Location: Sarasota , 34242
Do Not Show Listings
8767 MIDNIGHT PASS RD #101F, SARASOTA, FL 34242
$535,00081 Days on yellowkey MLS ID: A4680015
0 Days Off yellowkey (back on 4/11/2026)
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1768 Built: 1979 Tax: $9,388 (2025)Community: Island Reef Ii Ph 1 2 & 3Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,388
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. $50,000 Price Improvement — Now One of the Best Values on Siesta Key. At $535,000, this 1,700+ sq ft Island Reef condo is priced in line with nearby 1,300 sq ft units—creating a rare opportunity to own significantly more space without paying a premium. Located on the quieter south end of Siesta Key, this ground-floor residence overlooks Little Sarasota Bay and offers the kind of easy, coastal living that’s increasingly hard to find. The split-bedroom layout features two en suite bedrooms positioned on opposite sides of the condo, plus a half bath and a flexible space ideal for a small home office. Inside, the scale of the home stands out immediately—a massive living area, separate dining room, and an enclosed Florida room that captures peaceful bay and Intracoastal views. Natural light fills the space from morning through mid-day, while ceramic tile flooring throughout keeps maintenance simple and practical. The kitchen is equipped with butcher block countertops, abundant cabinetry, and a full-size layout that supports everyday living or extended stays. A full laundry room with standard-size washer and dryer adds to the convenience. What truly sets this unit apart is its ground-floor accessibility, generous square footage, and a strong track record of staying dry during past storms—an increasingly important consideration for waterfront buyers. Island Reef is a well-maintained, financially sound Gulf-to-Bay community with no upcoming assessments and on-site management. Residents enjoy deeded beach access just a short walk away, along with bayfront boat docks (with lift options), two heated pools, tennis and pickleball courts, fitness center, clubhouse, and an active social calendar. The free Siesta Key trolley stops right in front of the community, providing easy access to Siesta Village, dining, shopping, Turtle Beach, and nearby marinas. Offered turnkey furnished, this is a compelling opportunity for full-time living or seasonal enjoyment—especially for buyers who recognize value when they see it. Schedule your private showing today.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Mike Payne, Pa (941-928-8145)
3942 HAMILTON CLUB CIR #13, SARASOTA, FL 34242
$1,390,000202 Days on yellowkey MLS ID: A4666766
REDUCED by $85,000 (5.8%) on 04/07/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2691 Built: 1997 Tax: $9,668 (2024)Community: Hamilton ClubSingle Family
Taxes:$9,668
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Enter a coastal residence where architectural vision, designer finishes and direct access to the water create an exceptional lifestyle on Siesta Key. In the gated waterfront community of Hamilton Club, this fully reimagined home includes a private deeded dock on deep water, offering instant access to the Intracoastal, Sarasota Bay and the Gulf. Inside, the renovation reflects thoughtful design and custom craftsmanship throughout. The great room makes a dramatic impression with 20-foot ceilings, a floor-to-ceiling quartz feature wall with fireplace, floating wet bar, and glass sliders opening to a screened balcony overlooking the pool and pond. The kitchen was completely redesigned with imported cabinetry, premium appliances by Miele, Bosch, GE and KitchenAid, granite counters, and lighting that elevates function and style. An oversized two-car garage with additional golf cart space and additional storage adds a level of convenience rarely found in a coastal property. The residence offers three en-suite bedrooms and a loft, including two separate primary suites. The main floor suite features its balcony and spa-style bath. Upstairs, the primary suite includes a custom fireplace accent wall, walk in closet, and a travertine wrapped bath with freestanding tub, glass enclosed shower and extensive cabinetry. A third guest suite and spacious loft with custom iron railing complete the upper level. On the ground floor, a large climate-controlled bonus room with a half-bath opens to the lanai and offers flexible space for recreation, hobbies or fitness. Impact-rated windows, custom railings, hardwood floors, Nest thermostats, and central vac contribute to a lock and leave lifestyle with comfort of a single-family home. Hamilton Club is a private enclave of just 18 residences with a heated pool and tennis court, minutes from Siesta Village, Shell Road beach access and sugar sand shoreline of Siesta Beach. This is a rare opportunity to enjoy boating, privacy and elegant coastal living in an intimate, gated setting.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Mike Warm, Llc (941-525-2740)
3954 HAMILTON CLUB CIR #14, SARASOTA, FL 34242
$1,200,000294 Days on yellowkey MLS ID: A4656944
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2798 Built: 1997 Tax: $12,009 (2025)Community: Hamilton ClubCondo
Taxes:$12,009
