Location: Sarasota , 34239
Do Not Show Listings
1966 WISTERIA ST, SARASOTA, FL 34239
$3,349,000254 Days on yellowkey MLS ID: A4668324
0 Days Off yellowkey (back on 6/9/2026)
REDUCED by $51,000 (1.5%) on 05/15/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3934 Built: 2026 Tax: $9,291 (2025)Community: Desota ParkSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,291
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. Set within the coveted West of the Trail enclave, this newly constructed estate is a striking statement of contemporary design and quality craftsmanship. Thoughtfully designed with clean architectural lines and seamless indoor-outdoor flow. Exceptional attention to detail throughout the residence with 4-bedrooms + office/den + bonus loft and 6-bathrooms. European engineered hardwood and porcelain tile flooring, 9-foot interior doors, recessed ceilings and lighting, and a Level 5 wall finish. PGT impact-resistant, Low-E windows and expansive sliding glass doors flood the interiors with natural light. The open-concept great room is a dramatic focal point, featuring a soaring double-height ceiling and a striking slatted wood accent wall. State-of-the-art kitchen with premium Thermador appliance package, custom Studio Luxe cabinetry by Miralis, quartz countertops, and a waterfall island with designer breakfast bar seating. Opening seamlessly to the dining area and covered lanai, creating an ideal setting for entertaining. Large walk-in pantry, dedicated laundry room with Electrolux washer and dryer, elevator-ready storage space, and private office ensure everyday convenience is met with elegance. The main-level primary suite serves as a private retreat, featuring a spa-inspired bathroom and professionally designed, boutique-style custom closet. The second level offers three en-suite bedrooms, each with beautifully finished bathrooms and walk-in closets. Bathrooms are appointed with quartz countertops, LED mirrors, frameless glass shower enclosures, designer tilework, multiple shower heads, built-in niches, and integrated bench seating. A spacious loft lounge includes a wet bar with beverage refrigerator. Two expansive balconies provide additional space for relaxation or entertaining. Enjoy serene moments by the heated saltwater pool and integrated spa, covered lanai with summer kitchen, including grill, sink and refrigerator, and a dedicated poolside half bath. The backyard is fully enclosed with a six-foot privacy fence and includes green space suitable for pets or gardening. The pool area is screen-enclosure ready for year-round enjoyment. Ideally located just minutes from downtown Sarasota, top-rated schools, dining, shopping, and cultural attractions, this exceptional residence offers a rare opportunity to enjoy sophisticated West of Trail living with uncompromising design integrity and quality. Offering a one-year full developer warranty.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Linda Driggs (941-374-2920)
2945 UPPER TANGELO DR, SARASOTA, FL 34239
$660,00060 Days on yellowkey MLS ID: A4690742
2 Days Off yellowkey (back on 6/9/2026)
REDUCED by $35,000 (5.0%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1439 Built: 1960 Tax: $6,132 (2025)Community: South GateSpa: NoSingle Family
Taxes:$6,132
Remarks: A rare offering within Sarasota’s desirable South Gate community, this meticulously restored Atomic Ranch embodies the essence of authentic Mid-Century Modern design. Revered as one of the foundational architectural styles of the 20th century, this residence has been thoughtfully preserved and elevated by discerning owners who understood the importance of honoring its original integrity. Ideally positioned in the heart of Sarasota, the home offers effortless access to world-class beaches, premier shopping and dining, top-rated schools, Sarasota Memorial Hospital, and the vibrant downtown district. The residence unfolds with a seamless, open-concept design, featuring three spacious bedrooms and two bathrooms, an inviting eat-in kitchen area, and expansive living areas designed for both comfort and entertaining. Walls of vintage sliding glass doors dissolve the boundary between indoors and out, opening to a generous pool terrace. Both covered and open-air, this creates a true indoor-outdoor lifestyle synonymous with classic Florida modernism. Authentic details remain beautifully intact, including original terrazzo flooring throughout, vintage architectural elements, and curated mid-century finishes that speak to the home’s heritage. An oversized garage, along with substantial fenced exterior space, provides flexibility for additional parking, including room for a boat or recreational vehicles. The home has been featured on Sarasota’s renowned “MOD Tour,” celebrated for its originality and preservation. As noted during the tour, the residence showcases vintage sliding glass walls, vibrant period kitchens and baths, and a fluid connection to the pool area. Carefully selected furnishings that reflect the era enhance the spirit of 1960s design. This is a truly special opportunity to own a piece of architectural history. Thoughtfully restored, exceptionally located, and ready to be experienced.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kelly Gettel (941-315-2525)
