Location: Sarasota
Do Not Show Listings
7230 SHEPHERD ST, SARASOTA, FL 34243
$414,900216 Days on yellowkey MLS ID: A4671336
1 Days Off yellowkey (back on 6/16/2026)
REDUCED by $10,100 (2.4%) on 05/04/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2000 Built: 1953 Tax: $5,243 (2024)Community: Whitfield Estates Blks 14-23 & 26Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,243
Elementary School: Florine J. Abel Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Electa Arcotte Lee Magnet
Remarks: Under contract-accepting backup offers. ***HUGE PRICE REDUCTION- MOTIVATED SELLER!!!*** West of the Trail – Endless Potential in a Prime Sarasota Location! Vacation Rentals Allowed! APPRAISED AT $450,000 - OWNER HAS APPRAISAL Welcome to this charming and newly renovated 3-bedroom, 3-bath home offering nearly 2,200 sq. ft. of living space in highly desirable Whitfield Estates, where opportunity meets location. Whether you’re seeking your first home, a seasonal retreat, or a high-performing short-term rental, this property is a rare find — with no HOA or CDD fees! Set on a large corner lot, fully fenced quarter-to-half-acre lot, the backyard is designed for entertaining, featuring a turfed gazebo area perfect for Florida sunsets, plus a cement pad prepped with water and electric—ready for your custom outdoor kitchen. Inside, the home features a bright open-concept layout with an expansive family room, dining area, and designer kitchen. The kitchen renovation is a true showpiece, boasting shaker cabinetry, quartz countertops, and premium gold-accent fixtures. The entire living space is finished in large-format tile, providing a seamless flow throughout. The owner’s suite offers private access to a tranquil garden patio, along with a renovated bath featuring a walk-in shower and a spacious walk-in closet. Both guest bedrooms feature new carpet and stylish updates. A newly added bar area off the hallway connects perfectly to the dining room for entertaining ease. Enjoy peace of mind with double-pane impact windows, a new stone fireplace, and an additional family/bonus room—perfect for a game room, office, or sunroom. Major updates include a roof (2017) and dual A/C systems, with one unit replaced in 2019. Just a 5-minute walk to Sara Bay Country Club, offering optional golf, social, and dining memberships. Conveniently located less than 10 minutes to SRQ Airport and Ringling Museum, and within 15–20 minutes to the Gulf beaches, St. Armands Circle, Downtown Sarasota, UTC Mall, and Lakewood Ranch. Whether you’re an investor or a homeowner, this move-in ready entertainer’s paradise delivers prime Sarasota living with Airbnb flexibility (with proper registration). Schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Kimberly Rainey (678-764-6767)
4244 CENTRAL SARASOTA PKWY #726, SARASOTA, FL 34238
$300,00033 Days on yellowkey MLS ID: A4694637
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1147 Built: 1999 Tax: $3,300 (2025)Community: Plaza De FloresCondo
Taxes:$3,300
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: Virtually Staged. Welcome to Plaza De Flores, a gated enclave tucked into the heart of Palmer Ranch where palm-lined courtyards, a tiled fountain, and lush tropical landscaping set a serene, resort-like tone the moment you arrive. This second-floor, two-bedroom, two-bath residence lives bright and open, with soaring vaulted ceilings and neutral tile laid on the diagonal carrying you through a spacious great room bathed in natural light. Fresh paint throughout and new ceiling fans give the home a crisp, move-in-ready feel, while solid concrete block construction keeps it remarkably quiet and well insulated from the world outside. At the center of it all is a thoughtfully updated kitchen, where granite counters, white shaker cabinetry, and a warm stone backsplash pair beautifully with the appliances and a breakfast bar made for easy mornings. Smart touches like an added custom cabinet with a pull-out, open wood shelving, and a window above the sink make the space as functional as it is inviting, all flowing into the dining and living areas so no one ever feels far from the conversation. The primary suite is a true retreat, generously sized with a large closet and an ensuite bath featuring a dual-sink vanity, fresh mirrors, and a beautiful custom marble walk-in shower with a frameless glass enclosure and built-in niche. A comfortable guest bedroom and second full bath with a tub-and-shower combination offer private, welcoming accommodations for visitors. A dedicated in-unit laundry closet with a newer washer and dryer adds everyday ease, and recent upgrades including a 2025 tankless water heater and a 2024 tile roof bring real peace of mind. Just off the living room, a large screened lanai is the home's quiet showstopper, finished with cool tile underfoot, two sets of sliding glass doors, new screening, and custom pull-down shades for sun and privacy. It is the perfect perch for morning coffee or for unwinding to the area's incredible evening sunsets over the treetops. Beyond your door, Plaza De Flores delivers the lifestyle, with a sparkling community pool and spa, a tennis court, charming gazebos, and a clubhouse complete with a fitness room, library, and full kitchen. Newer carports and freshly repaved parking round out a community that is beautifully maintained. The location is hard to beat, moments from the Legacy Trail, Oscar Scherer State Park, and nearby kayak launches, with the dining and shopping of Gulf Gate and downtown Sarasota an easy drive away. When the beach calls, Siesta Key, Nokomis, Venice, and Caspersen are all within reach. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.*
