Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
2170 ROBINHOOD STREET #A3-305, SARASOTA, FL 34231
$477,4401230 Days on yellowkey MLS ID: A4558375
3 Days Off yellowkey (back on 5/5/2023)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 744 Built: 2023Community: Sarasota Bath And Racquet, A CondominiumCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$0
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Pre-Construction. To be built. One or more photo(s) has been virtually staged. Preconstruction. To be built…Welcome Home to the Active lifestyle of the new Bath and Racquet Community available now for pre-sale. The new iconic First of its kind, Bath and Racquet Residences and Club consists of 256 condominiums featuring 1,2, and 3 bedroom units built around the Brand new Bath and Racquet tennis facility & state of the art Pickleball courts. This beautiful complex features a residences swimming pool, 1 kilometer walking trail, playground, dog park, cabanas, and the option to be a member of the exclusive Bath and Racquet Club, which will feature multiple Tennis and Pickleball courts, Resort style swimming pool, a restaurant and a fitness center. Pickleball courts will be available both outdoor and indoor. We are approximately 4 miles to the award winning Siesta Key beaches, 3 miles to downtown Sarasota, right next to Trader Joe's Grocery, and walking distance to CineBistro Cinemas and many restaurants. This luxurious community features floor to ceiling windows, a superb kitchen appliance package, Quartz countertops and a washer and dryer hook up in all of the units. Elevators and covered parking is also part of this world class project. Priced from the mid $400,000s, Homebuyers have a selection of 29 different floor plans and the option to lease their unit for seven night minimum stay.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Tanya Keith (817-995-1559)
2170 ROBINHOOD STREET #A3-301, SARASOTA, FL 34231
$483,7901230 Days on yellowkey MLS ID: A4558370
0 Days Off yellowkey (back on 4/8/2023)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 754 Built: 2023Community: Sarasota Bath And Racquet, A CondominiumCondo
Listing Agent: Michelle Shiver (352-895-5779)
2170 ROBINHOOD STREET #A3-205, SARASOTA, FL 34231
$477,4401230 Days on yellowkey MLS ID: A4558331
3 Days Off yellowkey (back on 4/25/2023)
Remarks: Pre-Construction. To be built. One or more photo(s) has been virtually staged. Preconstruction. To be built…Welcome Home to the Active lifestyle of the new Bath and Racquet Community available now for pre-sale. The new iconic First of its kind, Bath and Racquet Residences and Club consists of 256 condominiums featuring 1,2, and 3 bedroom units built around the Brand new Bath and Racquet tennis facility & state of the art Pickleball courts. This beautiful complex features a residences swimming pool, 1 kilometer walking trail, playground, dog park, cabanas, and the option to be a member of the exclusive Bath and Racquet Club, which will feature multiple Tennis and Pickleball courts, Resort style swimming pool, a restaurant and a fitness center. Pickleball courts will be available both outdoor and indoor. We are approximately 4 miles to the award winning Siesta Key beaches, 3 miles to downtown Sarasota, right next to Trader Joe's Grocery, and walking distance to CineBistro Cinemas and many restaurants. This luxurious community features floor to ceiling windows, a superb kitchen appliance package, Quartz countertops and a washer and dryer hook up in all of the units. Elevators and covered parking is also part of this world class project. Priced from the $400,000s, Homebuyers have a selection of 29 different floor plans and the option to lease their unit for seven night minimum stay.
2170 ROBINHOOD STREET #A3-201, SARASOTA, FL 34231
$483,7901230 Days on yellowkey MLS ID: A4558304
4 Days Off yellowkey (back on 5/2/2023)
2170 ROBINHOOD STREET #A1-405, SARASOTA, FL 34231
$1,006,2251230 Days on yellowkey MLS ID: A4558143
3 Days Off yellowkey (back on 12/18/2023)
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1381 Built: 2023Community: Sarasota Bath And Racquet, A CondominiumCondo
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. One or more photo(s) has been virtually staged. Preconstruction. To be built…Welcome Home to the Active lifestyle of the new Bath and Racquet Community available now for pre-sale. The new iconic First of its kind, Bath and Racquet Residences and Club consists of 256 condominiums featuring 1,2, and 3 bedroom units built around the Brand new Bath and Racquet tennis facility & state of the art Pickleball courts. This beautiful complex features a residences swimming pool, 1 kilometer walking trail, playground, dog park, cabanas, and the option to be a member of the exclusive Bath and Racquet Club, which will feature multiple Tennis and Pickleball courts, Resort style swimming pool, a restaurant and a fitness center. Pickleball courts will be available both outdoor and indoor. We are approximately 4 miles to the award winning Siesta Key beaches, 3 miles to downtown Sarasota, right next to Trader Joe's Grocery, and walking distance to CineBistro Cinemas and many restaurants. This luxurious community features floor to ceiling windows, a superb kitchen appliance package, Quartz countertops and a washer and dryer hook up in all of the units. Elevators and covered parking is also part of this world class project. Homebuyers have a selection of 29 different floor plans and the option to lease their unit for seven night minimum stay.
