Location: Sarasota , 34242
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5830 MIDNIGHT PASS RD #32, SARASOTA, FL 34242
$499,90015 Days on yellowkey MLS ID: A4694962
Bed: 0 Bath: 1.0 Liv Area Sq Ft: 392 Built: 1962 Tax: $2,441 (2025)Community: Jamaica RoyaleSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,441
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Welcome to Jamaica Royale, a Gulf-side development on Siesta Key, with its award-winning, crystal powder soft sandy beach, just nearby. This studio offers a main-floor villa that has been renovated for comfort and durability. Enjoy the new kitchen with new stainless steel appliances, quartz counters throughout and a new bath. All furnishings have been tastefully replaced with a focus on quality and functionality. The water heater is new, freshly painted, and waiting for its new owner. The location of the rear patio is conveniently near one of three pools. An on-site office offers an optional rental program, so you may generate potential income when not in residence. While you go out your rear patio to the beach, you will pass Jamaica Royale's additional pools, beach cabana and white sands of Siesta Key. The clubhouse offers a full kitchen, a meeting room, on-site association services and rental management. Outside offers barbecue grills, a table and chairs, a lounging area and shuffleboard, a great area to gather with family and friends. Siesta Key offers public transportation to many of the area's local coastal attractions, restaurants, shopping and Sarasota, with all that it offers.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Dennis Girard (941-809-0041)
6157 MIDNIGHT PASS RD #E63, SARASOTA, FL 34242
$420,000294 Days on yellowkey MLS ID: A4662792
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1101 Built: 1974 Tax: $5,101 (2024)Community: Bay OaksCondo
Taxes:$5,101
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: BAY OAKS - JUST MINUTES FROM WORLD FAMOUS SIESTA KEY BEACH. Now is the time to make this 2-bedroom, 2-bath condo your island paradise. With weekly rentals allowed, this condo is perfect for a vacation getaway, short-term rentals, your personal island retreat, or full-time Florida living. Fully furnished and move-in ready. Enjoy poolside views from your screened porch, low HOA fees, and resort-style amenities including a heated pool, tennis courts, waterfront BBQ area, community room with pool table, and a fishing dock set in a lush, park-like setting along the bay. Centrally located on Siesta Key, you’re minutes from North and South Village shops, restaurants, and the free island trolley.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Greg Hudson (941-302-1485)
6100 MIDNIGHT PASS RD #201, SARASOTA, FL 34242
$6,499,000178 Days on yellowkey MLS ID: A4672432
2 Days Off yellowkey (back on 3/13/2026)
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3882 Built: 2019 Tax: $55,984 (2024)Community: Halcyon Siesta KeySpa: NoCondo
Taxes:$55,984
Remarks: Under contract-accepting backup offers. Welcome to Residence #201 at Halcyon Siesta Key—a rare opportunity within one of the island’s most exclusive boutique communities. With only six Gulf-front residences, Halcyon offers the ultimate in privacy, luxury, and architectural sophistication. This exquisite coastal retreat blends modern design with relaxed seaside living. Engineered hardwood floors, soft coastal hues, and floor-to-ceiling hurricane-impact windows frame sweeping views of the turquoise Gulf waters. Step off your private elevator into a bright, open floor plan designed for effortless entertaining. The gourmet kitchen features Wolf appliances, a wine fridge, and an oversized island flowing seamlessly into the dining and living spaces. The Gulf-front primary suite is a serene escape with a spa-inspired bath boasting dual vanities, a soaking tub, and a glass-enclosed shower. Two additional guest suites—each with private en-suite baths—offer exceptional comfort, while a versatile den/office provides flexibility for work or an additional bedroom. Unwind on your private Gulf-front terrace, where sunsets and sea breezes set the tone for everyday tranquility. Enjoy direct private beach access and the exclusive front amenity cabin, complete with a fitness center, bathrooms, comfortable lounge area, and an expansive deck ideal for entertaining or relaxing after a day by the water. A private two-car garage and resort-style amenities—including a beachfront pool and fire pit—complete this one-of-a-kind coastal lifestyle!
