Location: Sarasota
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
1065 LEWIS AVE, SARASOTA, FL 34237
$389,90016 Days on yellowkey MLS ID: A4695338
REDUCED by $10,000 (2.5%) on 06/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1295 Built: 1996 Tax: $2,544 (2025)Community: FairwaySpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,544
Elementary School: Tuttle Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: NO HOA • NO FLOOD ZONE • BLOCK CONSTRUCTION • NEW ROOF 2022 • OVERSIZED 2-CAR GARAGE Welcome to this beautifully maintained 3-bedroom, 2-bath home ideally located in the heart of Sarasota. Built with durable block construction and featuring a new roof installed in 2022, this property offers peace of mind, flexibility, and exceptional value. Inside, you'll find a bright open floor plan filled with natural light, updated finishes, and a spacious kitchen featuring granite countertops, stainless steel appliances, and modern cabinetry—perfect for both everyday living and entertaining. Step outside to enjoy the large screened lanai overlooking a fully fenced backyard complete with a storage shed, offering plenty of space for pets, gardening, outdoor gatherings, or simply relaxing in your own private retreat. One of this home's biggest advantages is its unbeatable location. Just minutes from Downtown Sarasota, Payne Park, Sarasota Memorial Hospital, Ed Smith Stadium, shopping, dining, and Sarasota's world-famous beaches, you'll enjoy easy access to everything that makes Sarasota one of Florida's most desirable places to live.Whether you're a first-time homebuyer, looking to downsize, or searching for a solid investment opportunity, this home offers the perfect combination of location, comfort, and everyday convenience. Schedule your private showing today.
Listing is courtesy of: PARADISUS REALTY GROUP CO (941-281-4973)
Listing Agent: Andres Salgado (941-875-2949)
1709 N TAMIAMI TRL #416, SARASOTA, FL 34234
$525,00053 Days on yellowkey MLS ID: A4690932
Bed: 1 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 855 Built: 2022 Tax: $6,366 (2025)Community: The Strand Of SarasotaCondo
Taxes:$6,366
Elementary School: Gocio Elementary
Remarks: Exceptional opportunity to experience a premier waterfront lifestyle in this contemporary condo, located just minutes from the vibrant energy of downtown Sarasota and our award-winning local beaches. Amazing water views from sunrise to sunset right outside your door. This gated community offers a suite of high-end amenities, including a state-of-the-art fitness center, a serene pool, and direct water access—perfect for launching a kayak or paddleboard through Whitaker Bayou into Sarasota Bay. A community dog park and fire pit are also available. The residence itself features modern styling with clean lines and is complemented by practical luxuries such as custom designer shades and curtains throughout and a large organized walk in closet in the owners suite. Additional features of this property include: -Den/Office with built in closet. - Dedicated underground parking space, additional storage, and secure elevator access. - A full-size front-load washer and dryer conveniently located adjacent to the owner's suite walk-in closet. - Significant investment potential, with the rare benefit of permitting weekly rentals. Whether you are seeking a personal sanctuary or a high-performing income-generating property, this residence is an ideal choice.
Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)
Listing Agent: Anne Friedland (941-894-7248)
1659 DEVONSHIRE LN, SARASOTA, FL 34236
$2,495,000196 Days on yellowkey MLS ID: A4673505
REDUCED by $100,000 (3.9%) on 05/14/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2754 Built: 2024 Tax: $23,612 (2024)Community: Burns Realty Co SubSpa: NoSingle Family
Taxes:$23,612
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2024
Remarks: Virtually Staged. Welcome to Downtown Sarasota luxury living at its finest. Perfectly positioned in the sought-after Laurel Park neighborhood, just steps from Historic Burns Court, Marie Selby Botanical Gardens, Bayfront Park, Marina Jack, and only minutes to Lido Beach and St. Armands Circle, this custom-built 2024 coastal modern residence offers an exceptional blend of sophistication, comfort, and walkable downtown convenience. Designed for those who value effortless entertaining and an active Sarasota lifestyle, this meticulously constructed two-story residence spans 2,754 square feet and features four bedrooms, three and a half baths, a heated saltwater pool, outdoor kitchen, and thoughtfully curated designer finishes throughout. The heart of the home showcases an expansive open-concept living space centered around a chef's kitchen appointed with premium Thermador stainless appliances, gas cooking, built-in coffee and beverage center, oversized island seating for seven, walk-in pantry, dedicated ice maker, dual wine refrigeration