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
4553 LINWOOD ST, SARASOTA, FL 34232
$372,00023 Days on yellowkey MLS ID: A4693155
1 Days Off yellowkey (back on 6/6/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1373 Built: 1995 Tax: $2,653 (2025)Community: Sarasota SpgsSingle Family
Taxes:$2,653
Elementary School: Brentwood Elementary
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. This house checks all the boxes and move in ready. Enjoy outside living on this lighted expansive deck flowing into screen porch overlooking private lush greenery. This newly beautifully stained deck offers solitude for morning coffee and space for large gathering. Remote retractable sunshade awning offers year round functionality with firepit area. Walking up to front door notice the new paver deck. Split bedrooms, with updated baths, decorator ceiling fans and lights, custom walk in master closet adjoins the master bath. Kitchen has lots of natural light, double oven offers lower convection unit and updated appliances . Also included are new HVAC in 2025 with 2 UV lights, electrical panel and newer hot water heater. Don't miss the owned solar assist panels, resulting in low electrical bills. All appliances, plumbing, HVAC, water heater and termites have warranties which can be assumed by new owner with all inspections current. Some furniture available for purchase separate agreement. Ride, walk or jog the nearby Legacy Trail, enjoy the world famous beaches, golf, with all the culture Sarasota adds to Florida.
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Ida Kay Tidwell (941-356-1146)
6499 SILVERSTAR DR, SARASOTA, FL 34240
$365,00013 Days on yellowkey MLS ID: A4696304
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1455 Built: 2023Monthly Fee: $217 Tax: $4,962 (2025)Community: Avanti/WatersideVilla
Taxes:$4,962
Elementary School: Tatum Ridge Elementary
High School: Booker High
Middle School: McIntosh Middle
Remarks: Welcome to Avanti at Waterside, where modern, maintenance-free living is paired with one of Sarasota’s most desirable lifestyle destinations. Located just minutes from Waterside Place, you’ll enjoy easy access to waterfront dining, boutique shopping, community events, farmers markets, live entertainment, and scenic walking paths in the heart of Lakewood Ranch’s Waterside district. This beautifully maintained home with a versatile flex room offers an open-concept floor plan designed for both everyday comfort and easy entertaining. The flex room provides the perfect space for a home office, den, hobby room, or guest retreat. Hurricane-impact windows provide added peace of mind, storm protection, energy efficiency, and noise reduction. Enjoy Florida living year-round from the screened rear lanai and private fenced outdoor space, a rare feature in the community. Additional highlights include an epoxy-coated garage floor and maintenance-free living with lawn care included. Whether you’re looking for a full-time residence or a seasonal retreat, this move-in ready home offers the perfect combination of comfort, convenience, and low-maintenance living in sought-after Avanti at Waterside.
Listing is courtesy of: LIVE MODERN (941-587-8871)
Listing Agent: Mara Daniel (941-587-8871)
9698 CRYSTAL ISLES CIR, SARASOTA, FL 34241
$888,99950 Days on yellowkey MLS ID: R4911214
REDUCED by $55,926 (5.9%) on 06/16/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2942 Built: 2026Monthly Fee: $358 Tax: $500 (2025)Community: Grand ParkSingle Family
Taxes:$500
Elementary School: K-8 At Clark And Lorriane
High School: Riverview High
Middle School: Sarasota Middle
Remarks: Pre-Construction. To be built. ****SPECIAL FINANCING AVAILABLE FOR A LIMITED TIME ONLY FROM PREFERRED LENDER. RESTRICTIONS APPLY, FOR QUALIFIED BUYERS, SUBJECT TO APPLICABLE TERMS AND CONDITIONS. SUBJECT TO CHANGE WITHOUT NOTICE**** Welcome to the Calusa. Boasting over 2,900 square-feet, this stunning five-bedroom, four-bathroom home, has a second-story bonus room and two-car garage. Located in the beautiful Grand Park neighborhood in Sarasota, this property offers a spacious and modern living experience. Step inside this two-story home and prepare to be impressed by the high-quality craftsmanship and attention to detail. There is plenty of room for you to spread out and enjoy. Entering from the foyer, you will find two bedrooms and full bath off to one side, with an additional bedroom and en-suite bath down an adjacent hallway. Further into the home is the main living space. The kitchen in this home features ample counter space and a sleek design that will make meal preparation a breeze. Whether you're hosting a dinner party or simply enjoying a cozy breakfast, this kitchen will be a hub of culinary delight. The owner's suite is located off the great room for a private oasis complete with dual sink vanity, water closet and walk-in shower. Upstairs, you will find the bonus room, bedroom and full bath. In addition, this property has a two-car garage, providing ample space for parking and storage. You'll have peace of mind knowing your vehicles are protected and secure. This property combines quality, comfort, and convenience in one remarkable package.
