Location: Sarasota , 34231
Do Not Show Listings
6470 HOLLYWOOD BLVD #208, SARASOTA, FL 34231
$320,00015 Days on yellowkey MLS ID: A4696425
0 Days Off yellowkey (back on 6/19/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 910 Built: 1978 Tax: $3,022 (2025)Community: Almeria On The BayCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,022
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Updated waterfront condo just a short stroll to Crescent Beach and the fun and funky South Siesta Key Village! A Five-minute drive or trolley ride to the main Siesta Village. Lounge by the heated pool or pull your boat up to this nicely remodeled 2 bedroom/2 bath Almeria by the Bay unit. Located on the 2nd floor (with an elevator) , this unit boasts a coastal kitchen with a convenient breakfast bar, new luxury vinyl floors (2026), and amazing Intercoastal water views from the primary bedroom and screened lanai. Both bathrooms have been thoughtfully updated, and this unit is being offered turn-key furnished. It features a Beachy décor throughout. Fish or Kayak right from your own complex ! Monthly rentals are allowed and sought after. There's also a large, private storage area. Whether it is a forever home, vacation get-away or investment property, this is one of the most affordable move-in ready units located so close to the beach.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Donna Portale (716-308-8189)
6723 AVENUE C, SARASOTA, FL 34231
$1,949,000142 Days on yellowkey MLS ID: C7521189
REDUCED by $50,000 (2.5%) on 06/19/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1851 Built: 1999 Tax: $5,412 (2025)Community: Bay View AcresSingle Family
Taxes:$5,412
Elementary School: Pine View School
High School: Pine View School
Middle School: Pine View School
Remarks: Location, location, location! Siesta Key - Private Boat Slip - Completely Updated - NOT in a FLOOD ZONE & No Hurricane damage!! Situated on Avenue C just before the South Siesta Key Bridge, this beautifully updated home offers an unbeatable coastal lifestyle. Enjoy less than a mile walk to the world-famous Siesta Key Beach, where you can take in stunning sunsets, white sand beaches, and relaxing weekends by the water. Boaters will love the easy access to the Intracoastal, just minutes away, with approximately 15 minutes to reach the Gulf of America. The home is also within walking distance to local restaurants and beaches, while being tucked inside a peaceful bird sanctuary, offering a rare blend of convenience and natural surroundings. Inside, the home has been fully updated. Improvements completed in 2020 include a NEW ROOF, tile flooring throughout, a brand-new kitchen, and updated bathrooms. The floor plan offers three bedrooms, including a SECOND PRIMARY SUITE, three bathrooms, and an oversized two-car garage. The backyard is designed for true Florida living, featuring a large heated pool, a spacious lanai with new panoramic screening, and a PRIVATE BOAT SLIP, one of only two slips in the entire neighborhood. The pool was resurfaced with new tile in 2025, and the dock was completed in 2025 as well. This home captures the best of coastal Florida living with walkability, boating access, and thoughtful updates throughout. Enjoy the neighborhood with a short walk to popular spots including Daiquiri Deck, Siesta Key Oyster Bar, Captain Curt’s Crab & Oyster Bar, The Old Salty Dog, Abel's ice cream, Ruth’s Chris Steak House, and Carrabba’s Italian Grill. With Publix Super Market and shopping just down the road, you can enjoy peace and quiet while still being close to everything you need. Schedule your own personal tour today!
