Location: Sarasota , 34242
Do Not Show Listings
1249 S BASIN LN, SARASOTA, FL 34242
$8,950,00053 Days on yellowkey MLS ID: A4690355
Bed: 6 Bath: 7.0 Gar: 8 Liv Area Sq Ft: 10642 Built: 1951Monthly Fee: $933 Tax: $40,641 (2025)Community: Siesta Properties IncSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$40,641
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Rarely does a property of this caliber become available on Siesta Key. Spanning approximately 1.6 acres, this exceptional waterfront estate is framed by majestic oak trees and lush, mature landscaping, creating a private, quiet, and timeless retreat. This legacy property showcases expansive bayfront views that wrap gracefully around to a protected canal, offering both breathtaking vistas and sheltered water access. At its heart stands a classic and formal Southern-style residence, remodeled in 2008, rich in character and designed for an elegant lifestyle. Grand, beautifully proportioned rooms are designed for effortless entertainment, highlighted by a stately formal dining room worthy of the most important occasions. The expansive country kitchen is both functional and refined, featuring a professional-grade Wolf range with custom copper hood, an oversized Sub-Zero refrigerator, vintage tile flooring, and a striking chandelier that brings a touch of timeless elegance to space. A classic wood-burning fireplace adds warmth and character to the cozy wood paneled den with charming French doors opening to bayfront views. With six spacious bedrooms, six full bathrooms, and two additional half baths, this home offers exceptional comfort and ample space to accommodate family and guests with ease. Car enthusiasts will appreciate the 8 garages. Boaters will appreciate the ample opportunities to enhance this property with custom docks or lifts. For those envisioning a custom estate, the property also offers a rare opportunity to build your dream home while comfortably residing on-site in the charming guest cottage, complete with bedroom suite and kitchen—allowing you to plan, design, and construct at your own pace without ever leaving this exceptional setting. Additionally, the property can be split into 3 separate waterfront parcels with the smallest water frontage being 99 ft. This is a true legacy offering, where expansive space and stunning waterfront beauty come together seamlessly, enhanced by breathtaking views that elevate every moment in this extraordinary setting. The Sanderling Club, the only guard-gated, single-family neighborhood on Siesta Key, offering residents tennis and pickleball courts, playground, and deeded access to a pristine stretch of Siesta Beach. Located minutes from Siesta Village, this property provides the perfect balance of serene seclusion and proximity to Sarasota’s vibrant cultural and culinary attractions.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
3441 GULFMEAD DR, SARASOTA, FL 34242
$10,500,00019 Days on yellowkey MLS ID: A4693315
Bed: 6 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 4769 Built: 2026 Tax: $16,553 (2025)Community: Gulfmead EstatesSingle Family
Taxes:$16,553
Remarks: Pre-Construction. To be built. This luxurious grand canal-front estate offers direct deep-water boating to the Gulf, out of one of the most exclusive neighborhoods on north Siesta Key. This in progress New Construction property by Pham Development is on an expansive 17,842 SF and 0.41 acre lot, with a 4,769 SF traditional-style home to be built. Enjoy two separate guests suites on top of the two 2-car garages, for a total of 4 garage spaces, both with elevator access to the above suites. The master bedroom will have water views, and the grand entry home hosts a total of 6 bedrooms, 6 baths, and 1 powder bath. This property's deep-water grand canal with no bridges is ideal for yachts and boats, with up to a 13-foot draft. A new dock and boat lift is set to be installed. Inside, expansive living spaces boast high-end finishes and top-of-the-line appliances, blending timeless elegance with modern comfort. Enjoy the water, and a large backyard perfect for entertaining, a private pool, and new lush landscaping—making this the ultimate waterfront estate for family.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
5019 COMMONWEALTH DR, SARASOTA, FL 34242
$600,000567 Days on yellowkey MLS ID: A4630299
2 Days Off yellowkey (back on 5/31/2026)
REDUCED by $35,000 (5.5%) on 05/22/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1373 Built: 1955 Tax: $6,363 (2025)Community: Siesta BeachSingle Family
Taxes:$6,363
