Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
3751 S SCHOOL AVE #29, SARASOTA, FL 34239
$124,999169 Days on yellowkey MLS ID: A4670178
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1972 Tax: $1,874 (2025)Community: Sunland AptsCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,874
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Recently updated with a new roof in August and no assessments! Prime location! Welcome to Sunland Garden Apartments, a charming 55+ condo community nestled behind The Crossings at Siesta Key Mall, which is currently undergoing redevelopment into a vibrant mixed-use development featuring retail shops, restaurants, and offices. Notably, Connors Steak & Seafood and Cinebistro are expected to remain! Ideally situated in central Sarasota, just a short drive to our stunning beaches. This third-floor unit offers two bedrooms with en-suite baths, walk-in closets, and the largest screened porch in the community equipped with hurricane roll shutters. Enjoy peaceful courtyard views, along with access to the community pool, BBQ area, and shuffleboard court. Being on the top floor means there are no neighbors above. Both bedrooms and the living room have sliding glass door access to the spacious, covered porch. The unit features a new front storm door, replaced A/C and hot water heater (both in 2019) with biannual maintenance, and a brand-new garbage disposal. The laundry room and a large storage cage are just steps from your front door, near the elevator and stairs for easy access. Your assigned parking spot and adjacent guest parking are conveniently located right in front of the unit. Enjoy proximity to Sarasota’s vibrant downtown scene, less than 3 miles away, with numerous entertainment venues, dining, theaters, and art galleries. Numerous parks and golf courses are also just minutes from the community. This property is perfect as a part-time escape or full-time residence!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Angie Unzicker (941-809-9119)
850 S TAMIAMI TRL #831, SARASOTA, FL 34236
$319,90023 Days on yellowkey MLS ID: A4687444
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1224 Built: 1998 Tax: $4,340 (2025)Community: Central Park Sec 2 Ph 1Condo
Taxes:$4,340
Remarks: AS PROMISED! Townhome so close to downtown, but priced considerably less! This 2BR/2.5BA second floor "Fiji" model condo has newer laminate flooring throughout except for the staris and hallway, and is offered totally turnkey furnished with a couple of exceptions. Air Conditioner, Water Heater & Washer/Dryer stack unit replaced in 2023. 2 screened lanais (1 downstairs and 1 upstairs) and 2 separate master suites each with an ensuite bath. Great room downstairs, in-unit laundry and a powder room. kitchen with breatfast bar, plus a large closet under the stairs which could be used as a small office if needed. Each lanai has a small storage room too. Unit overlooks the tennis court (which is mainly used now for pickleball) and is just a short distance to the heated pool and spa, and clubhouse with small fitness center. Active friendly community with kayak launch available to residents. Property is currently leased until September 30, 2025, so could be ready for you to spend the next winter season here. Monthly fee includes cable, internet, water, sewer, trash removal, use of the community recreational facilities, professional management along with exterior maintenance and insurance. Right across the street is a Publix supermarket for your convenience. Close to Sarasota Memorial Hospital, Marie Selby Botanical Gardens, and just minutes away from St. Armand's Circle shopping and world-famous Siesta Key Public Beach. Sarasota'a active and cultural downtown is less than a mile away, offering fine dining and the best of the arts with the Sarasota Ballet, Van Wezel Performing Arts Center, the Sarasota Orchestra and much more live entertainment, along with a welcoming night life with something for everyone. Easy access to Sarasota International Airport. Perfect for year-round living, rental, or just for seasonal use. Pet friendly for owners.