accommodating over 200 bottles, and seamless indoor-outdoor flow ideal for entertaining. Step outside into a private resort-inspired setting where textured stucco privacy walls frame a heated saltwater pool with waterfall feature, fountains, ambient lighting, covered entertaining spaces, outdoor kitchen, pool bath, and outdoor shower. Constructed entirely of concrete block and engineered for peace of mind with CAT 5 hurricane windows, metal roof construction, whole-house Generac generator, water filtration systems, and exceptional finish quality throughout. The second level owner's retreat creates a private sanctuary with spacious walk-in closet and spa-inspired bath, while two guest suites share a beautifully appointed Jack-and-Jill bath. A first-floor bedroom with adjacent full bath offers flexibility for guests, office, fitness, or multigenerational living. Additional features include marble exterior decking, porcelain tile balconies, epoxy garage flooring, irrigation system, quartz surfaces throughout, and premium construction rarely found in downtown Sarasota. Leave the car behind and experience Sarasota the way it was meant to be lived — morning walks to Selby Gardens, evenings in Burns Court, waterfront sunsets along Bayfront Park, and effortless access to world-renowned beaches. Luxury. Lifestyle. Location. 1659 Devonshire Lane delivers all three. Some photos have been virtually staged. All measurements are approximate and should not be relied upon as exact.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Julie Kell (330-309-7022)
630 CORWOOD DR, SARASOTA, FL 34234
$799,00057 Days on yellowkey MLS ID: A4690643
REDUCED by $25,500 (3.1%) on 06/14/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1897 Built: 1963 Tax: $7,711 (2025)Community: Corwood ParkSpa: NoSingle Family
Taxes:$7,711
Elementary School: Emma E. Booker Elementary
Remarks: Welcome home to Corwood Park—where Sarasota living feels effortless. Tucked into one of the area's most sought-after pockets west of the Trail, this beautifully updated home offers the rare combination of move-in-ready comfort, a sparkling pool, and a lush, private setting on nearly a quarter acre. From the moment you arrive, mature tropical landscaping sets a peaceful, resort-like tone that continues throughout the property. Inside, the renovated kitchen is a standout, featuring crisp shaker cabinetry, new countertops, and stainless-steel appliances—a space designed for both everyday living and entertaining. New tile flooring flows throughout the home, the bathrooms have been tastefully updated, and impact-rated patio doors add both style and peace of mind. A new high-efficiency washer and dryer round out the thoughtful upgrades, so all you need to do is unpack and settle in. Step outside to your own private oasis: a refreshed pool area perfect for morning swims, weekend barbecues, or simply unwinding under the Florida sun. The spacious, beautifully shaded lot offers room to garden, play, or simply enjoy the outdoors in privacy. The location is hard to beat—just minutes from the shimmering waters of Sarasota Bay (hello, sunset views), the Ringling Museum, Sarasota Jungle Gardens, downtown Sarasota's dining and arts scene, SRQ Airport, and some of the area's most beautiful beaches. Whether you're searching for a forever home, a seasonal escape, or simply a place that feels like vacation every day, this Corwood Park gem checks every box—comfort, character, and an unbeatable address.
Listing is courtesy of: CCI REALTY (954-667-6692)
Listing Agent: Oscar Betancourt (954-854-3959)
5526 CHANTECLAIRE #31, SARASOTA, FL 34235
$449,90039 Days on yellowkey MLS ID: A4689277
REDUCED by $10,100 (2.2%) on 06/08/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 1985Monthly Fee: $617 Tax: $2,477 (2025)Community: ChanteclaireVilla
Taxes:$2,477
Remarks: Virtually Staged. Welcome to this beautifully reimagined villa in the highly sought-after Meadows community, where timeless design meets modern sophistication. This fully renovated residence offers 2 bedrooms with a flexible third space that can serve as a private den, office, or easily function as a third bedroom tailored to fit your lifestyle. Every detail has been thoughtfully curated, showcasing a light, bright interior with an elegant, airy aesthetic. As reflected in the virtual staging, the open-concept design is complemented by clean lines, upscale finishes, and a seamless flow between living spaces perfect for both relaxed everyday living and effortless entertaining. Natural light fills the home, enhancing the soft, neutral palette and creating a warm yet refined ambiance throughout. Ideally located in The Meadows, known for its lush landscapes, walking trails, and proximity to dining, shopping, and Sarasota’s finest amenities, this residence offers the perfect balance of tranquility and convenience. Unlock exceptional living in one of Sarasota’s most desirable communities.