Remarks: A $100,000 price improvement! A unique opportunity to renovate and create your dream coastal retreat in one of Siesta Key’s sought-after gated enclaves, Hamilton Club, an exclusive boating community on North Siesta Key. Rarely available, this spacious, elevated townhome is one of only 18 residences in a private, pet-friendly, deep-water boating community offering a deeded dock with sailboat water access—no fixed bridges to Sarasota Bay and direct access to the Intracoastal Waterway and the Gulf. Bring your vision and design ideas—this property is ready for a full renovation and offers incredible potential. Generous square footage, soaring ceilings, and an open floor plan provide the canvas. The main level features a welcoming foyer, expansive living and dining areas, a large eat-in island kitchen, a spacious bedroom/den with a full bath, a laundry room, a pantry closet, and a powder room. Go out to the screened lanai overlooking lush, tropical landscaping, a tranquil lagoon and fountain, and the community pool, complete with spiral stair access to the lower level. Upstairs, a bonus room is flanked by two bedroom suites. The oversized primary suite offers a walk-in closet and a large bath with a soaking tub and a separate shower. A second en-suite guest bedroom and bath ensure comfort for family and guests. The elevator services all three levels, though it is not operational and not warranted. Downstairs, the ground floor offers flexible bonus space—ideal for an exercise room, game room, or hobby area—along with a screened lanai, two-car garage, and additional storage room. Residents enjoy maintenance-free living, a heated community pool, and access to tennis and pickleball courts. On the north end of Siesta Key, just minutes to the Shell Road Beach, quaint Siesta Village, and the powdery white sands and aqua waters of world-famous Siesta Beach. Only 10 minutes by car to downtown Sarasota's shopping, dining, vibrant nightlife, and cultural amenities. Rarely does a home in Hamilton Club become available—this is a must-see opportunity to create something special.
Listing Agent: Judie Berger (941-928-3424)
6287 MIDNIGHT PASS RD #103, SARASOTA, FL 34242
$685,00041 Days on yellowkey MLS ID: A4685468
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1550 Built: 1982 Tax: $7,057 (2025)Community: Excelsior Beach To Bay 6Condo
Taxes:$7,057
Remarks: 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 take 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.
Listing Agent: Peg Davant (941-356-4552)
6275 MIDNIGHT PASS RD #6275, SARASOTA, FL 34242
$1,195,00065 Days on yellowkey MLS ID: A4682650
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2200 Built: 1981 Tax: $6,153 (2025)Community: Excelsior Beach To Bay 3Spa: YesCondo
Taxes:$6,153
Remarks: New price - $100K less! Offered for the first time, this rare three-bedroom, three-bath waterfront villa at Excelsior’s coveted Beach-to-Bay community presents an exceptional opportunity to own one of only eight residences of its kind. Positioned on Sarasota Bay and the Intracoastal Waterway, the villa enjoys extraordinary privacy, peacefulness, and sweeping 180-degree water views from the expansive 36-foot lanai and most principal rooms. This light-filled corner residence lives beautifully like a single-family home, elevated above a private two-car garage and framed by windows on three sides. The open floor plan is spacious and airy, enhanced by vaulted ceilings in the living room, primary suite, and guest bedroom, hardwood flooring, and sliding glass doors that invite the waterfront setting indoors. A wood-burning fireplace adds warmth and character, while ceiling fans, custom window treatments, and 3M hurricane film on windows provide comfort and peace of mind. The updated kitchen opens seamlessly to the main living areas, creating an ideal space for entertaining or relaxed island living. The primary suite features a walk-in closet, a walk-in shower, and an updated bath. A new HVAC system, in-residence washer and dryer, and thoughtful upgrades throughout add to the villa’s move-in-ready appeal. Excelsior’s villas are uniquely situated directly on Sarasota Bay’s Intracoastal Waterway, with no other residences between you and the water. Only eight villas exist in total, four three-bedroom residences and four two-bedroom villas, making this a limited opportunity. Residents of Excelsior enjoy an unparalleled resort lifestyle with deeded beach access to Siesta Key’s world-renowned white sands, turquoise Gulf waters, and mango-colored sunsets. Amenities include two large, heated pools, two hot tubs, tennis and pickleball courts, shuffleboard, a fitness center, a library, a community room, and tranquil, tree-lined walkways with ponds and fountains. The fishing and lounging pier, grilling areas and picnic spaces are just moments away. The community is pet-friendly (small dogs), offers easy access to South Bridge and a short distance to Crescent Village, with free trolley service to Siesta Village. With a two-week minimum rental policy and on-site property management services available, the residence also offers attractive flexibility for seasonal or investment use. From morning experiences along the shoreline to breathtaking sunsets over the Gulf, every day on Siesta Key feels like a vacation. And when you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering world-class dining, arts and culture, including the Ringling Museum, Van Wezel Performing Arts Hall, and St. Armands Circle. Rarely available and exceptionally positioned, this waterfront villa captures the best of Siesta Key living, privacy, views, resort amenities and effortless access from beach to bay.
