Location: Sarasota
Do Not Show Listings
5132 JUNGLE PLUM RD, SARASOTA, FL 34242
$5,985,000385 Days on yellowkey MLS ID: A4651663
Bed: 5 Bath: 6.0 Gar: 10 Liv Area Sq Ft: 6928 Built: 2008Monthly Fee: $247 Tax: $45,860 (2024)Community: Hidden HarborSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$45,860
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm textures and elegant proportions create an atmosphere that is refined and welcoming. Just over a mile from the world-renowned sands of Siesta Key Beach, this is a home that celebrates the best of Sarasota’s lifestyle, a water connection, a celebration of indoor-outdoor living and architectural details that convey quiet luxury. Set on more than half an acre with 135 feet of water frontage, the residence opens with a stunning walnut-domed foyer, where soaring ceilings and floor-to-ceiling windows flood the space with light. Rich finishes—including Birdseye maple, tongue-and-groove cypress tray ceilings, and handcrafted millwork—are woven throughout the home, delivering a consistent sense of quality and character. The kitchen is a dream for chefs and entertainers alike, appointed with quartz countertops, a large center island, professional-grade appliances, a built-in espresso machine, and a walk-in butler’s pantry that seamlessly connects to formal and casual living areas. The owner’s suite is a private retreat, complete with a sitting room, dual walk-in closets, a spa-style bath with steam shower and a peaceful balcony overlooking the water. Each of the four guest suites offers its own en-suite bathroom and generous closet space, with three featuring walk-in closets and one boasting a built-in wall closet, ensuring privacy and comfort. Whether you need a quiet office, a vibrant game room or a cozy retreat, the bonus room, game room and loft offer the flexibility to suit your lifestyle. True to its coastal character, the home opens fully to expansive covered terraces designed for year-round enjoyment. Retractable screens, a wood-paneled ceiling, integrated fans, and ambient lighting create an outdoor living room atmosphere, complete with a fireplace and a full summer kitchen with built-in grill and bar seating. Beyond, the resort-style pool and raised spa are surrounded by tropical landscaping and natural stone decking, with multiple lounge areas designed for sun and shade. A custom fire pit anchors the space, offering a cozy, elegant setting for evening gatherings with water views. Water enthusiasts will appreciate the boat dock, built to accommodate a large vessel, complete with a boat lift. With quick access to the Intracoastal Waterway, the location is as functional as it is beautiful. Below, the expansive under-building garage offers room for more than 10 vehicles across five bays, plus a workshop, EV charging station and golf cart storage. A brand new whole-house generator was installed in June of 2025, creating peace of mind. Set on a quiet cul-de-sac just minutes from Sarasota’s best beaches, shopping, dining and cultural destinations, this rare offering is a seamless blend of timeless design, superior craftsmanship and the relaxed elegance of coastal Florida living.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
7223 CLOISTER DR #111, SARASOTA, FL 34231
$250,000205 Days on yellowkey MLS ID: C7517166
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1257 Built: 1984Monthly Fee: $525 Tax: $2,876 (2024)Community: Gulf Gate GardensCondo
Taxes:$2,876
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: This thoughtfully updated and coveted corner/end unit is ready for you to call it home! A rare 2 Bedroom 2-1/2 bath townhome that boasts newer updates which include granite countertops and soft close cabinetry throughout, a stylishly designed dining room ceiling, luxury vinyl plank flooring, and an enclosed rear porch so you can enjoy the outdoors in comfort 365 days a year. Conveniently close parking and a community pool are just steps away from your door! With an abundance of shopping and restuarants in the area as well as plans for more in the old Sarasota mall location, there will be no shortage of activities. Located approximately 6 miles away from the white sands of Siesta Key beach, know that you picked a great location with all of SW Florida's prized amenities at an excellent price point! Book your showing today!
Listing is courtesy of: ERA ADVANTAGE REALTY, INC. (941-255-5300)
Listing Agent: Khari Nixon (317-503-5350)
1339 22ND ST, SARASOTA, FL 34234
$475,00051 Days on yellowkey MLS ID: TB8497340
REDUCED by $5,000 (1.0%) on 05/23/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1681 Built: 1959 Tax: $3,260 (2025)Community: Cocoanut HeightsSingle Family
Taxes:$3,260
Elementary School: Gocio Elementary
Tax Year: 2025
Middle School: Booker Middle
Remarks: Charming Updated 3BR/2.5BA Home in Sarasota – Move-In Ready! Discover this beautifully renovated gem at 1339 22nd St, Sarasota, FL 34234 (1,681 sq ft living space on an 8,871 sq ft lot). Perfect blend of modern updates and classic Florida charm! Key Features: Prime Corner Lot with Double Street Access: Unique lot connecting to two streets (22nd & adjacent), offering exceptional curb appeal and flexibility. Ample Parking + 2-Car Attached Garage: Wide driveway spaces multiple vehicles easily – no parking hassles! Brand New Luxury Vinyl/Porcelain Tile Flooring Throughout: Sleek, durable, and easy-care for coastal living. Fully Updated Bathrooms: 2.5 modern baths with contemporary finishes. New AC System: Efficient, quiet cooling for year-round comfort. All-New Electrical & Plumbing: Complete modern rewiring and piping for safety and peace of mind. Gourmet Kitchen Shines: White shaker cabinets, stunning gray granite counters, blue subway tile backsplash, stainless steel appliances (fridge, dishwasher, range, microwave), and spacious breakfast bar open to the living/dining area. No HOA! Walk to Ringling College, minutes to Siesta Key beaches, downtown Sarasota dining/shopping, and SRQ airport. Built 1959, feels brand new inside. Zoned RSF3 – ideal for families, investors, or downsizers.