2170 ROBINHOOD STREET #A1-207, SARASOTA, FL 34231
$1,167,6801230 Days on yellowkey MLS ID: A4558136
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1768 Built: 2023Community: Sarasota Bath And Racquet, A CondominiumCondo
2170 ROBINHOOD STREET #A1-206, SARASOTA, FL 34231
$1,153,7101230 Days on yellowkey MLS ID: A4558135
5 Days Off yellowkey (back on 6/28/2023)
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1746 Built: 2023Community: Sarasota Bath And Racquet, A CondominiumCondo
Remarks: Under contract-accepting backup offers.Pre-Construction. To be built. One or more photo(s) has been virtually staged. Preconstruction. To be built…Welcome Home to the Active lifestyle of the new Bath and Racquet Community available now for pre-sale. The new iconic First of its kind, Bath and Racquet Residences and Club consists of 256 condominiums featuring 1,2, and 3 bedroom units built around the Brand new Bath and Racquet tennis facility & state of the art Pickleball courts. This beautiful complex features a residences swimming pool, 1 kilometer walking trail, playground, dog park, cabanas, and the option to be a member of the exclusive Bath and Racquet Club, which will feature multiple Tennis and Pickleball courts, Resort style swimming pool, a restaurant and a fitness center. Pickleball courts will be available both outdoor and indoor. We are approximately 4 miles to the award winning Siesta Key beaches, 3 miles to downtown Sarasota, right next to Trader Joe's Grocery, and walking distance to CineBistro Cinemas and many restaurants. This luxurious community features floor to ceiling windows, a superb kitchen appliance package, Quartz countertops and a washer and dryer hook up in all of the units. Elevators and covered parking is also part of this world class project. Priced from the mid $400,000s, Homebuyers have a selection of 29 different floor plans and the option to lease their unit for seven night minimum stay.
2170 ROBINHOOD STREET #A1-201, SARASOTA, FL 34231
$695,2451230 Days on yellowkey MLS ID: A4558062
5 Days Off yellowkey (back on 8/23/2023)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1087 Built: 2023Community: Sarasota Bath And Racquet, A CondominiumCondo
Remarks: Under contract-accepting backup offers.Pre-Construction. To be built. One or more photo(s) has been virtually staged. Pre-construction. To be built…Welcome Home to the Active lifestyle of the new Bath and Racquet Community available now for pre-sale. The new iconic First of its kind, Bath and Racquet Residences and Club consists of 256 condominiums featuring 1,2, and 3 bedroom units built around the Brand new Bath and Racquet tennis facility & state of the art Pickleball courts. This beautiful complex features a residences swimming pool, 1 kilometer walking trail, playground, dog park, cabanas, and the option to be a member of the exclusive Bath and Racquet Club, which will feature multiple Tennis and Pickleball courts, Resort style swimming pool, a restaurant and a fitness center. Pickleball courts will be available both outdoor and indoor. We are approximately 4 miles to the award winning Siesta Key beaches, 3 miles to downtown Sarasota, right next to Trader Joe's Grocery, and walking distance to CineBistro Cinemas and many restaurants. This luxurious community features floor to ceiling windows, a superb kitchen appliance package, Quartz countertops and a washer and dryer hook up in all of the units. Elevators and covered parking is also part of this world class project. , Homebuyers have a selection of 29 different floor plans and the option to lease their unit for seven night minimum stay.