Listing is courtesy of: FLORIWEST REALTY GROUP, LLC (941-334-4934)
Listing Agent: Elizabeth Stephens (941-334-4934)
4057 N CROCKERS LAKE BLVD #23, SARASOTA, FL 34238
$205,000218 Days on yellowkey MLS ID: S5138795
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1989Monthly Fee: $626 Tax: $2,104 (2024)Community: Vintage GrandCondo
Taxes:$2,104
Elementary School: None
Remarks: Welcome to 4057 Crockers Lake Blvd #23, a beautifully updated 3-bedroom, 2-bath condo in the highly desirable Vintage Grand at Palmer Ranch community of Sarasota. This bright, open-concept home features vaulted ceilings, luxury vinyl plank flooring, and a private open-air balcony overlooking lush tropical landscaping — perfect for enjoying morning coffee or evening breezes. The modern kitchen offers stainless steel appliances, updated cabinetry, solid-surface countertops, and a convenient breakfast bar that opens into the spacious living and dining areas — ideal for entertaining or relaxing. The primary suite features a walk-in closet and en-suite bath, while the two guest bedrooms provide ample flexibility for family, guests, or a home office. Residents enjoy true resort-style living with two community pools, a fitness center, tennis and basketball courts, playground, picnic and grill areas, and a car-wash station. The community is pet-friendly and ideally situated near Siesta Key Beach, Legacy Trail, Sarasota Square Mall, Costco, Publix, and top-rated schools. This move-in-ready condo offers exceptional comfort, convenience, and value — perfect as a primary home, seasonal retreat, or investment opportunity.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Brandon Cooke (330-849-0560)
5301 SADDLE OAK TRL, SARASOTA, FL 34241
$1,999,000131 Days on yellowkey MLS ID: A4680226
0 Days Off yellowkey (back on 6/8/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3978 Built: 2003Monthly Fee: $114 Tax: $10,477 (2025)Community: Saddle Oak EstatesSingle Family
Taxes:$10,477
Elementary School: Lakeview Elementary
Remarks: Under contract-accepting backup offers. Set on 6.34 private acres within the gated equestrian community of Saddle Oak Estates, this fully renovated estate has been reimagined for modern luxury living while preserving the rare sense of space and tranquility that defines the neighborhood. A long, impressive paver driveway introduces the nearly 4,000-square-foot residence, where estate privacy meets refined design just minutes from Sarasota’s everyday conveniences. Inside, wood-look tile flows seamlessly throughout the entire home, anchoring an open-concept layout designed for effortless indoor-outdoor living. The living room makes a striking first impression with a custom stone accent wall, fireplace, and built-ins that create a warm focal point for gathering. At the heart of the home, the chef’s kitchen is both elegant and functional, featuring a beautiful cabinetry with lighted upper cabinets, large island, gas range, stainless farmhouse sink, dine-in area, and a butler’s pantry that adds exceptional storage and prep space. A sunlit oversized dining room with custom cabinetry and high tray ceilings was designed for large family celebrations and entertaining. Walls of glass open directly to the pool terrace, blurring the line between inside and out. This impressive space is equally suited to function as a great room or media lounge, with the formal dining room positioned at the front of the home — currently styled as an inviting sitting area. A half bath is conveniently positioned here, and the second primary suite is located on this wing, creating the ideal setup for a private guest retreat or multigenerational living. The home offers two spacious primary suites, each with updated spa-inspired baths that feel like personal retreats. One suite includes a flexible den — perfect as a home office, gym, nursery or even a 5th bedroom. Two additional bedrooms and a full bath provide comfortable accommodations for family or guests. Thoughtful storage is built into every corner, including a cabinet-lined hallway leading to the oversized laundry room complete with granite counters, cabinetry, and utility sink. Plantation shutters, crown molding, and designer lighting elevate the interiors, adding warmth and sophistication throughout. Step outside to a true backyard oasis. The expansive paver patio surrounds a sparkling pool and flows into a large covered area with a wood-accent ceiling designed for lounging and outdoor dining. A pergola grilling area invites relaxed evenings entertaining under the stars, while a fenced dog run offers space for pets to roam. With flexible living spaces that adapt to your needs, expansive acreage, and the serenity of Saddle Oak Estates, this property delivers the rare combination of estate privacy and modern luxury, just minutes from Sarasota’s dining, shopping, and beaches.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Toma Milbank Pllc (941-720-5174)