Listing is courtesy of: RADIUS REALTY GROUP LLC (407-541-0779)
Listing Agent: Guillermo Gomez (407-497-9846)
2383 LAKESIDE MEWS #D3, SARASOTA, FL 34235
$295,00019 Days on yellowkey MLS ID: A4693236
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1382 Built: 1979 Tax: $3,214 (2025)Community: Meadowlake ISpa: NoCondo
Taxes:$3,214
High School: Booker High
Remarks: Beautifully renovated and move-in ready, this stunning 2-bedroom, 2-bath single-story residence offers the perfect blend of comfort, style, and convenience. Featuring luxury vinyl plank flooring throughout and an open concept layout, the home is filled with beautiful natural light through 5 sets of sliding glass doors. The spacious lanai has been thoughtfully converted into additional air-conditioned living space, creating even more room to relax and entertain. Enjoy the best of Florida living with 3 private lanai spaces perfect for morning coffee, outdoor dining, or evening unwinding surrounded by peaceful tropical scenery. The updated kitchen features stainless steel appliances, and upgraded light fixtures throughout, creating a fresh and elevated feel in every room. Located just a short walk to the community pool and the shops, dining, and walking trails of The Meadows, this home also offers unbeatable proximity to University Town Center shopping and dining, just minutes away. Whether you are looking for a full-time residence, seasonal retreat, or investment opportunity, this beautifully updated home checks every box.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Angelica Ridley (908-377-7243)
7790 FAIRWAY WOODS DR #1201, SARASOTA, FL 34238
$324,000177 Days on yellowkey MLS ID: A4672965
1 Days Off yellowkey (back on 5/22/2026)
REDUCED by $26,000 (7.4%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1956 Built: 1985 Tax: $2,278 (2025)Community: Fairway WoodsSpa: NoVilla
Taxes:$2,278
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Experience the ultimate Florida lifestyle with this maintenance-free villa, nestled in a vibrant community designed for those who appreciate comfort and privacy. Welcome to this first-floor end unit, which offers a flexible layout that can easily accommodate dual primary suites, when needed. Boasting a total of three bedrooms and two bathrooms, enhanced with delightful features like a cozy fireplace, an elegant, mirrored bar, sophisticated crown moldings, stylish built-ins, pocket doors, gorgeous granite countertops, and quality cabinetry, along with track and recessed lighting. Wooded privacy can be seen through the sliding glass doors from the gracious formal living room. Formal dining is located between here and the kitchen, including a morning room. This inviting space showcases stunning maple cabinetry, sleek stainless-steel appliances, a lovely, tiled backsplash, a granite breakfast bar, and a convenient pantry, all highlighted by custom offset tile. It also leads through sliding glass doors to the private covered and screened lanai. Double doors at the front of the home provide a quiet area for a home office. This space has a built-in closet and features a pocket door to the secondary en suite, making it suitable as a bedroom or bonus area. A modern bathroom has an impressive walk-in shower with a glass door, contrasting granite countertops, and white raised-panel cabinetry, drop lighting, and tile floors. The Owner's Suite, the largest of all bedrooms, features a window seat overlooking private wooded views, two built-in closets, and a large walk-in closet in the personal bath. It includes a single vanity with a makeup table and dual sinks, a garden soaking tub, and a separate accessible shower. The interior is thoughtfully finished with a convenient laundry room and a door leading to the attached two-car garage. Located in Fairway Woods, a charming private community near Siesta Key Beach, which is known as one of the best beaches in the world. Surrounded by magnificent, mature trees, this area is a true gem that offers fantastic opportunities for boating, biking, and hiking. Golf enthusiasts will appreciate the nearby top-rated TPC golf course. Additionally, residents have convenient access to grocery stores, healthcare facilities, and the vibrant cultural scene in Downtown Sarasota. The association fee covers roof and exterior maintenance, enhancing homeowners' convenience. The community fosters a warm spirit and features amenities such as a heated pool, along with a variety of enrichment classes and social events. You can meander through the beautifully landscaped grounds and enjoy the peaceful conservation areas—making it a wonderful place to call home!