Listing is courtesy of: SELLSTATE VISION REALTY (941-336-5400)
Listing Agent: Savannah Zarris (941-807-4304)
3165 REGATTA CIR, SARASOTA, FL 34231
$459,000117 Days on yellowkey MLS ID: A4683961
REDUCED by $5,900 (1.3%) on 06/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1193 Built: 1964Monthly Fee: $6 Tax: $3,638 (2025)Community: Gulf GateSingle Family
Taxes:$3,638
Remarks: Completely remodeled with all work permitted and completed to the highest standards, this move-in ready Gulf Gate home lives large and showcases exceptional quality, thoughtful design, and true craftsmanship. Live where others vacation — perfectly positioned just 2.4 miles from the nearest Siesta Key beach access, placing world-renowned white sand beaches and breathtaking Gulf sunsets just minutes from your doorstep! The designer-curated kitchen features solid wood white shaker cabinetry, premium quartz countertops, a custom tile backsplash, and new stainless-steel appliances. Just off the kitchen, a spacious dining area is anchored by a beautifully crafted custom solid wood banquette with an integrated bookcase, bench seating, and built-in storage — a rare and functional design feature. Both full bathrooms have been beautifully renovated with new vanities, updated countertops, and custom tiled showers. Additional interior upgrades include new luxury vinyl plank flooring, fresh interior and exterior paint, new doors and trim, and updated lighting & fixtures. Indoor laundry adds everyday convenience. Major system improvements provide peace of mind, including new PVC underground sewer drain lines, new water lines, a new water heater, updated electrical panel, HVAC (2020), and a *BRAND NEW ROOF* (2026)! All windows are equipped with hurricane shutters. Designed for seamless indoor/outdoor living, multiple sliding glass doors open to a spacious screened and covered back porch featuring upgraded Trex decking — the perfect space for morning coffee or relaxed evenings under the twinkle lights. The backyard is truly special, highlighted by a custom PAVER FIRE PIT with built-in bench seating. Enjoy fresh landscaping, a new front paver walkway, and a large fenced backyard. Covered carport parking includes an outdoor storage closet, plus an additional shell parking space which provides plenty of parking. Centrally located on a quiet circle in prime Gulf Gate, this home offers easy access to world-famous Siesta Key Beach and is within walking or biking distance to an array of local restaurants and shopping in Gulf Gate. Publix, Trader Joe’s and Costco are all just minutes away, and Gulf Gate Elementary School is right around the corner. Turnkey furnishing option is also available which could make for an easy second home. Bright, cheerful, and beautifully finished — this home is truly move-in ready! Buyer’s agent to verify all MLS information including room sizes, utilities and HOA if applicable.
Listing is courtesy of: CARMEL PROPERTIES (941-416-6300)
Listing Agent: Jonah Wright (941-932-1661)
1630 STICKNEY POINT RD #101, SARASOTA, FL 34231
$269,90092 Days on yellowkey MLS ID: A4687288
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 800 Built: 1975 Tax: $2,758 (2025)Community: Castle Del MareCondo
Taxes:$2,758
Remarks: Fantastic opportunity to own a beautifully updated 1BR/1BA first-floor unit in highly desirable Castel Del Mare! This light and bright residence features a tiled entry and kitchen, with attractive laminate flooring throughout the remaining living areas. The spacious kitchen is equipped with white cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining. The generously sized primary suite offers a private, updated en-suite bath complete with granite counters and a walk-in shower. What truly sets this unit apart is the in-unit washer and dryer—a rare convenience—along with an expansive double, oversized lanai just steps from the pool, creating the perfect space to relax and enjoy the Florida lifestyle. Castel Del Mare is a sought-after waterfront community ideally located just steps from the South Bridge to Siesta Key—offering the best of both worlds with easy access to the beach while enjoying the convenience of mainland living.
Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)
Listing Agent: Tony Andrews (941-921-5999)
1646 STICKNEY POINT RD #1646-101, SARASOTA, FL 34231
$379,900145 Days on yellowkey MLS ID: O6376065
REDUCED by $7,500 (1.9%) on 06/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1975Monthly Fee: $993 Tax: $3,529 (2025)Community: Castel Del MareSpa: NoTownhouse
Taxes:$3,529
Remarks: Escape to Saltwater Daydreams, your own slice of paradise just steps from the best of Siesta Key and Sarasota. A SUPERIOR UNIT that has been beautifully remodeled. This 2-bedroom, 1.5-bath townhomeis just across the south bridge from Siesta Key. Fully updated in 2022 with new furnishings, in-unit WASHER AND DRYER, a screened lanai, and a PRIVATE BACKYARD OFF the living area and master bedroom. Crescent Beach (access #12) in Siesta Key and multiple restaurants and shops are a short 10-MINUTE WALK! Fully updated in 2022 with designer decor and furnishings, in-unit WASHER AND DRYER, a screened lanai, and a completely private patio overlooking a very PRIVATE BACKYARD off the master bedroom and living area. Located in the sought-after Castel Del Mare complex, you'll enjoy two pools (one right on the Intracoastal Waterway), tennis, pickleball, shuffleboard, a mangrove walk, and gazebo views of the waterway. The off-island location is a bonus during peak season — easy in-and-out without the bridge traffic. Townhome features tranquil and private greenbelt views from both levels. Assigned parking is located directly in front of the home, with ample guest parking nearby. The HOA fee covers exterior and roof maintenance, landscaping, amenities, on-site management, strong reserves, cable TV, water, sewer, trash recycling, and weekly pest control! Whether as a primary residence, seasonal getaway, or investment opportunity, this home offers privacy, comfort, and the ultimate Siesta Key lifestyle! With flexible rental guidelines, you can offset ownership costs by renting out part of the year, and take advantage of lucrative peak-season rental revenues!” Near public transit with easy access to Siesta Key Beach, Siesta Village dining, and the Stickney Point Bridge. Nearby dining includes Merci Café and La Dolce Vita. Publix and Detwiler's Farm Market within 1 mile. Red Bug Slough Preserve and Gulf Gate Village nearby.