2507 BENEVA RD #10, SARASOTA, FL 34232
$159,900152 Days on yellowkey MLS ID: A4679145
REDUCED by $5,100 (3.1%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1964 Tax: $2,318 (2025)Community: Forest Lakes Country Club EstateCondo
Taxes:$2,318
Remarks: Welcome to your Sarasota retreat in a highly desirable central location close to everything. This charming 2 bedroom, 2 bath corner condo on the second floor offers an ideal blend of comfort, convenience, and opportunity. The spacious layout provides a bright, open feel. Enjoy Florida living year-round from your enclosed private balcony, perfect for morning coffee, quiet afternoons, or relaxed evenings with friends. The well-maintained community features a sparkling pool, making it easy to unwind and enjoy the sunshine just steps from your door. For golf enthusiasts, The Palms Golf Club at Forest Lakes is nearby, offering a picturesque setting to practice your swing. Downtown Sarasota is just a short drive away, where you'll find a wonderful array of shops, restaurants, and cultural attractions, while the Legacy Trail, just around the corner, is perfect for biking, walking, jogging, and enjoying the natural beauty of the area. Plus, the pristine beaches of Siesta Key and Lido Key are within easy reach as well. Rentals are allowed, making this an excellent option for investors. Whether you’re looking for a primary residence, a second home, or an income-producing property, this condo offers endless potential in one of Sarasota’s most convenient locations. Schedule your private showing today and envision the possibilities!
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Ellen Gesell (941-320-3432)
2551 WILKINSON RD, SARASOTA, FL 34231
$399,90013 Days on yellowkey MLS ID: A4696791
Bed: 3 Bath: 0.0 Liv Area Sq Ft: 1469 Built: 1955 Tax: $3,559 (2025)Community: Forest HillsApartment
Taxes:$3,559
Elementary School: Phillippi Shores Elementary
Middle School: Brookside Middle
Remarks: Virtually Staged. A Piece of Sarasota History Meets Modern Opportunity: The "Siesta Key Style" Duplex with TWO separate electrical panels! Own a landmark piece of Sarasota history. Nestled on an expansive, wooded double lot at the western end of Wilkinson Road, this "Siesta Key style" bungalow offers a rare blend of timeless character and modern updates. Surrounded by a lush, quarter-acre canopy of mature bamboo, majestic oaks, and tropical palms, this property is a private sanctuary just minutes from the best of the Gulf Coast. Two units, endless potential and fully remodeled between 2023 and 2024, this versatile duplex is an ideal setup for savvy investors, multi-generational families, or those looking to "house-hack". Unit 1: A spacious 2-bedroom, 2-bathroom layout. Unit 2: A charming 1-bedroom, 1-bathroom retreat. Modern Upgrades & Peace of Mind: Every major system has been addressed so you can enjoy "turn-key" living or immediate rental income. Roof: New commercial-grade TPO membrane roof (2022) with a 30-year life. Climate: Brand new, energy-efficient mini-split AC systems in both units. Infrastructure: New plumbing throughout and separate electrical panels for each side. Interior: A fresh mix of new and restored flooring, newer appliances in unit 1, and stylish finishes. Exterior: Extra storage in the outdoor shed and plenty of room to roam & garden on the oversized lot. Location is Everything!!! Whether you’re heading to the beach, to work or to the city, you are perfectly positioned: 5 Minutes to the North Siesta Key Bridge. 12 Minutes to the vibrant culture and dining in Downtown Sarasota. 11 Minutes to the freeway for easy commuting. Don't miss this rare chance to own a functional, fully updated landmark in one of Sarasota’s most convenient locations. Some photos are visually staged. Schedule your private tour today!