Listing is courtesy of: THE SARASOTA REAL ESTATE COMP. (941-321-5595)
Listing Agent: David Lehrman (941-321-5595)
70 AVENIDA VENECCIA #204, SARASOTA, FL 34242
$5,400,000500 Days on yellowkey MLS ID: A4637710
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4154 Built: 2025 Tax: $7,518 (2023)Community: Sunset BeachSpa: YesCondo
Taxes:$7,518
Tax Year: 2023
Remarks: One or more photo(s) has been virtually staged. Under Construction. One or more photos have been virtually staged. Currently under construction with an estimated completion in the first half of 2026, Sunset Beach embodies the pinnacle of luxurious beachfront living on Siesta Key. Nestled within a neighborhood-inspired enclave surrounded by newly built homes, it offers a prime location just steps from the vibrant shops and restaurants of Siesta Key Village. This exclusive collection of 11 exquisitely designed residences redefines coastal luxury, offering unparalleled Gulf views and seamless integration with the natural beauty of its surroundings. At Sunset Beach, every detail of the residences has been thoughtfully crafted to elevate your living experience while embracing the beauty of Siesta Key’s Gulf-front serenity. Each home begins with direct private elevator entry, ensuring privacy and exclusivity from the moment you arrive. Once inside, you’ll be greeted by 10-foot ceilings, floor-to-ceiling windows, and oversized terraces that frame spectacular Gulf views, offering seamless indoor-outdoor living. The spacious layouts are perfect for living, dining, and entertaining, featuring custom kitchens and bars equipped with Sub-Zero and Wolf appliances, ensuring a culinary experience as refined as the setting. The solid-core 8-foot-high entry and interior doors, floor-to-ceiling hurricane-resistant balcony sliders with laminated solar-tint glass, and glass balcony railings harmonize style with durability, ensuring your home is both beautiful and secure. To enhance your comfort and convenience, the residences are pre-wired for state-of-the-art Smart Home technology, allowing you to tailor your living environment with ease. Outdoors, the terraces feature elegant stained tongue-and-groove ceilings, providing a warm, timeless aesthetic to complement the panoramic Gulf views. Whether you’re relaxing in solitude or entertaining guests, these terraces are the perfect space to savor the beauty of the coastline. At Sunset Beach, the thoughtful design and high-end finishes ensure every moment feels luxurious, from your private retreat to the breathtaking surroundings of Siesta Key. Every feature has been carefully curated to provide the ideal balance of comfort, style, and functionality in a beachfront sanctuary that truly redefines coastal living. Don’t miss your opportunity to own one of these exclusive residences. Spend your day relaxing by the poolside or take a few steps to a beachside lounge chair, where you can relax under an umbrella and enjoy the stunning views of crystal-clear water and white sand. Amenities include a beachfront swimming pool, spa, cabanas, and fire pit, lounge chairs, umbrellas, kayaks, paddle boards, and bikes, a state-of-the-art fitness center, beachfront grilling area, and private on-site storage units.Contact us today to schedule your private tour of Sunset Beach and take the first step toward living your coastal dream. Your new chapter of beachfront luxury begins here.