262 ISLAND CIR, SARASOTA, FL 34242
$3,995,000186 Days on yellowkey MLS ID: A4668568
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3455 Built: 2023 Tax: $24,321 (2024)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$24,321
Remarks: Waterfront Sanctuary on Siesta Key - Outdoor Living Enthusiasts This is the One! Your party is in the back with your own Very Private Backyard and Pool Area ready for family gatherings, sunset hot tubs, sunrise fishing, & poolside cocktails. Being sold furnished. Move right in! Newer construction meeting all hurricane standards and building codes. All living space is above base flood elevation. Welcome to an unparalleled blend of sophistication and coastal charm. Located on the exclusive Palm Island neighborhood of Siesta Key, this exquisite residence offers an extraordinary island lifestyle—perfectly positioned along the Grand Canal with close proximity to the pristine, sand Beach of Siesta Key and the vibrant energy of Siesta Village. Spanning close to 3,500 square feet of meticulously designed living space, this newly built, custom home provides the ultimate in luxury and island living. The home includes 4 bedrooms, 4 full bathrooms, plus 2 additional half baths. Enjoy an additional, comfortable family room on the second floor. Every detail has been carefully curated to create a seamless balance of form and function. From the moment you enter, you'll be captivated by the open-concept layout, soaring ceilings, and walls of glass that flood the home with natural light, offering breathtaking panoramic views of the Grand Canal, playful manatees, water birds, and lush tropical landscapes. The chef-inspired kitchen is a culinary dream, featuring top-of-the-line Thermador appliances, custom cabinetry, and an expansive, Quartzite island perfect for both cooking and entertaining. The spacious living and dining areas flow effortlessly into the outdoor oasis, where a resort-style pool, hot tub, gas fire pit and outdoor kitchen await. Whether you're hosting guests or simply enjoying a quiet evening, this home offers the ideal setting for any occasion. The first floor primary suite is a true retreat, with ship lap ceiling and accent wall and a spa-like bathroom that includes a walk-in shower and dual vanities. Each additional bedroom/en-suite has been designed with comfort and luxury in mind, providing private, serene spaces for family and/or guests. In addition to the gorgeous interior, the property offers 80 feet of water frontage and unrivaled outdoor amenities including a private dock with 10,000 lb. boat lift ideal for boating enthusiasts to access Sarasota Bay and beyond. Situated just moments from the world-famous Siesta Key Beach, Iconic Siesta Village, and the vibrant downtown Sarasota scene, 262 Island Circle is the epitome of coastal, waterfront living. This is more than a home—it's an island lifestyle. This magnificent residence offers the perfect fusion of luxury, tranquility, and location. Discover your own slice of paradise on Siesta Key today. Call for a private showing.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Joe Kesslak (941-321-8585)
5334 CALLE FLORIDA, SARASOTA, FL 34242
$1,870,000114 Days on yellowkey MLS ID: A4676260
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2838 Built: 1998 Tax: $5,619 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$5,619
Remarks: Fantastic opportunity to own a unique home on Palm Island, in this exceptional Siesta Key residence, ideally located at 5334 Calle Florida. Situated on a large lot and elevated approximately 10 feet above sea level, the main home has never flooded during any storms, offering peace of mind along with island luxury. This 4-bedroom, 3-bathroom home features 2,838 square feet of thoughtfully designed living space highlighted by a dramatic great room with soaring 20-foot ceilings, creating an open and airy coastal feel. The large primary suite has a custom built window seat, 2 walk in closets and an oversized primary bathroom. The entire home features built in speakers, including the back porch. Designed for comfort and efficiency, the home is equipped with a three-zone air conditioning system and hurricane-rated Kevlar screens, hurricane rated garage and front door for added protection. The spacious two-car garage provides ample storage, perfect for island living. The exterior is landscaped with outdoor lights and power in soffits for seasonal or all year round lighting. Outdoor living is elevated—literally—with an elevated, heated pool and hot tub, an outdoor shower, and plenty of space to relax or entertain in true Florida style. Located on Palm Island, just moments from the world-renowned Siesta Key Beach, this property offers the perfect blend of privacy, elevation, and coastal charm. Whether as a primary residence or luxury retreat, this home is a rare opportunity to own a high-and-dry island property in one of Sarasota’s most sought-after neighborhoods. Roof replaced 2021, Pool resurfaced 2024, Pool cage repainted and rescreened 2025, Water heater 2025. Unique Architectural Details *** Custom Built *** Oversized Primary Suite *** Soaring Ceilings *** Open Concept *** Elevated Key West Style *** Screened Lanai