1870 JASMINE DR, SARASOTA, FL 34239
$2,860,00019 Days on yellowkey MLS ID: A4696318
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4165 Built: 2026 Tax: $7,657 (2025)Community: Hartland ParkSpa: YesSingle Family
Taxes:$7,657
Middle School: Booker Middle
Remarks: Experience modern luxury in this stunning new construction home located in Sarasota's highly sought-after West of Trail area. Offering 5 bedrooms, 5.5 bathrooms, and 4,165 square feet under air (5,614 total square feet), this exceptional residence combines custom design with everyday functionality. A grand entry welcomes you with soaring 12-foot ceilings, a spacious foyer, and a striking staircase that sets the tone for the home's contemporary elegance. The open-concept floor plan seamlessly connects the living, dining, and kitchen areas, creating the perfect space for entertaining and daily living. The chef-inspired kitchen features custom solid wood cabinetry, quartz countertops, premium Thermador appliances, and an oversized island designed for gathering with family and friends. A custom built-in feature wall in the living room adds both style and practicality. The bright first-floor office, complete with convenient bathroom access, can easily function as a guest suite and overlooks the beautifully landscaped front yard. Upstairs, 10-foot ceilings enhance the spacious feel throughout. The luxurious primary suite serves as a private retreat, accessed through double doors and opening to a private balcony that extends the second-floor living space. Each additional bedroom offers its own en-suite bathroom and walk-in closet, providing comfort and privacy for family and guests alike. A spacious second-floor laundry room with built-in cabinetry adds convenience. Outside, lush tropical landscaping and a full irrigation system complement the home's impressive curb appeal. Premium upgrades include impact-rated windows and doors, epoxy-coated garage floors, designer exterior lighting, pre-wiring for security cameras, and dual HVAC systems for enhanced comfort and energy efficiency. Ideally located West of Trail, this exceptional home is just minutes from downtown Sarasota, Sarasota Memorial Hospital, premier dining and shopping, local parks, and the world-renowned beaches of Siesta Key. Schedule your private showing today and discover the perfect blend of luxury, location, and modern living.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Samantha Jennen (941-321-6095)
1731 CUNLIFF LN, SARASOTA, FL 34239
$2,750,000112 Days on yellowkey MLS ID: A4684577
REDUCED by $45,000 (1.6%) on 06/02/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3239 Built: 1948 Tax: $9,273 (2025)Community: Mcclellan ParkSpa: NoSingle Family
Taxes:$9,273
Middle School: Sarasota Middle
Remarks: Hidden behind lush, curated gardens on a rare .34-acre parcel in McClellan Park, west of Osprey, this is more than a home—it’s a private in-town compound designed for those who value beauty, privacy, and a deeply connected lifestyle. A winding approach reveals a residence that unfolds with intention, where indoor and outdoor living exist in perfect harmony. At its heart, a 2024 architectural addition creates a breathtaking great room, where walls of glass disappear and the home opens entirely to a serene poolside setting—blurring the line between interior elegance and natural surroundings. The kitchen, dining, and living spaces flow effortlessly together, framed by garden views and natural light, creating an atmosphere that is both refined and grounding. This charming in-city home combines historic character with modern living. The property underwent a complete back-to-studs renovation, bringing it fully up to current Florida building codes with an official build date of 2013. You’ll enjoy the best of both worlds: a classic foundation refined by modern systems and standards. The main home spans 3,239 square feet with three bedrooms and three baths, fully customized with all the details valued by today’s buyers. Bonus rooms include an office/den, plus a sitting room in the primary suite. The striking 2024 addition, designed by Jimmy Thornton, features an open-concept great room, dining and kitchen with zero-corner, fully pocketing sliding glass doors, a dramatic architectural detail that opens the living space completely to the pool and outdoor areas. The kitchen is a true showpiece. It features high ceiling, super-organized European cabinetry with illuminated interiors, high-profile quartz and marble countertops, a glass window backsplash, and clerestory windows. Custom walnut open shelving add artistic flair. Appliance garages, interior drawers, workstation sink with two faucets, and oversize eat-in island add high-end functionality. The outdoors is incredibly lush and functional for an in-town location. Outdoor living rooms, fruit trees, trellises, native flowers, and an expansive food garden…plus a tree house for charm and fun. A heated saltwater pool anchors the backyard, while the detached guest house adds flexibility for recreation, home office, studio or guests. Energy independence is a standout advantage with a roof solar