviting. The thoughtfully designed floor plan features 3 BEDROOMS, EACH WITH ITS OWN ENSUITE BATH, providing exceptional privacy and comfort for family and guests. The spacious primary suite includes a private den/study and a luxurious spa-inspired bath, while the additional bedrooms are generously sized and beautifully appointed. A PRIVATE CASITA LOCATED JUST OFF THE PORCH adds even more flexibility—perfect for visiting guests, extended family, a private retreat, studio, or home office. Throughout the home, you’ll find wide-plank oil-finished wood flooring, handcrafted details, custom closets and built-ins that reflect the quality of this custom residence. At the heart of the home, the GOURMET CHEF’S KITCHEN was created for entertaining and features a 6-burner gas range, steam oven, two dishwashers, generous workspace and a large walk-in pantry. Open the sliders and embrace true Florida indoor-outdoor living. The extended courtyard and lanai enjoy DESIRABLE SOUTHERN EXPOSURE and a private tropical setting—perfect for morning coffee, entertaining friends, relaxing with an evening cocktail or unwinding in the spa. For boating enthusiasts, enjoy access to a DEEP-WATER BOAT DOCK WITH A 13,000-LB LIFT, making it easy to spend your days exploring Sarasota Bay and the surrounding waterways. An oversized THREE-CAR TANDEM GARAGE provides exceptional space for vehicles, storage and all your island toys. Spice Bay offers the rare combination of PRIVACY AND CONVENIENCE on Siesta Key. Walk or bike to the beach, nearby shops and restaurants, spend your days enjoying the world-famous quartz sands of Siesta Key Beach, then head downtown for Sarasota’s celebrated dining, arts and cultural scene. This exceptional TURNKEY FURNISHED custom residence captures the very best of luxury coastal living—private, refined and unmistakably Siesta Key.

1207 Sharswood Lane, Sarasota

8773 Midnight Pass Road Unit 504G, Sarasota

$615,000

2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code

Welcome home to your tropical retreat at Island Reef on south Siesta Key! Island Reef is a Gulf to Bay resort style community. Amenities include: 2 heated pools, private beach, pickleball, tennis, clubhouse and docks. There is an active social calendar and in-house rental management as well. This beautiful penthouse unit has a wonderful pool and courtyard view. 504G is being offered Turnkey Furnished. This beachy condo has been extensively upgraded including the kitchen, both bathrooms, a laundry with full-size washer and dryer, and a raised ceiling in the dining area. The knotty pine floors and doors are reminiscent of a coastal cottage. Indirect lighting can be dimmed to suite your needs. A new AC was installed in Oct 2026 and the warranty will be transferred to the new owners. The kitchen and bathrooms have solid wood paneled cabinets, granite countertops, and subway tile bath and shower surrounds. In the kitchen the lighted cabinets allow for a beautiful display of dishes, glassware, and favorite collectibles. The living room and dining area have comfortable coastal furniture. The large dining table holds 6-8. Glass sliding doors open to a garden style lanai with slate tile flooring. Enjoy the tropical breeze and pool view while sipping your morning coffee on this wonderful lanai. Throughout the condo there are several unique antique wood chests and other furniture pieces., which are perfect for additional storage. The coastal artwork and knick-knacks are included in the purchase of this home. From the primary bedroom, you can also access the lanai through sliding glass doors. There is a large walk-in closet and an ensuite bathroom with dual sinks and large shower. The guest bedroom has a three-piece full wall shelving /desk unit. There is also a full wall built-in closet. Across the hallway is a laundry and storage room. If you are ready to make a move to paradise, please call for a private showing. When you see 504G you will fall in love! Buy now and enjoy winter on Siesta Key!

8773 Midnight Pass Road Unit 504G, Sarasota

$4,500,000

5 Beds ⋅ 2 Baths ⋅ Sub Of Us Lt 7 Of 20-37-18 SubDv. ⋅ 34242 Zip Code

For the first time since 1925, the same Sarasota family is bringing 7535 and 7539 Midnight Pass Road to market, offered together as nearly one acre on Siesta Key. The two parcels total 0.95 acres, with 7535 offering over 100 feet of direct waterfrontage on Little Sarasota Bay, a reinforced concrete seawall, and access to the Intracoastal Waterway. The main home was designed by Jack West, a celebrated architect of the Sarasota School of Architecture. The charming second home on the adjoining parcel was designed by his onetime partner, Elizabeth Boylston, the first woman in Florida elected to the American Institute of Architects. This second residence offers two bedrooms, one bathroom, and 1,016 square feet, in addition to the MLS-listed totals. A detached two-car garage provides additional parking and storage. Walls of sliding glass and graceful midcentury lines open the main house to the garden and the water. Framed by lush tropical greenery, the combined site presents a rare opportunity to create a waterfront compound with a main residence, guest house and gardens. An additional adjacent 0.53-acre lot may also be available for purchase at an additional price, offering an opportunity to expand the property even further. A 2016 dock with a 13,000 lb boat lift provides access to the Intracoastal Waterway, where mornings begin with soft golden light over Little Sarasota Bay. Turtle Beach, Crescent Beach, and the powder-soft white sand of Siesta Beach are minutes away, with Siesta Key Village, downtown Sarasota, and Sarasota Bradenton International Airport all within easy reach. For the buyer who has been waiting for the right piece of Siesta Key, this is it: nearly an acre of land with direct bayfrontage, a seawall, dock and lift already in place, complemented by an architectural legacy and history that cannot be replicated. Create the waterfront home you have always imagined on land that has been cherished by the same family for over a century and is now ready for its next chapter.

7535 Midnight Pass Road, Sarasota

6312 Midnight Pass Road Unit 305S, Sarasota

$689,000

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

Picture your mornings starting with coffee on your screened lanai, a gulf view and soft sea breezes, then a few steps to the powdery white sand of world-famous Siesta Key beach. This 2-bedroom, 2-bath beachfront condo in a waterfront gated community is your own seasonal getaway when you want it and an established vacation rental when you don't. Weekly rentals are permitted, and the residence is already an active vacation rental with a proven booking history, so it can help offset the cost of ownership while you are away. Sold furnished and turnkey, it is ready to enjoy from the day you close. A split bedroom plan places a private en-suite bath with each bedroom, so guests and family each have their own retreat. Tile flooring throughout and a bright white kitchen with stainless appliances make for easy, low-maintenance coastal living. A large storage closet holds beach chairs, umbrellas and toys, and beach chairs are provided on the sand for owners and guests. Crescent Arms offers direct beach access, a community pool, tennis, an elevator and an assigned carport space, with a water view from the grounds and the Gulf just steps away. Stroll to nearby restaurants and shops, or hop on the free Siesta Key trolley to explore the island. A rare chance to own a piece of Siesta Key that works for you whether you are here or not.