Listing is courtesy of: CASEY REALTY CORPORATION (941-922-3391)
Listing Agent: Sue Jordan, Pa (941-920-6878)
1846 LINCOLN DR, SARASOTA, FL 34236
$2,095,000200 Days on yellowkey MLS ID: A4666374
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2618 Built: 1941 Tax: $17,701 (2024)Community: Avondale RepSingle Family
Taxes:$17,701
Tax Year: 2024
Remarks: Located in the highly sought-after Avondale neighborhood, this beautiful home has been extensively and tastefully UPDATED while maintaining its timeless charm. The SPLIT FLOOR PLAN includes three oversized ENSUITE BEDROOMS, an additional powder room, and a separate study/den conveniently positioned adjacent to the primary suite. FLOOR -TO-CEILING WINDOWS and an open floor plan allow for abundant natural light and views of the HEATED SALT WATER POOL, travertine deck, and generously sized backyard. Significant renovations in 2022 and 2023 include a new primary suite addition, an EXTENSIVE KITCHEN REMODEL WITH UPDATED PLUMBING AND ELECTRICAL and new flooring throughout. Exterior improvements are equally impressive, featuring IMPACT RATED WINDOWS AND DOORS throughout, enhanced landscaping with drainage systems, irrigation, front yard fencing, and updated lighting. Additional features include a 2-car garage with EPOXY FLOORING, METAL ROOF(2007/2021), and NEWER A/C (2021). The elevation of the house is above the based flood elevation and experienced no flood on the property during the 2024 storm season. Perfectly situated between Southside Village and the vibrant Downtown Sarasota Bayfront, the property is also located within the highly sought-after Southside Elementary School District, making it a premier choice for those seeking convenience, style, and location.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Fred Sassen (404-408-5956)
814 PARADISE WAY, SARASOTA, FL 34242
$1,995,00043 Days on yellowkey MLS ID: TB8483961
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1996 Built: 1962Monthly Fee: $17 Tax: $14,830 (2025)Community: Siesta IslesSingle Family
Taxes:$14,830
Elementary School: Phillippi Shores Elementary
Remarks: Exceptional Siesta Key waterfront residence offering a rare opportunity to own a turn-key, move-in-ready 4 bedrooms and 2 bathrooms home in one of the island’s most desirable and tranquil locations. Situated on a quiet cul-de-sac along a grand canal, the property provides privacy, scenic water views, and easy boating access to the Bay with only one higher bridge to navigate. A standout feature is the expansive Florida room, a light-filled living space designed for year-round comfort with floor-to-ceiling windows and seamless views of the water and surrounding greenery—ideal for relaxing or entertaining. The home has been thoughtfully maintained and is in excellent condition, allowing for immediate occupancy or rental income potential. Additional highlights include a heated pool, open and functional layout, and spacious living areas. Located just minutes from Siesta Key Beach and Siesta Key Village, this property combines prime location, generous living space, and waterfront charm, making it ideal as a primary residence, vacation home, or investment property. The house did not get flooded from the recent 2024 storms, a new roof was replaced in 2024, A/C was replaced in 2023, a pool heat pump was installed in 2023, re-piped and remodeled in 2022.
Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)
Listing Agent: Douglas Addeo (561-251-3408)
3360 HIGEL AVE, SARASOTA, FL 34242
$1,549,00066 Days on yellowkey MLS ID: A4682008
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2006 Built: 1960 Tax: $13,348 (2025)Community: Siesta Rev OfSingle Family
Taxes:$13,348
Remarks: Welcome to the home you've been waiting for! Your opportunity to own a fully updated island retreat pool home on world-famous Siesta Key. Imagine waking up minutes from powdery white quartz sand beaches, spending your afternoons poolside under the Florida sun, and ending your evenings with sunset walks along the water. This four-bedroom, three-bathroom home offers the flexibility, comfort, and lifestyle today’s buyers are looking for — whether as your primary residence, second home, or income-producing weekly rental. Inside, the home has been completely updated and thoughtfully designed for modern coastal living. With three separate living room areas, there is space for everyone to gather, relax, and spread out comfortably. Whether hosting friends, accommodating extended family, or welcoming vacation guests, the multiple living spaces provide both connection and privacy — a rare and valuable feature in Siesta Key homes. Natural light fills the interiors, creating a bright and inviting atmosphere that reflects the relaxed elegance of island life. Step outside to your new private pool and expansive outdoor living space designed for year-round enjoyment. Lounge poolside with morning coffee, host dinners, or unwind after a day at the beach. The seamless indoor-outdoor flow captures what Siesta Key living is all about. One of the most compelling features of this property is the one-week minimum rental allowance — a highly sought-after benefit on Siesta Key. Weekly rental flexibility allows you to generate strong short-term rental income while still enjoying personal time in your island home. With Siesta Key consistently ranked among the top beaches in the world, demand for updated weekly rental properties remains strong throughout the year. Residents of this neighborhood also enjoy private access to a beach area on the Pass — a peaceful waterfront setting perfect for sunset strolls, kayaking, paddle boarding, fishing, or simply relaxing away from the main beach crowds. Located just minutes from Siesta Key Village, you are close to dining, boutique shopping, live music, and vibrant island culture. Downtown Sarasota, marinas, golf courses, and Sarasota-Bradenton International Airport are all within easy reach. Whether you are searching for your own Siesta Key escape, a turnkey beach home with a pool, or a high-performing weekly rental investment in Sarasota, 3360 Higel Avenue offers the rare combination of lifestyle, flexibility, and location in one of Florida’s most coveted coastal communities.