system, two-car solar carport, and backup batteries. It’s a home that powers itself confidently and efficiently. Location is a major benefit here, and one you’ll appreciate every day. From this quiet McClellan Park street, you can walk to Southside School (or the Pine View bus stop), reach Southside Village in 0.5 mile, and be at Sarasota Memorial Hospital in 1.0 mile. Everyday convenience continues just beyond the neighborhood with shopping centers, restaurants, Downtown Sarasota and Gulf beaches all within five miles. And for buyers who love being on the water, you can roll your kayaks to the bay. There’s a convenient put-in at the end of the street. McClellan park homes like this one are few and far between. Quiet street, large lot, guest house and a full renovation already done. If you want Sarasota West of Trail without compromise, this is your moment.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Andrew Tanner (941-539-0998)
1775 STAPLETON ST, SARASOTA, FL 34239
$1,499,000239 Days on yellowkey MLS ID: A4670359
REDUCED by $26,000 (1.7%) on 06/02/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2853 Built: 2007Monthly Fee: $568 Tax: $8,620 (2024)Community: Granada ParkSingle Family
Taxes:$8,620
Tax Year: 2024
Remarks: Between North Siesta Key and Oyster Bay, this coastal craftsman contemporary residence offers the leisure of a maintenance-free lifestyle in a desirable location. Visit nearby shopping and dining, or just a quick drive to Siesta Key Beach or downtown Sarasota. Positioned across from the community pool, the home offers easy-care landscaping complemented by a charming herb garden. Built of solid concrete block construction for lasting durability, recent improvements include new UV purification in air-conditioning units, a new roof and fresh exterior paint. The well-designed floor plan offers four bedrooms and three baths, with a flowing open layout that connects the great room, dining area and kitchen beneath high ceilings filled with natural light. A private guest suite above the garage provides flexible space for multi-generational living, a studio or fitness retreat. Throughout the home, refined details like solid-wood cabinetry, deep-trimmed windows and fine millwork reflect craftsmanship and quality. The great room impresses with a two-story ceiling and fireplace, while the kitchen showcases shaker cabinetry, quartz countertops, a center island, stainless-steel appliances and a walk-in pantry. Living in Granada Park provides the ease of a lock-and-go lifestyle in a gated, established neighborhood. This pleasant haven is conveniently just .3 miles from Publix, .5 miles to CineBistro, 1.3 miles to Southside Village, two miles to Sarasota Memorial Hospital, 2.6 miles to downtown Sarasota and five miles to Siesta Key Beach. It’s the best of Sarasota living, wrapped in a maintenance-free, West of Trail lifestyle.
1642 BAHIA VISTA ST, SARASOTA, FL 34239
$3,995,000262 Days on yellowkey MLS ID: A4667508
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3809 Built: 2025 Tax: $10,995 (2024)Community: Seminole HeightsSingle Family
Taxes:$10,995
Elementary School: None
High School: None
Middle School: None
Remarks: Stunning New Construction by Award-Winning Architect Dan Lear in coveted West of Trail Neighborhood** This meticulously designed luxury home offers the perfect blend of modern elegance and timeless sophistication. Near Selby Gardens, Morton's Market, and Sarasota Memorial Hospital, this exceptional property provides both convenience and style. Spanning over 3,800sqft of living area, this expansive residence boasts four spacious bedrooms, five full bathrooms, a enormous den with terrace, and a dedicated office space, all thoughtfully crafted for contemporary living. The grand, open-concept great room is the heart of the home, seamlessly floating over the pool area with a stunning large corner pocketing glass door that connects the interior to the beautifully landscaped outdoor oasis. The second floor features three guest suites, each with its own private terrace, offering tropical views and tranquility. The home's striking exterior showcases luxurious vein-cut travertine, creating a refined, sophisticated look. This is an extraordinary opportunity to move right in to a worry free one-of-a-kind masterpiece.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Victoria Lear (941-350-1064)
3119 ROSE ST, SARASOTA, FL 34239
$625,00035 Days on yellowkey MLS ID: A4694570
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1132 Built: 1968Monthly Fee: $8 Tax: $5,566 (2025)Community: South GateSpa: NoSingle Family
Taxes:$5,566
Elementary School: Wilkinson Elementary