Remarks: Under contract-accepting backup offers. PRICED to Sell! A Rare Build Opportunity on Siesta Key! Located on one of Siesta Key’s most beloved streets, this .26-acre lot on Commonwealth Drive presents a unique opportunity to build new in an established, multi-million-dollar neighborhood. Surrounded by lush, mature landscaping and a peaceful, community-focused setting, the lot offers the ideal backdrop for your vision whether you’re seeking a full-time residence, vacation retreat, or long-term investment. The existing cottage, which holds no contributory value due to hurricane flooding, creates a true blank slate for new construction. As an added benefit, this property is being offered with the option to build a thoughtfully designed custom home by Yoder Construction. The proposed plan, The Oceana, is part of an exclusive ISLAND SERIES, developed with sustainability and the unique coastal conditions of Siesta Key in mind. Buyers may choose to build this elevated 2,735-square-foot home, or collaborate with the builder on a personalized design through the available design center. Commonwealth Drive is ideally located just minutes from the powdery sands of Siesta Key Beach and the vibrant charm of Siesta Village, with its shops, restaurants, and island lifestyle. Opportunities to build new in this highly sought-after location are increasingly rare. To explore this offering further, request details on the optional build package, and schedule a walk of the lot.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Dawn Bear (941-468-7224)
1020 SUN AND SEA DR #102, SARASOTA, FL 34242
$575,000242 Days on yellowkey MLS ID: A4667291
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 524 Built: 2009Monthly Fee: $822 Tax: $3,572 (2023)Community: Beach Club At Siesta KeyCondo
Taxes:$3,572
Elementary School: None
High School: None
Tax Year: 2023
Middle School: None
Remarks: Welcome to Beach Club at Siesta Key, where an unbeatable investment opportunity awaits just steps from the world-renowned Siesta Key Beach. This charming 1-bedroom, 1-bathroom first-floor condo is the ideal blend of personal escape and income-generating property, boasting a successful history in short-term rentals. As you step inside this fully furnished, turnkey unit, you’re greeted by an open living area is perfect for relaxation, featuring a TV for entertainment, while the kitchen comes equipped with stainless steel appliances. An in-unit washer and dryer add to the convenience, making longer stays comfortable and stress-free. The on-site professional management team handles all the details, from bookings to maintenance, giving owners peace of mind and ensuring that guests have a seamless experience. The property offers desirable amenities, including a heated pool, a soothing hot tub, complimentary Wi-Fi, and beach chairs and umbrellas for enjoying sun-soaked days by the ocean. Positioned mid-island and close to the Stickney Point Bridge, this condo provides easy access to all that Siesta Key has to offer. The Beach Club at Siesta Key is a hidden gem that is perfectly located within walking distance of South Siesta Village, Crescent Market, and local favorites for ice cream, coffee, dining, and more.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Cole Collins (941-350-8360)
5780 MIDNIGHT PASS RD #110, SARASOTA, FL 34242
$1,299,000109 Days on yellowkey MLS ID: A4683108
REDUCED by $50,000 (3.7%) on 05/29/2026
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 Agent: Natalie Gutwein (941-993-2660)
225 HOURGLASS WAY #103, SARASOTA, FL 34242
$500,000270 Days on yellowkey MLS ID: A4664460
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969 Tax: $3,529 (2024)Community: Whispering SandsCondo
Taxes:$3,529
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. GREAT PRICE IMPROVEMENT! Welcome to this RARE, 2 bed/2 bath, double lanai corner residence with peaceful lagoon views in the premiere Gulf front property of Whispering Sands! Nestled in the desirable Sunset House building, this freshly painted, updated unit offers a quiet, private setting, with serene views of lush landscaping and the shimmering lagoon with its abundant fish, turtles, and aquatic life. A wonderful entry hall leads into a spacious OPEN CONCEPT floor plan, where the kitchen, living and dining areas flow together to create a wonderful, flexible gathering space. The living space has been extended into what was originally an enclosed 24' x 7' lanai, resulting in the creation of additional valuable interior living space under air, flanked on all sides with floor to ceiling sliders. Sliders open into a private, sunny brick paver patio, perfect for grilling, gardening, or simply relaxing in the surrounding natural beauty. You'll enjoy hosting friends and family in your NEW 2025 kitchen featuring granite countertops, LG stainless appliances, soft-close cabinetry, tile backsplash, breakfast bar, & tray ceiling. The primary and guest bedrooms each include a set of charming French doors that open into the tiled, screened and glassed lanai with direct views into the lagoon. Updated in 2024, both bathrooms include new granite countertops, soft close vanities & fixtures, and recessed lighting. All of the sliders in this unit are Miami Dade hurricane impact rated. 2024 HVAC system. 2025 water heater. Whispering Sands is a 55+ Gulf front community ideally situated just steps to the colorful shops & restaurants of Siesta Key Village offering two heated pools, clubhouse with catering kitchen and fitness rooms currently undergoing complete remodeling, canoe/kayak storage, beachside Tiki Hut & grills, and 800’ of its own beach access on the Gulf! Thoughtfully updated, inviting, and perfectly private, this peaceful corner retreat offers the perfect blend of indoor/outdoor living on beautiful Siesta Key.