Listing is courtesy of: BEAR TEAM REAL ESTATE (407-228-1112)
Listing Agent: Bethanne Baer (407-228-1112)
4304 MIDLAND RD, SARASOTA, FL 34231
$340,00056 Days on yellowkey MLS ID: TB8502989
1 Days Off yellowkey (back on 6/19/2026)
REDUCED by $34,900 (9.3%) on 05/26/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1447 Built: 1952 Tax: $3,143 (2025)Community: Floral Park HomesteadsSpa: YesSingle Family
Taxes:$3,143
Elementary School: Wilkinson Elementary
Remarks: This meticulously maintained 3-bedroom residence offers the ideal blend of vintage Florida character and high-quality contemporary improvements—all in a prime Sarasota location. Metal roof (2011), new HVAC system (2023), and tankless water heater (2020). Original wall planking replaced with new Sheetrock and insulation to improve energy efficiency. New flooring installed in 2020 flows throughout the open-concept living areas. Private fenced backyard with a sparkling pool (2019) and an above-ground heated spa—perfect for year-round enjoyment. Conveniently situated near Sarasota’s most desirable destinations. Approximately 5 miles to the world-renowned Siesta Key Beach; it is also close to Lido Key Beach. Minutes to St. Armands Circle and Downtown Sarasota’s vibrant restaurant and cultural scene. Near major retailers, grocery stores, and the shops along Bee Ridge Road and Southside Village. Just around the corner from Bee Ridge Park with green space, playgrounds, and community activities.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Brenda Olivas (407-280-0208)
2227 CIRCLEWOOD DR #52, SARASOTA, FL 34231
$289,90020 Days on yellowkey MLS ID: A4696035
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1276 Built: 1974 Tax: $1,597 (2025)Community: Woodside VillageSpa: YesVilla
Taxes:$1,597
Elementary School: None
High School: None
Middle School: None
Remarks: Recently extensively remodeled villa just minutes from Siesta Key, surrounded by mature Old Florida landscaping in a private enclave of villa-style condos, close to Gulf Gate and US41. This inviting 2-bedroom, 2-bath condominium unit in Sarasota’s desirable Gulf Gate area, blending classic Florida charm with modern comfort. The spacious layout includes a bright Florida room, rear screened porch, and a covered carport. Recent updates feature a new modern kitchen w/ stainless steel appliances, new textured/painted ceilings and walls, newer HVAC system, newer electric wiring throughout the unit, newer electric panel, and newer water heater, plus newly paved neighborhood roads. The community offers a tennis/pickleball court and a large screened-in heated swimming pool. Not in a flood zone requiring insurance, this home is available for immediate occupancy, perfect for seasonal or year-round living. Just a 5-minute drive to world-famous Siesta Key Beach and close to shopping, dining, and entertainment, it’s ideal as a permanent home, vacation retreat, or investment property.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Sean Hickey (941-587-4244)
208 SOUTHWINDS DR, SARASOTA, FL 34231
$64,90064 Days on yellowkey MLS ID: A4690882
4 Days Off yellowkey (back on 6/19/2026)
REDUCED by $10,000 (13.4%) on 05/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 459 Built: 1966Monthly Fee: $195 Tax: $1,160 (2025)Community: South Winds Mhp Co-OpMobile Home
Taxes:$1,160
Remarks: Under contract-accepting backup offers. Welcome to an incredible opportunity in the highly desirable Southwind's 55+ co-op community, ideally located in the heart of Sarasota just minutes from the world-renowned Siesta Key Beach. Whether you’re searching for a full-time residence, seasonal getaway, or investment opportunity, this property offers exceptional value in an unbeatable location. This one-bedroom, one-bath residence features a spacious and functional layout with abundant natural light throughout. The living area flows nicely, creating a comfortable and inviting space to relax or entertain. One of the standout features is the oversized lanai; perfect for enjoying the Florida lifestyle year-round and easily serving as additional living space. The home also offers a private driveway, a dedicated laundry area located in the shed, and ample storage space. While the unit could benefit from some updating, it is priced