Remarks: This beautifully renovated South Gate home is the definition of move-in ready. Freshly updated from top to bottom, this mid-century gem combines timeless style with modern comfort in one of Sarasota’s most desirable neighborhoods. Step through the striking new front door into a bright, welcoming living space featuring gleaming polished terrazzo floors, a charming bay window, and an effortless open-concept layout. New recessed LED lighting throughout adds warmth and sophistication to every room. The stunning kitchen is both stylish and functional, showcasing quartz countertops, a pearl tile backsplash, a spacious island, and new Samsung appliances. An inviting eat-in area overlooks the large screened lanai, while glass French doors create the seamless indoor-outdoor living experience that makes mid-century homes so special. Whether gathering around the island or hosting dinner in the adjacent dining space, this home was designed for entertaining. The thoughtfully updated bedrooms and bathrooms continue the home’s fresh, clean aesthetic, while the oversized indoor laundry room offers abundant storage, new Samsung washer and dryer, and durable epoxy flooring. Outside, the expansive screened lanai and newly refinished pool create the perfect private retreat. With new pool equipment and plenty of outdoor space for relaxing or entertaining, the backyard is ready to impress. Major upgrades include a new metal roof, impact windows and doors, newer AC system, all-new plumbing, and a newer hot water heater — offering peace of mind for years to come. Located in the highly sought-after South Gate neighborhood, this home places you just minutes from Sarasota’s world-famous beaches, vibrant downtown, shopping, dining, and easy freeway access — all within 10 minutes. A renovation this exceptional is rare. Don’t miss your opportunity to make this stunning Sarasota home yours.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Thomas Arthur, Iii (941-400-7970)
2165 SUNNYSIDE LN, SARASOTA, FL 34239
$569,00031 Days on yellowkey MLS ID: A4690142
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1022 Built: 1952 Tax: $5,683 (2025)Community: Hibiscus Park 1Spa: NoSingle Family
Taxes:$5,683
Remarks: Great Opportunity to own your own Mid Century block built cottage near Sunnyside Park, Arlington Park and Sarasota Memorial Hospital, Or build NEW on the 9681 sq ft lot.... Ready to move right in, this 2 bedroom 1 bath home ...Enjoy the great back yard. AC 2014, Roof 2019.. Hot Water Heater 2020.....Located within the City of Sarasota limits, this home allows for weekly (7-day minimum) rentals, making it uniquely suited for those seeking both personal enjoyment and income potential.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Jonathan Woods (941-356-7583)
1734 WISCONSIN LN, SARASOTA, FL 34239
$1,599,00063 Days on yellowkey MLS ID: A4687427
REDUCED by $51,000 (3.1%) on 05/26/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2910 Built: 2024 Tax: $20,684 (2025)Community: BayviewSingle Family
Taxes:$20,684
Remarks: Less than 4 miles to Siesta Key Beach and under 3 miles to Downtown Sarasota, this newly built 4-bed modern home in Sarasota delivers luxury living, investment flexibility, and an exceptional West of the Trail location. Built in 2024, this contemporary residence offers approximately 2,900 square feet with 4 bedrooms+ den and 4.5 baths, featuring open-concept living spaces, clean modern design, energy-efficient construction, and seamless indoor-outdoor flow ideal for entertaining. Located within Sarasota city limits with 7-night minimum rental potential, this property is an outstanding opportunity for both investors and end users seeking a luxury lifestyle close to Downtown Sarasota, Southside Village, Sarasota Memorial Hospital, and Siesta Key Beach. Room for a future pool. Located within the coveted Southside school district. Seller financing available with a 5.5% interest-only loan for 2 years.
Listing Agent: Keith Kleppinger (941-525-2937)
2940 BOUGAINVILLEA ST, SARASOTA, FL 34239
$650,00072 Days on yellowkey MLS ID: A4689977
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1710 Built: 1960Monthly Fee: $17 Tax: $6,279 (2025)Community: South GateSingle Family
Taxes:$6,279
Remarks: Stunning, mid-century modern home in highly desirable South Gate with views you must see to believe! If you could have picked one of the best lots in South Gate back in the 1960’s this may have been it. The two-bedroom plus office, two bath home sits on a bluff overlooking a wide portion of Philippi Creek including a large aquatic preserve. You’ll be mesmerized by long, unobstructed views in every direction. A nature lovers delight and absolutely intoxicating. But while location is important, there are many more features in this classic home to consider. Entering through the large foyer you’ll immediately notice beautiful terrazzo floors throughout and a great room with vaulted ceilings. There’s an adjacent dining area off the kitchen and all of these spaces look out through what appears to be a “wall of glass” dedicated to the world class view of flora and fauna. The primary bedroom also has views and access to the back yard and the primary bathroom has been upgraded with a separate tub and walk in shower. The den/office can be made more private with sliding pocket doors and function as a guest bedroom. It even has a dedicated, enclosed patio and garden space. There’s an attached, oversized garage with room for your workshop and a double wide driveway with plenty of parking. While this home has been appropriately updated and improved over the years you’ll find it’s all been done with a great sensibility to the original intent, quality and “hipness” so many are learning to appreciate, again.