Listing Agent: Harriet Stopher (404-316-8944)
6287 MIDNIGHT PASS RD #103, SARASOTA, FL 34242
$685,00096 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 is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Peg Davant (941-356-4552)
1166 W PEPPERTREE DR #112D, SARASOTA, FL 34242
$725,000150 Days on yellowkey MLS ID: A4678257
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1974 Tax: $5,936 (2025)Community: Peppertree Bay IiiCondo
Taxes:$5,936
Remarks: Located on Siesta Key, this updated first-floor 2-bedroom, 2-bath condo at 1166 W Peppertree Drive offers an excellent combination of coastal living and rental potential. This home is offered TURN KEY! Just steps from the world-famous Siesta Key Beach, residents enjoy easy access to the island’s renowned white-sand shoreline, along with nearby shopping, dining, and local restaurants. The well-maintained open floor plan features an updated kitchen with granite countertops, custom cabinetry, and stainless-steel appliances. An enclosed lanai provides additional living space with a built-in quartz workspace and owner storage. Both bathrooms offer granite countertops and walk-in showers. Additional features include wood plank tile flooring throughout, updated windows, in-unit washer and dryer, and a remodeled kitchen. Peppertree is a Beach-to-Bay community with resort-style amenities, on-site management, optional rental program, and security, making this property ideal as a primary residence, seasonal retreat, or investment opportunity. Conveniently located near marinas, golf, Siesta village, and downtown Sarasota.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Mike Aveni (941-961-8730)
1345 MOONMIST DR #T6, SARASOTA, FL 34242
$620,000262 Days on yellowkey MLS ID: A4654050
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1575 Built: 1968 Tax: $3,545 (2024)Community: Polynesian GardensVilla
Taxes:$3,545
High School: Riverview High
Remarks: Welcome to your dream villa! This spacious coastal villa retreat on Siesta Key boasts 2-bedrooms and 2-bathrooms and offers 1,575 square feet of comfortable, open-concept living space, perfect for both relaxing and entertaining. Step inside to a freshly painted interior featuring a modern, neutral palette that complements any décor. This wonderful detached-villa is in a serene location just across the street from million-dollar residences on the Bay and offers low-maintenance living with a luxurious feel. It is high and dry and has never flooded. This villa has an impressive list of updates including a new Barrel Tile Roof and complete Air Conditioning System. The large open dinning/living room area has bamboo flooring and sliding glass doors leading to your retractable awning-covered paved patio. A separate office area with built in desk and shelving and the potential for adding a sleeper sofa. A spacious primary bedroom with en-suite bathroom has a walk in closet and separate storage area. The second bedroom is roomy, light and pleasant ideal for either family or guests. The kitchen was completely remolded in 2016 and has a built in pantry, shaker cabinets with pullout shelving and a breakfast nook. Don’t miss this move-in ready gem with big-ticket upgrades already done! Polynesian Gardens is ideally located and provides a tranquil and unique Siesta Key escape for owners and guests alike. Relax and enjoy the tropical palms, large heated pool and peaceful intracoastal pier that provide a relaxing Siesta Key experience. Either take a short walk or take the free trolley which stops directly in the front of the community to world famous Siesta Key Beach, local restaurants, shopping, boat and fishing charters and rentals for all outdoor and water activities. Additional Features: •New Barrel Tile Roof. •This home features a spacious carport, offering sheltered parking and added storage potential. •Laundry room with full-size washer & dryer. •Quiet, well-maintained community. •Community amenities included; landscaping, exterior maintenance, cable tv, water, intracoastal pier and large heated pool. *The Polynesian Gardens Home Owners Association has plans in effect to paint the exterior of this Villa at no cost to the owner. Potentially the new owner will have their choice of colors. The unit is VACANT!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Dean Hall (941-726-7197)
156 SIESTA DR, SARASOTA, FL 34242
$1,649,000305 Days on yellowkey MLS ID: A4661717
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2901 Built: 1977 Tax: $19,016 (2024)Community: Siesta Rev ResubSingle Family
Taxes:$19,016