accordingly, presenting a fantastic opportunity to customize and make it your own. With a little vision, this property has the potential to truly shine; making it especially appealing for investors or buyers looking to add value. Located in an X flood zone, this property has had no flood or water damage from recent storms, offering added peace of mind. Southwind is a vibrant and friendly community known for its active lifestyle and impressive amenities, including a heated pool, shuffleboard courts, horseshoe pits, library, and recreation hall. The community also offers guest parking along with designated areas for RV and boat storage. With low monthly fees of just $195, which include water, sewer, cable, and lawn care, it’s one of the best values in Sarasota. Conveniently located just 10 minutes to Siesta Key, 20 minutes to downtown Sarasota and UTC Mall, and close to shopping, dining, and everything South Sarasota has to offer. Affordable opportunities like this in such a prime location are rare. Priced to sell and offered as-is with the right to inspect; don’t miss your chance to make this your own slice of paradise.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Rachelle Golden (941-538-8998)
3225 GULF WATCH CT, SARASOTA, FL 34231
$399,0006 Days on yellowkey MLS ID: TB8519650
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1216 Built: 1990Monthly Fee: $133 Tax: $3,345 (2025)Community: Gulf Gate GlenSingle Family
Taxes:$3,345
Remarks: Nestled within the desirable Gulf Gate Glen community, this location offers the perfect blend of convenience, recreation, and the laid-back Florida lifestyle that makes Sarasota so sought after. Residents enjoy being just minutes from the powder-soft sands of Siesta Key Beach, consistently ranked among the best beaches in the country. Whether you're spending the day boating on Sarasota Bay, exploring nearby waterfront parks, or taking in a breathtaking Gulf Coast sunset, this location places the very best of Sarasota right at your fingertips while remaining outside of a flood zone. Stepping inside, you'll immediately notice the soaring vaulted ceilings, abundant natural light, and luxury vinyl plank flooring that flows throughout the home. This well-designed floorplan offers 2 bedrooms, 2 bathrooms, and a spacious 2-car garage, creating the perfect balance of comfort and functionality. The kitchen features stainless steel appliances and overlooks a dining area, making everyday living and entertaining effortless. The owner's suite serves as a private retreat with a walk-in closet and an ensuite bathroom complete with dual sinks and a walk-in shower. French doors lead to the screened-in lanai, providing the ideal space to enjoy your morning coffee, unwind in the evenings, or entertain guests while enjoying Florida's year-round sunshine. One of the biggest advantages of living here is the everyday convenience. Gulf Gate Village is just around the corner, offering an eclectic mix of locally owned restaurants, coffee shops, bakeries, live music venues, and neighborhood bars that create a true sense of community. For shopping, dining, and entertainment, you're only a short drive from Downtown Sarasota, St. Armands Circle, and the countless cultural attractions that make Sarasota one of Florida's premier destinations. Outdoor enthusiasts will appreciate easy access to Legacy Trail, one of the area's most popular biking and walking trails stretching for miles throughout Sarasota County. Nearby parks, marinas, fishing spots, kayak launches, golf courses, tennis facilities, pickleball courts, and fitness centers provide endless opportunities to enjoy an active Florida lifestyle. Families will appreciate the proximity to highly regarded schools, while commuters benefit from quick access to US-41, making travel throughout Sarasota, Venice, and Lakewood Ranch simple and convenient. Sarasota Memorial Hospital, medical offices, grocery stores, and everyday necessities are all just minutes away. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this exceptional Sarasota location delivers the coastal lifestyle buyers dream about. Close to world-famous beaches, vibrant dining and entertainment, outdoor recreation, and everything that makes Florida's Gulf Coast so special, schedule your showing today!