Listing Agent: Barbara May (404-822-9264)
1730 WISCONSIN LN, SARASOTA, FL 34239
$1,599,00088 Days on yellowkey MLS ID: A4687426
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2910 Built: 2024 Tax: $20,687 (2025)Community: BayviewSingle Family
Taxes:$20,687
3700 S OSPREY AVE #205, SARASOTA, FL 34239
$225,00079 Days on yellowkey MLS ID: TB8494655
REDUCED by $12,000 (5.1%) on 04/23/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 991 Built: 1979 Tax: $2,548 (2025)Community: Plaza GardensCondo
Taxes:$2,548
Remarks: This fully renovated West-of-the-Trail condominium offers a rare opportunity to enjoy one of Sarasota’s most desirable locations at an approachable price point. Thoughtfully updated with custom imported Italian cabinetry and modern finishes, the residence features generous, well-proportioned living spaces that provide a level of comfort and openness not typically found in this price range. The building’s solid concrete construction ensures exceptionally quiet interiors, while elevator access and an in-unit washer and dryer add everyday convenience, complemented by additional shared laundry facilities. Residents are welcomed by a charming interior courtyard with mature tropical landscaping, creating a peaceful and inviting atmosphere. Ideally located just 10–15 minutes from Siesta Key Village and its world-renowned beaches, this condo is also minutes from Southside Village on Hillview Street, where you’ll find popular dining spots such as Libby’s Neighborhood Brasserie, Veronica Fish & Oyster, Morton’s Gourmet Market, and Pacific Rim. Everyday essentials are within easy reach, including Trader Joe's, Publix, and Sarasota Memorial Hospital, along with additional shopping and dining along US-41 near Bay Road. While the community offers a more relaxed lifestyle without resort-style amenities such as a pool or gym, it makes up for it with larger living spaces, quiet construction, and an unbeatable location. This is an outstanding opportunity to own a move-in-ready Sarasota condo near Siesta Key at a highly competitive price.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Roman Donato Ruiz (813-619-0792)
1607 FLOWER DR, SARASOTA, FL 34239
$4,290,000382 Days on yellowkey MLS ID: A4653737
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 4769 Built: 2024 Tax: $16,090 (2024)Community: Harbor Acres Sec 2Spa: YesSingle Family
Taxes:$16,090
Remarks: One or more photo(s) has been virtually staged. LOWEST PRICED NEW CONSTRUCTION WEST OF TRAIL HOSPITAL/SOUTHSIDE VILLAGE AREA! Truly a Coastal Classic Modern Masterpiece Located in One of the MOST Sought After Neighborhoods West of the Trail in Sarasota! This Gorgeous HARBOR ACRES Home is NOT your Typical Very Traditional Boring Florida Home! This Home was Built for the Discerning Buyer who Appreciates Modern Art and Design! Every Room is Unique and Designed with Attention to Detail and Gracefully Incorporates the Outside Indoors via Walls with Large Picture Windows. This Amazing Property Features: A MAIN HOUSE w/5 Bedrooms, 5.5 Baths, 2 Master Suites (Up & Down) both w/Zen-like 5-Piece Master Baths w/Whirlpool Soaking Tubs and Separate Showers; Fabulous Great Room w/Soaring Ceilings, Wall Fireplace and Sliders Looking Out to the Aqua Pool and Spa and Tropical Landscape; Extra Flex Room off Kitchen w/Built in Art Niche makes a Perfect Dining Room, Den/Office w/Built-ins, Fabulous Kitchen w/Separate Refrigerator, Freezer & Wine Refrigerator, Luxury Dacor Appliances, Quartz Counters, Designer Kitchen Cabinetry, Pantry, Eating Bar; Media Bonus Room w/Balcony, Laundry Room w/Storage, Open Glass Staircase to Upstairs, Elevator Shaft to All Floors, Porcelain Tile and Elegant Lighting Fixtures throughout, Bosch AC Units, 2 Balconies Upstairs, En-Suite Bedrooms, Powder Room w/Glass Art Sink, Impact Windows and Sliders w/Low E Glass, Oversized 2 Car Garage and an Oversized 1 Car Garage w/Electric Charging Stations, Smart Home w/Fully Integrated Wifi System, Covered Lanai w/Fully Equipped Out Door Kitchen and Fire Pit. A Detached CASITA GUEST HOUSE w/Separate Entrance, Full Bath, Kitchenette and One Bedroom overlooking the Pool Court Yard, Perfect for a Nanny, House Keeper, Teen, MIL or Pool Party Room. The Outdoor Features: Gorgeous 35 Foot Saltwater Pool w/Waterfall, Huge Sun Shelf and Hot Tub Spa; Lush Tropical Landscaping, Tiered Flower Planters, Low Maintenance Yard, Irrigation, Circular Driveway and Privacy Wall. Home was Built nearly 2 FT above the Flood Zone and does NOT Require Flood Insurance. This Never Before Been Lived in Home is Ready and Waiting for It's New Owner! Located just Minutes to Sarasota Memorial Hospital and Medical Center, Morton's Market, Downtown Sarasota, Shopping, Dining, St Armand's and the Best Beaches!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Anne Thomas, Pa (941-993-7700)