6312 Midnight Pass Road Unit 305S, Sarasota

5855 Midnight Pass Road Unit 611, Sarasota

$599,000

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

Under contract-accepting backup offers. PRICED TO SELL! Walk into over $20,000 rental income! Discover the best of Siesta Key living at Harbor Towers Yacht & Racquet Club, where waterfront surroundings, resort-style amenities, and rental flexibility come together. Located on the sixth floor, this two-bedroom, two-bath condominium is being sold TURNKEY FURNISHED and has partial views of the Intracoastal Waterway—a relaxing backdrop for watching the boats go by. Whether you’re seeking a full-time residence, seasonal retreat, or investment property, this condo offers an appealing opportunity to own on one of Florida’s most beloved barrier islands. The building has undergone an extensive renovation, including all-new hurricane-impact windows and doors, adding to the appeal of this established waterfront community. A two-week minimum rental policy provides flexibility to enjoy your own island getaways while pursuing vacation-rental income when you’re away. Private storage locker included.

5855 Midnight Pass Road Unit 611, 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

$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

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

$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

$10,890,000

6 Beds ⋅ 8 Baths ⋅ Roberts Point SubDv. ⋅ 34242 Zip Code

Set on 1.34 waterfront acres in one of Sarasota’s most extraordinary settings, 4196 Roberts Point Circle presents a rare opportunity to own a private residential compound surrounded by water, mature tropical vegetation and sweeping views across Sarasota Bay. With over 400 feet of waterfront and an exceptional sense of privacy, the property offers a setting that is increasingly difficult to replicate on Siesta Key or anywhere in the Sarasota area. For a buyer drawn to architecture with history and individuality, the existing compound offers an opportunity for renovation and transformation. For those envisioning something entirely new, the acreage and waterfront position provide an exceptional canvas for creating a landmark Sarasota estate. The property also has the potential to be divided into multiple parcels and redeveloped as incredible bayfront homes. Most compelling is the location on the coveted north end of Siesta Key, an area prized for its privacy, larger properties and peaceful residential character while remaining close to everything that makes the island so desirable. The structures encompass approximately 8,500 square feet of living space with six bedrooms and eight baths. Distinctive architecture, extensive use of natural wood, vaulted and beamed ceilings, expansive walls of glass and wraparound outdoor living areas give the residence a character entirely its own. The main residence features generous gathering spaces framed by windows and French doors, warm wood flooring, a dramatic open staircase, and an expansive primary suite with vaulted ceilings. Multiple living and entertaining areas provide flexibility for reimagining the interiors while preserving the property’s architectural personality. The guest house is perfect for guests, extended family, private offices, studios, or multigenerational living. Outdoors, the expansive grounds unfold toward the shoreline with a swimming pool, mature landscaping and multiple docking options providing direct access to the water. From the shoreline and elevated living spaces, broad views stretch across Roberts Bay to the mainland while the scale of the 1.34-acre parcel creates a remarkable sense of openness and seclusion. Siesta Key is celebrated for its laid-back coastal lifestyle, vibrant Siesta Key Village and extraordinary beaches, including Siesta Beach, renowned for its powdery white quartz sand and previously named the No. 1 beach in the United States by Tripadvisor. From this private waterfront retreat, downtown Sarasota’s dining, shopping, and cultural attractions are also just minutes away, creating an exceptional combination of island seclusion and mainland convenience. This is a rare opportunity without compare on the Gulf Coast.

4196 Roberts Point Circle, Sarasota

6287 Midnight Pass Road Unit 103, Sarasota

$619,000

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

Priced to sell. Welcome to your sunny slice of paradise on Siesta Key. This bright and inviting south-facing condominium offers a great opportunity to enjoy island living just near the world-famous white quartz sand of Siesta Beach. This generously sized two-bedroom, two-bath residence has been well maintained by its original owner and occasionally occupied. The desirable southern exposure fills the condominium with natural light throughout the day, creating an open and welcoming atmosphere. The interior has been recently painted, giving the home a fresh, clean look, ready for your personal touches. The unit includes several updates, including a newer stack washer and dryer, newer air-conditioning system, plus energy-efficient LED lighting. The spacious layout provides comfortable living and dining areas along with a generously sized main bedroom en suite, making it ideal for year-round living, seasonal use or taking advantage of the Excelsior on-site rental program with a two-week rental minimum. Convenience is key with under-building assigned parking as well as a private storage closet for beach chairs, umbrellas and other beach essentials. This bay-to-beach complex offers an easy distance across the street to the powdery sand and turquoise Gulf waters of internationally recognized Siesta Key Beach. Residents and renters enjoy an impressive array of resort-style amenities. The property features tennis and pickleball courts, beautifully maintained grounds, bayside grilling areas, and bayside and Gulf-side swimming pools. Whether you prefer relaxing by the water, enjoying sunset walks along the beach or staying active with outdoor recreation, this community offers something for everyone. With its prime location, bright southern exposure and access to outstanding amenities, this Siesta Key condominium presents a wonderful opportunity to own a piece of Florida’s sought-after coastal lifestyle.

6287 Midnight Pass Road Unit 103, Sarasota

$2,295,000

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

Under contract-accepting backup offers. Beautifully updated homes can be recreated, however 320 feet of waterfront cannot. Add 2,510 square feet of sophisticated living, a 50-foot private dock, a short route toward open water, and this becomes a Siesta Key opportunity that is anything but ordinary. Designed for those who want the water to be part of everyday life, this beautifully updated residence combines three bedrooms, two-and-a-half baths, generous living spaces, thoughtful privacy and a clean contemporary aesthetic. Soaring ceilings, large windows and abundant natural light bring an airy energy to the open-concept living room that becomes the focal point of your island lifestyle. Plantation shutters offer privacy and architectural character, while gorgeous tile flooring creates cohesion and easy maintenance between Siesta Key adventures. The completely renovated kitchen makes a sophisticated statement with sleek gray and white cabinetry, quartz countertops and open shelving that turns favorite serving pieces into artful display. Privately positioned, the owner’s wing feels like a retreat of its own. The primary suite and separate study or recreation room sit adjacent to a secluded canal-side patio—the perfect perch for quiet morning coffee or sunset spirits. The renovated primary bath features modern cabinetry, a frameless glass shower and a luxurious soaking tub with water views. The additional bath has been equally thoughtfully renovated. Outside, Siesta Key living takes center stage. A screened pool, new pool deck and covered entertaining space offer plenty of room for lounging while overlooking the canal, while a private 50-foot Trex dock with a 5,000-pound boat lift makes boating an effortless extension of the day. Whether you like to tinker or simply appreciate being organized, even the garage is ready for you with painted flooring, extensive cabinetry and smart closet storage. Distinctive yet remarkably versatile, this is polished, move-in-ready Siesta Key living—with the kind of relationship to the water that simply cannot be recreated.

