Displaying: For Sale
Location: Sarasota
Property Type(s): Villas
Price: $200,000 to $299,000
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Sarasota - 83 properties found
2731 RIVERBLUFF WAY #V76, SARASOTA, FL 34231
$229,00012 Days on yellowkey MLS ID: A4696921
0 Days Off yellowkey (back on 6/22/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1480 Built: 1971Monthly Fee: $725 Tax: $3,438 (2025)Community: Strathmore Riverside ISpa: NoVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,438
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: TURN-KEY OR UNFURNISHED | FULLY RENOVATED | 55+ WATERFRONT COMMUNITY Less than 18 minutes to Siesta Key Beach, this renovated 2 bedroom, 2 bath villa with two bonus rooms offers the Florida lifestyle many buyers are searching for. Residents enjoy a heated and chilled waterfront pool overlooking the marina, clubhouse, fitness center, residents' library, shuffleboard courts, and marina access. Boat slips are available for rent, providing direct boating access through Phillippi Creek to the Gulf of America. This home offers more usable living space than many comparable units in the community, with two bonus rooms ideal for a home office, hobby room, reading area, or guest space. Major updates include impact windows (2020), newer roof, 2022 A/C, updated plumbing and electrical systems, a whole house surge protector, fresh insulation, laminate flooring, sliding barn doors, granite countertops, under-cabinet lighting, and modern finishes throughout. Offered turn-key, furnished or unfurnished, this move-in-ready home is conveniently located near shopping, dining, medical facilities, downtown Sarasota, St. Armands Circle, and Siesta Key Beach. A rare opportunity to enjoy boating, resort-style amenities, and a renovated home in one of Sarasota's desirable 55+ waterfront communities.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: David Valencia (941-223-3621)
266 OAK HILL DR #34, SARASOTA, FL 34232
$285,00012 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
Elementary School: Gocio Elementary
High School: Booker High
Middle School: Booker Middle
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)
SARASOTA, FL 34233
$269,90019 Days on yellowkey MLS ID: A4695930
1 Days Off yellowkey (back on 6/23/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1803 Built: 1989 Tax: $3,614 (2025)Community: Crestwood VillasVilla
Taxes:$3,614
Elementary School: None
High School: None
Middle School: None
Remarks: Priced for quick sale. This Villa is 1803 sq ft with 3 bedrooms and 2 baths. Crestwood Villas is located in the popular Centergate Area close to shopping and many other amenities. Master bath has new cabinets and granite counter tops, Kitchen has ample wood cabinet space with stainless steel appliances. Windows have plantation shutters or blinds. There is an alarm and exterior surveillance camera system which the new owner can have activated. The villa has a new Tile Roof. Outside screened patio is private and spacious for entertaining. Lanai has a remote electric hurricane role down shutter. The clubhouse offers year round social events. Play tennis or Pickleball then cool of int he shimmering pool which is geo thermal heated for those chilly days.
Listing is courtesy of: RAMPART HOMES INC (941-925-4835)
Listing Agent: Connie Belmont (941-228-9682)
4668 OAK HILL LN #40, SARASOTA, FL 34232
$280,000118 Days on yellowkey MLS ID: A4683176
REDUCED by $10,000 (3.4%) on 05/06/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1024 Built: 1985Monthly Fee: $559 Tax: $3,287 (2025)Community: Village Oaks Sec ASpa: NoVilla
Taxes:$3,287
Remarks: Your Private Sarasota Sanctuary Awaits! Discover true Florida living in this beautiful end unit villa situated on a quiet street. This 2 BR/2BA gem located in the Village Oaks Community is a breath of fresh air. Enjoy morning coffee on your screened front porch or sunsets drinks on the large rear lanai. Inside, the home features vaulted ceilings in living/dining areas and luxury vinyl plank flooring flowing throughout the main living space and bedrooms. The split-bedroom floor plan ensures maximum privacy for owners and visitors alike. The bright kitchen features stainless appliances and an eat-in nook filled with natural light. Best of all, the community pool and tennis court are just steps away from your front door! Perfectly located near UTC shopping and beautiful beaches nearby - this is the Florida lifestyle you've been searching for!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Laura Flood (941-725-2500)
365 OAK HILL WAY #32, SARASOTA, FL 34232
$280,000159 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.
7913 PINEGLEN CT #34, SARASOTA, FL 34238
$279,90017 Days on yellowkey MLS ID: A4695983
REDUCED by $5,000 (1.8%) on 06/20/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1466 Built: 1985Monthly Fee: $647 Tax: $1,718 (2025)Community: Pine Tree VillageSpa: NoVilla
Taxes:$1,718
Elementary School: Gulf Gate Elementary
Middle School: Sarasota Middle
Remarks: Discover this spacious and meticulously maintained 2 Bedroom, 2 Bathroom VILLA offering 1468 SQ FEET Of comfortable living space, complete with GARAGE. Located in the highly sought after PINE TREE COMMUNITY, You will be less than 5 miles from The world famous SW FL Gulf coast Beaches. Centrally located with easy access to Downtown Sarasota, St Armands Dining and shopping district and the long list of attractions that sarasota is famous for! Step inside and enjoy soaring ceilings, an open, and welcoming, immaculate VILLA. Enjoy the screened in lanai perfect to enjoy the FL sunshine! The estimated HOA of 600.00 includes: A HEATED POOL TENNIS COURTS LAWN CARE GARBAGE REMOVAL EXTERIOR MAINTENANCE Whether you are seeking winter getaway or, even better, A year round, full time residences, this very well could be the one with regards to comfort, convenience and LOOCATION! WELCOME TO ENDLESS SUMMER!