1829 BOUGAINVILLEA ST, SARASOTA, FL 34239
$4,100,00021 Days on yellowkey MLS ID: A4695800
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4857 Built: 1925 Tax: $13,902 (2024)Community: Poinsettia Park 2Spa: YesSingle Family
Taxes:$13,902
Remarks: Experience the timeless charm and distinctive elegance of this West of Trail luxury cottage, with modern finishes that remain true to its original allure, at 1829 Bougainvillea Street. Occupying three lots, it is nestled gracefully in Sarasota's most cherished neighborhood. Set on a tranquil, tree-lined avenue, moments from vibrant Southside Village, Sarasota Memorial Hospital, and the renowned sands of Siesta Key, this thoughtfully enhanced residence exudes a rare character and allure that newer homes simply cannot replicate. From the moment you step inside, you're captivated by a refined blend of historic charm and contemporary luxury. Rich hardwood flooring, detailed crown moldings, and designer lighting create a warm and refined ambiance throughout the spacious, open-concept layout. Anchoring this home is a beautifully reimagined gourmet chef's kitchen, showcasing high-end stainless steel appliances, luminous granite countertops, bespoke cabinetry, and an expansive island—ideally suited for gatherings both grand and intimate. The luxurious master suite is a serene retreat, illuminated by abundant natural light and offering generous closet space alongside a spa-inspired ensuite with a sumptuous walk-in shower and dual vanities. Additional bedrooms and versatile living areas effortlessly accommodate family, guests, or a tailored home office. Unique to this remarkable residence is the thoughtfully designed separate living quarters, complete with a private entrance, an inviting bedroom, a fully equipped kitchen, and a full bathroom. Ideal for hosting guests, housing extended family, or offering privacy to long-term visitors, these quarters are unique. Outside, the magic only continues—enchanting gardens burst with colorful bougainvillea, and mature greenery surrounds an inviting patio that effortlessly extends the living space outdoors, perfect for sunlit gatherings or quiet moments beneath Sarasota's famous skies. With meticulous care and modern upgrades, including a newer roof, advanced HVAC systems with two newly installed air conditioning units, recently replaced front-facing windows, and fully updated plumbing and electrical infrastructure, this home blends historic character with contemporary convenience, ensuring comfort, efficiency, and peace of mind. 1829 Bougainvillea Street represents more than just a renowned address; it offers a rare opportunity to own a property rich in Sarasota history and charm, distinctively set apart from uniformity and infused with authentic character. Welcome home to an extraordinary residence awaiting your personal story. Its roots run deep into our community. The prior owners have all remained friends to this day, and the resurgence of the modern cottage is now at the forefront of interior design and architecture. This property embodies that trend in a way no other home can. A true one-of-a-kind that will never be replicated.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Skrzypkowski (941-328-8307)
1640 WALDEMERE ST, SARASOTA, FL 34239
$6,500,000110 Days on yellowkey MLS ID: A4685215
INCREASED by $50,000 (0.8%) on 06/05/2026
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 5270 Built: 2026 Tax: $8,031 (2026)Community: Lewis Combs SubSpa: YesSingle Family
Taxes:$8,031
Tax Year: 2026
Remarks: Almost finished!!! Completion 3 weeks!!! Touch-ups and Staging in process now. Modern Luxury Villa | 1640 Waldemere St Experience the pinnacle of Gulf Coast luxury in this stunning Miami-style modern villa, perfectly situated West of Trail in one of Sarasota’s most coveted neighborhoods. This architectural marvel blends high-end technology with effortless coastal living, offering a sanctuary just minutes from the vibrant pulse of Downtown Sarasota and the world-renowned sands of Siesta Key and Lido Beach. The Residence Designed for the connoisseur of fine living, this home boasts a sleek, minimalist aesthetic defined by clean lines and expansive glass. Elevated Living: Move effortlessly between floors with your private elevator. The Great Indoors/Outdoors: Massive automated glass doors disappear to create a seamless transition to the resort-style pool deck, perfect for year-round entertaining. Privacy at Your Fingertips: Equipped with cutting-edge Smart Glass technology, windows transition from transparent to opaque instantly