Listing is courtesy of: LUXEKEY REAL ESTATE LLC (941-404-3173)
Listing Agent: Robin Eekhof (941-504-1941)
1221 N PALM AVE #202, SARASOTA, FL 34236
$425,00030 Days on yellowkey MLS ID: A4693884
0 Days Off yellowkey (back on 6/14/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 663 Built: 1924 Tax: $4,361 (2025)Community: Frances CarltonCondo
Taxes:$4,361
Elementary School: Alta Vista Elementary
Remarks: Under contract-accepting backup offers. Virtually Staged. Own a piece of downtown Sarasota history. Set along iconic Palm Avenue, the Frances Carlton is a 1924 Mediterranean Revival landmark listed on the National Register of HISTORIC Places, placing theaters, galleries, dining, and the marina nearby, while offering a sense of character and permanence rarely found today. This intimate boutique building of just 19 residences is thoughtfully maintained, with FULLY FUNDED RESERVES, completed Structural Integrity Inspection, and amenities including a private pool, garden areas, and gated assigned parking. This FULLY REMODELED second-floor residence has never been lived in since its renovation and offers a clean, modern interpretation of the building’s historic charm. With windows on three sides, a rare feature in condominium living, the home is filled with natural light throughout the day. The layout reflects its European-influenced design, with defined spaces, arched windows, and a sense of proportion setting it apart from more conventional layouts. The bright sunroom extends the living space and overlooks the pool below, ideal as a reading room, office, or quiet retreat. The residence offers one assigned, secured parking space. This is your opportunity to own a thoughtfully updated home in one of Sarasota’s most recognizable historic buildings, in a truly walkable downtown location. Don't let this one get away!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Justyna Michalowska (941-567-7300)
33 S GULFSTREAM AVE #404, SARASOTA, FL 34236
$375,0002 Days on yellowkey MLS ID: A4695460
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 754 Built: 1964 Tax: $4,270 (2025)Community: Gulfstream TowersSpa: NoCondo
Taxes:$4,270
Remarks: Discover the ultimate downtown Sarasota lifestyle from this beautifully maintained fourth-floor condominium offering partial Sarasota Bay, Bayfront Park, and Marina Jack views. Perfectly positioned at the coveted corner of Main Street and Gulfstream Avenue, this residence places the very best of Sarasota just outside your front door. Step inside to find expansive living spaces, wood-look tile flooring throughout, abundant natural light, and a warm modern aesthetic that complements the building's timeless mid-century architecture. The spacious primary suite offers comfort and privacy, while the retro-inspired bathroom preserves the character and charm that make this residence truly unique. Enjoy spectacular sunset skies from the comfort of your living room or take a short stroll to Sarasota's vibrant waterfront, renowned restaurants, boutique shopping, theaters, art galleries, farmers market, and year-round cultural events. Whether enjoying morning walks along the bayfront or evenings dining downtown, every day feels like a vacation. This well-maintained community offers exceptional amenities including a resort-style pool and expansive sun deck, social room with kitchen and dining area, refurbished lobby and common areas, updated elevators, impact-resistant windows, and attractive brick paver decking. Ideal as a primary residence, seasonal retreat, or investment opportunity, this is a rare chance to own in one of Sarasota's most desirable downtown locations where waterfront living, walkability, and urban convenience come together seamlessly.