Remarks: Situated in the sought-after Bay Isle community on Siesta Key, this exceptional three-level pool home combines the best of upscale coastal living with impressive rental performance. Designed to host gatherings of all sizes, it is perfectly suited as a primary residence, vacation escape, or income-producing property. In 2024, it brought in $132,419 in gross rental income, with 2025 projections at $120,681, showcasing its strong investment appeal. Just a short stroll to Shell Beach and minutes from Siesta Key Village and the world-renowned Siesta Key Beach, the home offers unmatched access to award-winning white sand, vibrant dining, and boutique shopping. A complete renovation in 2019 transformed the property with a new metal roof, hurricane-impact windows, patio and garage doors, upgraded AC systems, and an oversized resurfaced lap pool with all-new equipment, including a heat pump. Over 50 Areca palms frame the lush tropical landscaping, providing beauty and privacy while remaining easy to maintain. The outdoor living space rivals a private resort, featuring a sparkling pool, spacious patio, and tranquil surroundings ideal for lounging or entertaining. Inside, natural light fills the open floor plan, creating seamless flow to the outdoor areas and making it a true entertainer’s haven. Impeccably maintained and move-in ready, this Bay Isle residence offers a rare opportunity to enjoy the island lifestyle while benefiting from consistent rental income.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
548A BEACH RD, SARASOTA, FL 34242
$1,725,00044 Days on yellowkey MLS ID: A4691951
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2080 Built: 1981Monthly Fee: $1,500 Tax: $16,762 (2025)Community: Tiffany SandsTownhouse
Taxes:$16,762
Remarks: This beautifully renovated Tiffany Sands townhome on Siesta Key offers the perfect blend of space, style, and an unbeatable location with serene beach views. Featuring 3 bedrooms and 3.5 baths, the open and inviting floor plan is designed for both comfort and effortless coastal living, with each spacious bedroom offering its own walk-in closet. A versatile first-floor bonus room, complete with a full bath and private entrance, provides the ideal space for guests, a home office, or additional living flexibility. The home also includes a one-car garage with extra storage, multiple expansive decks, and a private patio—perfect for enjoying Gulf breezes and taking in the stunning turquoise waters that define Siesta Key. Just a short stroll away, deeded beach access leads to the island’s world-renowned powdery white quartz sand. Ideally located near Siesta Key Village, you’ll enjoy effortless access to boutique shopping, dining, vibrant nightlife, and everyday conveniences. This is a wonderful opportunity to own a move-in-ready coastal retreat in one of Siesta Key’s most sought-after locations.
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
4708 OCEAN BLVD #E4, SARASOTA, FL 34242
$2,199,00062 Days on yellowkey MLS ID: A4689440
REDUCED by $91,000 (4.0%) on 05/21/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2277 Built: 1981 Tax: $16,662 (2025)Community: Windward PassageCondo
Taxes:$16,662
Remarks: 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.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
5569 SHADOW LAWN DR, SARASOTA, FL 34242
$1,250,00049 Days on yellowkey MLS ID: A4691399
0 Days Off yellowkey (back on 5/31/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2074 Built: 1966Monthly Fee: $17 Tax: $7,312 (2025)Community: Siesta IslesSingle Family
Taxes:$7,312
Remarks: Under contract-accepting backup offers. NEW SOD AND LANDSCAPING JUST INSTALLED, and a brand-new irrigation system was installed as well to keep everything to paradise standards! Welcome to the heart of world-renowned Siesta Key, where coastal living meets modern luxury. This fully renovated, solidly constructed home offers exceptional quality and thoughtful upgrades throughout, including PGT hurricane-impact windows, multiple triple-panel sliding impact glass doors, and a 2019 tile roof. Step inside through beautifully etched, Florida-themed French doors into an open-concept floor plan filled with natural light streaming from the screened lanai. The spacious living and dining areas seamlessly connect to a chef-inspired kitchen, complete with an induction range, griddle, and premium finishes—perfect for entertaining. The home features wood-grain luxury vinyl flooring throughout and tastefully updated bathrooms. The private primary suite is situated on one side of the home and includes an attached office, offering a quiet retreat. Just beyond, you’ll find a generously sized laundry room with a brand-new stackable washer and dryer. The opposite side of the home hosts additional bedrooms and a guest bathroom, providing comfort and privacy for family or visitors. Outdoors, enjoy your own private oasis with a saltwater pool and a brand-new, state-of-the-art pump system. Located in the highly desirable Siesta Isles community, this property is ideally positioned for strong rental potential, offering opportunities for annual, monthly, or seasonal income. Enjoy the convenience of being just a 10-minute walk or 5-minute bike ride to Siesta Key Beach—without the need to access main roads. Move-in ready and perfectly situated, this exceptional home offers the ultimate in coastal living. Schedule your private showing today.