Listing is courtesy of: THE SARASOTA REAL ESTATE COMP. (941-867-9866)
70 AVENIDA VENECCIA #202, SARASOTA, FL 34242
$6,900,000500 Days on yellowkey MLS ID: A4637462
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3550 Built: 2025 Tax: $7,518 (2023)Community: Sunset BeachSpa: YesCondo
160 GARDEN LN, SARASOTA, FL 34242
$4,250,000288 Days on yellowkey MLS ID: A4663247
1 Days Off yellowkey (back on 4/16/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4086 Built: 2025 Tax: $10,687 (2024)Community: Siesta Rev Plat OfSpa: YesSingle Family
Taxes:$10,687
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Welcome to Your Dream Coastal Retreat Steps from Siesta Beach! This custom three-story home on Siesta Key’s coveted north end features five bedrooms, 4 full and 1 half bathrooms and combines elegant design, elevated construction, and thoughtful luxury finishes. The light-filled, open-concept floor plan seamlessly connects the great room, dining space, and a gourmet chef’s kitchen, which features a quartz waterfall island, custom cabinetry, and high-end appliances. **Expansive sliding glass doors open to over 1,200 square feet of covered outdoor living space, framing views of lush tropical landscaping and a resort-style pool with a sun shelf. The primary suite is a true sanctuary, complete with a free-standing soaking tub and an oversized walk-in shower. The outdoor living experience is unrivaled. Multiple covered lanais and balconies provide perfect spaces for entertaining, relaxing with morning coffee, or enjoying Sarasota’s sunsets. **Additional features include an elevator servicing all three levels, additional guest suites, flexible bonus spaces, a two-car garage, and storm-rated windows and doors for elevated construction. Stylish coastal architecture with Hardie board siding and a metal roof completes the package. **Located just steps from Siesta Key’s world-famous beaches and minutes from the vibrant shops and restaurants of Siesta Village, this location offers the perfect blend of luxury and island lifestyle. **Short-term rentals are permitted, providing a flexible investment opportunity. **This property is also conveniently located in close proximity to Downtown Sarasota, Southside Village, and top hospitals, restaurants, and entertainment. This is your chance to build a custom masterpiece in a truly unparalleled location. Build your dream home with us, or purchase the lot and plans separately. Use our trusted general contractor or bring your own builder. Are you ready to turn your vision into a reality?
Listing Agent: Chad Fonder (941-961-3865)
1249 S BASIN LN, SARASOTA, FL 34242
$8,950,00050 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
Taxes:$40,641
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
$10,500,00016 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
$600,000564 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)
1300 N PORTOFINO DR #406, SARASOTA, FL 34242
$499,00041 Days on yellowkey MLS ID: A4692022
REDUCED by $26,000 (5.0%) on 05/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 929 Built: 1969 Tax: $2,653 (2025)Community: Siesta Harbor IiSpa: YesCondo
Taxes:$2,653
Remarks: BEAUTIFUL RENOVQTION ON THE CANAL! WATERVIEWS! Live the Florida dream in this recently remodeled CANAL-FRONT home, designer 2 bedroom, 2 bathroom condo nestled within the coveted Siesta Harbor community, offering private beach access to world-famous Siesta Key Beach just across the street. Situated on the fourth floor with picturesque water views, this beautifully updated unit features gorgeous quartz countertops, gray shaker cabinetry, stainless steel appliances, and brand new ceramic tile flooring throughout. Enjoy peace of mind with the glass-enclosed lanai with sliding glass windows that provides a serene retreat year-round. The open-concept layout flows seamlessly from the modernized kitchen into a bright and welcoming living space, perfect for entertaining or relaxing. Both bathrooms have been tastefully renovated, including a fully remodeled primary and guest bath, and the entire unit was freshly painted. Additional features include a private storage closet, updated lighting, and high-speed fiber optic internet. Siesta Harbor is a vibrant 55+ waterfront community along the Intracoastal Waterway, offering a heated pool, spa, clubhouse, fitness center, shuffleboard, fishing dock, sauna, BBQ area, and boat slips for up to 30’ vessels. Whether enjoying your morning walk to the beach, walking to lunch just minutes away, catching the free trolley to Siesta Key Village, or heading over the nearby bridge to explore downtown Sarasota’s dining, shopping, and cultural scene, this location offers the ultimate in coastal convenience and lifestyle. With monthly rentals allowed 12 times a year, it’s ideal as a personal escape or investment property.