Listing Agent: Natalie Gutwein (941-993-2660)
450 BEACH RD #3, SARASOTA, FL 34242
$1,685,00059 Days on yellowkey MLS ID: A4682792
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1386 Built: 1977 Tax: $10,325 (2025)Community: Place 450Condo
Taxes:$10,325
Remarks: NEW 3-Day RENTAL APPROVED INVESTOR ALERT! SELLER MOTIVATED RECENT BUILDING IMPROVEMENTS! Experience refined Gulf-front living in this exquisitely renovated and fully furnished 3-bedroom, 2-bath coastal residence just steps from the powdery-quartz sand of world-renowned Siesta Key Beach. With deeded beach access and sweeping Gulf panoramas, this boutique retreat captures the essence of cosmopolitan island living. Professionally managed with flexible weekly rentals and proven year-round income potential, this property offers both lifestyle and investment appeal. A short stroll leads to the vibrant dining, live music, and charming boutiques of Siesta Key Village, while a peaceful path through the coastal preserve brings you directly to the shoreline and its mesmerizing turquoise waters. Located within an intimate five-residence enclave, the condominium has been thoughtfully renovated to reflect effortless coastal elegance. The open-concept interior showcases warm wood finishes, stainless steel appliances, and a beautifully designed kitchen that flows seamlessly into the living and dining spaces. Gulf views from the kitchen and a private balcony for sunset evenings elevate the experience even further. This charming boutique building, perfectly located for convenience, has been fully upgraded with major safety and community improvements! A new grill and lounge area are underway, alongside exciting game and entertainment spaces making it the ultimate spot to relax, socialize, and have fun. Additional features include an enclosed one-car garage, an assigned open parking space, and access to a beautifully maintained community pool and outdoor entertainment area complete with grilling space, lawn games, and a convenient private storage unit. Whether as a private seaside sanctuary, legacy family retreat, or high-performing investment, this exceptional property blends prestige, privacy, and prime location on coveted Siesta Key. An extraordinary coastal jewel exclusively presented.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Anne Schneider (310-562-9710)
1630 STICKNEY POINT RD #101, SARASOTA, FL 34231
$269,90025 Days on yellowkey MLS ID: A4687288
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 800 Built: 1975 Tax: $2,758 (2025)Community: Castle Del MareCondo
Taxes:$2,758
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: Fantastic opportunity to own a beautifully updated 1BR/1BA first-floor unit in highly desirable Castel Del Mare! This light and bright residence features a tiled entry and kitchen, with attractive laminate flooring throughout the remaining living areas. The spacious kitchen is equipped with white cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining. The generously sized primary suite offers a private, updated en-suite bath complete with granite counters and a walk-in shower. What truly sets this unit apart is the in-unit washer and dryer—a rare convenience—along with an expansive double, oversized lanai just steps from the pool, creating the perfect space to relax and enjoy the Florida lifestyle. Castel Del Mare is a sought-after waterfront community ideally located just steps from the South Bridge to Siesta Key—offering the best of both worlds with easy access to the beach while enjoying the convenience of mainland living.
Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)
Listing Agent: Tony Andrews (941-921-5999)
1700 COVE II PL #324, SARASOTA, FL 34242
$849,90029 Days on yellowkey MLS ID: A4686403
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1720 Built: 1979 Tax: $7,965 (2025)Community: Midnight Cove IiTownhouse
Taxes:$7,965
Remarks: 3 BEDROOMS ON SIESTA KEY! ONE WEEK RENTALS! DEEDED BEACH ACCESS! WATER VIEWS! DOCKS AVAILABLE! Fantastic 3 bedroom townhouse at Midnight Cove II. 2nd and 3rd floor with lovely views and deeded beach access. Plenty of room for family and friends. Large sized living, dining and kitchen area. Perfect for family gatherings! Midnight Cove II offers deeded beach access directly across the street, marina with slips available, beautiful grounds, grilling area, tennis, pickleball, basketball court, fitness center and a large, heated pool. And bring the large pup too! Great association with onsite rental and management office. Fully funded reserves, milestone inspections complete! Turnkey furnished too! Walk to nearby dining, shopping, water sports and more. See this unit today!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Kim Sheridan (941-313-0262)
1894 LOMA LINDA ST, SARASOTA, FL 34239
$2,500,00033 Days on yellowkey MLS ID: A4685717
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1867 Built: 1954 Tax: $11,627 (2025)Community: Floyd & Cameron SubSingle Family
Taxes:$11,627
Remarks: Discover this UNIQUELY RARE OPPORTUNITY in the Coveted West of the Trail Neighborhood, amongst other very beautiful multi-million-dollar homes (two back-to-back lots, 1894 Loma Linda with frontage of 78’ and 1891 Prospect with frontage of 88’ with depth of 296’ for a total of both properties). The property on Loma Linda side is located on a quiet cul de sac at the end of the street. The two properties situated over half an acre have sewer and electric ready at the property and mature grand palms. Explore the potential opportunities this unique property offers! In combining these two lots you will have endless opportunities to customize the property to your vision. Whether you're seeking a family compound, multi-family development, or a dream home with additional income potential, this property delivers unmatched flexibility. Generate immediate income with existing rentals—Loma Linda is currently rented at $5,500 annually, and the adjacent lot is listed at $2,600 for annual rental—or live in one home while you plan and build on the other. With no flood zone concerns and established electrical and sewer connections, the property is ready to bring your vision to life. Location is exceptional with “A” rated Southside Elementary School, minutes to Southside Village shops and dining options, minutes to Sarasota Memorial Hospital, Downtown Sarasota and all the cultural amenities, Siesta Key beach and St. Armand’s Circle. Don’t miss this rare opportunity to create your perfect Sarasota retreat! Sold "as is."
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Beth Harris (941-321-7148)
1891 PROSPECT ST, SARASOTA, FL 34239
$2,500,00033 Days on yellowkey MLS ID: A4685965
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1091 Built: 1950 Tax: $10,285 (2025)Community: Floyd & Cameron SubSingle Family
Taxes:$10,285
3234 RESTFUL LN, SARASOTA, FL 34231
$399,000275 Days on yellowkey MLS ID: A4658946
0 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1985 Built: 1957 Tax: $3,115 (2024)Community: Restful PinesSingle Family
Taxes:$3,115
Remarks: Under contract-accepting backup offers. NEW PRICE! MOTIVATED SELLER! Welcome to this beautifully remodeled 4-bedroom, 3-bath home located in the desirable Restful Pines neighborhood in South Sarasota’s 34231 zip code. Offering nearly 2,000 square feet of modern living space, this home features two spacious living areas, generously sized bedrooms, and a flexible layout perfect for families or entertaining. Enjoy peace of mind with a brand-new roof and air conditioning system, both installed in 2024. The home has been upgraded throughout with new windows and stylish modern doors that enhance both energy efficiency and curb appeal. The kitchen shines with sleek quartz countertops, stainless steel appliances, and a contemporary design that flows seamlessly into the main living spaces. All three bathrooms have been beautifully updated with new vanities, glass-enclosed showers, and modern tile finishes. Set on a quarter-acre lot in Flood Zone X, this home has never flooded and offers a large backyard with plenty of room to add a pool, detached garage, or storage building. Best of all, there are no HOA or CDD fees, giving you the freedom to enjoy your property without added restrictions or costs. Enjoy the convenience of walking to A+ rated Riverview High School and nearby Red Bug Slough Preserve with scenic trails and nature views. You're also just minutes from Siesta Key’s world-famous beaches, Detwiler’s Farm Market, and the vibrant Gulf Gate dining and shopping district. With a motivated seller, this move-in ready home is a fantastic opportunity in one of Sarasota’s most convenient and sought-after locations!