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Bona Nedelkovska (727-238-6302)
5720 ISANDA PL, SARASOTA, FL 34231
$785,00027 Days on yellowkey MLS ID: A4695097
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1971 Built: 1967 Tax: $5,994 (2025)Community: Phillippi Gardens 03Spa: NoSingle Family
Taxes:$5,994
Remarks: Welcome to your private piece of paradise! Situated on an expansive, oversized lot featuring a massive, fully fenced side yard, this masterfully renovated 4-bedroom, 2-bathroom residence perfectly blends modern luxury with an outdoor vacation lifestyle. From the moment you step through the beautiful front entrance into the large, welcoming foyer, the quality of craftsmanship is undeniable. The entire home features seamless, high-end wood-plank tile flooring that leads you into a show-stopping chef's kitchen. the kitchen is anchored by stunning quartz countertops with a dramatic waterfall edge, pristine white cabinetry, a modern tile backsplash, premium stainless steel appliances, and a convenient breakfast bar. The spacious owner's retreat is a true "wow" factor, boasting a spa-like bathroom complete with a custom walk-in shower, a deep soaking tub, and gorgeous wood-plank accent walls. Both bathrooms throughout the home have been meticulously updated with newer vanities, quartz countertops, and contemporary plumbing fixtures. The flexible 4th bedroom easily adapts to a private home den or executive office. Step outside to your ultimate outdoor sanctuary: a massive under-roof lanai area transitions smoothly to a shimmering 14x28-foot pool, creating the perfect backdrop for Florida entertaining. Beyond the aesthetics, this home offers unparalleled mechanical peace of mind and insurance efficiency: a newer roof (2018), complete hurricane impact windows and sliders (2018), a newer A/C system with all-new ductwork (2021), and a newer water heater (2019). All new landscaping in the back with shell comes with minimum maiantance and beach style yard. Tucked away in a highly desirable South Sarasota location, you are within arm's reach of premier shopping, local dining, and just minutes away from the world-famous quartz sands of Siesta Beach. Beautifully updated and completely move-in ready, this spectacular home will not last long. Schedule your private tour today!
Listing is courtesy of: VIVE REALTY (941-600-8162)
Listing Agent: Nicole Long (941-600-8162)
2037 and 2039 Jo an Dr JO AN DR, SARASOTA, FL 34231
$619,00053 Days on yellowkey MLS ID: A4692288
REDUCED by $10,000 (1.6%) on 06/08/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 1988 Built: 1955 Tax: $5,534 (2024)Community: High AcresSpa: YesHalf Duplex
Taxes:$5,534
Elementary School: Phillippi Shores Elementary
Tax Year: 2024
Remarks: Live the Florida Dream for Free – Premier Sarasota Duplex with Income Potential Why choose between a luxury home and a smart investment? At 2037 & 2039 Jo An Drive, you can have both. This meticulously maintained side-by-side duplex offers a rare opportunity to occupy a beautiful 2BR/2BA residence while the identical neighboring unit generates significant rental income to offset your costs. The Lifestyle: Enjoy your own private oasis featuring a luxurious swim spa and a massive, deep-bay garage perfect for boat storage—all just 3 miles from the world-famous Siesta Key Public Beach. The Income: With RMF-1 zoning, this property is a turnkey powerhouse. Whether you prefer stable long-term tenants or want to capitalize on the high-demand short-term rental market, the numbers work in your favor. The Location: Tucked away on a quiet street but only minutes from Southside Village, premier dining, and top-rated schools. Ideal for: The "House Hacker": Live in one side and let the other pay your mortgage. The Seasonal Resident: Live here in the winter and rent both units during the peak vacation season. The Savvy Investor: Maximize your ROI with two updated units in a prime coastal location. Don’t just buy a home—buy an asset. Contact us today for a private tour and a full rental income projection.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Marcus Mumm (920-960-0413)
6139 HOLLYWOOD BLVD, SARASOTA, FL 34231
$999,90028 Days on yellowkey MLS ID: TB8512156
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2088 Built: 1953 Tax: $9,362 (2025)Community: Pine Shores Estate 4Th SecSpa: YesSingle Family
Taxes:$9,362