Listing is courtesy of: IRONGATE REALTY INC (941-720-1003)
Listing Agent: Brittany Mccord (941-720-2640)
5830 MIDNIGHT PASS RD #48, SARASOTA, FL 34242
$558,00015 Days on yellowkey MLS ID: A4695273
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1963 Tax: $3,659 (2025)Community: Jamaica RoyaleCondo
Taxes:$3,659
Remarks: Welcome to your own slice of paradise at Jamaica Royale, located directly on the world-famous shores of Siesta Key Beach. This beautifully remodeled one-bedroom, one-bath condominium, complete with a queen sleeper sofa, and a twin sleeper sofa, offers the perfect combination of coastal sophistication and exceptional rental income potential. Thoughtfully updated throughout, the stunning kitchen features elegant quartz countertops, custom wood cabinetry, stainless steel appliances, and a convenient laundry closet with a stackable washer and dryer—ideal for effortless beachside living and entertaining. The spa-inspired bathroom showcases designer finishes, including a custom-tiled shower and sleek quartz top vanity. Designed with both comfort and style in mind, the open and inviting floor plan is offered fully furnished and turnkey, allowing you to begin enjoying the Siesta Key lifestyle immediately. Whether you're seeking a personal beachfront getaway, an investment property, or both, this residence delivers. Jamaica Royale is one of Siesta Key's most sought-after beachfront communities, offering flexible one-week minimum rentals, making it highly attractive to vacationers and investors alike. Residents and guests enjoy 3 heated community pools, designated BBQ areas, a shuffleboard court and approximately 300 feet of private beachfront, with direct access to the Gulf of Mexico's crystal-clear waters and powder-soft quartz sand. Perfectly positioned just minutes from Siesta Key Village, you'll enjoy easy access to award-winning restaurants, charming boutiques, entertainment, and vibrant nightlife. This is a rare opportunity to own a turnkey beachfront retreat in one of Florida's most desirable coastal destinations—where every day feels like a vacation.
Listing is courtesy of: PEPPERTREE BAY REALTY INC (941-914-3380)
Listing Agent: Eliza Miller (941-914-3380)
6140 MIDNIGHT PASS RD #902, SARASOTA, FL 34242
$925,000255 Days on yellowkey MLS ID: A4666851
REDUCED by $20,000 (2.1%) on 04/12/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 1000 Built: 1967 Tax: $10,547 (2025)Community: Horizons WestCondo
Taxes:$10,547
Elementary School: Gulf Gate Elementary
Remarks: Your Dream Beach Escape Awaits on Siesta Key! Tired of long winters or hectic city life? Discover the ultimate retreat in this luxurious 9th-floor penthouse overlooking Siesta Key’s world-renowned Crescent Beach. With uninterrupted Gulf views, you’ll enjoy breathtaking sunsets and the soothing sounds of the surf each day. This spacious 1-bedroom, 1-bath unit features a sleek open floorplan with panoramic views from the living, dining, and kitchen areas. Fully furnished and move-in ready, it includes impact windows and doors, 2021 AC, new glass railings for unobstructed beach views, and updated appliances. The bedroom offers custom closets and en-suite bath with a modern walk-in shower. A large walk-in pantry provides extra storage. Add a sleeper sofa or Murphy bed to easily host guests. Located in Horizons West, a 7-acre gulf-to-bay community with 300 feet of private beach, beachside pool and spa, grilling areas, clubhouse, and a bayside park with day dock—perfect for kayaking, fishing, or relaxing by the intracoastal waterway. A second pool is located next to the Community Clubhouse. Hop on the free Siesta Key trolley to explore local dining, shopping, and entertainment. This is more than a condo—it’s your gateway to paradise.