Listing is courtesy of: THE KEYES COMPANY - SARASOTA (941-362-4100)
Listing Agent: Joseph Mcdonald, Llc (941-375-9646)
140 S BLVD OF THE PRESIDENTS, SARASOTA, FL 34236
$2,350,000109 Days on yellowkey MLS ID: A4683280
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2206 Built: 1951 Tax: $19,449 (2025)Community: Saint Armands Div John Ringling EstatesSpa: NoSingle Family
Taxes:$19,449
Remarks: Welcome to an extraordinary opportunity on Lido Key, where refined coastal elegance meets exceptional investment potential. This beautifully appointed three-bedroom, two-bath pool home is being offered fully turnkey furnished and has an established history as a successful income-producing rental property, making it as smart as it is stunning. Nestled beneath mature shade trees on an oversized 10,285 square foot lot, the property offers rare privacy just moments from the beach. Lush tropical landscaping surrounds the home, creating a serene island setting that feels worlds away while remaining close to everything that makes Lido Key so desirable. Inside, soaring ceilings and expansive windows flood the home with natural light, enhancing the open-concept layout designed for effortless entertaining and everyday comfort. Warm wood floors, thoughtfully curated finishes, and a soft coastal palette create a relaxed yet sophisticated ambiance throughout. Every space feels intentional, welcoming, and ready to enjoy from day one. The chef’s kitchen is a true centerpiece, featuring rich custom cabinetry, granite countertops, stainless steel appliances, double ovens, a wine fridge, and an extended breakfast bar perfect for hosting family and guests. The adjacent dining area opens seamlessly through sliding glass doors to the outdoor living space, blurring the lines between indoor comfort and Florida sunshine. The spacious primary suite serves as a private retreat, complete with vaulted ceilings and a spa-inspired bath offering dual vanities, custom cabinetry, and a walk-in shower. Two additional guest bedrooms provide flexibility for visitors or vacation renters, while a full-size laundry area, built-in workspace, and generous storage add convenience to the home’s thoughtful design. Step outside and discover your own private resort. The sparkling pool and expansive patio create the ultimate backdrop for entertaining, relaxing, and soaking in the year-round Florida lifestyle. Covered dining areas and multiple lounging spaces make this backyard oasis ideal for everything from quiet mornings with coffee to lively sunset gatherings. Location is everything, and this home delivers. Just minutes from the pristine sands of Lido Beach and the iconic boutiques and dining of St. Armands Circle, you’ll enjoy immediate access to world-class shopping, waterfront restaurants, boating, and the vibrant arts and culture of downtown Sarasota. Lido Key continues to be one of the Gulf Coast’s most coveted destinations, prized for its laid-back luxury and strong vacation rental demand. Whether you are searching for a sophisticated island residence, a luxury vacation retreat, or a high-performing investment property with proven income history, this exceptional Lido Key home offers the rare combination of lifestyle, location, and long-term value. This is more than a home — it is the island dream realized.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
301 JACKSON DR, SARASOTA, FL 34236
$2,790,000110 Days on yellowkey MLS ID: A4683209
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2028 Built: 1951 Tax: $20,382 (2025)Community: Saint Armands Div John Ringling EstatesSpa: NoSingle Family
Taxes:$20,382
Remarks: Welcome to your private coastal sanctuary just moments from the powder-soft sands of Lido Beach and a short stroll to iconic St. Armands Circle. Perfectly positioned in one of Sarasota’s most coveted locations, this stunning residence captures everything buyers dream about when they imagine luxury living by the gulf. From the moment you arrive, lush tropical landscaping and swaying palms frame a beautifully maintained property that feels both secluded and inviting. The expansive paver drive and manicured lawn create a grand first impression, while mature greenery provides privacy rarely found this close to the beach. Inside, the home blends refined elegance with relaxed island charm. Sunlight pours through plantation-shuttered windows, illuminating spacious bedrooms designed for comfort and style. The primary suite is a tranquil retreat with soft coastal tones and garden views, while the guest rooms are thoughtfully appointed to accommodate family and visitors with ease. Every space feels bright, airy, and curated for effortless living. The bathrooms are nothing short of spa-worthy. Floor-to-ceiling tile, frameless glass showers, custom vanities with stone countertops, dual sinks, and elegant fixtures create a luxurious experience that rivals high-end resorts. Thoughtful details like recessed niches, designer mirrors, and soft lighting elevate each space. Step outside and the property truly comes to life. The private backyard oasis is designed for unforgettable gatherings and serene relaxation alike. A sparkling pool is surrounded by expansive decking, lounge seating, and tropical landscaping that transforms the space into your own secluded resort. String lights overhead add ambiance for evening swims, while shaded seating areas invite long afternoons under the palms. The fenced yard enhances privacy, creating a rare sense of retreat just minutes from everything. And the location — simply exceptional. Imagine morning walks to Lido Beach, sunset cocktails at St. Armands Circle, boutique shopping, award-winning dining, boating, and downtown Sarasota’s vibrant arts scene all just moments from your front door. Homes in this location with this level of finish and established rental success are incredibly rare. Whether you are searching for a luxury island residence, a sophisticated vacation retreat, or a high-performing investment property with proven appeal, this home delivers on every level. Offered in pristine condition and designed for both comfort and entertaining, it embodies the very best of coastal Florida living. This is more than a home. It is the St. Armands lifestyle — elevated, private, and unforgettable.