Remarks: Offered below appraised value at $999,900, this truly one-of-a-kind Sarasota property presents a rare opportunity to own a private family compound just minutes from Siesta Key and located West of the Trail in the highly desirable Pine Shores neighborhood. Set on an oversized 0.34-acre gated, fenced, and walled homesite, this exceptional property offers two separate living residences, incredible flexibility, and resort-style outdoor living — all with NO HOA and NOT located in a flood zone. This property also represents an outstanding investment opportunity with a proven rental history and strong income-producing potential, making it ideal for seasonal rentals, multigenerational living, guest accommodations, or long-term investment strategies. The beautifully maintained main residence features 3 bedrooms and 3 baths with approximately 1,685 square feet of living space and is being offered fully turnkey furnished. ROOF (3 - 4 years old), HVAC 2025, TANKLESS WATER HEATER 2025. Pride of ownership is evident from the moment you arrive, with a long paver driveway leading to a charming, gated breezeway entrance and lush, low-maintenance tropical landscaping. The main home showcases polished terrazzo flooring, crown molding, remodeled kitchen and baths, granite countertops, impact-resistant windows and doors, and a state-of-the-art water filtration system. Outdoor living is exceptional with a heated saltwater pool, spa, summer kitchen, and expansive entertaining areas designed for the ultimate Florida lifestyle. Built in 2013, the detached oversized two-car garage structure adds tremendous value and versatility. Upstairs, guests or extended family will enjoy a spacious studio apartment complete with a full kitchen, breakfast bar, custom cabinetry, hardwood flooring, upgraded lighting and fans, built-in hideaway bed, full bath, and private laundry area. The garage also includes built-in storage shelving and an additional side carport. The oversized paver driveway and side access provide abundant room for boat, RV, or recreational vehicle parking. The expansive lot also offers future flexibility with room to potentially expand, add additional structures, or create a custom luxury estate environment. Located just minutes from Siesta Key Beach, Phillippi Estate Park, shopping, dining, and Sarasota’s vibrant cultural attractions, this is a truly special property combining location, privacy, flexibility, lifestyle, and investment value in one extraordinary offering.
Listing is courtesy of: MARZUCCO REAL ESTATE (239-776-5194)
Listing Agent: Lisa Kohan (239-272-5901)
4078 GROVELAND AVE, SARASOTA, FL 34231
$335,000238 Days on yellowkey MLS ID: A4669478
REDUCED by $10,000 (2.9%) on 06/15/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1240 Built: 1981 Tax: $2,704 (2024)Community: Grove ParkSingle Family
Taxes:$2,704
Remarks: In a city where home prices often feel out of reach, this well-maintained three-bedroom, one-bath residence offers something increasingly rare: a real opportunity to plant roots in Sarasota without sacrificing location or potential. Set on a quiet, non-HOA neighborhood just minutes from the beach, downtown, shopping, and restaurants, this home proves that owning in Sarasota does not mean choosing between charm, location, and affordability. Inside, you will find an open layout with tile and laminate flooring, natural light throughout, and a warm, welcoming feel ready to be personalized. The kitchen has been thoughtfully updated with granite countertops and refreshed cabinetry that seamlessly blends function and simplicity, while unifying the living and dining areas. A cozy brick fireplace, featuring an above-mantel TV mount, anchors the living room, making it perfect for both quiet evenings with a book and hosting game day with friends. The primary bedroom features two closets and a dual-access ensuite bath that connects to the hallway leading to the home's two additional bedrooms. Step outside to a fully fenced backyard with a spacious deck, fire pit, and a large permitted shed that offers flexibility for storage or creative use, along with ample room for a home addition or pool, if desired. While it is not the biggest or flashiest house in town, it is real, it is ready, and it can be yours to shape. Whether you are a first-time buyer looking to stay in Sarasota on a budget, a seasonal visitor in need of a winter retreat, or someone who values authenticity, this is a home where you can begin to build not just equity, but a meaningful life. QUALIFIED BUYERS MAY HAVE THE OPPORTUNITY TO ASSUME THE EXISTING FHA LOAN AT A 2.9% INTEREST RATE. THIS RARE FINANCING OPTION COULD MEAN SIGNIFICANT MONTHLY SAVINGS COMPARED TO CURRENT MARKET RATES. ASSUMPTION IS SUBJECT TO LENDER APPROVAL AND BUYER QUALIFICATION. CONTACT THE LISTING AGENT FOR DETAILS.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Domanic Calamese (941-914-0038)
5917 OLIVE AVE, SARASOTA, FL 34231
$448,99926 Days on yellowkey MLS ID: O6411402
REDUCED by $24,001 (5.1%) on 06/18/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1330 Built: 1957 Tax: $3,209 (2025)Community: Golden AcresSingle Family
Taxes:$3,209
Remarks: Virtually Staged. Located in the desirable coastal community of Sarasota, this inviting home offers a relaxed Florida lifestyle with a comfortable layout and bright, open living spaces. The interior features a functional flow designed for everyday living and easy entertaining, with well-sized bedrooms and versatile common areas. Outdoor space provides room to enjoy the warm weather year-round, whether relaxing, gardening, or hosting gatherings. Conveniently situated near Gulf beaches, shopping, dining, and cultural attractions, this property delivers both lifestyle and location in one of Sarasota’s most sought-after areas.
Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)
Listing Agent: Raquel Littlejohn (470-279-6333)
2657 WOODGATE LN #E4, SARASOTA, FL 34231
$189,50097 Days on yellowkey MLS ID: A4686420
REDUCED by $5,500 (2.8%) on 06/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1980Monthly Fee: $563 Tax: $909 (2025)Community: Pinewood Village VCondo
Taxes:$909
Remarks: Well kept and updated first level condo. The kitchen has been updated cabiinets and countertops. The primary bathroom has been updated as well. This unit come partially furnished. Parking couldn't be easier with a carport parking spot right in front of the unit. The front porch has been screened in for the morning coffee and book. All the kitchen appliances convey including the washer and dryer. This community offers a community pool, community center that offers a pool table and fitness area.
Listing Agent: Eric Martin (941-274-8718)
2654 GRAND CAYMAN ST, SARASOTA, FL 34231
$357,00029 Days on yellowkey MLS ID: A4694859
REDUCED by $10,000 (2.7%) on 06/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1190 Built: 1959 Tax: $2,737 (2025)Community: Bahama HeightsSingle Family
Taxes:$2,737
Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT!! Step into this move-in ready 2-bedroom, 2-bath home just minutes from world-famous Siesta Key and downtown Sarasota with no HOA restrictions! Enjoy the ultimate Florida lifestyle with top-rated schools and restaurants all within short distance, including Riverview High School and Phillippi Shores Elementary School. The open-concept living area features beautiful hand-painted ceiling details, abundant natural light, and a warm atmosphere perfect for relaxing. Major upgrades include a 50-year metal roof (2019), upgraded windows, new hot water heater (2025), upgraded kitchen and primary bathroom, and fresh interior paint (2026). High and Dry no flood insurance required! Schedule your private showing today! Move-in ready. List agent is owner.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Mary Birkhold (941-266-8679)
2242 CIRCLEWOOD DR #24, SARASOTA, FL 34231
$225,00012 Days on yellowkey MLS ID: TB8517647
1 Days Off yellowkey (back on 6/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1176 Built: 1974Monthly Fee: $695 Tax: $1,028 (2025)Community: Woodside Village EastVilla
Taxes:$1,028
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 2242 Circle Wood Drive, a beautifully maintained 2-bedroom, 2-bath villa offering the perfect blend of comfort, convenience, and maintenance-free living in one of Sarasota’s most desirable locations. Inside, you'll find spacious living areas filled with natural light, an inviting floor plan, and a beautiful sunroom/den that provides the perfect space for a home office, reading room, or additional living area. Covered parking adds everyday convenience, while the lush tropical landscaping creates a peaceful setting you'll love coming home to. The community amenities elevate the lifestyle even further with a heated pool, tennis and pickleball courts, and beautifully maintained grounds. Location is everything, and this villa delivers. You're just minutes from Siesta Key Beach, St. Armands Circle, Downtown Sarasota, world-class dining, shopping, entertainment, and golf. Whether you're looking for a full-time residence, seasonal retreat, or low-maintenance Florida getaway, this villa offers the Sarasota lifestyle you've been dreaming of.
Listing is courtesy of: ELEVE REAL ESTATE LLC (813-562-5002)
Listing Agent: Danielle Davis (813-526-5002)
1436 PINE BAY DR, SARASOTA, FL 34231
$4,698,000100 Days on yellowkey MLS ID: A4683228
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 4128 Built: 2026Monthly Fee: $17 Tax: $7,062 (2025)Community: Johnson EstatesSpa: YesSingle Family
Taxes:$7,062
Remarks: Pre-Construction. To be built. Experience modern coastal living at its finest with the Coral Isle by Heritage Builders. Nestled on an expansive 20,000+ sq. ft. homesite in the highly coveted Oyster Bay neighborhood, this newly crafted ranch-style residence effortlessly blends contemporary design with timeless architectural elements. With 4,128 sq. ft. of air-conditioned living space all on one level, the home offers an ideal layout featuring four spacious bedrooms, a dedicated media room, private office, casual dining area, and an impressive four-car side-load garage. Inside, Heritage Builders’ signature high-end finishes take center stage. White oak flooring flows throughout the home, complemented by elegant arched entryways and thoughtfully designed details at every turn. The primary suite is a serene retreat, complete with an outdoor shower accessible directly from the luxurious primary bath—perfect for embracing the Florida lifestyle. The heart of the home is the expansive Great Room and open-concept kitchen, designed to bring family and friends together. A disappearing corner slider in the casual dining area blurs the lines between indoors and out, opening to the covered lanai, pool, and spa—an entertainer’s dream. The chef’s kitchen impresses with an oversized island, true walk-in butler’s pantry, and a full suite of Thermador appliances, offering ample space for prep, cooking, and hosting. Situated just 5 minutes from the world-famous Siesta Key Beach, a short walk to the exclusive Field Club, and mere minutes from the boutiques and dining of Southside Village, this location places you at the center of Sarasota’s most desirable amenities. Enjoy quick access to the arts and culture of downtown Sarasota, only 7 minutes away, all while residing in one of the area’s most charming and established neighborhoods. The Coral Isle brings modern luxury, thoughtful design, and unrivaled convenience together in one extraordinary home.