Listing is courtesy of: JUDITH GUZZI & ASSOCIATES LLC (914-490-9032)
Listing Agent: Judith Guzzi (914-490-9032)
4938 COMMONWEALTH DR, SARASOTA, FL 34242
$2,695,000101 Days on yellowkey MLS ID: A4683758
REDUCED by $205,000 (7.1%) on 05/22/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2169 Built: 1984 Tax: $12,150 (2025)Community: Siesta BeachSpa: YesSingle Family
Taxes:$12,150
Remarks: Experience the pinnacle of waterfront luxury on Siesta Key’s prestigious Grand Canal. This meticulously reimagined residence at 4938 Commonwealth Drive offers a rare blend of modern sophistication, structural integrity, and complete peace of mind. Extensively transformed both structurally and aesthetically, the home welcomes you into an expansive open-concept design filled with natural light. The newly expanded kitchen serves as the heart of the home, offering abundant cabinetry and storage, a double oven, generous pantry storage, striking custom beam detail, an open breakfast bar, and direct access to the wraparound decking—creating seamless indoor-outdoor living and effortless entertaining. A stylish powder room has also been thoughtfully added. New hurricane-impact windows and sliding glass doors frame the interiors, while designer flooring flows beautifully throughout both levels. Major system upgrades elevate the home’s value and efficiency, including a brand-new roof and a comprehensive solar power system with battery storage. A fresh, contemporary interior palette enhances the clean architectural lines and airy coastal feel. The lower level adds over 1,300 square feet of legal non-conforming living space with its own private entry, garage access, and elevator connection to the main living areas, leading directly to the pool deck. Redesigned for modern functionality, this space features a spacious family entertainment area, custom bar, and an additional guest suite with a walk-in closet and full bath—ideal for extended family, guests, or a private retreat. Outdoor living is equally impressive. The private backyard sanctuary showcases a heated pool and spa with a new heater and filtration system, sleek updated decking, professional landscaping, and premium artificial turf for effortless maintenance. For the boating enthusiast, the deep-water dock and boat lift provide direct access to the Intracoastal Waterway and open waters of Sarasota Bay, delivering the ultimate waterfront lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Maurice Menager (941-238-8119)
1020 SUN AND SEA DR #102, SARASOTA, FL 34242
$575,000239 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
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
$1,299,000106 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
$500,000267 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
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)
589 COMMONWEALTH LN, SARASOTA, FL 34242
$2,200,00041 Days on yellowkey MLS ID: R4910990
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2073 Built: 1972 Tax: $9,116 (2025)Community: Siestas Bayside Waterside EastSingle Family
Taxes:$9,116
Remarks: Welcome to your canal front pool home on beautiful Siesta Key. It is a 4 bedroom,2 full bathroom home on approximately .24 acres (10,623 sq ft).It was built in 1972 and now rebuilt in 2026. The house is 2,154 sq ft under air with a 2 car garage which is 462 sq ft. There are brand new Champion windows and sliders,throughout all hurricane impact resistant. The new HVAC system was put in in 2024, and since then the electric and plumbing systems were totally redone. The brand new flooring is a beautiful sandy tile, much like the color of the sand on world renowned Siesta Key beach. Take invigorating walks or bike rides and view the magnificent sunsets on the beach. The roof is older but has been inspected and is in excellent condition. There are lots of plush plantings and a dock right outside of the screened pool and lanai. Come see for yourself! This home should not be missed! Buy yourself a piece of paradise, there's only so much to go around!
Listing is courtesy of: PREMIER PLUS REALTY (941-228-0077)
Listing Agent: June Mceleavy (941-228-8139)
6287 MIDNIGHT PASS RD #103, SARASOTA, FL 34242
$685,00093 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)
1166 W PEPPERTREE DR #112D, SARASOTA, FL 34242
$725,000147 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
$620,000259 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
$1,649,000302 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
$1,725,00041 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)
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