6100 MIDNIGHT PASS RD #201, SARASOTA, FL 34242
$6,499,000224 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
High School: Sarasota High
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)
3441 GULFMEAD DR, SARASOTA, FL 34242
$10,500,00062 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
Tax Year: 2025
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)
5543 ASHTON WAY #5543, SARASOTA, FL 34231
$275,000132 Days on yellowkey MLS ID: N6143396
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1232 Built: 1993Monthly Fee: $315 Tax: $3,561 (2025)Community: Ashton Lakes 8Spa: YesCondo
Taxes:$3,561
Elementary School: Gulf Gate Elementary
Remarks: Welcome to this charming 2 bedroom, 2 bath walk up condominium in the highly desirable Ashton Lakes community. This light and bright residence features high ceilings that create a spacious and open feel throughout the home. Enjoy relaxing on the screened lanai while taking in peaceful lake views and the natural beauty of the surroundings. The comfortable floor plan includes a spacious primary bedroom with a walk in closet and private ensuite bath, creating a quiet and inviting retreat. The guest bedroom is conveniently located near the second bathroom and can easily serve as a guest room or home office. Additional features include an inside laundry room and an assigned carport. Ashton Lakes is set on 33 acres of beautifully maintained grounds with four scenic lakes and offers a resort style lifestyle with a wide range of amenities. Residents enjoy two heated swimming pools, including one large pool with a lap lane, tennis courts, pickleball courts, shuffleboard courts, grilling areas, and a welcoming clubhouse that hosts an active social calendar during the winter season. The community is connected by a convenient footbridge to Merchants Mart shopping center where you will find CVS, Ace Hardware, a liquor store, Dollar Store, and the popular Detwiler’s Farm Market. Ideally located just 3.5 miles from the world famous Siesta Key Beach, this home also offers easy access to I 75 and US 41. Shopping, dining, schools, and hospitals are all within a short drive. The condominium fee includes cable TV, internet, water, trash, exterior and grounds maintenance, and an on site manager, providing convenience and peace of mind. Whether you are looking for a winter retreat or a full time residence, this lake view condominium offers a wonderful opportunity to enjoy the Florida lifestyle in a prime and convenient location.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rick Tritschler, Jr. (941-928-1292)
5780 MIDNIGHT PASS RD #110, SARASOTA, FL 34242
$1,299,000152 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Natalie Gutwein (941-993-2660)
1611 HYDE PARK ST, SARASOTA, FL 34239
$3,750,000154 Days on yellowkey MLS ID: A4683619
REDUCED by $449,000 (10.7%) on 04/06/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2545 Built: 1920 Tax: $6,507 (2025)Community: NoneSpa: YesSingle Family
Taxes:$6,507
Elementary School: Southside Elementary
Remarks: Located in Sarasota’s established West of Trail neighborhood, this gated and fenced 1920 Craftsman residence offers a rare double lot and a guest cottage. Originally constructed in 1920 and comprehensively renovated in 2025 and 2026, the property preserves its architectural character while integrating modern systems, finishes and upgrades including all impact windows and doors. Spanning 3,609 total square feet, the estate is designed for privacy and flexibility. The main residence includes three bedrooms and two and one-half baths. The primary suite is positioned on the main level with direct access to the pool and courtyard, along with a spacious walk-in closet. Large-format porcelain block flooring extends throughout, complemented by updated lighting and professionally curated design elements introduced during the full vintage renovation. The kitchen supports both daily living and entertaining, anchored by a substantial island with quartz countertops, new appliances and a natural gas five-burner range. A dining nook overlooks the pool and courtyard, while adjacent living and lounge areas create seamless gathering spaces. Outdoor living centers around a private courtyard featuring a heated saltwater pool and spa with rock fountain feature, outdoor kitchen, multiple balconies and sitting areas, a sweeping front porch and the landscape lighting is strategically set among the mature Florida landscaping. A custom-built treehouse fort and chicken coop contribute additional character to the grounds. A detached, air-conditioned two-car garage includes a self-contained guest cottage above with one bedroom, office and one bath, with additional covered parking offering flexibility for extended family, guests or potential rental income. Conveniently located near Hillview Street dining and shopping, Morton’s market, the bayfront, Downtown Sarasota and Southside Elementary School, this property combines preserved Craftsman architecture with modern livability in one of Sarasota’s most desirable in-town locations. Can be sold furnished.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Lori Carey, Llc (941-780-3427)