Listing is courtesy of: HB REALTY GROUP INC. (941-378-3983)
Listing Agent: Sara Boudarga (941-321-6352)
2049 CHAMPION ST, SARASOTA, FL 34231
$65,00085 Days on yellowkey MLS ID: A4688156
REDUCED by $10,000 (13.3%) on 06/18/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 736 Built: 1963Monthly Fee: $215 Tax: $958 (2025)Community: Mobile EstatesMobile Home
Taxes:$958
Remarks: Opportunity awaits with this Sarasota property located in a 55+ community in a convenient area near US-41, Bee Ridge Road, and the Gulf Coast beaches. The home is being offered as-is and presents strong potential for buyers looking to renovate, update, or create value through thoughtful improvements. This property offers a compelling opportunity for those seeking a project in a desirable Sarasota location. With the right vision, the home can be transformed into a comfortable full-time residence or a seasonal retreat. Ideally positioned just minutes from Siesta Key Beach, downtown Sarasota, shopping, dining, and everyday conveniences, the location provides access to many of the area's most desirable amenities. Nearby parks, retail centers, and major roadways allow convenient connectivity throughout Sarasota and surrounding communities. For buyers looking to take on a renovation project and customize a property to their preferences, this home offers solid potential within a well-located Sarasota neighborhood. The property is being sold as-is. Buyers are encouraged to conduct their own due diligence and verify all information.
Listing is courtesy of: KONA REALTY (941-718-8293)
Listing Agent: Dan Ivanov (941-544-0475)
4003 BOOTH PL, SARASOTA, FL 34231
$355,90069 Days on yellowkey MLS ID: A4690238
REDUCED by $19,100 (5.1%) on 05/02/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1306 Built: 1952 Tax: $2,979 (2025)Community: BrooksideSingle Family
Taxes:$2,979
Remarks: Under contract-accepting backup offers. Welcome to this FRESH and Bright centrally located home in Sarasota! It offers 3 bedrooms, 2 bathrooms, and valuable updates that provide both comfort and peace of mind. A BRAND NEW ROOF is scheduled for installation in mid-June 2026, while the freshly painted interior (May 2026), finished in a soft/neutral white, creates a light-filled and inviting atmosphere throughout the home. The beautifully updated kitchen features newer appliances, cabinetry, white quartz countertops, and fixtures, blending style and functionality for everyday living and entertaining. The spacious primary suite is complemented by a stunning bathroom renovation completed in March 2026, showcasing modern finishes and thoughtful design. The water softener is also new. UPDATED PHOTOS WILL BE TAKEN after the new roof is completed. Step outside and enjoy the spacious screened lanai, an ideal setting for morning coffee, evening relaxation, or gathering with family and friends. The large private backyard is shaded by mature trees, offering both beauty and privacy. A one-car carport under the main roofline adds convenience and enhances the property's overall value. Located within the highly sought-after Riverview School District, this home is just minutes from Siesta Key's world-famous beaches, vibrant downtown Sarasota, premier shopping and dining, parks, and major medical facilities. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this exceptional location offers enduring appeal. With many of the major improvements already completed—including the new roof, fresh interior paint, updated kitchen, renovated primary bathroom, and new water softener—this property presents an outstanding opportunity to enjoy the Sarasota lifestyle from day one. Combining desirable updates, a prime location, and room to make it your own, this home is ready to welcome its next owner.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Julie Shaw (941-408-4760)
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