500 Venice Lane, 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

$1,400,000

3 Beds ⋅ 3 Baths ⋅ Summer Cove On Siesta SubDv. ⋅ 34242 Zip Code

Under contract-accepting backup offers. Rarely available at Summer Cove on Siesta Key, this exceptional 3-bedroom, 2.5-bath residence offers an elegant opportunity to enjoy the best of island living. Set within a gated Gulf-to-Bay community built in 2005, the residence features beautiful views from every window, abundant natural light, and deeded beach access. A private elevator opens directly to the residence, where comfort and coastal sophistication come together effortlessly. The thoughtfully designed kitchen serves as a beautiful centerpiece, while two expansive balconies extend the living space outdoors. Two tandem garage spaces provide secure, convenient parking. There is deeded beach access and a kayak launch for an easy way to enjoy the surrounding waterways and explore the coast. At the heart of the community is a beautifully renovated clubhouse. It was formerly the renowned Summerhouse Restaurant and a memorable part of Siesta Key history. Today, this distinctive gathering space features a new fitness center, game room, pool tables, library, and more—creating an inviting setting for recreation, entertaining, and relaxation. Outdoor amenities include a resort-style pool and spa, and a barbecue area. With its private elevator, generous outdoor spaces, secure garage parking, deeded beach access, and exceptional community amenities, this rarely offered residence presents a distinctive opportunity to experience Siesta Key in comfort and style. Siesta Key shops, restaurants, and beaches are just minutes away. Also, it’s just a short drive downtown Sarasota, St. Armand’s Circle, and Longboat Key. Schedule your private tour today!

1640 Summerhouse Lane Unit 40, 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. Excelsior just voted to allow one week rentals outside of high season.

6285 Midnight Pass Road Unit 406, Sarasota

6300 Midnight Pass Road Unit 1005, Sarasota

$1,200,000

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

Full gulf views and right on the beach! Experience breathtaking coastal living from this spectacular 10th-floor condominium at Crystal Sands on Siesta Key being offered turnkey furnished. Enjoy panoramic beach and gulf views from the living areas and both bedrooms, creating an incredible backdrop for morning coffee, relaxing afternoons, and unforgettable sunsets. From this elevated vantage point, you'll also enjoy beautiful views of downtown Sarasota. Located directly on Siesta Key's desirable Crescent Beach, this residence offers the quintessential Florida beach lifestyle. The comfortable floor plan features spacious living areas, luxury vinyl plank flooring, newer appliances and a 30-foot lanai accessible from the living room and both bedrooms. Excellent rental income opportunity with 2-week rentals permitted and an onsite rental management staff to handle every detail. Enjoy the flexibility of using the condominium as your own private beach retreat while generating rental income when you're away. Whether you're looking for a vacation home, investment property, or the perfect combination of both, this is a rare opportunity to own a gulf-view residence in one of Sarasota's most desirable locations. Pet friendly.

6300 Midnight Pass Road Unit 1005, Sarasota

$649,000

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

Sweeping water views across Big Pass to the Gulf of Mexico and year-round sunsets set the stage for this oversized 2-bedroom, 2-bath residence in Siesta Towers on Siesta Key. A rare 40+ foot-long balcony stretches across the residence, while inside, 1,435 square feet, generously sized rooms and a flexible floor plan offer endless possibilities to create your own coastal retreat. Similar floor plans have been reimagined to include a den or flex space, and an in-unit washer and dryer may be added. Hurricane-impact sliders and windows frame the views and fill the residence with natural light. Siesta Towers has undergone extensive improvements, including a new seawall, renovated exterior, new landscaping, rebuilt fishing and social piers, renovated pool and fencing, Garrison flood-control system, replaced electrical system and key-fob/app-controlled access. Residents also enjoy a fitness center, social room, outdoor grills, bike room and private storage.

4822 Ocean Boulevard Unit 8B, 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

5855 Midnight Pass Road Unit 221, Sarasota

$634,900

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

Beautiful turnkey 2-bedroom 2 bath condo in Harbor Towers! All new hurricane windows, window shades, new plumbing for entire home and hot water heater 2025. Master bedroom has walk in closet, renovated bath with floating vanity and tub/ shower combo. Second bedroom is large with lots of windows and connected bath with tub / shower and floating vanity. Dining room and Living room combo with open floor plan. Hurricane windows across the entire front of condo give lots of sun and nice view of the lake. This unit includes a covered parking spot ($15.000 value). Rental income is very strong with on-site management. Unit currently rented Feb 13, 2027- March 20th, 2027. Great rental Income! This property features many amenities, including, heated pool with kiddie pool, 2 BBQ areas, social room with renovated kitchen, Har-Tru tennis courts, fitness room, kayak storage, harbor with boat slip rental. Close proximity to Siesta Key beach. Harbor Towers also offers one of the lower HOA fees on the key for all that is included.