1804 N LAKE SHORE DR, SARASOTA, FL 34231
$4,995,000187 Days on yellowkey MLS ID: A4679067
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 6854 Built: 2004 Tax: $22,275 (2025)Community: Oyster Bay EstatesSingle Family
Taxes:$22,275
Remarks: A residence of sophistication and luxury, this exceptional home was thoughtfully designed to bring family and friends together—sharing good food, meaningful connection, and the enjoyment of elevated everyday living. Ideally located just 8 miles from Sarasota-Bradenton International Airport, 12 minutes to Siesta Key Beach, and 10 minutes to downtown Sarasota, the property is in close proximity to The Ringling, Van Wezel, Selby Gardens, Asolo, premier dining and shopping, The Field Club, and the Sarasota Yacht Club—creating a seamless blend of culture, convenience, and coastal lifestyle. Elegant yet warm and approachable, the home blends refined architecture with tropical elements, including stone columns, metal pergolas, concrete textures, and lush landscaping, creating a relaxed oasis unlike any other. A surrounding stucco wall enhances privacy, allowing you to unwind to the soothing sound of a tranquil fountain within a peaceful, secluded setting. The main living spaces were intentionally designed for gathering, featuring bead-board stained ceilings in the family room, formal living room, and dining area. The cook’s kitchen is both striking and highly functional, highlighted by a glazed pressed-tin ceiling, unpolished concrete floors, and views into the kitchen garden through multiple French doors and expansive windows—perfectly suited for both everyday living and entertaining.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Bridget Spiess (941-720-6304)
5600 BEACH WAY DR #201, SARASOTA, FL 34242
$575,000419 Days on yellowkey MLS ID: A4654536
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1259 Built: 1970Monthly Fee: $1,467 Tax: $5,918 (2024)Community: Beachway AptsSpa: NoCondo
Taxes:$5,918
Remarks: SELLER SAYS BRING ALL OFFERS! MAJOR PRICE IMPROVEMENT!! Reduced over 75k! Have you ever wondered what it's like to own a Siesta Key sunset? Throw on your swimsuit, grab a towel and take a short stroll across the street, because here at Beach Way, you can't get much closer! Embrace your very own next-level Florida lifestyle with this exceptional opportunity. This second floor 2-bedroom, 2-bathroom condo is ideally situated and directly across the street from the world-renowned Siesta Key Beach, continuously celebrated for its powdery soft, white quartz sands and clear waters. This property is being offered fully furnished and is move in ready, presenting a unique chance to personalize your very own dream retreat whether as a permanent residence or a vacation getaway. This unit beams with natural light throughout, showcasing its rare beauty. With a minimum lease period of one month, up to twelve times a year, it also offers potential for rental income. Rental Proforma attached. As you enter the front doors to this beach oasis, prepare to be impressed by an open-concept kitchen that seamlessly flows into the living and dining areas, extending out to a private screened-in lanai where you can take in partial glimpses of the Gulf, creating a perfect setting for relaxation and entertaining. Need a little space? Both bedrooms feature walk-in closets, providing ample storage and comfort. In addition, the unit overlooks the community's heated pool which is maintained at 85 degrees year-round. This well-maintained community was built in 1970, offering a host of amenities designed for convenience and leisure. Residents have access to a community room with a full kitchen for social gatherings, picnic and grilling areas, elevators, laundry facilities on each floor, and a personal storage unit. In addition, your deeded carport is located just steps from your front door, ensuring ease of access. Recent updates to building include a new roof in 2020, an updated elevator installed in 2019, re-plumbed stacks completed in 2018, the addition of new vinyl fencing in 2021. The quarterly condo association fee covers access to all the amenities, pest control, basic cable, water/sewer services, grounds maintenance, weekend on-site maintenance, and community insurance. Living on Siesta Key means more than just proximity to the beach; it's about embracing a lifestyle where every day feels like a vacation. Start your mornings with a peaceful walk along the shoreline, enjoy paddleboarding in the calm Gulf waters, or partake in beach yoga sessions at sunrise and drum circle