Listing is courtesy of: CANDY SWICK & COMPANY (941-954-9000)
Listing Agent: Candy Swick (941-376-9000)
7340 PALOMINO TRL, SARASOTA, FL 34241
$6,950,000230 Days on yellowkey MLS ID: O6352294
Bed: 11 Bath: 9.5 Gar: 10 Liv Area Sq Ft: 15311 Built: 1981Monthly Fee: $150 Tax: $22,398 (2024)Community: Saddle CreekSingle Family
Taxes:$22,398
Elementary School: Lakeview Elementary
Remarks: Welcome to The Palomino Estate — a private, 17-acre gated oasis unlike anything else in Sarasota County. Located just 10 miles from Siesta Key Beach and 15 miles to downtown Sarasota, this extraordinary property blends resort-style living with the peace and privacy of the countryside. Set within the equestrian community of Saddle Creek, where horse enthusiasts are welcome to use the 31 miles of riding trails, this multi-residence estate offers over 15,000 sq ft under air across multiple structures, including two custom homes, a 5,000 sq ft air-conditioned “barndominium” and entertainment pavilion, and multiple garages. Behind an eight-foot perimeter fence with dual gated entries, you’ll find lush tropical landscaping, privacy berms, and nature trails weaving through the property. You can stroll through the bamboo forest and reflection garden while enjoying multiple ponds for fishing or kayaking. A raised wooden boardwalk winds through the property offering biking and hiking adventures, while a lighted pickleball, tennis, and basketball court with gazebo creates endless opportunities for recreation. In the center of the compound, a massive stone firepit anchors the grounds for gatherings under the stars. There is plenty of space to have a garden or raise livestock.This expansive estate features two custom residences with pools, plus an entertainment barn constructed of solid block. The barn includes two bedrooms, two bathrooms, a full-saloon-style bar, kitchenette, gym, sauna, golf simulator, movie theater, game room, and outdoor kitchen, creating a space that feels like a private resort. A separate air-conditioned garage with 11-foot ceilings offers space for cars, boats, equipment, and more, while another detached garage adds even more covered parking and storage.Together with the barn, the two homes offer eleven bedrooms, nine and a half bathrooms, and over fifteen thousand square feet under air (more than twenty-two thousand total), making this property ideal for multi-generational living, entertaining, or use as a private retreat.Each structure is equipped with whole-home generators, water filtration systems, and impact windows and doors, along with modern security and digital gate entry panels.Recent improvements include new roofs on every structure in 2023, resurfaced pools with travertine and flagstone decking, composite decking and railings, landscape lighting, golf simulator and sauna installations in 2023, and freshly paved asphalt and concrete driveways, and fencing for pets.The main residence offers expansive living areas, soaring ceilings, a massive stone fireplace great room, multiple en-suite bedrooms, an in-law suite with its own kitchen, and relaxing poolside views. The guest residence has been completely renovated with high quality finishes and could serve as a primary home for your extended family. It features a bright open floor plan with gourmet kitchen and second story wrap-around deck for 360-degree nature views. This home also features a private resort-style outdoor area overlooking the lake. This estate was designed for comfort, recreation, and peace of mind, with every detail crafted for privacy and long-term enjoyment.Whether used as a private family compound, equestrian hideaway, or corporate retreat,The Palomino Estate represents a property that truly has it all—green space, activities, security, luxury, and serenity—all just minutes from Sarasota's world-famous beaches, dining, and shopping.
Listing is courtesy of: ORLANDO PROPERTY ADVISORS (407-808-3695)
Listing Agent: Justin Pekarek (407-808-3695)
4119 VIA SIENNA CIR, SARASOTA, FL 34243
$385,000152 Days on yellowkey MLS ID: TB8460377
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1910 Built: 2022Monthly Fee: $250 Tax: $3,747 (2025)Community: Sienna Park Twnhms/UniversityTownhouse
Taxes:$3,747
Elementary School: Emma E. Booker Elementary
Remarks: STUNNING TOWNHOME WITH EXPANSIVE POND VIEWS! This impeccably maintained 3-bedroom, 2.5-bath townhome offers approximately 1,920 square feet of thoughtfully designed living space, complete with a one-car garage and serene water views that create a truly peaceful setting. Upon entering, you are welcomed into a spacious and open great room with plenty of room for both living and dining—perfect for everyday comfort and entertaining alike. The stylish kitchen features quartz countertops, stainless steel appliances, abundant cabinetry, and bar seating, making it both functional and inviting. A convenient pantry provides additional storage, while the open layout allows natural light to flow throughout the space. The entire first floor is finished with elegant wood-look ceramic tile, adding warmth and durability. Upstairs, upgraded wood flooring continues through the stairway and hallway, leading to a well-designed split bedroom layout. The spacious owner’s suite overlooks the tranquil pond and features a large walk-in closet and an oversized en-suite bathroom with dual sinks. Two additional bedrooms are nicely sized and finished with plush carpeting, offering flexibility for family, guests, or a home office. The upstairs laundry room adds everyday convenience and ease. Step out onto the lanai and relax while enjoying peaceful pond views and abundant wildlife, creating a private and serene outdoor retreat. This home is move-in ready, very well maintained, and offers modern finishes throughout. Ideally located near shopping, dining, and everyday conveniences, this townhome combines low-maintenance living with comfort, style, and beautiful water views—an exceptional opportunity you won’t want to miss.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Robert Johnson (813-364-2250)
350 GOLDEN GATE PT #62, SARASOTA, FL 34236
$1,175,000174 Days on yellowkey MLS ID: A4674150
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1677 Built: 1969 Tax: $9,359 (2024)Community: Bay Point AptsCondo
Taxes:$9,359
Elementary School: Southside Elementary
Remarks: The first thing you notice is the view: a full sweep of Sarasota Bay through a wall of windows that defines the main living space. Natural light fills the open living and dining areas, where the water, the John Ringling Bridge, and the downtown skyline sit in clear, uninterrupted sight. A sizeable, light-filled great room anchors the floor plan, offering generous space for living, dining, and relaxing. The kitchen is designed for function and ease, with quartz countertops, white soft-close cabinetry, glass-front display cabinets, and stainless-steel appliances. A peninsula with bar seating connects the kitchen to the main living area, and a built-in desk overlooks the bay as an ideal workspace or breakfast bar with a true waterfront backdrop. The primary suite continues the same water-facing views, offering a wide picture window, recessed lighting, and an en-suite bath with a dual-sink vanity, quartz countertops, tall storage cabinetry, and a seamless-glass walk-in shower. The guest bedroom offers bay views as well, and a second full bathroom features an updated vanity and walk-in shower. Tile flooring runs throughout, maintaining a cohesive flow from room to room. Bay Point Apartments offers a relaxed waterfront lifestyle with a community pool, outdoor lounging space, and a day dock for fishing, launching kayaks, or welcoming friends arriving by boat. Located on quiet Golden Gate Point, the building is minutes to downtown Sarasota, St. Armands Circle, and Lido Beach.