5103 GREENCROFT RD, SARASOTA, FL 34235
$295,000641 Days on yellowkey MLS ID: N6134516
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1487 Built: 1979Monthly Fee: $567 Tax: $3,642 (2023)Community: Vivienda At The MeadowsVilla
Taxes:$3,642
Tax Year: 2023
Remarks: Resort-Style Living Maintenance-Free includes Tile Roof. One of Sarasota’s most desirable communities. This spacious 2 bedroom, 2 bath, car garage home offers multiple living areas, including a living room, open-concept kitchen/family/dining area, and tranquil greenbelt view from the lanai. Ideally positioned not direct-facing neighbors, this home boasts a generous front yard and privacy. Enjoy true ease of living—landscaping and TILE roof maintenance are covered by the HOA, with reserves in place for future care. Recent upgrades include HVAC (2021), Water Heater (2023), Washing Machine (2024), Refrigerator (2022), as well as a new kitchen faucet, range hood fan, and light (2024). The Meadows Country Club offers membership access to 54 holes of golf, 17 Har-Tru tennis courts, pickleball, a junior Olympic-size pool, fitness center, two restaurants, and over 200 annual events. Explore 14 miles of scenic walking, biking, and nature trails, all just minutes from downtown Sarasota, UTC Mall, and I75. Come home to comfort, community, and the carefree lifestyle you’ve been looking for. Resort-Style Living in The Meadows Golf & Country Club Welcome to The Vivienda, a maintenance-free enclave within The Meadows, one of Sarasota’s most desirable communities.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY (941-207-5055)
Listing Agent: Janet Linaburg (941-225-5289)
1010 VILLAGIO CIR #106, SARASOTA, FL 34237
$249,9001222 Days on yellowkey MLS ID: A4560093
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 2002Monthly Fee: $329 Tax: $2,049 (2021)Community: Villagio CondominiumCondo
Taxes:$2,049
Tax Year: 2021
Remarks: WONDERFUL. UNIQUE SARASOTA CONDO ON A VERY CONVENIENT PLACE. NEAR DOWNTOWN, BEACHES, ST. ARMANDS CIRCLE SHOPPING-RESTAURANTS AND ORIOLES BASEBALL STADIUM. AFFORDABLE PRICE.
Listing is courtesy of: WHITE SANDS REALTY GROUP FL (941-260-3350)
Listing Agent: Gloria Insua Massa (941-302-8123)
1020 23RD ST, SARASOTA, FL 34234
$465,0009 Days on yellowkey MLS ID: A4695931
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 856 Built: 1954 Tax: $4,267 (2025)Community: Sylvan ShoresSpa: NoSingle Family
Taxes:$4,267
Remarks: TAKE A STROLL back in time to "OLD FLORIDA" and land in an incredible location WEST of N. Trail in RINGLING PARK! What a fabulous, and WELL PRESERVED home complete with a large fenced back yard, private driveway and carport. You will fall in love with the beautiful, Terrazzo Floors accented by 1950's interior architectural features such as arched vestibules and Plaster Cove Ceilings. This is a 2 bedroom bungalow with a front and rear porch, ample size living room, fabulous Florida room and a large laundry room. Updates include a new kitchen and updated bathroom, almost new HVAC, updated 150 amp electric panel, all 20 windows have been updated with tilt in, single pane windows, Terrazzo floors updated and new LPV flooring in the Florida room. This Fantastic home is a great opportunity! $465,000
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Scotty Ledford (941-400-7360)
365 OAK HILL WAY #32, SARASOTA, FL 34232
$280,000150 Days on yellowkey MLS ID: A4677958
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1174 Built: 1985Monthly Fee: $559 Tax: $570 (2025)Community: Village Oaks Sec BSpa: NoVilla
Taxes:$570
Remarks: Virtually Staged. Nestled in the quiet, pet friendly community of Village Oaks features this Immaculate updated 2-bedroom, 2 bathroom Condo/Villa that offers a move-in-ready retreat. This fully updated unit features a new hot water heater installed in January 2026 and boasts a freshly repainted interior throughout. The modernized kitchen offers a pass-through to the dining area. Updated Master Bath with dual sinks, and walk in shower. Enjoy the look of luxury vinyl that flows seamlessly through every room. The open-concept living room boasts of high ceilings, while an enclosed Florida room (lanai) provides a private space to enjoy the lush surroundings. The villa features a convenient in unit laundry area with a washer and dryer tucked into a dedicated laundry closet.Enjoy the convenience of a private one car garage with remote access, plus two dedicated exterior parking spots right outside your villa. Community pool overlooking lake along with tennis/pickleball court for outdoor activities. Ideally situated between I-75 and downtown Sarasota, offering quick access to the University Town Center Mall (UTC), local dining and world-class beaches.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Laura Flood (941-725-2500)