for ultimate privacy. Space for Everything: Featuring 5 spacious bedrooms, a dedicated executive office, and a private home gym, there is no better lifestyle or utility. Tech-Forward Luxury This is a fully realized Smart Home, designed for total control and ambiance: Integrated Smart Home System: Control lighting, climate, and security from your device. Whole-Home Audio: An immersive sound system flows through every room and out to the pool deck. Modern Finishes: Premium materials and high-end fixtures throughout reflect a commitment to quality and contemporary style. The Location Located West of 41, 1640 Waldemere St places you in the heart of Sarasota’s most desirable "West of Trail" district. You are seconds away from: Sarasota Memorial Hospital and the medical district. Downtown Sarasota’s fine dining, opera, and boutiques. St. Armands Circle and local beautiful sand beaches. Live the Future of Luxury. This villa isn't just a home; it’s a statement. Call for all details…
Listing is courtesy of: JOSEPH RUSSO, LICENSED R.E. BROKER (941-928-1613)
Listing Agent: Joseph Russo (941-928-1613)
1340 HARBOR DR, SARASOTA, FL 34239
$10,995,000149 Days on yellowkey MLS ID: A4680096
Bed: 4 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5157 Built: 1950 Tax: $23,499 (2024)Community: Harbor AcresSpa: YesSingle Family
Taxes:$23,499
Remarks: Under Construction. Superb New Construction opportunity in Harbor Acres, a one-third-acre waterfront property on the widest part of the neighborhood's deep-water harbor on Sarasota Bay. The views are great and the home is located on a protected, sailboat water basin with no bridges to the Gulf of Mexico. Newer boat dock and boat lifts accommodate up to 15,000-pound boat plus two recreational water craft, making easy access to Sarasota's waterways and the gulf, AND the home was designed by one of the BEST architectural firms, MHK, and under construction by one of the BEST waterfront builders, Voigt Brothers. The floor plan is amazing and the home is available for purchase during the construction phase, which makes it easy for future owners to modify the interior plans to their desires and choose their finishes. Harbor Acres is considered one of the best neighborhoods in Sarasota— and speaking of BEST, it has it all….location, waterfront, appreciation, neighbors. A close-knit community that is close to Downtown Sarasota and in-town amenities yet a half mile to Sarasota Memorial Hospital and Southside Village shops and restaurants. Call for floor plans or to walk the property.
3751 S SCHOOL AVE #29, SARASOTA, FL 34239
$124,999238 Days on yellowkey MLS ID: A4670178
0 Days Off yellowkey (back on 6/5/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1972 Tax: $1,874 (2025)Community: Sunland AptsSpa: NoCondo
Taxes:$1,874
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 Agent: Angie Unzicker (941-809-9119)
3018 ARLINGTON ST, SARASOTA, FL 34239
$399,90078 Days on yellowkey MLS ID: A4689348
REDUCED by $14,100 (3.4%) on 06/04/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1626 Built: 1952 Tax: $3,869 (2025)Community: Cottage In The PinesSpa: YesSingle Family
Taxes:$3,869
Remarks: Storybook Charm Meets Modern Luxury in Highly Desirable Arlington Park! Nestled in the unique, tree-lined "Cottage in the Pines" section of south downtown Sarasota, this beautifully updated 1952 residence perfectly blends timeless mid-century character with smart, modern improvements. From the moment you arrive, the brand-new vinyl siding and welcoming farmer’s porch create undeniable curb appeal, while the wide stone driveway offers plenty of extra parking. Step inside to discover a bright and spacious 3-bedroom, 2-bathroom, 1,626-sqft floor plan designed for effortless living. Durable tile flooring sweeps through the main living areas, leading to a charming kitchen complete with a closet pantry, custom tile backsplash, and a convenient pass-through window to the dining area. Safety and efficiency are already taken care of with hurricane-impact windows installed across the front and bedrooms. The expansive primary suite is a true private retreat, boasting an extended sitting area, a large walk-in closet, a remodeled spa-like bath, and private sliding door access to the backyard. Outside, your personal Florida oasis awaits. The fully fenced, oversized 0.21-acre lot features a relaxing hot tub, a handy utility shed, and endless space to design a future pool or gardening paradise. Located just minutes from downtown Sarasota, the world-class sands of Siesta Key, Sarasota Memorial Hospital, and the vibrant recreation at Arlington Park, this home offers unparalleled central convenience. Schedule your private tour today and fall in love!