2727 WALDEMERE ST, SARASOTA, FL 34239
$2,085,00030 Days on yellowkey MLS ID: A4692394
1 Days Off yellowkey (back on 5/23/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2809 Built: 2026 Tax: $4,732 (2025)Community: Brunks Add To City Of SarasotaSpa: YesSingle Family
Taxes:$4,732
Elementary School: Alta Vista Elementary
Remarks: Under contract-accepting backup offers. Welcome to this exceptional new construction home, ideally located in Arlington Park, one of Sarasota’s most desirable neighborhoods on a rare oversized 11,230 SqFt lot. This spacious and thoughtfully designed one-story residence offers 4 bedrooms and 4.5 bathrooms, featuring soaring ceilings and an impressive “wow” factor the moment you walk through the door. Designed for both comfort and style, the home showcases custom cabinetry, high-end finishes throughout, and a chef’s kitchen equipped with premium Thermador appliances, a walk-in pantry, and abundant storage. TVs and speaker system (indoor and outdoor) convey with the home, and additional features include built-ins and a dedicated pool bath- every detail has been carefully considered. Step outside to your private backyard retreat, complete with a sparkling saltwater pool and spa, all enclosed within a massive panoramic screen enclosure. The expansive lanai serves as a true extension of the living space, perfect for entertaining or relaxing year-round. The beautifully landscaped yard offers both privacy and curb appeal, along with ample space to park an RV or additional vehicles. Located just a short walk to Arlington Park, you’ll enjoy access to walking trails, a dog park, public swimming pool (home to the Tsunami Swim Team), as well as tennis and basketball courts. With easy access to downtown Sarasota and the area’s world-renowned beaches, this home offers the perfect blend of luxury, convenience, and lifestyle. A rare opportunity to own a truly move-in-ready home that checks every box—this one is guaranteed to impress.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Izabela Fratczak (941-525-7828)
5191 LAKE VILLAGE DR #2, SARASOTA, FL 34235
$249,00014 Days on yellowkey MLS ID: A4694247
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1065 Built: 1981 Tax: $2,877 (2025)Community: Village LakeCondo
Taxes:$2,877
Remarks: Bright, airy, and move-in ready! This turnkey furnished corner unit offers peaceful lake views, abundant natural light, and excellent income potential. Featuring hurricane-impact windows installed in 2026 and a 2018 A/C, this well-maintained Sarasota property is perfect as a vacation getaway, seasonal rental, or full-time residence. Relax and enjoy the serene water views while being just minutes from shopping, restaurants, golf, downtown Sarasota, and world-famous Gulf beaches.