435 S GULFSTREAM AVE #1004, SARASOTA, FL 34236
$895,000224 Days on yellowkey MLS ID: A4670726
REDUCED by $55,000 (5.8%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1829 Built: 1972 Tax: $10,813 (2025)Community: Regency HouseSpa: NoCondo
Taxes:$10,813
Remarks: One or more photo(s) has been virtually staged. Welcome to waterfront living at Regency House, nestled in the heart of Sarasota on a serene, tree-lined street—ideally located between Gulfstream and Palm Avenue. Enjoy sweeping views of Sarasota Bay, breathtaking sunsets, and effortless walkability to the city’s premier dining, shopping, cultural attractions, and the bayfront. This beautifully updated 1,829 sq. ft. residence is designed with both style and function in mind, featuring a spacious split floor plan that maximizes privacy. The living room opens to spectacular north- and west-facing views, where sparkling city lights, Marina Jack’s Park, and Sarasota Bay create a stunning backdrop. Thoughtfully integrated shelving adds versatility and easily adapts to a dedicated home office set up. Modern upgrades include new flooring, a fresh neutral palette, and a sleek kitchen with stainless LG appliances and a Bosch induction cooktop. With abundant storage and generous counter space, the designer kitchen is ready for everything from casual meals to lively entertaining. Each bedroom is a private retreat, offering gorgeous sunset views, updated baths, and abundant closet space—including brand-new California Closet custom buildouts. A full size, in-residence washer and dryer make this home as practical as it is luxurious and a versatile bonus/storage room provides additional flexibility for work, hobbies, or extra belongings. Enjoy Resort-style amenities and maintenance free living: a heated pool, fitness center, stylish club room with catering kitchen, and the peace of mind of 24/7 concierge service and a professional on-site manager provide ease of living just steps from the beautiful waterfront. This residence offers a fabulous lifestyle just moments from Marina Jack, boutique shopping and world -class dining, Opera and Theatre, Whole Foods, St. Armands Circle and Lido Beach. Enjoy the best of the Gulf Coast and peace of mind at Regency House. The building maintains healthy reserves and has completed the Milestone Inspection and Structural Integrity Reserve. Don’t miss this rare opportunity to experience vibrant downtown living with every convenience right at your doorstep.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dianne Anderson (941-350-3513)
5552 BENTGRASS DR #7-116, SARASOTA, FL 34235
$250,0004 Days on yellowkey MLS ID: A4695756
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1615 Built: 2002 Tax: $2,892 (2025)Community: Las Palmas Of SarasotaCondo
Taxes:$2,892
Remarks: GORGEOUS AND PRICED TO SELL! Impressive upgrades, stylish, and great location! Step into the largest three-bedroom, two-bath floor plan in Las Palmas, where thoughtful design meets exceptional updates. This unique residence offers peaceful water views, lush mature landscaping, and a layout that truly stands out. From the moment you enter, you'll be captivated by the second story soaring ceilings, enhanced by an impressive catwalk feature that allows natural light to flood the space. The beautifully updated kitchen, modern laminate flooring, and meticulous upkeep make this home move-in ready. Newer AC system, a newer hot water heater, upgrades kitchen floors, and modern updates throughout. Las Palmas is a highly sought-after gated community offering an unparalleled lifestyle. Enjoy direct access to Benderson Park through a private gate, making morning walks, bike rides, or trips to UTC effortless. No need to worry about parking for special events ... simply stroll or cycle to Sarasota's premier shopping and dining destination. Residents also have access to resort-style amenities, including two heated swimming pools, tennis courts, two clubhouses with a TV room, two fitness centers , a car wash station, a dog park, and even extra storage for RVs and large trucks. This home is a rare find and beautifully maintained, thoughtfully updated, and priced to sell. Don't miss your chance to own one of the best values in Sarasota. This condo is not only exciting to view but it's also priced below well below it's value, and incredibly well taken care of by it's current owners. Schedule your showing today!