5855 Midnight Pass Road Unit 221, 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

$4,295,000

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

A boater’s paradise and an entertainer’s dream, this exceptional waterfront residence captures the very best of the Siesta Key lifestyle. Set along 83 feet of waterfront with direct access to Sarasota Bay and just a short walk to Beach Access 1 on Shell Road, the expansive home was thoughtfully designed for luxurious indoor-outdoor living and sophisticated entertaining. Featuring a grand entrance with an automated front gate, expansive stone-paver driveway, and abundant parking for entertaining, this waterfront property makes an undeniable statement. Inside, glistening water views greet you at the door. Soaring 11-foot ceilings, 8-foot solid-core doors, impact-rated windows, and wide-plank luxury LVP flooring create a refined yet inviting atmosphere. At the heart of the home, the open-concept great room flows seamlessly through oversized sliding glass doors to the expansive 50-foot lanai. The chef’s kitchen features custom wood cabinetry, quartz countertops, premium Thermador and Bosch appliances, and an entertaining bar complete with a wine cooler, two beverage refrigerators, and an ice maker. The primary suite provides a private retreat with his-and-hers walk-in closets and a spa-inspired bath featuring dual rain showerheads, a steam shower, soaking tub, and elevated stone finishes. Three additional bedrooms offer exceptional accommodations, including ensuite bathrooms with beautifully appointed finishes. Outside, a heated pool with sun shelf, luxurious spa, and custom, in-ground fire pit create the perfect, private waterfront oasis. The newly installed dock, 10,000lb boat lift, and two jet ski lifts make getting out on the water effortless, with Sarasota Bay just minutes away. A private putting green, integrated indoor-outdoor speaker system, beautifully landscaped grounds, and whole-property fencing complete the resort-like setting. The lower level offers more than 2,500 square feet of ADDITIONAL space for vehicles, water toys, equipment, a home gym, game room, workshop, etc. Overlooking Bayou Nettie, this premier waterfront setting places Sarasota Bay just moments away by boat. This is a home designed around the pleasures of waterfront living, uninterrupted entertainment and everyday enjoyment.

3920 Roberts Point Road, Sarasota

$1,400,000

4 Beds ⋅ 2 Baths ⋅ Ocean View SubDv. ⋅ 34242 Zip Code

WELCOME TO THE SIDE OF SIESTA KEY YOU NEVER WANT TO LEAVE. Glistening Heron Lagoon stretches peacefully behind this beautifully restored and renovated income producing single family home, while just beyond, the Gulf of Mexico makes its presence known through salty breezes and the sound of waves in the distance. Surrounded by lush tropical greenery on a deep Siesta Key lot, this is an exceptional combination of island lifestyle, 5 Star vacation home with income potential and long term land value. Tax records reflect four bedrooms, with the fourth currently enjoyed as an office, plus two full baths. Single story, built to enhance the open, airy feeling inside, while the home's connection to the outdoors keeps the peaceful lagoon and tropical setting at the center of everyday life. Following the 2024 storms, the home was extensively renovated, fully permitted and improved creating a fresh and beautifully finished property. The new kitchen and baths, gleaming tile floors and light filled interiors are perfectly suited to relaxed island living. Your private pool and spa are surrounded by tropical greenery with the peaceful waters of Heron Lagoon beyond. Spend afternoons by the pool and enjoy spectacular sunset colors. The deep lot provides a wonderful sense of space and privacy, while the substantial brick paver driveway offers abundant parking for owners and guests, an increasingly valuable feature on Siesta Key and an important advantage for a successful vacation rental. For the investor or second home buyer, the opportunity becomes even more compelling. This highly sought after vacation rental generates approximately $114,000 in annual gross rental revenue despite being only self managed by an out of state owner. It offers an established income stream with the flexibility to enjoy the property yourself, creating the possibility of owning a Siesta Key getaway that can also work for you when you are away. Prior to the extensive restoration and improvements that followed, the property received an appraisal with an opinion of value of $1,300,000 as of September 2024. Since that time, substantial additional work and improvements were completed. What cannot be duplicated is the setting and the land. A deep single family homesite on Siesta Key overlooking Heron Lagoon, surrounded by tropical greenery with the Gulf just beyond offers tremendous possibilities. Continue its successful vacation rental use, make it your island getaway, enjoy it as a full time residence, or hold an increasingly scarce piece of Siesta Key real estate for the future. The property offers approximately 1,625 square feet of living area, four bedrooms per tax records, two full baths, a garage, private pool and spa, dock, covered outdoor living space, and extensive brick paver parking. Glistening lagoon views. Gulf breezes and the sound of the waves. Tropical privacy. Deep lot. Generous parking. Proven rental income. Extensive post storm restoration and renovation. Long term Siesta Key land value. This is more than a successful vacation rental. It is a beautiful single family home, an island escape, an income producing property and an opportunity to own a special piece of Siesta Key. Property documentation reflects a 2017 roof, 2020 plumbing re pipe, 2021 water heater and 200 amp electrical service. Flood insurance is 8,734.00 per year, Homeowners insurance is 7,788 per year and there is no HOA. Come for the opportunity. Stay because you may never want to leave.

8302 Midnight Pass Road, Sarasota

$7,900,000

5 Beds ⋅ 6 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code

Pre-Construction. To be built. ......YOU WILL BE IMPRESSED by this Permitted & Custom Designed Residence along Hansen Bayou---deep Sailboating Water with Immediate Access to the Gulf....."Tucked-Away" on a 18,000+ sq ft lot on a QUIET STREET near the North Bridge of Siesta, allowing Privacy as well as Quick and Easy Proximity to both all the Arts/Dining/ Shopping of downtown Sarasota Bayfront as well as just MOMENTS to TOP RATED SIESTA KEY BEACH!.....Upon entering the main living area you will be greeted by WALLS OF GLASS seamlessly blending Indoor/Outdoor Living Spaces. In addition the Main Living Areas, this home also features a Private Den/Study, Sumptuous Primary Suite w/balcony; (3) Secondary En-suite Bedrooms as well as a PRIVATE GUEST QUARTERS..... Sleek Architectural Lines; Generous 3 Car Garage with High Ceilings--with optional 6 car garage with "Lifts"; ELEVATOR; Level 5 Finishes Throughout and over 4500 sq ft of Sophistication & Barefoot Elegance*****Every Design Element Commands Attention*****Build Package by Waterfront Specialist, Coastal Tide Construction with ability to CHOOSE YOUR FINISHES---allowing for the PERFECT OPPORTUNITY to Customize your Island Estate and ENJOY the Ideal Beach and Boating Florida Lifestyle.