Listing is courtesy of: BOUDRIE REAL ESTATE GROUP INC (941-730-5674)
Listing Agent: Rebekah Boudrie (941-730-5674)
1807 UNIVERSITY PL #151, SARASOTA, FL 34235
$199,00093 Days on yellowkey MLS ID: A4686953
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1195 Built: 1964 Tax: $2,296 (2025)Community: Strathmore Villa Sec 09Villa
Taxes:$2,296
Remarks: Welcome to maintenance-free Florida living in the highly desirable 55+ community of Strathmore Villas! This rare beauty offers the privacy of a single-family home with only the carport and storage area attached, perfect for buyers seeking low-maintenance, and easy living in a convenient location. This 2 bedroom, 2 bathroom home features a spacious airy layout with a large living room, a separate dining area, and abundant natural light throughout, ideal for both relaxing and entertaining. The fully equipped kitchen is designed to impress with ample cabinetry, matching appliances, a butcher block center island, and unique backsplash and countertops that create a charming coastal, beach-inspired feel. The primary suite is a true retreat, complete with a private en-suite bathroom featuring a relaxing walk-in shower. The second bedroom and full guest bathroom offers flexible space, perfect for overnight guests, a home office, or hobby room. Enjoy your own tropical backyard oasis with lush landscaping, making it the prime spot for morning coffee, gardening, or soaking up the Florida sunshine in peace. Residents of Strathmore Villas enjoy resort-style, maintenance-free amenities, with HOA fees covering roof, exterior maintenance, grounds care, pest control, water, sewer, trash, basic cable, escrow reserves, plus access to a community pool and clubhouse, making this an excellent option for snowbirds or full-time residents. Location is everything, and this home delivers! You’re just minutes from UTC Mall, downtown Sarasota, St. Armands Circle, championship golf courses, top-rated restaurants, shopping, and world-famous Gulf beaches. If you’re searching for a move-in ready villa, this is the one. Don’t miss your chance to own a piece of paradise, call today to learn more!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Joey Lamielle (941-350-0016)
5313 SAN JUAN DR, SARASOTA, FL 34235
$295,000140 Days on yellowkey MLS ID: N6142648
Bed: 2 Bath: 1.0 Gar: 2 Liv Area Sq Ft: 1258 Built: 1972 Tax: $3,039 (2025)Community: De Soto LakesSpa: NoSingle Family
Taxes:$3,039
Elementary School: Emma E. Booker Elementary
Middle School: Booker Middle
Remarks: Custom Built -Great starter home with Water Views in DeSota Lakes community located in highly desirable Sarasota FL. Expansive water views from Living Room - Kitchen- Dining and both bedrooms. Sliding glass doors lead out to the covered patio with a large backyard. Wood burning fireplace will take the nip out of the air on that rare occasion. Plenty of parking for your boat/RV. This home has a lot of potential to make your very own. NO HOA or CDD fees here.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Tammy Kitt (941-284-7274)
1315 WESTPORT LN #1412, SARASOTA, FL 34232
$289,00012 Days on yellowkey MLS ID: A4696836
0 Days Off yellowkey (back on 6/16/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1861 Built: 1972Monthly Fee: $620 Tax: $3,694 (2025)Community: Village Green Forest Lake 14Villa
Taxes:$3,694
Remarks: Experience carefree Florida living in this beautifully updated contemporary villa located in a desirable 55+ community. This elegant two-bedroom, two-bath residence with a one-car garage showcases an open-concept design enhanced by designer porcelain tile flooring throughout, custom cabinetry, quartz countertops, and premium Wolf appliances. Smart home features, LED lighting, Hunter Douglas blinds, and impact windows provide both style and peace of mind. The spacious floor plan flows effortlessly to a private setting overlooking some of the community's most lush and picturesque Florida foliage. Just steps away, residents enjoy easy access to the sparkling community pool and shuffleboard courts, creating the perfect backdrop for an active and social lifestyle. Major updates create exceptional value, including a new A/C system (2022) with Nest thermostat, water heater (2020), and both tile and flat roofs replaced in 2017. Lawn care is included, allowing more time to enjoy everything Florida has to showcase. Whether relaxing among the tropical landscaping or gathering with friends at the pool, this villa delivers the ideal combination of sophistication, comfort, and low-maintenance living. Close by are several Sarasota famous restaurants. In 1972 the construction of these villas was superior and sound. Built to last!