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Nelson Reyes (813-843-7003)
5424 AMERICA DR, SARASOTA, FL 34231
$1,350,000131 Days on yellowkey MLS ID: A4679427
REDUCED by $145,000 (9.7%) on 05/15/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1706 Built: 1983 Tax: $14,691 (2025)Community: Phillippi Gardens 08Spa: NoSingle Family
Taxes:$14,691
Remarks: Nestled on a quiet cul-de-sac in Sarasota, this stunning three-bedroom, three-bath waterfront home offers the perfect blend of tranquility and lifestyle. Enjoy your own private pool with sweeping views over the water, plus direct Intracoastal Waterway access via Philippi Creek. Deep water and a nine-foot bridge clearance make it easy for most 30-foot center console boats to come and go. Just across the creek lies a protected Sarasota watercourse barrier and wildlife refuge, preserving breathtaking, unobstructed views. Recent updates include a brand-new roof, a freshly painted exterior, and the timeless charm of a paver-brick driveway. It also features a 1.5 car garage, perfect for parking a full-size vehicle and a golf cart, bikes, or beach gear. While the interior would benefit from cosmetic updates, the bones and location of this property are truly unbeatable. From your private waterfront retreat, every day feels like a vacation. Best of all, you’re just a five-minute drive from world-famous Siesta Key Beach. Call the listing agent today to schedule your private showing!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Bradley Kayser (941-809-7396)
7944 BERGAMO AVE, SARASOTA, FL 34238
$370,000110 Days on yellowkey MLS ID: A4681762
REDUCED by $19,000 (4.9%) on 04/04/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1672 Built: 2004Monthly Fee: $471 Tax: $4,394 (2025)Community: VillagewalkSpa: NoTownhouse
Taxes:$4,394
Elementary School: Ashton Elementary
Remarks: Priced to sell! A Wonderful Buy! Fantastic Sun Rises as you sip your morning coffee from your large lanai (screen recently replaced) with waterview and retractable awning. Large side yard. Beautifully maintained home with engineered hard wood flooring in most of the home. Tile in wet areas has been recently cleaned and sealed. Large living area with built in wall unit for TV and your favorite Treasures. Newer appliances in kitchen and laundry, new large stainless sink in kitchen. Laundry and 1/2 bath conveniently located on the first floor. Hot Water heater replaced in 2021. Freshly painted throughout. Village Walk is a wonderful unique community, built hurricane safe with poured concrete walls and foundations. Every home in Village Walk is considered to be a Single Family Home, roofs are tied down to the structures, per the Florida Building Codes and considered to be above average. Inspectors, roofers and Insurance agents that are familiar with Village Walk will share this information with you. Village Walk is in Flood Zone X, an area that is determined to be outside the 1% and 0.2% chance of flooding. FEMA updated, 8/2/24. Flood Zone provided by Sarasota County Tax reports. Evacuation zone D, flood insurance is not mandatory, but flood insurance is available. Village Walk power lines are underground with a Sarasota Fire Department just down Honore. Seldom losing power. Amenities include 24 hour guarded gate, geo-thermal heated and cooled lap & lagoon pools, six Har-Tru Tennis courts, Pickle ball, Bocce' ball and Basketball courts, State of the Art fitness Center, Miles of walking and bike paths, over 500 acres of lakes and preserves. There are over 50 activity groups who meet daily, weekly, or monthly. Plus there is a full service Cafe with full service Bar, Gas Station, Barber shop/Hair Salon, and Gift Shop. A special NOTE is that Village Walk did not lose power during the hurricanes and there was No flooding. What a Fantastic Place to Call HOME!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kim Klee (941-400-8922)
1264 18TH ST, SARASOTA, FL 34234
$475,00068 Days on yellowkey MLS ID: A4687775
REDUCED by $50,000 (9.5%) on 05/23/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1921 Built: 1947 Tax: $5,774 (2025)Community: EdgewaterSingle Family
Taxes:$5,774
Elementary School: None
High School: None
Middle School: None
Remarks: Multifamily investment opportunity (RMF Zoning) on the near north side of Sarasota in the heart of the highly sought-after Central Cocoanut Historic District. BLOCK CONSTRUCTION, three-bedroom, two-bathroom home WITH a one bed, one bath, 566 square foot in-law suite created from a garage conversion. The home is a split plan and all three bedrooms have exterior access. The kitchen is bright and updated and opens to the shared lanai and utility room. In addition to the “in law” suite there is an attached 220 square foot studio with plumbing, offering creative or rental potential. Situated in a vibrant, walkable neighborhood with bike lanes, you’ll enjoy easy access to downtown Sarasota, along with its renowned dining, shopping, arts, and cultural amenities. The Ringling College of Art and design is just a few blocks away and the adjacent North Trail Corridor is experiencing some of Sarasota’s most dynamic development. A short 10-minute drive over the Ringling bridge lands you in St. Armands Circle and the beaches of Lido and Longboat Key.
Listing Agent: David Jennings (941-650-7354)
3301 BAY SHORE RD, SARASOTA, FL 34234
$3,995,000702 Days on yellowkey MLS ID: A4613341
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2703 Built: 1914 Tax: $9,843 (2023)Community: Indian Beach Map OfSpa: NoSingle Family
Taxes:$9,843
Tax Year: 2023
Remarks: Exotic and extremely private bay front property on the market for the first time in 40 years. In fact, this is only the third time it’s been available in 100 years. Travel back in time to find ancient oaks and large palms, Banyans, and cedars. It’s an idyllic paradise reminding us of why people have come to these shores for millennia. Even the beachfront appears unadulterated as do several others along Sarasota’s north shore. Although this is direct waterfront, most of the land is not in the flood zone creating many possibilities for new structures on or near grade. What is most unique is the 444-foot lot depth. This is almost 4 times that of other bayfront parcels being redeveloped in the area. This extreme distance provides complete privacy from Bay Shore Road and with each adjacent property a multi-acre estate, the feeling of spaciousness and seclusion is complete. Leave the world behind on the long, winding shell drive through tree canopy and lush vegetation. At “the end of the road” is the original homesite on a small bluff directly on and overlooking Sarasota Bay. Your views are of Longboat and Lido Key and out New Pass to the Gulf of Mexico. Looking south you see our bustling little city of Sarasota and the John Ringling Bridge. Enjoy sea breezes in the afternoon and sunsets all year round. The original home on property evokes a bygone era but land values, building codes and FEMA regulations point toward new construction. A parcel like this is an architects dream providing the size necessary to create what anyone might want, elevation allowing cascading terraces down to the waterfront and multiple, potential “footprints” for accessory dwellings, accessory structures and more. Bay Shore Road has become an eclectic location for the grandest homes in Sarasota. This has led to sales over 10 million dollars and have exceeded 15 million. But you could not put a price on the most spectacular neighbor, Ca’ d Zan. John Ringling’s gilded Venetian palace anchors the neighborhood to the north and downtown Sarasota is just 2 miles south. Other nearby cultural & educational institutions include the Ringling Museum of Art, the Asolo Theater of Performing Arts, the Sarasota Ballet, the Ringling College of Art & Design and our newest amenity, The Bay Park Conservancy redeveloping 53 acres of City waterfront into a world class public park.