Listing Agent: Roni-Marie Gold, Pa (941-487-0105)
5727 RIEGELS POINT RD, SARASOTA, FL 34242
$4,595,000626 Days on yellowkey MLS ID: A4618421
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 3616 Built: 1982Monthly Fee: $125 Tax: $19,884 (2024)Community: Riegels LandingSingle 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)
2989 GREENBRIAR ST, SARASOTA, FL 34237
$475,00037 Days on yellowkey MLS ID: TB8484848
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1237 Built: 1956 Tax: $843 (2025)Community: Greenbriar Homes 1St AddSingle Family
Taxes:$843
Elementary School: Alta Vista Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated TRUE MID CENTURY MODERN three-bedroom, two-bathroom home in Sarasota, where modern upgrades and thoughtful design come together to create a move-in-ready retreat. With a 2021 water heater, 2019 AC, and updates throughout the entire home, including brand-new luxury vinyl plank flooring, a completely renovated kitchen and bathrooms, new fixtures, and fresh landscaping, this property offers stylish living inside and out. An inviting, large front porch and new front door welcome you into a light and bright interior featuring an open floor plan. The spacious living room and dining room combination flows seamlessly into the stunning brand-new kitchen, designed with both functionality and style in mind. The kitchen features stainless steel appliances, a striking waterfall peninsula, new backsplash, and modern cabinetry, creating the perfect space for cooking, entertaining, and gathering. Both bathrooms have been fully renovated with new vanities, mirrors, lighting, and beautifully tiled showers with updated hardware. The primary suite offers double closets for ample storage and a private en-suite bathroom with a modern tiled shower, a lighted mirror, and new vanity. The additional bedrooms are nicely sized and share a fully updated bathroom with a tub/shower combination. Modern ceiling fans throughout the home add comfort, while the open layout enhances the bright, airy feel of the living spaces. Outside, enjoy a large fenced backyard with plenty of room for outdoor entertaining, gardening, or relaxing in the Florida sunshine. The home also features carport parking and additional storage space with A/C, providing flexibility for hobbies, storage, or workspace. Ideally located close to parks, dining options, and zoned schools, this home is also just 20 minutes from the vibrant shopping and dining of St. Armands Circle and the beautiful sands of Lido Key Beach. Enjoy the perfect combination of modern upgrades, comfort, and convenient Sarasota living. Schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (866-308-7109)
Listing Agent: Jeffrey Borham, Pa (866-308-7109)
3799 FLAMINGO AVE, SARASOTA, FL 34242
$18,500,000330 Days on yellowkey MLS ID: A4653658
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 8138 Built: 2016 Tax: $109,657 (2024)Community: Siesta Key / Bay IslandSingle Family
Taxes:$109,657
Remarks: Relax and take in the positive energy of Lotus-style living in this one-of-a-kind Balinese-inspired resort compound on north end of the world-famous Siesta Key. Nothing is needed to begin your Zen journey as the property comes completely furnished down to dishes, silverware and a Buddha living wall. The coexistence of indoor and outdoor space blends over 8,000 square feet of indoor space with thousands of square feet of patio and pool area. An outdoor oasis offering an infinity-edge pool with a swim-up bar, a sunken fire pit lounge within the pool, a spa, an outdoor kitchen, a dining pavilion with a living plant wall and an open-air living room with a fireplace. A