Listing Agent: Suki Scollo (941-587-2289)
8456 MIDNIGHT PASS RD, SARASOTA, FL 34242
$1,900,00060 Days on yellowkey MLS ID: TB8497342
REDUCED by $300,000 (13.6%) on 05/30/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 966 Built: 1962 Tax: $7,269 (2025)Community: Heron Lagoon Lodge SubSingle Family
Taxes:$7,269
Elementary School: Southside Elementary
Remarks: Rare Opportunity: Last Unrestricted Deed Waterfront Property on Midnight Pass Siesta Key’s Heron Lagoon. Discover one of the most unique waterfront opportunities left on the Turtle Beach end of Siesta Key. This last unrestricted deed property on legendary Midnight Pass sits directly on the serene Heron Lagoon side, offering unparalleled flexibility with no HOA and endless possibilities for your dream coastal retreat. The existing home is a charming 2-bedroom, 1-bathroom Old Florida bungalow (966 sq ft) that has been thoughtfully remodeled while preserving its authentic island character. Oak trees frame the property, and the one story design blends seamlessly with the natural surroundings on this oversized 0.39-acre lot (approximately 47 ft of direct lagoon frontage). Step outside to your private dock complete with shower and electricity — perfect for kayaking, paddle boarding, straight into Heron Lagoon with quick, effortless access to the Gulf of America via Midnight Pass. Enjoy breathtaking west-facing sunsets every evening as the sky paints vibrant colors over the ocean — a year-round spectacle right from your backyard. Whether you envision keeping the classic bungalow, adding a pool, expanding the home, or building new under Siesta Key’s flexible zoning, this rare unrestricted parcel delivers the ultimate blank canvas. Property Highlights: 2 beds | 1 bath | 966 sq ft living area, 0.39-acre lot with direct Heron Lagoon frontage, Private boat dock with shower & electric, No HOA — unrestricted deed, West-facing Gulf sunsets, Remodeled Old Florida charm, Prime southern Siesta Key location on one of Florida’s most coveted barrier islands, and the recently opened Midnight Pass intercoastal passage to the Gulf. Don’t miss your chance to own a true piece of Siesta Key history and lifestyle. This one-of-a-kind waterfront gem will not last.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
5727 RIEGELS POINT RD, SARASOTA, FL 34242
$4,295,000683 Days on yellowkey MLS ID: A4618421
REDUCED by $300,000 (6.5%) on 04/22/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3616 Built: 1982Monthly Fee: $125 Tax: $19,884 (2024)Community: Riegels LandingSpa: YesSingle Family
Taxes:$19,884
Remarks: When home feels like a permanent vacation, every day becomes a tropical escape where time slows down, the water is always nearby, and every day begins and ends with a coastal breeze. That’s the essence of 5727 Riegels Point—a casually luxurious, resort-style property where the lifestyle is as effortless as it is extraordinary. Nestled within the gated enclave of Riegels Landing on Siesta Key, an exclusive community with fewer than 30 estate homes, this unique property offers a lifestyle where outdoor living is as exceptional as the interior. Step into your own island sanctuary, surrounded by 357 feet of deep-water shoreline on a private basin with direct Intracoastal access. It’s a true boater’s paradise, complete with two 10,000-lb boat lifts, a floating kayak launch, water and electricity at the dock, and lit pilings perfect for nighttime fishing. The water is deep enough for a large-scale yacht to sit comfortably at your dock. Expansive Shellstone patios wrap around the home, offering countless spaces to relax, dine, and entertain. The saltwater pool and raised spa, framed by fire and water features anchor this private resort experience. Remote smart controls make it easy to unwind in the pool and spa after a sunset cruise. The front entry showcases coastal curb appeal with double frosted glass doors, leading into an interior that blends casual sophistication with the ease of turnkey living. The great room is open and airy, with engineered wood floors and abundant natural light. Large sliders provide seamless access to the outdoor amenities, creating a perfect space for both entertaining and casual relaxation. The chef’s kitchen is designed for both form and function, featuring Wolf cooking appliances, a Sub-Zero refrigerator, a Miele dishwasher, a galley sink, and custom cabinetry throughout. Hidden outlets at the cabinet base and multiple pantries, plus clever storage built into the island, keep everything organized with ease. The primary suite is a serene retreat with engineered hardwood floors, a access to a waterfront terrace with Trex decking that wraps around the entire home, and well-thought-out blind and electrical automation. The luxurious bath features lighted mirrors, dual sinks, a makeup vanity, a free-standing tub, a walk-in shower, and a Toto commode. The suite also includes a spacious walk-in closet with