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Niall Phelan (941-914-8589)
413 ISLAND CIR, SARASOTA, FL 34242
$3,299,00012 Days on yellowkey MLS ID: A4689084
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2994 Built: 2026Monthly Fee: $4 Tax: $10,496 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$10,496
Remarks: Experience the pinnacle of coastal luxury in this newly constructed masterpiece, ideally located just moments from the beach and a short walk to the vibrant shops, dining, and entertainment of Siesta Village. Situated on an oversized lot, this exceptional property offers added privacy, space, and presence rarely found in this sought-after location. Featuring 4 bedrooms, a private office, and 4.5 bathrooms, the home blends modern elegance with thoughtful design at every turn. A striking first impression begins at the grand entry, where sleek modern pivot doors set the tone for the refined finishes found throughout. Inside, soaring ceilings and expansive living spaces are filled with natural light, while oversized sliding glass doors create a seamless connection between indoor and outdoor living. The chef’s kitchen is a true centerpiece, showcasing custom flat-panel cabinetry, premium Thermador appliances, and a hidden entrance to a spacious walk-in pantry—offering both style and function. Every detail has been carefully curated, from custom built-ins in select bedrooms to the high-end finishes that create an atmosphere of refined comfort. The main living spaces open effortlessly to a private outdoor retreat featuring a resort-style pool and spa, sun shelf, and panoramic screened enclosure with elegant glass railings—perfect for entertaining or relaxing in complete privacy. Car enthusiasts and those in need of extra storage will appreciate the impressive three-car garage with 17-foot ceilings and a built-in car lift, allowing space for a fourth vehicle or additional elevated storage—an exceptional and rare amenity. Designed with both luxury and resilience in mind, this home offers peace of mind in any season. Built elevated and engineered for coastal living, it is equipped with a buried 500-gallon propane tank and a whole-house generator—providing reliable, uninterrupted power during outages. Combined with modern construction standards and durable materials, this residence delivers a level of security and preparedness rarely found in homes this close to the water. Complete with integrated smart home features including a whole-home speaker system and security cameras, this residence offers the very best of modern coastal living. More than just a home, this is a lifestyle opportunity in one of Siesta Key’s most sought-after locations—where luxury meets lasting peace of mind.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Daniel Dabrowski (847-274-2960)
339 TREASURE BOAT WAY, SARASOTA, FL 34242
$3,000,00020 Days on yellowkey MLS ID: A4685922
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2689 Built: 1957 Tax: $16,361 (2025)Community: Harmony SubSpa: YesSingle Family
Taxes:$16,361
Remarks: Elegant Siesta Key Waterfront Living. Don’t just move. Arrive! Enter into your residence, and the world falls away. Picture-perfect postcard views from nearly every room await to welcome you home. Nestled on an unrivaled point at the intersection of the Grand Canal’s most impressive waterways, this newly renovated, rare find offers you the complete package. Luxury finishes, high-tech resilience, and the quintessential Siesta Key lifestyle are prepared for you to move in ready. A brief stroll from the vibrant energy of Siesta Key Village and the quartz sands of Siesta Beach. With an astounding approximately 240 feet of private seawall and offering long-range canal views creating a lagoon-like setting, this opportunity simply cannot be replicated. While offering crisp, clean lines of modern contemporary style, the infrastructure is strictly 2026-ready. This unique residence provides both luxurious aesthetic appeals, featuring a fully updated chef’s kitchen and designer baths, and "invisible luxury". The peace of mind that comes from the resilience of a durable metal roof, new seawall, and all-new high-velocity hurricane windows and doors, new flooring, wood burning fireplace, and new electrical, plumbing, as well as new three-zone HVAC and mechanical systems, has been thoughtfully provided. And, for your peace of mind, professional night vision high-tech security cameras and systems were installed in 2026. The preferred split plan offers three additional bedrooms, including a private guest suite with its own separate entrance and ensuite bath. Life at 339 Treasure Boat Way centers around the water. Venture out onto the paved, open-air pool deck to find a 2026 freshly re-finished Aqualink-controlled, saltwater, heated pool and spa with LED lighting. Enjoy gentle, golden morning sun and cool, shaded afternoons—perfect for entertaining and alfresco dining. An oversized detached two-car air-conditioned garage, fenced yard for pets, and ample guest parking.