koi pond with stunning built-in footbridges stretches nearly the entire length of the home, enhancing the serene ambiance of the outdoor space. Spanning over an acre with more than 700 feet of waterfront, the property is a masterpiece of luxury, designed for effortless relaxed living or island-style entertaining. A custom-designed driveway welcomes you to a breathtaking entrance, where waterfalls and fire features set the tone for the experience that awaits inside. Expansive walls of glass, seamless indoor-outdoor transitions, and rich wood and stone flooring throughout create a striking, cohesive aesthetic. The thoughtfully designed interior boasts multiple living spaces, including a game room, home theater, fitness room, meditation space and an impressive 8-plus-car garage. For the waterfront enthusiast, a well-equipped boat dock, a separate waterfront garage, and a paddleboard/canoe launch provide unparalleled access to pristine waters. This exceptional residence also features a newer seawall, full-house generator, Crestron home automation, a three-stop elevator and a whole-house reverse-osmosis water filtration system, ensuring convenience and peace of mind. An island paradise, this estate offers unmatched privacy while remaining just moments from Sarasota’s vibrant shopping, dining and world-renowned cultural attractions. Don’t miss this rare opportunity to own a move-in-ready masterpiece on Siesta Key – home to the #1 beach in the USA (Tripadvisor).
943 POMELO PL, SARASOTA, FL 34236
$4,950,00038 Days on yellowkey MLS ID: A4685163
2 Days Off yellowkey (back on 3/30/2026)
Bed: 5 Bath: 5.0 Liv Area Sq Ft: 5764 Built: 2025 Tax: $15,949 (2025)Community: Prime SubSingle Family
Taxes:$15,949
Remarks: Take advantage of a rare opportunity to own a thoughtfully remastered residence West of the Trail, perfectly positioned in one of Sarasota’s most desirable neighborhoods, Hudson Bayou. Rebuilt by Nautilus Homes, this exceptional single-family home offers over 5,700 square feet of refined living space, creating a rare chance to own a new home custom designed and built with intention and quality throughout. This expansive residence features five bedrooms, four full baths, and two half baths, including an optional second primary suite or private in-law suite, offering flexibility for multi-generational living or extended guests. A primary suite on the main level opens to its own private screened terrace, creating a tranquil retreat. The first floor also includes a dedicated office, ideal for working from home. The interior showcases timeless finishes, high-end materials, and abundant natural light throughout. At the heart of the home is a stunning chef’s kitchen with premium appliances, generous prep space, and a walk-in pantry, seamlessly connecting to the main living and entertaining areas. Multiple screened porches and terraces extend the living space outdoors, where a private tropical oasis awaits. The beautifully landscaped backyard features a resort-style pool and spa, surrounded by lush tropical plantings that create a private secluded setting for relaxation and entertaining. Perfectly sited on a large lot directly across from Pomelo Park, the home enjoys both privacy and green park views, as well as a generously large front yard. This coveted location places you in one of the few walkable neighborhoods to downtown Sarasota and Southside Village, with easy access to boutiques, restaurants, and everyday conveniences. Combining timeless design, exceptional craftsmanship, and an unbeatable location, this remarkable residence presents a rare West of the Trail opportunity to create your ideal Sarasota lifestyle.