4100 TEE RD, SARASOTA, FL 34235
$399,00013 Days on yellowkey MLS ID: A4694503
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1798 Built: 1971 Tax: $3,991 (2025)Community: Kensington ParkSingle Family
Taxes:$3,991
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Tucked away at the end of a quiet cul-de-sac in a charming neighborhood, this beautifully renovated 4-bedroom, 2-bath residence offers the perfect blend of style, comfort, and convenience. Ideally located just minutes from Downtown Sarasota, world-renowned beaches, dining, shopping, and cultural attractions, this move-in-ready home is a rare find. Inside, enjoy a light and inviting interior featuring brand-new luxury vinyl wood-look flooring, fresh interior paint throughout, and a thoughtfully redesigned floor plan with four true bedrooms — a feature not often found. The fully updated kitchen showcases new cabinetry, modern finishes, and a fresh contemporary feel perfect for everyday living and entertaining alike. Both bathrooms have been tastefully renovated with stylish updates and timeless appeal. The spacious garage offers excellent storage and functionality, complete with a laundry sink, washer, and dryer. Additional highlights include a newer roof and quality renovations throughout, providing peace of mind for years to come. Privately positioned at the end of the street with minimal traffic, this home combines the tranquility of a tucked-away setting with close proximity to everything Sarasota has to offer.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Courtney Tarantino (941-893-7203)
4813 BENCHMARK CT, SARASOTA, FL 34238
$949,00030 Days on yellowkey MLS ID: A4690988
4 Days Off yellowkey (back on 5/23/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2809 Built: 1997Monthly Fee: $275 Tax: $5,549 (2025)Community: Turtle RockSingle Family
Taxes:$5,549
Remarks: Under contract-accepting backup offers. Come live the Florida lifestyle to the fullest in this truly exceptional CUSTOM -BUILT residence, ideally positioned behind the gates of the highly sought-after Turtle Rock community in Palmer Ranch. Every once in a while, a home comes along that stands apart from the rest—this is unquestionably one of those rare opportunities. Offering an expansive 4-bedroom, 3-bathroom layout with a SPACIOUS 3 CAR GARAGE, this residence is perfectly situated on a quiet street where homes seldom become available, and showcases TRANQUIL LAKE VIEWS paired with a BRAND NEW ROOF (2023) for added peace of mind. From the moment you arrive, the home’s superior curb appeal is evident. An extra-wide pavered driveway provides ample parking and leads you to an elegant double-door entry, enhanced by majestic Royal Palms trees and a charming private courtyard framed by an iron gate—a welcoming prelude to the interior that awaits. Step through the Brazilian oak doors with leaded glass accents and be immediately captivated by the grand foyer, where soaring ceilings, double tray details, and crown moldings create a refined and inviting atmosphere. The thoughtfully designed split floor plan offers optimal privacy, with the primary suite on one side and guest accommodations on the other. The generously sized primary suite serves as a peaceful retreat, complete with dual walk-in closets featuring custom built-ins and a spacious en-suite bath with a roomy walk-in shower with a frameless shower door. At the heart of the home, the open and inviting kitchen is perfectly suited for both everyday living and entertaining, featuring rich warm wood cabinetry, granite countertops, stainless steel appliances, and a natural gas range (Turtle Rock is a natural gas community). Three additional guest bedrooms—one currently utilized as a home office—along with two additional bathrooms, including a CONVENIENT pool bath, ensure comfort and flexibility for family and guests alike. Step outside to your OWN PRIVATE OASIS. The OVERSIZED screened lanai offers exceptional privacy with no direct views from the neighboring homes, ( both adjacent homes have court yard style pools, enhancing this welcoming residence's privacy ) creating a serene setting to relax and unwind. Enjoy the resurfaced, natural gas-heated pool WHILE TAKING IN THE BREATHTAKING LAKE VIEWS, where both sunrises and sunsets provide a stunning daily backdrop.Enjoy an "al fresco" dining experience with the fully automated lanai awning system. Other great features include, a natural gas, tankless instant water heater , Two AC systems for extra energy savings, the home has also been repipped for additional peace of mind. Residents of Turtle Rock enjoy a vibrant lifestyle with access to miles of scenic walking and biking trails,( The Lagacy Trail is also literrarly around the corner) a community center with a heated pool, tennis and pickleball courts, and beautifully maintained natural surroundings. All of this is just minutes from premier shopping, dining, top-rated schools, and the world-renowned Siesta Key Beach. This is a rare opportunity to own a home that combines space, privacy, location, and lifestyle in one of Sarasota’s most desirable communities. Schedule your private showing today.