Listing is courtesy of: DENISE OYLER PA (941-914-6526)
Listing Agent: Denise Oyler (941-914-6526)
3537 S SCHOOL AVE, SARASOTA, FL 34239
$690,00048 Days on yellowkey MLS ID: A4691686
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1988 Built: 1961Monthly Fee: $17 Tax: $3,895 (2025)Community: South GateSpa: NoSingle Family
Taxes:$3,895
Elementary School: Southside Elementary
High School: Sarasota High
Remarks: PRICE ADJUSTMENT of $25k. Private Oasis Awaits! This home is perfect for year round living, a Florida get away or an income generating property. It offers 3 bedrooms and 2 bathrooms and just under 2,000 square feet of comfortable living. The layout is thoughtfully designed, with 3 separate sitting areas with an abundant natural light through the large windows. The tiled flooring provides a clean, modern aesthetic, complemented by the neutral color palette. The updated kitchen is spacious, with ample wood cabinetry and a quartz countertop, providing plenty of storage and preparation space. The primary bedroom is generously sized with a bathroom, offering a comfortable retreat and a door to walk out onto covered lanai. Additional features include an inside laundry room, newer appliances, energy-efficient double-pane windows, tile roof only 10 years old and plantation shutters throughout for added charm. The outdoor space is perfect private oasis for relaxation while enjoying the sparkling resurfaced pool with a screened enclosure. The oversized lot features lush landscaping and spacious paved driveway, creating a welcoming outdoor atmosphere. In addition, the backyard is fenced in for pets with plenty of room to store watercraft. If desired, the property is Airbnb-ready and is within city limits so weekly rentals are approved. The city location makes for an ideal choice to call home to escape and relax on Siesta Key beaches or explore downtown Sarasota and all it has to offer.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Kimberly Mcmahon (941-812-5092)
6144 MIDNIGHT PASS RD #3N, SARASOTA, FL 34242
$1,385,00015 Days on yellowkey MLS ID: A4696434
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1967 Tax: $16,658 (2025)Community: Island HouseCondo
Taxes:$16,658
Remarks: Island House Dream Condo on Siesta Key! Experience the best of beachfront living at Island House on world-famous Siesta Key, where breathtaking Gulf views, unbeatable location, and effortless island living come together. Perfectly positioned in one of the most desirable beachfront buildings in the community, this second-floor condo offers truly unobstructed beach and water views with no other condo or building standing in your way. From the moment you arrive, the view takes center stage. Enjoy stunning beach views from all living areas, including the living room, guest bedroom, and master bedroom. New hurricane-impact windows and expansive glass bring the beauty of Siesta Key inside, creating a bright, open, coastal retreat from every angle. This is as close to the sand as it gets—literally beachfront and just steps from the world-famous powdery sand and warm Gulf waters. The elevated second-floor setting gives you the privacy and peace of mind you want, with no past water intrusion or storm damage to the unit, while still offering easy access to the beach and a convenient ramp for luggage. Inside, the condo is move-in ready and designed for easy beach living, featuring tile flooring throughout, an updated kitchen with solid-surface/granite counters, and beautifully updated bathrooms with elegant tiled showers. Whether you are looking for your own Siesta Key escape or an income-producing investment, the flexible 3-night minimum rental policy makes this an outstanding opportunity. Island House offers everything you need for the perfect beach lifestyle, including on-site management, refreshed landscaping, outdoor dining and game areas, beach chairs, chaise lounges, shaded beach cabanas, shuffleboard, cornhole, a heated community pool, and a clubhouse with billiards, foosball, board games, and puzzles. When you are ready to explore, hop on the free trolley or local ride-share vans to Siesta Key Village for shopping, dining, and nightlife, or venture to Turtle Beach, downtown Sarasota, restaurants, boating, fishing charters, performing arts, museums, parks, and the Legacy Trail. This is more than a condo—it is your front-row seat to Siesta Key’s legendary beach lifestyle. Bring your toothbrush, swimsuit, and love for sunsets, because this one is ready to enjoy!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Christine Walker (941-779-4342)
5610 MIDDLE AVE, SARASOTA, FL 34243
$373,90028 Days on yellowkey MLS ID: A4694925
REDUCED by $10,000 (2.6%) on 06/16/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2430 Built: 2004 Tax: $5,506 (2025)Community: Desoto AcresSingle Family
Taxes:$5,506
Remarks: INVESTOR SPECIAL / VALUE-ADD OPPORTUNITY IN DESOTO ACRES! Situated on OVER 1/2 ACRE in the desirable Desoto Acres area of Sarasota, this 2004-built 3 bedroom, 3 bathroom home offers 2,430 sq ft of living space with tremendous upside potential. Spacious layout, attached garage, and large lot create an excellent canvas for renovation, modernization, or long-term hold. Property needs TLC and updates but has strong bones and plenty of potential for the right buyer. Ideal opportunity for investors, rehabbers, contractors, or buyers looking to customize a larger home on acreage in a highly sought-after Sarasota location. Rare chance to secure a newer-built home on .59 acres with room to add value. Conveniently located near University Pkwy, shopping, dining, SRQ Airport, and downtown Sarasota. Property being sold AS-IS. Cash or hard money financing preferred. Bring your vision and unlock the potential!