Listing is courtesy of: COLDWELL BANKER REALTY (941-739-6777)
Listing Agent: Tonna Gruber (941-232-8950)
4712 OCEAN BLVD #W10, SARASOTA, FL 34242
$2,700,00013 Days on yellowkey MLS ID: A4688159
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3903 Built: 1981 Tax: $20,311 (2025)Community: Windward PassageCondo
Taxes:$20,311
Remarks: A rare opportunity to reimagine a Gulf-front penthouse on Siesta Key. Set in a boutique condominium community near Siesta Village, this expansive four-bedroom, four-bath residence offers over 3,900 air-conditioned square feet, full Gulf views and the kind of scale, frontage and location that are seldom available. With nearly 80 feet of linear Gulf frontage, the penthouse captures sweeping vistas of the azure Gulf waters, Big Pass, Lido Key and downtown Sarasota from nearly every room. The floor plan is exceptionally spacious, with grand living areas, high ceilings, a fireplace, two balconies, an attached two-car garage and the rare flexibility that comes with a residence of this size and presence. The two-building, 22-unit complex features a pool overlooking the Gulf, offering a relaxed setting to enjoy the waterfront lifestyle. This residence presents a unique canvas for a complete custom renovation. A new owner can transform this property into a spectacular coastal showplace, tailored to today’s luxury lifestyle. The existing floor plan includes generous entertaining spaces, a large kitchen footprint, two primary-suite areas, one with a private sauna, all ready to be reinterpreted with a fresh vision and design. Just moments from Siesta Village, with its restaurants, boutiques, boating and waterfront activities, this residence also enjoys proximity to Siesta Key’s world-famous white quartz sand beach. It is an extraordinary chance to create a one-of-a-kind Gulf-front penthouse in one of the island’s desirable locations. Beyond the island, vibrant downtown Sarasota’s cultural, shopping, dining and entertainment areas are just minutes away.
9226 MIDNIGHT PASS RD #3B, SARASOTA, FL 34242
$725,00081 Days on yellowkey MLS ID: A4679789
REDUCED by $25,000 (3.3%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1223 Built: 1982Monthly Fee: $500 Tax: $4,453 (2025)Community: Castaway CoveSpa: NoCondo
Taxes:$4,453
Remarks: PRICE IMPROVEMENT!! It’s time to SIMPLIFY! Sun. Sand. Surf. 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 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. Furnishings may be available for a truly turnkey opportunity.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Dawn Bear (941-468-7224)
915 BEACH RD #216, SARASOTA, FL 34242
$575,00088 Days on yellowkey MLS ID: A4677981
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1972 Tax: $3,708 (2025)Community: La SiestaCondo
Taxes:$3,708
Remarks: An exceptional investment opportunity on Siesta Key, located directly across the street from the highly rated Siesta Key Beach. This updated second-floor condominium features two bedrooms and one bathroom, offering a highly desirable layout for both personal use and income production in one of Florida’s most sought-after vacation destinations. The residence includes a private balcony overlooking the pool, providing a relaxing, resort-style experience for owners and guests alike. The second-floor location offers added privacy, while elevators servicing each floor ensure easy access and convenience. Designed with investors in mind, the community offers a dedicated on-site management office, creating a truly turnkey rental opportunity with seamless guest coordination and peace of mind. Community laundry facilities are conveniently located on each floor, adding to the ease and appeal for short- and long-term stays. Just steps from world-famous sugar-sand beaches and minutes from Siesta Village dining, shopping, and entertainment, this condo presents a rare opportunity to own a low-maintenance, income-producing property that combines strong rental potential with the ultimate island lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Sheryl Vanduren (720-384-4884)
6500 MIDNIGHT PASS RD #208, SARASOTA, FL 34242
$835,000123 Days on yellowkey MLS ID: A4675137
1 Days Off yellowkey (back on 4/8/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1086 Built: 1974 Tax: $7,216 (2024)Community: SeashellSpa: NoCondo
Taxes:$7,216
Remarks: Welcome to your slice of effortless Siesta Key living at the desirable Seashell Condominiums. This inviting second-floor residence, Unit 208, offers two bedrooms and two baths wrapped in a light, coastal aesthetic that immediately sets the tone for island life. Thoughtfully laid out and easy to maintain, the space feels comfortable and welcoming, while new impact windows and sliders offer peace of mind. Seashell is a boutique community of just 48 residences, creating a relaxed, neighborly atmosphere without sacrificing amenities. Residents enjoy private beach access, a heated pool, outdoor grilling areas, and a tiki hut perfect for hosting casual gatherings or enjoying lunch in the shade. The gated property also features under-building parking and onsite rental management, making ownership simple and flexible—ideal for personal use, rental income, or both. Location is key, and Seashell delivers. Situated near Captain Curt’s Plaza—often referred to as Siesta Key’s South Village—you’re moments from popular restaurants, live music, and everyday island conveniences. With the Stickney Point Bridge directly across the street, on-and-off island access is refreshingly easy. Laid-back, well-located, and designed for easy coastal living, this is Siesta Key ownership made simple.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
6204 MIDNIGHT PASS RD #201, SARASOTA, FL 34242
$790,000346 Days on yellowkey MLS ID: A4652172
0 Days Off yellowkey (back on 3/31/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1173 Built: 1979 Tax: $7,204 (2024)Community: Siesta Dunes BeachCondo
Taxes:$7,204
Remarks: Under contract-accepting backup offers. Virtually staged to showcase the full potential of this beautiful Siesta Key condo! Just steps from the powdery sands of Siesta Key Beach, this turnkey 2-bedroom, 2-bath unit offers the perfect blend of comfort, style, and value. The unit features vaulted ceilings that create a spacious feel, along with a covered parking space and private storage area. New hurricane-impact windows and doors have already been purchased and are scheduled for installation, providing added peace of mind for future owners. A new roof is also coming soon. This unit has no history of flood damage during current ownership and delivered strong rental income in 2023, generating $62,000 net in just 9 months as the owners reserved 3 months for personal use. Residents and guests enjoy access to resort-style amenities including a clubhouse, sparkling pool, tennis courts, and 24-hour security. Owners also benefit from maximum rental flexibility with the option of short-term rentals through Airbnb, VRBO, or the on-site rental office. Plus, you are just moments from Siesta Key’s top restaurants, bars, and boutique shops. Whether you are seeking a stress-free getaway or a high-performing property, this condo checks every box: location, lifestyle, and long-term value.