Listing is courtesy of: CP REALTY INTERNATIONAL (941-685-8441)
Listing Agent: Claude Pierre (941-685-8441)
1204 HILLVIEW DR, SARASOTA, FL 34239
$18,900,000126 Days on yellowkey MLS ID: A4677344
Bed: 6 Bath: 8.0 Gar: 3 Liv Area Sq Ft: 7687 Built: 2008 Tax: $85,253 (2025)Community: Harbor AcresSpa: NoSingle Family
Taxes:$85,253
Remarks: Set within the prestigious Harbor Acres neighborhood—one of Sarasota’s most sought-after waterfront enclaves, this stunningly renovated gated estate occupies an exceptional lot on the Hillview Point with 171 feet of Sarasota Bay frontage and sweeping, unobstructed panoramic views. This magnificent two-story residence, designed by renowned architect Cliff Scholz, offers six bedrooms, seven full baths, and two half baths, complemented by an oversized three-car garage—providing a seamless blend of architectural grandeur and everyday livability. A dramatic two-story foyer welcomes you inside, where expansive west-facing walls of glass capture breathtaking water vistas and bathe the home in natural light. The main level is thoughtfully designed for both refined entertaining and comfortable living, featuring a waterfront living room, an inviting family room, and an elegant dining room. At the heart of the home, the gourmet kitchen showcases authentic zebrawood cabinetry celebrated for its exotic grain patterns and rich natural character, paired with Quartz countertops, a generous center island, premium appliances, and a breakfast area with a dedicated coffee bar—perfectly suited for intimate mornings or hosting on a grand scale. Additional highlights include a private library, executive office, a full-service bar, and secondary laundry room. The owner’s suite is a serene waterfront sanctuary, offering tranquil Sarasota Bay views, dual spa-inspired bathrooms, three walk-in closets, and a private laundry—creating a truly elevated retreat experience. Ascend the sweeping staircase or take the private elevator to the second level, where five beautifully appointed guest suites provide exceptional comfort and privacy. Two of these suites, along with the upstairs library, enjoy coveted waterfront positioning and direct access to a spectacular 35-foot terrace overlooking Sarasota Bay—an ideal setting for morning coffee, sunset cocktails, or quiet moments of reflection. An additional laundry room on this level adds to the home’s thoughtful functionality. Outdoor living is equally impressive. Host unforgettable gatherings on the expansive 76-foot elevated terrace with summer kitchen or unwind poolside at the resort-style terrace featuring a 55-foot heated pool and generous lounging areas. For boating enthusiasts, private dockage delivers effortless access to Sarasota Bay and the open waters beyond. This extraordinary waterfront estate embodies the very essence of Sarasota luxury—where timeless design, exceptional craftsmanship, and unparalleled coastal views come together in a truly rare offering.
Listing Agent: Stephanie Church (941-724-5448)
6290 BUCKINGHAM ST, SARASOTA, FL 34238
$500,000113 Days on yellowkey MLS ID: A4681325
REDUCED by $30,000 (5.7%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1835 Built: 1997Monthly Fee: $83 Tax: $3,021 (2025)Community: Wellington ChaseSpa: NoSingle Family
Taxes:$3,021
Remarks: Under contract-accepting backup offers. Welcome to your private oasis in the heart of Wellington Chase, one of Sarasota’s most desirable and centrally located communities. This charming 3 bedroom, 2 bathroom pool home presents a rare opportunity to own a piece of paradise where you can add your own personal touches to create the ultimate dream home. From the moment you step inside, you are greeted by a bright and airy living room that feels spacious, thanks to large sliding glass doors that lead directly to the screened-in pool area. This seamless indoor-outdoor flow is perfect for entertaining or simply enjoying the peaceful, sun-drenched Florida lifestyle. The floor plan is thoughtfully designed for both comfort and functionality, featuring a dedicated dining space and a kitchen equipped with Corian countertops and a convenient closet pantry. Nearby, the oversized laundry room with a brand NEW washer and dryer and built-in shelving offers plenty of extra storage and utility space. The master suite serves as a true sanctuary, boasting a massive walk-in closet and a master bathroom complete with dual sinks, a relaxing soaking tub, and a separate shower. Ensuring privacy for family or guests, the second and third bedrooms are joined by a Jack-and-Jill bathroom. Outside, the backyard is a hidden gem, offering a level of privacy that is hard to find. Whether you are lounging by the pool or enjoying the lush surroundings, this space feels like a personal retreat. Best of all, Wellington Chase offers incredibly low annual HOA fees while keeping you close to everything Sarasota is famous for; including world-class beaches, top-rated schools, and the Legacy Trail. This home is ready for its next chapter and is waiting for someone to unlock its full potential in a premier location.