Listing Agent: Jennifer Linehan (941-266-7555)
3227 BENEVA RD #203, SARASOTA, FL 34232
$165,000228 Days on yellowkey MLS ID: A4663437
0 Days Off yellowkey (back on 3/29/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1979Monthly Fee: $425 Tax: $2,099 (2024)Community: Village Brooke Sec 3Condo
Taxes:$2,099
Elementary School: Wilkinson Elementary
Remarks: Under contract-accepting backup offers. ******PRICE IMPROVEMENT****** **Resort-Style Living at an Exceptional Value** Enjoy the best of Florida living in this beautifully located condo, just minutes from Siesta Key, Lido Key, and vibrant downtown Sarasota. With public transit and shopping just steps away, convenience meets coastal charm. This rarely available 2-bedroom, 2-bath residence offers low HOA fees and numerous recent updates, including a brand-new A/C system and appliances, fresh interior paint, and a modern raised ceiling in the kitchen that enhances the open feel. Relax or entertain in the spacious lanai featuring storm sliders—expand your living space year-round or open them to enjoy tranquil views of the pool and sparkling lake with water feature. Located on the second floor in the rear of Village Brooke, this unit includes a private parking space, ample guest parking, and a convenient storage room just outside the front door. Village Brooke is a meticulously maintained community offering two pools, tennis and pickleball courts, shuffleboard, and a large clubhouse complete with billiards and gathering spaces. Perfect as a full-time residence or seasonal retreat, this home is move-in ready and waiting for your personal touch. Opportunities like this don’t last—schedule your showing today!
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Jodi Fleming (941-993-6331)
1826 BOYCE ST, SARASOTA, FL 34239
$2,150,000109 Days on yellowkey MLS ID: TB8459204
4 Days Off yellowkey (back on 3/16/2026)
Bed: 5 Bath: 5.0 Liv Area Sq Ft: 3270 Built: 2001 Tax: $23,215 (2025)Community: HartsdaleSingle Family
Taxes:$23,215
Remarks: Under contract-accepting backup offers. Welcome to this stunning 5-bedroom, 5-bathroom home ideally located near the Hillview District, downtown Sarasota, and just minutes from to Southside Elementary School. Enjoy the best of “West of the Trail” living in this beautifully updated residence that blends timeless architectural charm with modern luxury. The home features a brand-new gourmet kitchen highlighted by a striking double island with quartz waterfall countertops, stainless steel appliances including a gas cooktop and hood, a wine refrigerator, and a custom buffet offering abundant storage. A true formal dining room provides the perfect setting for entertaining. Original travertine tile floors flow throughout the expansive first floor, leading to the primary suite with a large walk-in closet and a spa-inspired ensuite with direct access to the pool deck. The split floor plan also includes a private guest suite with its own ensuite bath. Floor-to-ceiling windows fill the home with natural light and showcase views of the exceptional backyard. Upstairs, you’ll find three additional bedrooms and two fully updated bathrooms. The backyard is truly a rare find—a private oasis featuring a spacious pool, covered lanai, pergola, outdoor shower, storage shed, and full fencing. With its generous size and proximity to downtown, this outdoor space is perfect for relaxing, entertaining, or creating lasting memories. This exceptional home offers comfort, elegance, and an unbeatable location—an opportunity not to be missed.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Mirvate Thrower (702-480-3086)
1500 COVE II PL #524, SARASOTA, FL 34242
$849,900108 Days on yellowkey MLS ID: A4676444
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1720 Built: 1979 Tax: $8,269 (2025)Community: Midnight Cove IiCondo
Taxes:$8,269
Remarks: RARE OPPORTUNITY TO OWN A 3 BEDROOM ON SIESTA KEY! With Deeded beach access and one-week rentals! Maximize your investment while enjoying this fantastic 2 level townhouse in Midnight Cove II. Enjoy the views from your screened lanai or open air balcony on the second level. This unit offers space! Great sized living and dining areas, nice large, bright kitchen with updated appliances, powder room on the main level plus 2 more full baths upstairs. In unit laundry, deeded covered parking and offering a great rental history! Ideally located for quick deeded access to Crescent Beach just across the street! Midnight Cove II is a highly desirable community offering a marina with slips available and direct access to the intracoastal. Other amenities include tennis, pickleball, basketball court, fitness center and large heated pool. In addition, there is a grill and picnic area, car wash, pet walk, canoe storage and more! The property features beautiful mature landscaping with frontage on the intracoastal with paths and seating throughout the property. Midnight Cove II offers fully funded reserves, onsite rentals and management, and a rental friendly environment to maximize your income. Milestone Report is complete. Roof was replaced in fall of 2025 as well. Offered turnkey furnished with a small list of exceptions. Great opportunity - don't miss it!