3601 White Lane, 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

$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

$2,250,000

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

TURNKEY. FULLY FURNISHED. INCOME PRODUCING. Welcome to an exceptional Siesta Key property offering the rare combination of a fully renovated luxury residence, private tropical setting and proven rental income. The home is being offered fully furnished and can include essentially everything needed to operate and enjoy it immediately—from designer furnishings and décor to pots, pans, dishes, silverware, linens, towels and other household essentials. Truly turnkey, the next owner can simply bring a suitcase and begin enjoying the Siesta Key lifestyle or continue the established rental operation. Extensively renovated with a focus on modern comfort, durability and style, the approximately 2,500-square-foot residence features an open, light-filled floor plan, expansive impact windows and doors, durable wood-grain tile flooring, custom wood cabinetry, quartz waterfall countertops and curated designer lighting. The split-bedroom layout offers privacy and flexibility, making the home equally well suited for full-time living, family vacations or rental guests. The spacious primary suite features private outdoor access and a beautifully renovated bath with a freestanding soaking tub and oversized marble walk-in shower. Three additional bedrooms are located on the opposite side of the home, including a junior suite with its own private bath, floor-to-ceiling marble tile and oversized picture window overlooking the pool and outdoor living area. The home comes equipped with a 30-year commercial-grade roof, high-impact windows and doors throughout, new HVAC, pool equipment, water heater and major appliances, designer finishes and bathrooms that feature floor to ceiling marble detailing. Outside, the property becomes a private tropical retreat. The heated saltwater pool and screened enclosure are surrounded by lush landscaping and the expansive double lot provides exceptional privacy and space for entertaining, relaxing or enjoying the Florida lifestyle. For the owner-user, this is a beautifully renovated and fully furnished Siesta Key home requiring little to nothing to do. For the vacation-home buyer, it offers a private escape that can generate income when not in use. For the investor, the established rental history and strong NOI create a compelling income-producing opportunity. A rare opportunity to acquire a fully renovated, fully furnished and income-producing Siesta Key property where luxury, lifestyle and investment potential come together. Located just blocks from Roberts Bay and less than one mile from the world-famous sands of Siesta Key Beach, the location provides convenient access to the beach, dining, shopping and everything that makes Siesta Key one of Sarasota’s most desirable destinations.

4879 Commonwealth Drive, 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

$3,150,000

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

A boater’s paradise on Siesta Key! This sprawling single-story waterfront residence positioned on a half-acre home site adjacent to the Grand Canal comes with two lifts and dual personal watercraft platforms. Everything about this home invites its owners to relax and embrace the Siesta lifestyle. From the abundant outdoor space including a heated saltwater pool and spa, multiple entertaining areas overlooking the lush landscaping and water, to the easy-flowing floor plan with generous gathering areas, 829 Idlewild Way invites you to stay a while, every day. With 4 bedrooms and 3 and a half baths (two are en suites) positioned at the corners of the home, privacy is ensured for everyone. The extraordinary primary suite offers a luxurious respite at the end of the day with spa-like bath awash in natural light, with a dual-entry shower of travertine and glass and multiple showerheads, sliding privacy glass doors to the outdoor area, jetted spa tub, dual separate vanities and a water closet with a bidet, a large walk-in closet with custom built-ins and dressing area and a spacious bedroom featuring an architectural ceiling, fireplace and with abundant natural light, this elevated retreat awaits you. The center of the home is where everything and everyone comes together. Separate yet open areas flow seamlessly from dining to entertaining to lounging, ultimately leading through the four sets of impact-rated double doors to the resort-like environs beyond. At the center of all this is a kitchen that will inspire and satisfy accomplished and aspiring chefs. Miele appliances including dual ovens, microwave drawer, cooktop, two-drawer dishwasher, built-in separate refrigerator and freezer and central cooking island are surrounded by contemporary custom cabinetry, exotic granite surfaces and accent lighting throughout. Of course, if you prefer to present and serve alfresco, everything you need is just nearby. For those who value a bit of practicality beyond luxury, the oversized three-plus-car garage (a lift is included to accommodate four vehicles) will provide ample space for vehicles and toys. Additional practicality is possible given the orientation of two guest rooms, full bath and separate living room, potentially providing a generous guest/in-law suite within the home. If you are dreaming of a laid-back beach and boating lifestyle at the number one beach in the U.S., this is your place.

829 Idlewild Way, Sarasota

$1,175,000

4 Beds ⋅ 2 Baths ⋅ Siesta Cove Sub SubDv. ⋅ 34242 Zip Code

Tucked away on a quiet, secluded street in Siesta Cove, this beautifully renovated four-bedroom residence offers exceptional privacy, generous living spaces and the relaxed elegance of island living. Thoughtfully designed for everyday comfort and effortless entertaining, the home is filled with natural light and enhanced by extensive custom finishes throughout. A gracious foyer opens to an inviting, open-concept interior with a spacious living, dining, and family room. At the heart of the home, the well-appointed kitchen features maple cabinetry, stone countertops, stainless-steel appliances and an open connection to the main living areas, including the family room creating an ideal setting for gatherings with family and friends. Privately positioned, the expansive primary suite serves as a peaceful retreat with a large walk-in closet and spa-inspired bath featuring an oversized shower. Three additional guest bedrooms, convenient pool bath and an indoor laundry room provide comfort and flexibility for family members and visitors alike. Sliding glass doors create a seamless transition to the private outdoor living area, where a brick-paver lanai, heated pool and outdoor shower invite year-round relaxation. The fully fenced backyard offers generous space for pets, play or gardening. The home has been extensively improved for comfort, efficiency and peace of mind. Notable updates include a 2023 roof, impact-resistant windows and doors, whole-house replumbing, a hurricane-rated garage door, updated irrigation, a newer pool heat pump and saltwater system, interior and exterior painting, updated ceiling fans and LED lighting, upgraded electrical switches and outlets, refreshed landscaping, landscape lighting, and a brand new white PVC fence. A two-car garage completes the property. Located just a short walk from Siesta Beach, the residence places one of Florida's most celebrated coastal destinations within easy reach. Known for its powder-soft quartz sand and clear Gulf waters, Siesta Beach was named the No. 1 beach in the United States and No. 4 in the world in Trip advisor's 2025 Travelers Choice Awards. This desirable mid-key location also provides convenient access to Siesta Key's dining, shopping and recreational offerings, as well as downtown Sarasota's cultural attractions, restaurants, hospital and top-rated schools. Whether enjoyed as a full-island residence or a private coastal retreat, this exceptional property captures the very best of the Siesta Key lifestyle.