custom built-ins. Upstairs, two generous guest suites share a well-appointed full bathroom. Two loft areas provide the perfect space for reading, working, or relaxing. The lower level offers a multifunctional space, featuring a living space, fitness room, sliders to access the outdoor space, and a wine room with plumbing for a cooler. Additional features include a spacious 2-car garage with custom built-ins, Control4 smart home technology for lighting, AV, security, and more, four HVAC zones for comfort, turnkey furnishings, a whole-house water softener system (salt and carbon filters), a whole house generator and an oversized laundry room with custom organization. At 5727 Riegels Point, enjoy island living with easy access to Sarasota and Siesta Key Village’s dining, shopping, and entertainment. Siesta Key Beach, recently named the No. 1 beach in America by Tripadvisor, is just moments away, offering powdery sand, clear waters, and stunning sunsets. From dockside mornings to poolside evenings, this is coastal living at its best—a full-time escape where your dream lifestyle unfolds.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
777 BEACH RD #1E, SARASOTA, FL 34242
$765,000221 Days on yellowkey MLS ID: A4670832
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1970 Tax: $8,392 (2024)Community: Crescent Royale 3Spa: NoCondo
Taxes:$8,392
Remarks: Get ready to be wowed by this completely reimagined 2-bedroom, 2-bath coastal gem in the highly sought-after Crescent Royale! Step inside to discover a stunning transformation where modern luxury meets timeless coastal charm. The new kitchen, now seamlessly integrated into the great room by the removal of a wall, creates a spacious and inviting open-concept layout perfect for entertaining or relaxing in style. Both bathrooms have been beautifully redesigned, featuring fresh, contemporary finishes. As an end unit, this residence shines with upgrades from top to bottom – including new plumbing, electrical, and flooring – ensuring every detail has been thoughtfully addressed. Enjoy the ease of first-floor living with no elevators or stairs to navigate, plus the convenience of a covered parking space located just steps from your door. From your living room and lanai, take in breathtaking Gulf views and relish the unbeatable location directly across from world-renowned Siesta Key Beach. Crescent Royale’s amenities complete the picture of resort-style living, featuring a vibrant clubhouse with a fitness center and game room, a sparkling heated pool, and a grilling/picnic area perfect for outdoor gatherings. All this, and you are just a short stroll or bike ride to Siesta Key Village, where dining, shopping, and entertainment await. Whether you are seeking your own beachside retreat or an exceptional investment property, this condo truly has it all. With outstanding rental potential, you can enjoy it when you wish and generate income while you are away. Don’t miss this rare opportunity to own your slice of paradise at Crescent Royale — where luxury, location, and lifestyle come together beautifully.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Scott Rickards, Pa (941-356-7040)
765 SIESTA KEY CIR, SARASOTA, FL 34242
$3,290,00034 Days on yellowkey MLS ID: C7525634
REDUCED by $210,000 (6.0%) on 05/30/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3446 Built: 1972Monthly Fee: $83 Tax: $20,136 (2025)Community: Siestas BaysideSingle Family
Taxes:$20,136
Remarks: Hidden behind an expansive 250-foot circular driveway, the residence is designed for those who appreciate luxury waterfront living and effortless entertaining. Offering approximately 3,500+ square feet, the home features 5 bedrooms, 2 bonus rooms, and dual primary suites, including a spacious main-level owner’s retreat and an additional upstairs suite ideal for guests or multigenerational living. Inside, timeless elegance meets modern functionality with marble flooring, GE Café appliances, spray foam insulated walls for enhanced efficiency and sound reduction, and expansive living spaces filled with natural light and tranquil water views. Recent improvements include three newer HVAC systems, a newer pool heater, major mechanical updates, and an oversized deep-water dock capable of accommodating larger vessels. Outdoor amenities create a true resort-style setting with a heated pool, private basketball court, lush tropical landscaping, and multiple areas for relaxation and entertaining. The oversized waterfront lot is the true centerpiece of the property, providing remarkable privacy and unobstructed boating access with no waterway limitations — an increasingly rare offering on Siesta Key. Conveniently located just minutes from Siesta Key Beach, marinas, fine dining, private clubs, and downtown Sarasota, this extraordinary property presents a rare opportunity to own a premier waterfront estate in one of Southwest Florida’s most desirable coastal destinations.