1401 KENILWORTH ST, SARASOTA, FL 34231
$7,950,00095 Days on yellowkey MLS ID: A4676504
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 4042 Built: 2024Monthly Fee: $333 Tax: $32,760 (2025)Community: Oyster Bay LandingsSingle Family
Taxes:$32,760
Remarks: Tucked behind the gates of Oyster Bay Landings, the only gated community in Oyster Bay Estates, this one-of-a-kind 2024 Sweet Sparkman–designed residence offers exceptional privacy and boating access in a premier West of Trail location. One of just 12 homes in this intimate enclave, the property includes a deeded boat dock along a protected cove on Roberts Bay with dual water inlets leading directly out to the bay. At the end of a quiet dead-end street surrounded by boatable water, the 4,042-square-foot residence (6,678 square feet total) features clean-lined contemporary architecture, floating stairs with glass railings, an elevator to all levels and walls of glass that fill the interiors with natural light. Premium finishes include a custom European kitchen with DOCA cabinetry and porcelain countertops, LED lighting throughout, motorized shades and a whole-house generator. Balconies on second and third floors frame views toward Roberts Bay. The West of Trail address places you close to the best of Sarasota. The Field Club is within short distance, Publix is one mile away, Sarasota Memorial Hospital is only two miles north, downtown Sarasota is about three miles, and Siesta Key Beach, with its world-famous white quartz sand, is only five miles from your door. A unique, modern, coastal home with gated privacy, waterfront access and everyday convenience in one of Sarasota’s desirable neighborhoods. Inquire about the adjacent lot to the west, an opportunity to expand or create a private estate compound, while preserving uninterrupted waterfront views.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Andrew Tanner (941-539-0998)
2170 ROBINHOOD ST #C1406, SARASOTA, FL 34231
$1,095,00068 Days on yellowkey MLS ID: A4681719
0 Days Off yellowkey (back on 2/9/2026)
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1465 Built: 2026 Tax: $46,289 (2025)Community: Sarasota Bath And Racquet Club, A CondominiumCondo
Taxes:$46,289
High School: Booker High
Remarks: Under Construction. Pre-construction. Experience refined luxury living at Bath & Racquet Residences, where modern elegance meets Sarasota’s storied legacy. This spacious three-bedroom, 2.5-bath residence features floor-to-ceiling windows, custom Italian cabinetry, quartz countertops, premium Bosch appliances, and serene views overlooking the beautifully landscaped courtyard. A separate laundry room is one of the many thoughtful design elements enhancing everyday comfort. Beyond your doorstep, enjoy an unparalleled collection of resort-style amenities. The community and club feature a private pool, expansive two-acre park, dog park, playground, and a scenic 1-kilometer walking trail—perfect for an active outdoor lifestyle. Sports and wellness enthusiasts will appreciate 13 tennis courts, 2 pickleball courts, 4 panel courts, a resort-style club pool, on-site restaurant, state-of-the-art fitness center, and a full-service wellness spa. Located just 4 miles from the world-famous Siesta Key beaches and 3 miles from vibrant Downtown Sarasota, this address offers the perfect blend of luxury, convenience, and coastal sophistication. Bath & Racquet Residences presents a unique opportunity for both full-time residents and investors, with short-term rentals permitted (7-night minimum), offering flexibility and income potential. Under the guidance of Tommy Haas, former World No. 2 and official club ambassador, this iconic redevelopment reimagines the historic Bath & Racquet Club, originally founded in 1969. Once the home court of tennis legends such as Chris Evert and Martina Navratilova, the property now enters a new era—honoring its rich heritage while embracing modern elegance, wellness, and active living. Designed by the acclaimed Halflants + Pichette Architects, Bath & Racquet Residences and Club presents 256 luxury condominiums with low HOA fees.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Cari Miller (203-722-4509)
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