5333 Siesta Court, Sarasota

$1,399,000

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

Private beach access, heated pool access and an oversized two-car garage—all within walking distance of South Siesta Key’s restaurants and shops. Located near Point of Rocks, 6796 Sarasea Circle #3 offers a multilevel layout with three bedrooms, three full baths and flexible space for guests or extended family. Partially Furnished, Short-term rentals are permitted, subject to applicable association rules and regulations. The residence includes 1,890 square feet in the main home plus a separate 333-square-foot air-conditioned downstairs studio/efficiency, providing a combined 2,223 square feet of air-conditioned space. The main living level features an open kitchen, dining area and family room with volume ceilings, a fireplace and access to a spacious balcony. The upper level includes the primary suite with an ensuite bath. A second bedroom and full bath provide additional guest accommodations. The downstairs studio serves as the third bedroom and bathroom, with its own kitchenette and private exterior entrance. This space offers added privacy for visiting guests or extended family. A fenced courtyard provides another inviting setting for relaxing or entertaining. Recent improvements include a complete new A/C system in 2026, a metal roof in 2023 and new window coverings. All appliances, including the washer and dryer, are included. Enjoy beach days near Point of Rocks, time by the heated pool and the convenience of nearby dining—all with the space and flexibility of a townhome.

6796 Sarasea Circle Unit 3, 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

1200 E Peppertree Lane Unit 505, Sarasota

$610,000

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

SUNSETS, SUNSETS, SUNSETS! Experience the Siesta Key lifestyle in this turnkey furnished 5th-floor residence located in the highly desirable Peppertree Bay community. Situated on the Bayside, this 2-bedroom, 2-bath condo offers panoramic views of Siesta Key and spectacular Florida sunsets, along with private deeded beach access just across the property. Tile flooring flows throughout the residence, while the custom kitchen features granite countertops, a tile backsplash, abundant cabinetry, and brand-new stainless steel appliances. The open-concept dining and living areas extend into the enclosed lanai, creating additional space to relax, entertain, and enjoy the beautiful views. Additional features include a newer (2024) HVAC system, a new 80 gallon hot water heater, an in-unit washer and dryer, generous storage, and convenient under-building parking. Offered turnkey furnished, this residence is ready to enjoy from day one. Peppertree Bay is a sought-after Gulf-to-Bay community offering an exceptional array of amenities, including private deeded beach access, two heated swimming pools, two clubhouses with full kitchens, tennis and pickleball courts, a fitness center, fishing pier, BBQ grills, picnic areas, and an active social calendar in season. Ideally located on Siesta Key with easy access to Siesta Key Village, enjoy nearby dining, shopping, live entertainment, and everything Sarasota offers. Whether you're searching for a full-time residence, seasonal retreat, or investment property, this condo delivers the location, amenities, and lifestyle that make Siesta Key so desirable.

1200 E Peppertree Lane Unit 505, 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

8710 Midnight Pass Road Unit 203B, Sarasota

$610,000

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

Embrace the Siesta Key lifestyle at Tortuga Beach Club! This spacious 2-bedroom, 2-bath residence offers 1,650 square feet of living space in an intimate 77-unit Gulf-front community on the desirable south end of Siesta Key. From relaxing days along the private beachfront to unforgettable sunsets over the Gulf of Mexico, Tortuga offers the coastal lifestyle you've been dreaming of. Step inside and discover a light and inviting split-bedroom floor plan with an enclosed lanai that extends the living space and provides the perfect spot to relax and unwind. The spacious kitchen features wood cabinetry, granite countertops, abundant storage and a convenient pass-through breakfast bar overlooking the living area. A separate dining room just off the kitchen provides additional space for entertaining family and friends. The primary suite offers generous closet space, with the washer and dryer conveniently located within the primary closet. A new A/C system adds comfort and peace of mind. Tortuga Beach Club offers an impressive array of amenities designed for enjoying the best of island living. Spend your days on the private Gulf-front beach, take a swim in the heated indoor/outdoor community pool, relax in the sauna, or gather with friends on the sun deck featuring grills and seating areas. The community clubhouse offers a kitchen, library and entertainment space, while tennis and pickleball courts are conveniently located across Midnight Pass Road. Boating enthusiasts will appreciate access to boat slips across the street on the bay, with slips currently available for annual rental by application. A community laundry facility provides additional convenience when needed. The residence also includes covered parking conveniently located near the building entrance and elevator, making loading and unloading a breeze. The location completes the package! Enjoy close proximity to Turtle Beach, where you can spend the day along the shoreline, launch a kayak or simply soak up the laid-back atmosphere of south Siesta Key. You're also near some of the island's favorite dining destinations, including Ophelia's on the Bay, Turtles Restaurant and other nearby waterfront and casual dining options. Siesta Key Village, shopping, entertainment and the world-famous quartz sands of Siesta Beach are just a drive up the island. Whether you're searching for a full-time island residence or your own Siesta Key getaway, this spacious Tortuga Beach Club condominium brings together private Gulf-front beach access, boating, resort-style amenities and an exceptional south Siesta Key location. Spend your days enjoying the water and your evenings watching spectacular Gulf sunsets this is Siesta Key living at its best!

8710 Midnight Pass Road Unit 203B, 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

$1,675,000

4 Beds ⋅ 4 Baths ⋅ Princes Gate SubDv. ⋅ 34242 Zip Code

RARE SIESTA KEY WATERFRONT OPPORTUNITY — BUILD YOUR DREAM HOME ON A PRIVATE STREET AND A SHORT WALK TO THE BEACH. This exceptional property is a .41-acre waterfront lot with rare deep water frontage with quick access to the Intercoastal Waterway and no bridges. Offering approximately 240 feet of sailboat-capable concrete seawall, potentially two private boat docks and direct access to the Intracoastal Waterway, this is a remarkable opportunity for the boating enthusiast looking to create a custom luxury residence on Siesta Key. Custom luxury home rendering and plans are available, providing a vision for what can be created on this unique homesite. The plans can be imagined to the buyer's preferences with an in-house architect and designer, offering the opportunity to tailor the residence, finishes, layout, and waterfront lifestyle to suit your individual vision. The location is equally impressive. Leave the boat at your backyard dock and walk, golf cart or take the Trolley to Siesta Key Beach or one of the many outstanding hotspots. Enjoy the rare combination of boating from your backyard and walking to the beach, while remaining close to Siesta Key's restaurants, shopping, entertainment, and island lifestyle. Stickney Point Road is approximately a half-mile away, providing convenient access to the mainland. The property currently features a nearly 3,000-square-foot, 4-bedroom, 3-bath pool home, allowing a buyer the flexibility to renovate, enjoy the existing residence, or start fresh with a new luxury waterfront home. The existing home features spacious indoor-outdoor living areas, an expansive kitchen, family room with fireplace, screened paver lanai, pool, tropical waterfront views, and a new roof completed in April 2024. Properties offering this combination of an oversized .41-acre lot, roughly 240 feet of seawall, sailboat-capable water, direct Intracoastal access, and walkability to Siesta Key Beach are increasingly difficult to find. The opportunity here is the land, the water, and the lifestyle—bring your boat and your vision and create an extraordinary Siesta Key waterfront estate. Visit the website for more information or to book your private showing.