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Nili Blaha (941-224-8363)
539 AVENIDA DEL NORTE, SARASOTA, FL 34242
$5,499,00090 Days on yellowkey MLS ID: A4679096
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4195 Built: 2026 Tax: $7,935 (2025)Community: Archibald ResubSpa: YesSingle Family
Taxes:$7,935
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. EXQUISITE NEW CONSTRUCTION ON SIESTA KEY: ISLAND LUXURY REDEFINED | Estimated to be substantially completed by 4/30/2026 | A rare opportunity to own a meticulously designed custom residence on a prime corner parcel of approximately one-quarter acre, just blocks from world-renowned Siesta Key Beach. Easily accessible from both the north and south bridges, this exceptional new build delivers the ultimate coastal lifestyle where refined interiors meet effortless outdoor living. | SIESTA Key Beach is frequently recognized as one of the best beaches in the U.S. and worldwide, celebrated for its powder quartz sand and crystal-clear waters. Its global reputation has been affirmed by TripAdvisor’s Travelers’ Choice Best of the Best Beaches and Dr. Beach’s annual rankings, making this location as iconic as it is desirable. | MOMENTS from Siesta Key Village, enjoy efficient access to boutique shopping, coffee shops, and acclaimed dining while still benefiting from an extraordinary amenity, your own private boat dock access on the canal just across the street. Spend the day boating and return home with ease, parking your vessel at your own dock, a true island luxury. | THIS thoughtfully curated residence reflects the vision of a hands-on developer deeply involved in every aspect of design, from interior finish selections to landscaping and amenities. Created for buyers who appreciate craftsmanship and fine detail, the home offers 4,195 sq ft of interior living space and an additional 3,756 sq ft of outdoor living, seamlessly blending indoor and outdoor environments. | THE chef’s kitchen is designed for both entertaining and everyday ease, complete with a “dirty kitchen” for behind-the-scenes preparation. The light-filled great room opens to a nearly 50-foot wraparound terrace, creating a spectacular setting for hosting family and friends. | TWO bedrooms are located on the main living level, ideal for guest suites or a secondary primary. Take the stairs or elevator one level up to access the private primary suite featuring a truly custom bath with bespoke tile, finishes, soaking tub and spacious shower that creates a spa-like retreat. Two additional bedrooms with a shared bath complete the upper-level.| FLEXIBLE, elegant, and intelligently executed, the suite of spaces within this home allows effortless tailoring to any family’s lifestyle from multi-generational living to a dynamic entertainer’s paradise. | IMAGINE a home where the luxuries of island beach life blend with a private, resort-style retreat: *Inground pool & spa for cooling off or casual lounging*Rooftop deck for sunset cocktails and starlit conversation*Private boating access just steps from your front door. | AND, when you’re ready for a taste of city life, Downtown Sarasota’s rich cultural tapestry with its farmers markets, arts, galleries, festivals, waterfront parks, and world-class dining is only a short drive away. |THIS is more than a home, it’s an invitation to own your piece of the new Siesta Key lifestyle: elevated, effortless, and extraordinary.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Lisa Otte (941-281-5472)
8555 HERON LAGOON CIR, SARASOTA, FL 34242
$2,725,000385 Days on yellowkey MLS ID: A4646820
INCREASED by $1,350,000 (98.2%) on 04/06/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2568 Built: 1951Monthly Fee: $75 Tax: $12,703 (2024)Community: Heron Lagoon LodgesSingle Family
Taxes:$12,703
Remarks: Pre-Construction. To be built. Rare Opportunity on Siesta Key – Expansive Corner Lot with Private Beach Access + Custom Coastal Estate by SeaSafe Homes. A truly rare opportunity to build your dream home on one of the largest privately owned parcels on Siesta Key. Situated on an expansive over ¾-acre corner lot with nearly 37,000 square feet, this exceptional homesite offers private beach access via an exclusive pedestrian bridge leading directly to your own slice of Siesta Key’s sugar-sand shoreline. Located within an intimate enclave of only 13 homes along Heron Lagoon, this hidden gem offers unmatched privacy, serenity, and exclusivity on the south end of the island, while remaining just minutes from Siesta