Listing is courtesy of: TREND REALTY (941-928-3449)
Listing Agent: Liz Wiggins (941-666-3964)
1395 HARBOR DR, SARASOTA, FL 34239
$5,750,00022 Days on yellowkey MLS ID: A4691667
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4940 Built: 2027 Tax: $8,003 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$8,003
Remarks: Under Construction. Situated on a prized 1/3-acre homesite in the prestigious Harbor Acres community, this extraordinary custom residence by the award-winning team at Allegra Homes masterfully blends timeless coastal elegance with modern luxury. The two-story “Lakeshore Traditional” floor plan offers the ease and comfort of exceptional living with nearly 5,000 square feet of impeccably designed interiors. Featuring five bedrooms, five full baths, a powder bath, a dedicated office with custom built-ins and a game room with wet bar, every detail of this residence has been intentionally crafted to deliver a sophisticated yet effortless lifestyle. This solidly constructed home is enhanced with a brick paver motor court, a three-car garage, and professionally designed landscaping with irrigation and architectural lighting adding to its tropical ambiance. A dramatic great room serves as the centerpiece of the home, highlighted by soaring architecturally detailed ceilings, a stunning entertainment feature wall with fireplace, and expansive glass sliders that seamlessly connect the indoor living spaces to the spectacular outdoor retreat. Designed for year-round enjoyment, the beautifully finished lanai showcases a heated saltwater pool and spa, outdoor kitchen with grilling station and beverage center, and enclosed with Clear View screening that elevates the home’s refined coastal aesthetic. The gourmet kitchen is both functional and striking, anchored by an oversized island and appointed with an exceptional suite of Sub-Zero and Wolf appliances, including a 42-inch refrigerator, wine cooler, 36-inch cooktop, oven, and drop-down microwave—creating an ideal setting for entertaining and everyday living alike. Privately positioned, the luxurious owner’s suite offers a tranquil retreat with elegant wall detailing, a custom headboard feature wall, sitting area, and an indulgent bath featuring a freestanding soaking tub, oversized frameless glass shower, floating mirrors, split vanities, and a private water closet. Additional features include hurricane-impact windows and shutters, tankless recirculating water heater, tray ceilings with cove molding, recessed lighting, finished closets, 8-foot solid-core doors, and outdoor shower. Harbor Acres is widely considered one of Sarasota’s most established and prestigious waterfront neighborhoods — an ultra-prime West of the Trail enclave in one of Sarasota’s most desirable intown settings. Live moments from world-class boating, beaches, dining, and arts scene in a spectacular home designed to capture the essence of coastal luxury.
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
1880 LOMA LINDA ST, SARASOTA, FL 34239
$1,795,00081 Days on yellowkey MLS ID: A4688301
REDUCED by $100,000 (5.3%) on 06/04/2026
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2904 Built: 1954 Tax: $17,468 (2025)Community: Floyd & Cameron SubSpa: YesSingle Family
Taxes:$17,468
Remarks: Sought after West of Trail location close to Southside Village and on a cul-de-sac street. The home boasts almost 3000 square feet of airy living space and an open floor plan with vaulted ceilings. The kitchen with countertop seating overlooks the great room and dining room. The bedroom layout is a split plan with the large primary suite opening to the pool area and featuring a rainfall shower and garden tub plus double vanities. Two guest bedrooms share an updated bathroom with the fourth bedroom on the other side of the home and a separate bathroom with shower in hallway. A large family room is off the kitchen and dining room areas and has another full bathroom and French doors that open to the pool. An over-sized utility room off the kitchen has an extra refrigerator and built in cabinetry. The expansive caged in pool area with spa allows for ample entertaining space with plenty of fenced backyard beyond, allowing for wonderful indoor/outdoor entertaining.
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