6937 Midnight Pass Road, Sarasota

6300 Midnight Pass Road Unit 809, Sarasota

$1,795,000

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

From its elevated eighth-floor setting at Crystal Sands, this turnkey-furnished residence captures an extraordinary panorama of the Gulf of Mexico and Siesta Key’s renowned white-sand shoreline. Completely renovated in 2022, this two-bedroom beachfront retreat pairs sophisticated coastal interiors with an expansive screened Gulf-front terrace, storm-rated windows and sliding glass doors, and an impressive rental history—all within one of Siesta Key’s most recognizable beachfront communities. Beyond its appeal as a personal beachfront escape, #809 offers an established rental history. The residence averages more than $80,000 in annual gross rental income (2024 – 2026), with bookings extending through year-end, offering a compelling opportunity for buyers seeking to combine personal enjoyment with income potential. Inside, the 1,271-square-foot residence has been thoughtfully reimagined with a fresh coastal aesthetic, luxury vinyl wood-plank flooring throughout, custom architectural ceiling treatments, and an open floor plan that keeps the Gulf firmly in view. The designer kitchen is both polished and functional, featuring granite countertops, custom Shaker-style cabinetry, stainless steel appliances, and a refrigerator cleverly concealed behind coordinating custom cabinet panels. The kitchen opens naturally to the dining area, where a built-in banquette creates an inviting gathering space beneath a dramatic coffered ceiling accented by designer lighting and naturally stained solid-wood beams. Beyond, the Gulf-front living room is framed by walls of glass, drawing your eye directly toward the water and opening to the screened terrace. The terrace is where the Siesta Key lifestyle truly takes center stage. Stretching across the Gulf-facing side of the residence, this generous outdoor living space provides a front-row seat to turquoise water, passing boats, and spectacular Gulf sunsets. A desirable split-bedroom floor plan provides privacy for owners and guests, with both bedrooms positioned to enjoy Gulf views and direct access to the screened terrace. Each bedroom also features a walk-in closet with built-in organization. The primary suite is complemented by a beautifully renovated en-suite bath with dual sinks, granite countertops, extensive built-in linen storage, and an oversized walk-in shower with bench seating. The second bath is also well appointed with newer cabinetry, stone counters and a tub/shower combination. Crystal Sands is an iconic Siesta Key beachfront community distinguished by its classic architectural presence and exceptional location directly on the Gulf of Mexico. Residents and guests enjoy a heated community pool, gated entry, elevators, recreation facilities, covered and guest parking, and direct access to the beach and Gulf. The residence also includes one covered carport space. And when you are ready to venture beyond the beach, some of Siesta Key’s favorite destinations are close at hand. Head north to Siesta Key Village for its lively collection of restaurants, boutiques, cafés, and nightlife, or south toward Crescent Beach, Point of Rocks, and the restaurants and conveniences surrounding Stickney Point Road. The Siesta Key trolley makes exploring the island especially easy, with service along the Key connecting beaches, dining, shopping, and Siesta Key Village.

6300 Midnight Pass Road Unit 809, Sarasota

5855 Midnight Pass Road Unit 222, Sarasota

$620,000

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

TURNKEY, FULLY FURNISHED & JUST MINUTES FROM SIESTA KEY BEACH! Your Florida getaway awaits at Harbor Towers Yacht & Racquet Club! One of the building's largest floor plans, this spacious residence offers a desirable split-bedroom layout, with a private bathroom for each bedroom. Sold completely furnished, it's ready for you to arrive, unpack, and start enjoying the Florida lifestyle—or explore its potential as a rental property. Enjoy peaceful mornings sipping coffee on the enclosed patio overlooking the tranquil pond, followed by a game of tennis or a relaxing afternoon at the beautiful waterfront pool overlooking the docks. When it's time for the beach, Siesta Key's world-famous quartz sugar sand and turquoise waters are just a short drive or trolley ride away. Spend your evenings exploring the restaurants, boutiques, happy hours, and live music of Siesta Key Village. An especially appealing feature is the existing electric washer and dryer hookups beneath the kitchen counter, reportedly grandfathered under current building restrictions. A shared laundry room is also conveniently located on the second floor, just a few doors away. Whether you're searching for a seasonal escape, a furnished Florida retreat, or an opportunity to generate rental income, this residence offers flexibility in a desirable Siesta Key-area location. Short-term rentals are permitted with a two-week minimum, subject to applicable rules and restrictions. Owners may also have the option of using the community's on-site property management or selecting their own provider, subject to association requirements. Beach days, waterfront amenities, tennis, and the Siesta Key lifestyle are waiting for you. Schedule your private showing today! Buyer to independently verify all association rules and fees, laundry hookup permissions, boat slip availability and rental terms, property management options, and rental restrictions.

5855 Midnight Pass Road Unit 222, Sarasota

9000 Blind Pass Road Unit B114, Sarasota

$815,000

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

Virtually Staged. Some room are virtually staged. Wake up to breathtaking, unobstructed views of the Gulf of Mexico on Turtle Beach from this beautifully remodeled 2-bedroom, 2-bath beachfront condominium on the peaceful south end of Siesta Key at Turtle Beach. This End Unit provides additional natural light and privacy! Whether you're searching for a private coastal retreat or an income-producing investment, this residence offers the best of both worlds. Sunsets are stunning! Every detail has been thoughtfully updated with upscale finishes, including a designer kitchen featuring quartz countertops, stainless steel appliances, porcelain tile flooring throughout, and hurricane-impact windows for peace of mind. Both spa-inspired bathrooms boast elegant walk-in showers with frameless glass doors, while the private in-unit laundry room adds everyday convenience. Just minutes from waterfront restaurants, marinas, and all the attractions of Siesta Key, you'll enjoy the serenity of Turtle Beach while remaining close to everything the island has to offer. With an onsite management team available to assist with rentals and a highly desirable one-week minimum rental policy, owners can enjoy the condo whenever they choose while generating outstanding rental income the rest of the year. Luxury finishes, panoramic Gulf views, beachfront living, and exceptional flexibility—this is your opportunity to own a slice of paradise on Siesta Key. Custom shades have been ordered and should arrive soon! Property has been in the rental program at Fisherman's Cove to offset expenses, but Owners used the unit personally in March and October.