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Dawn Bear (941-468-7224)
1100 IMPERIAL DR #108, SARASOTA, FL 34236
$569,00031 Days on yellowkey MLS ID: A4692243
REDUCED by $30,000 (5.0%) on 06/10/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1262 Built: 1971 Tax: $7,769 (2025)Community: Bays Bluff Atps Sec 1Spa: YesCondo
Taxes:$7,769
Remarks: MOTIVATED SELLER! DON'T MISS THIS OPPORTUNITY! This 1st floor end-unit directly faces Sarasota Bay and offers the ability to walk right out to the bayfront. As the largest floor plan available in Bay’s Bluff, the residence spans the entire width of the building and, with its expansive windows, offers either sunrise or sunset views from every room - - - and wonderful cross breezes! * * * Nicely updated, this unit is move-in ready with some furniture included. Hurricane-impact windows provide added peace of mind. The screened lanai is a wonderful place to sit, relax and watch the seabirds, sailboats, and breathtaking sunsets. * * * Bay’s Bluff is a charming, pet-friendly mid-rise community. Are you a dog lover? Imagine being able to take your dog out directly from your unit and walk with them along the bayfront. * * * The waterfront heated pool and grill area are ideal for hosting a sunset cocktail party or cookout. Or relax at the water’s edge in an Adirondack chair on the community’s 267-foot private seawall, where the soothing sounds of the bay will calm your mind and spirit. * * * Location, location, location! Publix grocery is conveniently located just across the street; The Bay Park, Sarasota’s 53-acre cultural and waterfront destination, is only two blocks away; downtown Main Street is just one mile away, offering easy access to world-class dining, theaters, galleries and shopping; the Sarasota-Bradenton Airport is 4 miles away; and one of Sarasota’s many wonderful beaches lies just on the other side of the Ringling Bridge that you can see from the lanai. * * * Don’t miss this rare opportunity to own a premier bayfront residence in downtown Sarasota, with water views and a prime location.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Marilyn Kneafsey (941-373-0999)
5071 BARRINGTON CIR #1602, SARASOTA, FL 34234
$149,90051 Days on yellowkey MLS ID: A4691290
0 Days Off yellowkey (back on 5/19/2026)
REDUCED by $15,000 (9.1%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1078 Built: 1982 Tax: $497 (2025)Community: Barrington WoodsVilla
Taxes:$497
Remarks: Spectacular Sarasota end-unit villa offering 2 bedrooms and 2 bathrooms, perfectly positioned with a 1-car carport conveniently located near the unit entry. Enjoy serene pond views from the primary bedroom, living room, and glass-enclosed lanai, creating a peaceful and private retreat. Features include a screened front entry leading into a welcoming foyer, a spacious kitchen with eat-in area and breakfast bar, and an in-unit laundry closet with full-size washer & dryer. Additional highlights include a large exterior storage closet, security system, central vacuum, impact glass windows, and major updates with a new AC (October 2023) and hot water heater (February 2022). Offered as an estate sale and sold with all contents in the unit and storage closet. Residents also enjoy access to a community pool and a prime location just minutes from Gulf beaches, the Ringling Museum, Sarasota-Bradenton International Airport, and vibrant downtown Sarasota.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Mike Bridges (941-316-6530)
5019 STEVENS DR, SARASOTA, FL 34234
$635,000111 Days on yellowkey MLS ID: A4683765
1 Days Off yellowkey (back on 6/13/2026)
REDUCED by $5,000 (0.8%) on 06/11/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1592 Built: 1957 Tax: $5,172 (2025)Community: Sapphire HeightsSpa: NoSingle Family
Taxes:$5,172
Remarks: Under contract-accepting backup offers. Fully renovated mid-century gem in the charming and highly coveted Indian Beach Sapphire Shores neighborhood of Sarasota. This exceptional three-bedroom, two-bathroom home has been lovingly preserved and thoughtfully restored with a strong emphasis on period-appropriate mid-century design and timeless style. Original terrazzo floors sparkle throughout the main living areas, honoring the home’s architectural roots. The fully renovated kitchen features new high-end appliances and blends seamlessly with the home’s classic aesthetic. The former Florida room has been transformed into comfortable year-round living space with permanent climate control, with the design anchored by an authentic vintage 1960s Preway wood-burning cone fireplace — a true statement piece. High-end mid-century light fixtures are showcased throughout, including multiple authentic Herman Miller pieces. Major updates provide peace of mind, including a new roof (2023), brand-new HVAC system and ductwork (2024), and a new solid wood privacy fence (2024). All bedrooms