Sundays. The island's laid-back atmosphere is complemented by its vibrant community, offering a mix of friendly full-time residents and seasonal visitors. Ready to venture out for some more fun? Siesta Key Village, just a short distance away, is the heart of the island's social scene. Here, you'll find an array of casual bars, eateries, and boutiques, perfect for evening outings or weekend brunches. The community's eclectic vibe ensures there's always something happening, from local festivals to live music events. Other close by attractions include the Ringling Bridge, Downtown Sarasota and St. Armands, close proximity to top rated schools and hospitals, SRQ Airport and University Town Center. Don't let another Season pass you by from owning your own slice of paradise in the sand. Schedule your showing today.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Ashley Nevadomski (941-769-7627)
1537 SIESTA DR, SARASOTA, FL 34239
$2,995,00082 Days on yellowkey MLS ID: A4692775
REDUCED by $105,000 (3.4%) on 05/29/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3727 Built: 2023 Tax: $31,404 (2025)Community: Sunset Bay SubSingle Family
Taxes:$31,404
Remarks: Welcome to 1537 Siesta Drive—an exceptional custom coastal contemporary residence ideally positioned between Downtown Sarasota and world-renowned Siesta Key Beach. Built in 2023, this stunning luxury home offers 4 bedrooms, 4 full baths, 2 half baths, a dedicated office, and over 3,700 square feet of thoughtfully designed living space. From the moment you enter, you’re greeted by soaring ceilings, rich hardwood flooring, and an open-concept floor plan flooded with natural light. The chef’s kitchen is a showpiece, featuring premium appliances, designer finishes, a wine refrigerator, and seamless flow into the expansive great room—perfect for both entertaining and everyday living. The first-floor primary suite is a private retreat, complete with spa-inspired bath, oversized walk-in closet, and outdoor access. Upstairs, additional ensuite bedrooms and private balconies offer elevated comfort with peekaboo Sarasota Bay views. Step outside to your resort-style backyard oasis featuring a heated saltwater pool, outdoor kitchen, putting green, expansive covered lanai for dining and lounging, and lush tropical landscaping—all designed for effortless Florida living. Additional highlights include a 3-car garage, metal roof, impact windows/doors, and a premier West of Trail location just minutes from Southside Village, downtown dining, marinas, and the beaches. Located within city limits, this home has operated as a successful short and long-term rental. Financials are available upon request. Luxury, location, and lifestyle converge at this remarkable Sarasota residence.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Tina Ellis (512-550-1117)
9200 MIDNIGHT PASS RD #25, SARASOTA, FL 34242
$429,00084 Days on yellowkey MLS ID: A4692488
REDUCED by $20,000 (4.5%) on 05/26/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 906 Built: 1972 Tax: $4,028 (2025)Community: Inlet AptsCondo
Taxes:$4,028
Remarks: Introducing Inlet Apartments - Siesta Key, a charming, quaint coastal retreat for a tropical vacation or a beach getaway. This second-floor, one-bedroom, one-bath is quiet and peaceful on the Blind Pass Lagoon at far south end of Siesta Key and just beyond your sliding glass doors. You will be instantly captivated by views of paddleboarders and kayaks going by, plus a heated swimming pool and a partial view of the Gulf. With 906 square feet, this residence is sold turnkey furnished, blending modern sophistication with relaxed coastal living. Contemporary new kitchen with new appliances, white quartz countertops, an oversized island, and crafted for effortless everyday living. The open-concept layout flows through the dining room, with a queen-size Murphy bed for extra guests, and living spaces, enhanced by luxury vinyl wood flooring and modern compact ceiling fans that adjust with touch of a button. Wake up to enchanting lagoon views in the tranquil primary suite, and beautifully updated bath. Go outside to a spectacular 200-square-foot screened lanai with pull-down shades for privacy, ideal for morning espresso, sunset cocktails or simply soaking in Siesta Key’s year-round beauty. There are convenient elevators, laundry facilities and assigned parking for each unit. HVAC in 2021, water heater in 2022. Life at Inlet boating amenities included private boat dockage for sailboats and powerboats up to 26 feet (first-come, first-serve basis). The Blind Pass Lagoon leads into Sarasota Bay and onto the Gulf. There are fishing, kayak storage and launch, waterfront pool, all just minutes from Turtle Beach and a short trolley ride to Crescent Key Village. This is more than a condominium at the beach, it’s a one-of-kind opportunity to own a piece of Siesta Key.