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
1817 6 TH ST, SARASOTA, FL 34236
$999,99933 Days on yellowkey MLS ID: A4694609
REDUCED by $95,001 (8.7%) on 06/12/2026
Bed: 8 Bath: 3.0 Liv Area Sq Ft: 2211 Built: 1932 Tax: $12,519 (2025)Community: Gillespie Park SubSpa: NoSingle Family
Taxes:$12,519
Elementary School: Alta Vista Elementary
Remarks: Under contract-accepting backup offers. Build your downtown Sarasota legacy on one of the largest and most strategically positioned parcels to come to market in Gillespie Park in years. This rare ±19,400 SF double lot (100' x 194') sits in the heart of one of Sarasota's most actively transforming neighborhoods, offering a blank canvas for contractors, custom builders, developers, and end users ready to capitalize on the city's most compelling infill corridor. DTN (Downtown Neighborhood) zoning allows for this ±0.45-acre site the potential to support approximately 5 residential units, a luxury single-family estate, a multi-generational compound, or a boutique townhome project (buyer to verify all uses with the City of Sarasota). The two combined lots create a 100-foot-wide buildable footprint that is extraordinarily rare at this proximity to downtown. Located in Flood Zone X, the property carries no mandatory flood insurance requirement and faces none of the elevation and construction cost burdens that affect so much of coastal Sarasota — a significant competitive advantage for any development pro forma. The site is clean and ready for permitting. Gillespie Park is not an emerging neighborhood — it has arrived. Adjacent to the Rosemary District (Sarasota's most walkable neighborhood with a Walk Score of 88), the area is surrounded by completed and ongoing new construction. Residents walk to Main Street dining, the Sarasota Farmers Market, Whole Foods, Sprouts, Regal Cinema, the Van Wezel Performing Arts Hall, and The Bay — Sarasota's transformative 53-acre waterfront park. Siesta Key Beach is approximately 20 minutes away. Opportunities to acquire nearly half an acre with this zoning flexibility, this location, and this lot dimension do not come along often. Whether you are a developer looking for your next high-margin project or a buyer ready to build a custom urban oasis, this is the site.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Vincent Lamaida (941-416-5654)
3927 DESOTO RD, SARASOTA, FL 34235
$725,00079 Days on yellowkey MLS ID: A4689010
REDUCED by $24,000 (3.2%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1782 Built: 1983Monthly Fee: $13 Tax: $3,686 (2025)Community: Desoto PinesSingle Family
Taxes:$3,686
Remarks: Under contract-accepting backup offers. PRICE REDUCED!!!!Set on an expansive 1.06-acre lot, 3927 DeSoto Road in Sarasota offers a rare combination of space, privacy, and versatility. The oversized parcel provides endless possibilities—whether you envision lush landscaping, additional structures, or simply enjoying the open room to spread out. At the heart of the outdoor space is a huge pool, perfect for entertaining, relaxing, or creating a true backyard retreat. With this much land surrounding it, the pool area feels private and resort-like, offering plenty of room for outdoor seating, dining, and recreation. Inside, the home features a spacious interior layout with generous living areas designed for comfort and functionality. Large rooms, open flow, and abundant natural light create an inviting atmosphere that’s ideal for both everyday living and hosting guests. This property stands out for its rare lot size, impressive outdoor amenities, and roomy interior, making it a unique opportunity in Sarasota for anyone looking for space without sacrificing convenience. Home is located very close to UTC, Benderson Park and all local beaches and downtown Sarasota.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Gabe Gadah (941-376-4229)
7524 WESTMORELAND DR, SARASOTA, FL 34243
$5,500,00014 Days on yellowkey MLS ID: A4695898
Bed: 6 Bath: 5.5 Gar: 5 Liv Area Sq Ft: 6215 Built: 2001 Tax: $15,233 (2025)Community: Whitfield Estates Unit 1Spa: NoSingle Family
Taxes:$15,233
Remarks: Set on a premier waterfront lot in the Sarasota/Bradenton area, this single-family estate offers panoramic water views, a separate guest house, and the kind of indoor-outdoor living buyers expect at the luxury level. The main residence (3806 sq ft) is designed for entertaining and everyday comfort, with expansive living spaces, a well-appointed kitchen, and seamless access to the pool and outdoor areas, while the guest house (2409 sq ft) provides ideal accommodations for visitors, extended family, or a private office retreat. Comfortable luxury living on a combined 1+ acre lot (there are 2 parcels included in this offering) with a spectacular panoramic water view. Beautifully kept grounds accented by Royal palms create the feel of a family compound that elegantly states, "You've made it!" The three-story main house has a twin grand winding staircase and an elevator to the second-floor main level. Tall double-trey ceilings w/ uplighting and massive impact glass windows and doors provide an absolutely breathtaking view of the swimming pool and the Sarasota Bay. Built on 38 concrete and steel reinforced pilings, the main house was constructed in 2001, and the windows and