Listing is courtesy of: RE/MAX PALM REALTY (941-743-5525)
Listing Agent: Taylor Brady (239-896-6433)
5600 BEACH WAY DR #201, SARASOTA, FL 34242
$575,000376 Days on yellowkey MLS ID: A4654536
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1259 Built: 1970Monthly Fee: $1,467 Tax: $5,918 (2024)Community: Beachway AptsSpa: NoCondo
Taxes:$5,918
Remarks: SELLER SAYS BRING ALL OFFERS! MAJOR PRICE IMPROVEMENT!! Reduced over 75k! Have you ever wondered what it's like to own a Siesta Key sunset? Throw on your swimsuit, grab a towel and take a short stroll across the street, because here at Beach Way, you can't get much closer! Embrace your very own next-level Florida lifestyle with this exceptional opportunity. This second floor 2-bedroom, 2-bathroom condo is ideally situated and directly across the street from the world-renowned Siesta Key Beach, continuously celebrated for its powdery soft, white quartz sands and clear waters. This property is being offered fully furnished and is move in ready, presenting a unique chance to personalize your very own dream retreat whether as a permanent residence or a vacation getaway. This unit beams with natural light throughout, showcasing its rare beauty. With a minimum lease period of one month, up to twelve times a year, it also offers potential for rental income. Rental Proforma attached. As you enter the front doors to this beach oasis, prepare to be impressed by an open-concept kitchen that seamlessly flows into the living and dining areas, extending out to a private screened-in lanai where you can take in partial glimpses of the Gulf, creating a perfect setting for relaxation and entertaining. Need a little space? Both bedrooms feature walk-in closets, providing ample storage and comfort. In addition, the unit overlooks the community's heated pool which is maintained at 85 degrees year-round. This well-maintained community was built in 1970, offering a host of amenities designed for convenience and leisure. Residents have access to a community room with a full kitchen for social gatherings, picnic and grilling areas, elevators, laundry facilities on each floor, and a personal storage unit. In addition, your deeded carport is located just steps from your front door, ensuring ease of access. Recent updates to building include a new roof in 2020, an updated elevator installed in 2019, re-plumbed stacks completed in 2018, the addition of new vinyl fencing in 2021. The quarterly condo association fee covers access to all the amenities, pest control, basic cable, water/sewer services, grounds maintenance, weekend on-site maintenance, and community insurance. Living on Siesta Key means more than just proximity to the beach; it's about embracing a lifestyle where every day feels like a vacation. Start your mornings with a peaceful walk along the shoreline, enjoy paddleboarding in the calm Gulf waters, or partake in beach yoga sessions at sunrise and drum circle Sundays. The island's laid-back atmosphere is complemented by its vibrant community, offering a mix of friendly full-time residents and seasonal visitors. Ready to venture out for some more fun? Siesta Key Village, just a short distance away, is the heart of the island's social scene. Here, you'll find an array of casual bars, eateries, and boutiques, perfect for evening outings or weekend brunches. The community's eclectic vibe ensures there's always something happening, from local festivals to live music events. Other close by attractions include the Ringling Bridge, Downtown Sarasota and St. Armands, close proximity to top rated schools and hospitals, SRQ Airport and University Town Center. Don't let another Season pass you by from owning your own slice of paradise in the sand. Schedule your showing today.
Listing Agent: Ashley Nevadomski (941-769-7627)
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