Key Village Featured here is the Wave Crest Model by SeaSafe Homes, thoughtfully designed for elevated coastal living. Built for luxury and resilience, this home features a superior 2x12 floor system and 2x6 wall construction, engineered to withstand winds up to 180 MPH, exceeding typical coastal building standards and providing peace of mind. With advanced off-site construction methods, build time can be reduced by up to 75%, minimizing weather-related construction delays and allowing you to enjoy your new home sooner. The thoughtfully designed floor plan offers 4 bedrooms, 3.5 bathrooms, and an open-concept layout ideal for full-time living, seasonal enjoyment, or luxury rental potential. The spacious kitchen flows seamlessly into the living and dining areas and includes a large walk-in pantry and extended island, perfect for entertaining. The primary suite features direct porch access, a spa-inspired bath and walk-in closet. A secondary en-suite bedroom with optional private exterior entrance offers ideal flexibility for guests or lockout rental use. Every SeaSafe home also includes energy-efficient sealed systems and upgraded insulation as standard, combining strength, efficiency, and thoughtful design. Whether you envision a legacy family estate, luxury island getaway, or investment opportunity, this extraordinary homesite paired with a premier coastal build offers a once-in-a-lifetime chance to own something truly special on Siesta Key. Private tours, lot walks, and builder consultations available upon request.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Conner Ashley (941-374-1024)
925 BEACH RD #310, SARASOTA, FL 34242
$599,000231 Days on yellowkey MLS ID: TB8422646
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1972Monthly Fee: $758 Tax: $5,378 (2024)Community: La SiestaCondo
Taxes:$5,378
Remarks: Siesta Key 2BR/1BA condo updated in 2021 with sweeping Gulf views from a private balcony. Bright, open living area flows to the outdoors. Prime island location close to dining and shops. A standout coastal retreat or investment. Come enjoy the Siesta Key lifestyle!
Listing is courtesy of: BRICK STREET REALTY (727-512-6615)
Listing Agent: Colin Mooney (727-512-6615)
704 TROPICAL CIR, SARASOTA, FL 34242
$1,375,00021 Days on yellowkey MLS ID: A4687678
2 Days Off yellowkey (back on 4/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2073 Built: 1976Monthly Fee: $54 Tax: $12,410 (2025)Community: Siesta BeachSpa: NoSingle Family
Taxes:$12,410
Middle School: Sarasota Middle
Remarks: Nestled in one of Siesta Key’s most sought-after neighborhoods, this beautifully updated tropical retreat offers the perfect blend of coastal charm, modern comfort, and an active waterfront lifestyle. Whether you’re searching for a full-time residence or a private vacation escape, this home delivers an exceptional opportunity in an unbeatable location—just under a mile from the world-renowned white quartz sands of Siesta Key Beach. Set on a tropically landscaped low maintenance lot, the home has been thoughtfully updated to create a light, inviting interior centered around a modernized kitchen. A generously sized island anchors the space, serving as the heart of the home, ideal for entertaining family and friends. The open dining area overlooks the newer heated saltwater pool and screened enclosure, creating a seamless indoor-outdoor flow for relaxed coastal living. Evenings here are unforgettable, whether enjoying dinner al fresco or taking a moonlit swim beneath the warm tropical sky. The residence offers three spacious bedrooms, including a flexible guest room with a Murphy bed, allowing for both everyday comfort and effortless hosting. An additional office space off the pool area also features a Murphy bed, providing even more versatility for guests or extended stays.What truly sets this property apart is its connection to nature and the water. A charming boardwalk travels through lush mangroves, leading to your private dock perfect for launching kayaks and exploring the serene waters of the Bayside Club estuary. From here, you’ll enjoy quick access to the Intracoastal Waterway and beyond, opening the door to endless days of coastal adventure. All of this natural beauty comes with the assurance that this home had no damage nor flooding from previous storms. Offered with timely occupancy, this is a rare opportunity to secure your place in one of Siesta Key’s most desirable enclaves and begin enjoying the best of island living without delay for this summer.