doors were upgraded to hurricane standards. In fact, the owner has a flood policy on the main house for just $1,200 per year. There is an oversized 3 car garage with an expanded work area and 220V power if you have an electric car. Plus, a massive unfinished storage and fun area with non-conforming pool bath below the main living area elevated approximately 18' above. The completely separate guest house also with views of the bay includes an additional 3 bedrooms, great room, dining room, full kitchen, office and attached 2 car garage. The guest house was built in 1950 and remodeled to mimic the Coastal Mediterranean style of the main house. The pool ranges from 3' to 7' in depth and includes remote control lighting and a water feature. The pool and outdoor area create the perfect setting for parties or special events. The pool is surrounded by a huge concrete deck that extends as a patio under the cover of the massive main observation and entertainment deck above. There are rough ins for an outdoor kitchen on the ground floor patio. There is also an additional observation deck off the 3rd floor living room that, with a slight zoom on your camera, provides a nice view of John Ringling bridge. Longboat Key provides night lights beyond the bay, and your own private Osprey nest adds to the natural symphony of life on the water. Boaters, you are less than a mile away from Sara Bay Marina. Commuters, you are less than 3 miles away from SRQ. Beach goers, you are less than 10 miles from Lido Beach and St Armands Circle. Professionals, you are less than 7 miles from downtown Sarasota. Kayakers, walk to the Riprap and launch! Be sure to watch the individual videos showing each interior. They are not just slideshows. This is the first time this property has been offered for sale since the builder owned it. An acre of mainland bayfront land is rare in the Sarasota/Manatee waterfront community. Don't Daydream and miss out on your Dream home. The main home is being sold partially furnished with a few exclusions. The guest house is unfurnished. Capture the Zen of waterfront living for yourself and future generations now.
Listing is courtesy of: FLORIDA INTERNET REALTY LLC (941-961-4983)
Listing Agent: Steve Rider (941-504-5163)
411 BURNS COURT, SARASOTA, FL 34236
$1,075,00033 Days on yellowkey MLS ID: A4694679
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1345 Built: 1926 Tax: $4,644 (2025)Community: Burns Court Sub OfSingle Family
Taxes:$4,644
Remarks: Under contract-accepting backup offers. This iconic commercial/residential Burns Court bungalow, the ultimate live/work space, offers a rare opportunity to restore and personalize a truly unique downtown property in one of Sarasota's most coveted historic neighborhoods. The Burns Ct. facing 2-bedroom, 1-bath main residence features a private masonry-walled back courtyard leading to a large 1-bedroom, 1-bath detached unit. This unit, with frontage on Pineapple Avenue, is ideal for commercial or residential use, a guest apartment, private office/studio, small shop... Located in the heart of nationally designated Historic Burns Court, one of downtown Sarasota’s most walkable neighborhoods, the property is just steps from an award-winning cinema, restaurants, boutiques, and the Bayfront, yet notably outside of a flood zone. Many original architectural details remain intact, including decorative ironwork, moisture-resistant plaster walls, crown molding, and original hardwood floors. A beautiful, mature oak tree provides valuable shade and enhances the home’s historic charm. The home has excellent bones for a dream restoration project, the main house featuring a 2023 roof and 2019 HVAC. Built-in equity: Zoned Downtown Core (DTC), the property includes confirmed transferable development rights (TDRs), which may be sold to a developer or investor thanks to a new historic preservation ordinance effective as of December 2025. Whether you envision creating a stunning live/work environment, generating income from a detached apartment, or designing an elegant commercial space, this charming property offers exceptional flexibility and historic character.
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Erin Difazio (941-870-8060)
8340 WINGATE DR #1023, SARASOTA, FL 34238
$335,00035 Days on yellowkey MLS ID: A4694124
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1604 Built: 1999 Tax: $4,083 (2025)Community: Pinestone At Palmer RanchCondo
Taxes:$4,083
Remarks: Light-filled, spacious, and perfectly positioned to enjoy tranquil lake views, this beautifully refreshed 3-bedroom, 2-bath condo offers 1,604 square feet of effortless Florida living. Vaulted ceilings create an airy sense of space, while the lanai and two lakeview bedrooms invite you to relax and unwind in a peaceful setting. What truly sets this property apart is the exceptional lifestyle offered by the community—where impressively low HOA fees unlock an amenity package rarely found at this price point. Enjoy a resort-style pool, full fitness center, clubhouse, movie room, tennis, pickleball, shuffleboard, library, and a vibrant social atmosphere with regular resident events. This is low-maintenance living without compromise.
Listing Agent: Daria Fairchild (941-650-7207)
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