offer sizable closets, and the large zero-scaped front yard ensures beauty with minimal maintenance. The expansive backyard is a private retreat, featuring a generous paver patio and ample space for a pool or future additions. A newly installed barrel sauna and cold plunge create a spa-like sanctuary along the side yard, with convenient access from the principal suite. The true highlight of the home is the architect-designed principal bedroom and bathroom suite, completed in 2025 — an incredibly rare feature for this neighborhood and era. Designed as a private oasis, the light-filled bedroom includes a picture window and charming window seat, thoughtfully separated from the two guest bedrooms on the opposite wing of the home. The spacious en-suite bathroom is professionally interior designed and features high-end fixtures, a large walk-in shower, a freestanding spa tub, double vanity, and a walk-in closet. An exterior door provides direct access to the outdoor spa area for seamless indoor-outdoor living. Ideally located, this home is within a short distance to multiple beautiful waterfront parks and the renowned The John and Mable Ringling Museum of Art. Just five minutes to downtown Sarasota and ten minutes to the pristine beaches of Lido Key, you’ll enjoy the very best of Sarasota’s natural beauty and vibrant cultural scene — all from the comfort of your exquisitely restored mid-century home in one of the city’s most beloved neighborhoods.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Agnes Cameron (941-388-3966)
266 OAK HILL DR #34, SARASOTA, FL 34232
$285,0003 Days on yellowkey MLS ID: A4696620
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1024 Built: 1985Monthly Fee: $559 Tax: $2,638 (2025)Community: Village Oaks Sec AVilla
Taxes:$2,638
Remarks: Welcome to this beautifully maintained 2BR/2BA villa with a private single-car garage, offering comfort, updates, and peace of mind in a prime Sarasota location. Major improvements have already been done, including impact windows and sliding glass doors (2025), a new A/C system (2025), new roof and gutters (2024), and water heater (2020), updated master bathroom making this home truly move-in ready with lower maintenance costs for years to come Located in a quiet, established community surrounded by mature oak trees and lush green space, this villa offers a relaxed Florida lifestyle just minutes from everything: Downtown Sarasota, I-75, UTC Mall, St. Armands Circle, and the world-famous Lido Key beaches. Residents enjoy resort-style amenities including a lakeside heated pool, tennis courts, and pickleball—perfect for staying active or socializing with neighbors in a friendly, well-kept neighborhood.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Julianna Kovacs (941-518-6485)
1350 5TH ST #402, SARASOTA, FL 34236
$695,00027 Days on yellowkey MLS ID: A4691938
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 784 Built: 2019Monthly Fee: $724 Tax: $5,936 (2025)Community: Risdon On 5ThSpa: NoCondo
Taxes:$5,936
Remarks: Stunning one bedroom penthouse in the heart of the Rosemary District, one of downtown Sarasota’s most vibrant and sought after neighborhoods, featuring an exclusive private garage, an exceptionally rare offering in luxury condo living. Positioned on a private penthouse level with only four residences, this sophisticated urban retreat combines privacy, security, contemporary design, and unmatched walkability. Filled with natural light, the residence features soaring ceilings, impact rated windows and doors, electric blinds, and refined modern finishes throughout. The open concept layout is complemented by a beautifully appointed kitchen with a premium appliance package, sleek cabinetry, and an oversized single cell sink designed for both style and functionality. Designed by Halflants + Pichette Studio for Modern Architecture, Risdon on 5th showcases striking contemporary architecture and an elevated downtown Sarasota lifestyle. Step outside your door to enjoy the rooftop pool and observation lounges, offering resort style amenities and an elevated atmosphere perfect for relaxing or entertaining. The gated community provides peace of mind while placing you in the center of downtown Sarasota’s thriving arts and entertainment scene. Residents enjoy unbeatable walkability to the Sarasota Opera House, theaters, acclaimed dining, rooftop bars, art galleries, boutique shopping, coffee shops, nightlife, and waterfront attractions. The private one car garage is a true rarity for downtown Sarasota penthouse living, adding convenience and long term value rarely found in the Rosemary District. Ideal as a full time residence, seasonal retreat, or investment opportunity, this exceptional penthouse offers the perfect lock and leave lifestyle in one of Sarasota’s most desirable urban locations.
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