9000 Blind Pass Road Unit B114, Sarasota

5920 Midnight Pass Road Unit 501, Sarasota

$1,800,000

2 Beds ⋅ 2 Baths ⋅ Sarasota Surf & Racquet SubDv. ⋅ 34242 Zip Code

Luxury on Siesta Key with impressive square footage offering an elevated experience and more room to live. Encompassing an impressive 1,724 square feet, this rarely available fifth-floor tower residence delivers the spaciousness of a single-family home with the effortless ownership, resort amenities, and income-producing flexibility of a premier Gulf-front condominium. Sweeping, unobstructed Gulf views and beautifully curated interiors complete a residence that's as functional as it is unforgettable. Inside, every detail has been thoughtfully curated to create a warm, sophisticated coastal retreat. Plantation shutters frame the natural light, while bamboo and leather furnishings, woven rattan accents, and a striking chain-link wall mirror in the primary suite lend personality and designer appeal. The updated kitchen and bathrooms feature timeless solid-surface countertops and clean, contemporary finishes that complement the home's relaxed elegance. The spacious primary suite is a true sanctuary, offering room for a dedicated sitting area large enough for a sofa—perfect for enjoying a quiet morning with Gulf views or unwinding after an evening in Siesta Key Village. An enclosed lanai extends the living space and showcases breathtaking, panoramic views of the turquoise water and legendary white sand beaches that have made Siesta Key world-renowned. Beyond your front door, Sarasota Surf & Racquet Club offers an exceptional collection of resort-style amenities, including private beach access, two heated swimming pools, tennis and pickleball courts, a well-equipped fitness center, barbecue areas, and beautifully maintained tropical grounds. This exceptional residence proves you don't have to choose between the space of a home, the ease and earning potential of a condominium, and the lifestyle of Gulf-front living—you can have all three.

5920 Midnight Pass Road Unit 501, Sarasota

$2,250,000

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

Under contract-accepting backup offers. Location, waterfront, boating and income potential come together at 4937 Oxford Drive, an exceptionally spacious, one-story pool home with desired frontage on Siesta Key's Grand Canal. Offering an impressive 2,539 square feet of living space with three bedrooms plus an office, this home stands out for its generous proportions, wide-open living areas and rare single-level floor plan. Even more noteworthy, the home has experienced no water intrusion, according to the owner, an important distinction for island living. A previous remodel raised the ceilings, creating a wonderful sense of volume, light and openness throughout the main living spaces. Go outside and the reason for owning on Siesta Key becomes even more compelling. The screened lanai surrounds a heated saltwater pool, while beyond it lies the Grand Canal, one of the island's defining waterways and a tremendous advantage for those who want to embrace the Siesta Key boating lifestyle. Although the former dock was lost years ago, the existing pilings remain, presenting a potential opportunity to reestablish a dock and create your own waterfront setup, subject to applicable permitting and approvals. Beyond its appeal as a full-time residence or island retreat, this property has been a superb income producer, offering potential for an owner seeking lifestyle and investment opportunity. And the location is hard to beat, close to Siesta Key Village, world-famous Siesta Beach, restaurants, shopping and all the energy of island life, with convenient access to the mainland. Large, one-story homes offering this much living space, a private pool, Grand Canal frontage, boating potential, strong income history and no water intrusion are difficult to find. Whether you envision a personal waterfront retreat, a potential income-producing investment or the best of both, 4937 Oxford Drive delivers a rare combination of space, location and Siesta Key lifestyle.

4937 Oxford Drive, Siesta Key

$2,795,000

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

For the buyer who believes the best of Siesta Key is experienced by boat, 5178 Oakmont Place delivers an exceptional combination of deep-water canal frontage, estate-sized privacy, refined island living, and effortless access to Sarasota Bay. Set on more than half an acre along Siesta Key’s coveted Grand Canal, this tastefully updated custom residence pairs Caribbean-inspired architecture with 93 feet of waterfront, a private dock, and impressive 30,000-lb boat lift—creating a true luxury retreat for boating enthusiasts just minutes from the bay. A winding paver driveway introduces the private tropical setting, leading to a gracious residence by award-winning builder Lee Wetherington. Inside, high ceilings, substantial crown molding, elegant archways, tray ceilings, recessed lighting, and expansive windows create an airy sense of scale, while warm bamboo flooring brings natural sophistication throughout the primary living spaces. Designed for relaxed island living and entertaining, the open great room is anchored by a striking coral stone gas fireplace and framed by French doors connecting the interior to the expansive covered veranda. The updated kitchen features crisp white cabinetry, granite countertops, stainless steel appliances, breakfast-bar seating, generous storage, and an adjacent service bar, complemented by a separate dining area for effortless entertaining. The spacious primary suite overlooks the tropical grounds, pool, and waterway and features a tray ceiling, two walk-in closets, dual vanities, large shower, and jetted soaking tub. A desirable split-bedroom floor plan provides two additional bedroom suites, while a large private office offers flexibility for working from home, a media room, or additional lounge space. Outdoor living is a defining feature of this Siesta Key waterfront home. The wide covered veranda provides generous spaces for dining and lounging while overlooking the private swimming pool and lush tropical landscape. Beyond the pool, a pathway leads directly to the Grand Canal and an outstanding boating setup featuring approximately 93 feet of deep-water frontage, a large dock, and 30,000-lb boat lift. Cruise to Sarasota Bay, waterfront dining, or Gulf waters before returning home to enjoy sunset along the canal. Built with quality and longevity in mind, the residence was constructed above base flood elevation and includes hurricane shutters, UV window film, foil roof insulation, floored attic storage, central vacuum, and construction to Miami-Dade standards. An oversized three-car garage offers excellent space for vehicles, bikes, kayaks, paddleboards, fishing equipment, and additional storage. Despite its private, estate-like setting, the home is ideally positioned near Siesta Village, world-famous Siesta Key beaches, boating, dining, and island attractions, with downtown Sarasota approximately 15 minutes away by car. For the luxury buyer seeking a Siesta Key waterfront pool home with deep-water boating access, substantial boat lift, oversized private lot, and proximity to Sarasota Bay, 5178 Oakmont Place offers an extraordinary opportunity to embrace the coastal Florida lifestyle

5178 Oakmont Place, Sarasota

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