Listing Agent: Jeff Hinrichs (941-456-1251)
5780 MIDNIGHT PASS RD #110, SARASOTA, FL 34242
$1,349,00054 Days on yellowkey MLS ID: A4683108
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $10,806 (2025)Community: Gulf & Bay ClubCondo
Taxes:$10,806
Remarks: Welcome to the effortless rhythm of island living at Gulf & Bay Club, one of Siesta Key’s most prestigious beachfront communities. Behind the 24-hour guard-gated entrance, this beautifully remodeled, rarely available, three-bedroom residence offers the perfect blend of comfort, privacy, and resort-style living in a setting that feels worlds away from the everyday. Positioned on the first floor as a bright end unit, the home is surrounded by windows on three sides, filling the interior with natural light and creating a relaxed coastal atmosphere throughout. The thoughtfully redesigned floor plan opens beautifully for entertaining, with elegant finishes and carefully curated upgrades that make the residence feel both sophisticated and welcoming. The kitchen was designed with gathering in mind, featuring custom cabinetry, quartz countertops, marble backsplash, and premium Bosch appliances including induction cooktop and stainless vent hood. An additional built-in entertaining area with beverage refrigeration and extra storage makes hosting friends and family effortless. Living and dining areas flow naturally to the private lanai overlooking tropical landscaping and a tranquil lagoon, just steps to one of the community’s three pools, where evenings are often spent enjoying the peaceful surroundings and the soft glow of Siesta Key sunsets. The three-bedroom layout provides exceptional flexibility, whether for hosting guests, accommodating family, or creating a quiet home office. The primary suite offers a peaceful retreat with a walk-in closet and a beautifully updated bath featuring custom cabinetry, quartz countertops, and an expanded designer-tiled shower. Extensive renovations throughout the home include raised ceilings, smooth-finish walls, luxury flooring, updated lighting and electrical systems, new ductwork, upgraded panel box, air handler, and quick-recovery water heater. Importantly, the residence did not experience water intrusion during the recent hurricanes, offering additional peace of mind. Life at Gulf & Bay Club is defined by its resort-style amenities across 32 gated beachfront acres and 800 feet of Siesta Key’s famous quartz sand beach. Residents enjoy three heated pools including a lap pool, tennis and pickleball courts, racquetball, a large fitness center, beautifully landscaped walking paths surrounding the freshwater lagoon, clubhouses for gatherings, electric vehicle charging stations, and professional on-site management — all within a secure 24-hour guard-gated community. Just beyond the gates, the vibrant charm of Siesta Key Village awaits with its locally loved restaurants, boutiques, and island nightlife, while downtown Sarasota’s renowned arts and cultural scene is only a short drive away. This is more than a residence — it is an opportunity to experience the best of beachfront living on Siesta Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Natalie Gutwein (941-993-2660)
6536 PEACOCK RD, SARASOTA, FL 34242
$5,650,00013 Days on yellowkey MLS ID: A4688703
Bed: 7 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 4697 Built: 2024 Tax: $46,507 (2025)Community: Stickney Point SubSingle Family
Taxes:$46,507
Remarks: There is only one — Siesta Sun Sets. Set against the quiet backdrop of Sabal Lake, with glimpses of the Gulf beyond, this residence unfolds with a sense of irresistible intention. Influenced by West Indies architecture, the design blends expansive indoor-outdoor living with natural textures, layered spaces, and a palette that mirrors its surroundings — soothing, sun-washed, and enduring. Across more than 4,000 square feet, the home offers seven incredible en-suite bedrooms and multiple living areas designed for both gathering and restful retreat. The great room anchors the experience, where kitchen, dining, and living spaces open outward to twin balconies — one overlooking the extensive grounds, the other framed by mature oaks, offering a quiet contrast of shade and light. Above, a private club level introduces a more intimate setting — a theater-style lounge, additional suites, and access to the rooftop deck. It is here, at the highest point of the home, that the name reveals itself. As day transitions to evening and the Gulf reflects gold, the softening sky reveals stunning sunsets, becoming the backdrop against which you count your blessings. Below, the grounds are equally considered. A multi-sport court — rare in both scale and versatility — sits alongside a resort-style pool and 360-degree spillover spa, creating a setting as seductive as it is serene. Covered outdoor living spaces extend the home’s presence, offering multiple areas for dining, gathering, and quiet retreat, all within a private, fully enclosed landscape. Siesta Sun Sets is not defined by any one feature, but by the way it brings them together — water, light, elevation, and space — into a residence that feels both grounded and removed, exclusive and secluded. A masterwork of resilient engineering and high-end coastal construction, this estate is architecturally primed to withstand coastal elements while serving as a premier venue for grand-scale entertaining and lucrative seasonal retreats. More than a home, Siesta Sun Sets is part of an exclusive Vunique collection with a proven history of strong rental performance — each residence one-of-one, purpose-built to balance bold design and bespoke experience. Here, ownership transcends address; it becomes a mark of belonging to something beautifully uncommon.
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