Listing Agent: Mairead Smialek (847-334-4848)
2639 BOUGAINVILLEA ST, SARASOTA, FL 34239
$844,999110 Days on yellowkey MLS ID: A4681333
REDUCED by $19,001 (2.2%) on 04/23/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2435 Built: 1960Monthly Fee: $17 Tax: $8,234 (2025)Community: South GateSpa: NoSingle Family
Taxes:$8,234
Remarks: Under contract-accepting backup offers. Enjoy life to the fullest in this 3 bedroom, 3 bath mid-century modern style ranch home, nestled on a near 1/3 acre lot in the sought-after South Gate neighborhood, offering over 2,400 square feet of architecturally updated and meticulously maintained living space. From the moment you arrive, this private sanctuary impresses with iconic palm trees, a custom circular paver driveway, professionally lit landscaping, and a vivid one-of-a-kind patio with a colorful front entry. Inside, the light and bright open-concept floorplan showcases flawless terrazzo flooring and a striking modern contrasted kitchen with stainless steel appliances and a large island with bar-top seating. The kitchen and living areas flow seamlessly into the family and dining room, providing ample gathering space and an entertainment center ready for modern electronics. French doors lead to an almost 40-foot screened lanai overlooking a professionally manicured, fenced, and irrigated backyard accented with coping. The primary bedroom features a private exterior entrance, space for a desk or seating area, and an en-suite bath with a walk-in closet with built-in shelving and safe, a wall-to-wall glass shower with multiple massage jets and bench seating, and a separate water closet. Two additional contemporary bedrooms and bathrooms are located on the opposite side of the home. The remodeled two-car garage is climate controlled and includes a full laundry room with utility sink. Major upgrades and systems include a standing seam metal roof, hurricane-rated impact windows and garage door, tankless water heater, whole-home generator, updated electrical system with new controls, and a plumbing system rerouted with exterior clean-outs for easy access. The home includes both a 100-gallon and 500-gallon propane tank, with the generator operating from the 500-gallon tank and the water heater capable of running from either tank, all serviced on a regular basis. Indoor comfort is enhanced by a professionally maintained HVAC system with in-duct air purification, including UV lighting and a whole-home purification system. Smart-home features allow remote control of the irrigation system, HVAC, alarm system, front door lock, and security cameras. The driveway has been recently resealed, and exterior security lighting surrounds the home. Optional membership to the South Gate Community Association offers social activities and pool access at the historic community center for a nominal fee. Ideally located just minutes to golf courses, boat clubs, Downtown Sarasota dining, shopping, nightlife, cultural events, and the world-famous beaches of Siesta Key.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alan Macloughlin (941-780-8628)
4244 CENTRAL SARASOTA PKWY #726, SARASOTA, FL 34238
$300,00012 Days on yellowkey MLS ID: A4694637
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1147 Built: 1999 Tax: $3,300 (2025)Community: Plaza De FloresCondo
Taxes:$3,300
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Laurel Nokomis Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to Plaza De Flores, a gated enclave tucked into the heart of Palmer Ranch where palm-lined courtyards, a tiled fountain, and lush tropical landscaping set a serene, resort-like tone the moment you arrive. This second-floor, two-bedroom, two-bath residence lives bright and open, with soaring vaulted ceilings and neutral tile laid on the diagonal carrying you through a spacious great room bathed in natural light. Fresh paint throughout and new ceiling fans give the home a crisp, move-in-ready feel, while solid concrete block construction keeps it remarkably quiet and well insulated from the world outside. At the center of it all is a thoughtfully updated kitchen, where granite counters, white shaker cabinetry, and a warm stone backsplash pair beautifully with the appliances and a breakfast bar made for easy mornings. Smart touches like an added custom cabinet with a pull-out, open wood shelving, and a window above the sink make the space as functional as it is inviting, all flowing into the dining and living areas so no one ever feels far from the conversation. The primary suite is a true retreat, generously sized with a large closet and an ensuite bath featuring a dual-sink vanity, fresh mirrors, and a beautiful custom marble walk-in shower with a frameless glass enclosure and built-in niche. A comfortable guest bedroom and second full bath with a tub-and-shower combination offer private, welcoming accommodations for visitors. A dedicated in-unit laundry closet with a newer washer and dryer adds everyday ease, and recent upgrades including a 2025 tankless water heater and a 2024 tile roof bring real peace of mind. Just off the living room, a large screened lanai is the home's quiet showstopper, finished with cool tile underfoot, two sets of sliding glass doors, new screening, and custom pull-down shades for sun and privacy. It is the perfect perch for morning coffee or for unwinding to the area's incredible evening sunsets over the treetops. Beyond your door, Plaza De Flores delivers the lifestyle, with a sparkling community pool and spa, a tennis court, charming gazebos, and a clubhouse complete with a fitness room, library, and full kitchen. Newer carports and freshly repaved parking round out a community that is beautifully maintained. The location is hard to beat, moments from the Legacy Trail, Oscar Scherer State Park, and nearby kayak launches, with the dining and shopping of Gulf Gate and downtown Sarasota an easy drive away. When the beach calls, Siesta Key, Nokomis, Venice, and Caspersen are all within reach. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.*
Listing Agent: Toni Zarghami (941-248-2147)
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