Listing Agent: Lisa Gullick (941-364-4000)
2690 TEMPLE ST, SARASOTA, FL 34239
$749,00060 Days on yellowkey MLS ID: A4695132
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1955 Built: 1986 Tax: $4,399 (2025)Community: Arlington ParkSpa: NoSingle Family
Taxes:$4,399
Elementary School: Alta Vista Elementary
Remarks: Welcome to a refined corner-lot home directly across from Arlington Park — one of Sarasota's most beloved neighborhood amenities. With 1,955 sqft of thoughtful living space, three bedrooms with walk-in closets, two updated baths, and a true 2-car garage, this property offers a combination that simply doesn't exist at this price point in the heart of the city. Every detail has been considered for Florida living. A 2022 metal roof with a 50-year warranty, two new Trane HVAC systems, impact-resistant windows, and a new water heater mean lower insurance, lower utilities, and no deferred maintenance. Located in evacuation Zone E and high and dry through every recent storm season, this is the rare home that lets you stop worrying about Florida ownership. Inside, character meets quality: stained solid wood doors, crown molding, hardwood bamboo flooring, a maple stairwell, and warm wooden ceilings. Walk out to a generous screened lanai, private hot tub, and lush tropical landscaping framed by palms, bamboo, and fruit trees. The fully fenced yard provides quiet privacy in a setting most Sarasota buyers only dream about. Step out your front door to Arlington Park's 50-meter lap pool, tennis courts, basketball courts, dog park, and walking trails. Sarasota Memorial Hospital, Southside Village dining, and downtown are all within minutes. Beaches at Siesta Key are a short drive away. Zoned for top-rated Southside Elementary (A-rated). A rare opportunity: turnkey, insurable, and irreplaceable location — directly across from the park.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Leslie Emery (941-400-9710)
1400 SIESTA DR, SARASOTA, FL 34239
$4,000,000153 Days on yellowkey MLS ID: A4678496
REDUCED by $500,000 (11.1%) on 05/28/2026
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 4660 Built: 1978 Tax: $22,924 (2025)Community: Acreage & UnrecSpa: YesSingle Family
Taxes:$22,924
Remarks: Welcome to 1400 Siesta Drive, where refined waterfront living becomes your everyday reality. This home is quietly tucked away behind a gated entrance, with an additional secondary gate providing exclusive access to the residence. Thoughtfully designed to embrace breathtaking, unobstructed views of Sarasota Bay, this modern residence is a showcase of light, space, and coastal elegance. Expansive floor-to-ceiling windows frame the ever-changing scenery, offering front-row views of passing boats and unforgettable sunsets from nearly every room. The primary suite is a private sanctuary, featuring a generous walk-in closet, a spa-inspired ensuite bath, and a dedicated office—each enhanced by stunning bay views. Outdoors, your personal oasis awaits with a heated pool, abundant sun-drenched lounging space, and a newly constructed dock ready for effortless boating and waterfront adventures. Ideally located near Sarasota’s world-class dining, shopping, and cultural attractions, this exceptional bayfront retreat offers the perfect balance of privacy and convenience. Offered turn-key furnished, this is a rare opportunity to step seamlessly into an elevated waterfront lifestyle.
Listing Agent: Matthew Voss (941-402-8799)
1022 S OSPREY AVE, SARASOTA, FL 34236
$1,599,000300 Days on yellowkey MLS ID: A4666624
4 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2284 Built: 1922 Tax: $4,185 (2024)Community: Rigbys SubSingle Family
Taxes:$4,185
Remarks: Situated in the highly desirable West of Trail neighborhood of Hudson Bayou, this fully restored 1922 residence is the perfect blend of historic charm and modern conveniences. The property offers 2,284 square feet with two bedrooms and two bathrooms in the main house, plus a one-bedroom, one-bathroom guest house. Renovations include a 2006 conversion of the garage into a guest house with a stucco privacy wall and Chicago brick driveway. In 2018, a spacious primary suite with double closets, a large bath, and French doors to a screened lanai was added. High ceilings, oversized impact windows, and refinished hardwood floors (2024) add to the home’s appeal. Recent updates include a recoated roof with a 10-year transferable warranty (2025), A/C (2023), water heater (2024), encapsulated crawlspace with dehumidifier (2024), foundation reinforcement with new support jacks (2024/2025), and hurricane-rated windows. The kitchen and dining area were fully renovated, featuring custom Conestoga cabinetry and designer appliances (2024/2025). Additional features include recessed lighting, custom closets, a Murphy bed, and a natural gas fireplace. A wellness room with an infrared sauna (2025) completes the interior. Exterior highlights include enhanced landscaping, three all-weather sheds, a pergola with natural gas grill hookups, and a serene brick courtyard surrounded by mature landscaping for privacy. The location is unparalleled, with proximity to Southside Village, the downtown Sarasota bayfront, St. Armands Circle, and the world-famous beaches of Lido and Siesta Key.
Listing Agent: Barbara May (404-822-9264)
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