Listing is courtesy of: PREMIER PROPERTIES OF SRQ LLC (941-526-3113)
Listing Agent: Michael Panichelli (941-777-3450)
5915 TIDEWOOD AVE #4, SARASOTA, FL 34231
$284,900188 Days on yellowkey MLS ID: A4675716
REDUCED by $15,000 (5.0%) on 06/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1155 Built: 1973 Tax: $1,857 (2025)Community: Baywood Colony Sec 1Villa
Taxes:$1,857
Remarks: Virtually Staged. Completely renovated and ideally located in the waterfront community of Baywood Colony, this beautifully updated villa offers the perfect blend of modern comfort and coastal lifestyle. Just one block from Little Sarasota Bay and only moments to Siesta Key, this home places you right where you want to be. Inside, the updates shine from the moment you walk in. The open living and dining areas feel bright and welcoming, enhanced by new flooring and a warm wood-paneled ceiling that adds character and charm. Large sliding glass doors lead to the enclosed lanai, creating a seamless indoor-outdoor flow and offering a versatile space to relax or entertain. The kitchen has been fully renovated with new cabinetry, countertops, and stainless steel appliances, delivering a clean, modern look with functional design. Both bathrooms have also been beautifully updated, and new hurricane impact windows in the main living areas provide added peace of mind along with energy efficiency. The layout offers two comfortable bedrooms, including a spacious primary suite with its own private bath. The second bedroom is well-positioned for guests or flexible use as a home office. Step outside and enjoy the community’s true highlight—direct access to Little Sarasota Bay, where residents can take in stunning water views, launch a kayak, or simply relax by the water. Baywood Colony also features a heated community pool and well-maintained grounds, creating a laid-back, coastal atmosphere. Whether you're looking for a full-time residence or a seasonal retreat, this move-in ready villa combines thoughtful updates, a functional layout, and an unbeatable location near Siesta Key, dining, and shopping. **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)
1141 MERLE WAY #14, SARASOTA, FL 34232
$210,000146 Days on yellowkey MLS ID: TB8470330
REDUCED by $10,000 (4.5%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1500 Built: 1974 Tax: $2,581 (2025)Community: Glen Oaks Ridge Villas 1Villa
Taxes:$2,581
Elementary School: Tuttle Elementary
Remarks: SELLER CONCESSION** SELLER IS OFFERING 1K TOWARDS CLOSING COSTS IF BUYER USES PREFERRED LENDER. As you step into 1141 Merle Way, you’re welcomed into a bright and comfortable living space designed for easy everyday living. The home has been thoughtfully maintained and updated, with fresh interior paint completed in 2021, giving it a clean and inviting feel throughout. The layout flows effortlessly from the living room into the kitchen and dining area, creating a functional and open atmosphere. The kitchen has been upgraded with new cabinetry and Formica countertops that were redesigned and shortened to improve both movement and usability. Brand-new LG fluorescent lighting enhances the space, making it bright and practical for daily cooking and entertaining. Automatic shades in the living room, kitchen, dining area, and bedroom provide added convenience and light control at the touch of a button. Moving through the home, you’ll find a comfortable bedroom with new blinds installed in 2025, providing privacy and a fresh, updated look. The bathroom has been thoughtfully renovated to include a walk-in sit-in tub, offering both comfort and accessibility. Hurricane-rated doors add peace of mind, while a sensor light outside enhances safety and security. Recent upgrades continue outside the home, including new gutters installed in 2025. The property is located in a welcoming 55+ community known for its friendly atmosphere and well-maintained amenities. Residents enjoy access to a clubhouse, workout center, pool, and outdoor shower, as well as nearby nature trails and close proximity to three golf courses. With easy access to Honore Avenue via 17th Street, the location provides a perfect balance of tranquility and convenience. HOA INCLUDES exterior maintenance, water, sewer, cable, and amenities This home offers a comfortable, low-maintenance lifestyle, ideal for those looking to enjoy Sarasota living with ease.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Rotosha Cormier (941-210-2062)
3280 SOUTHFIELD LN #804, SARASOTA, FL 34239
$219,900630 Days on yellowkey MLS ID: TB8309229
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1323 Built: 1969 Tax: $2,672 (2023)Community: South Gate Village Green 08Villa
Taxes:$2,672
Tax Year: 2023
Remarks: *UPDATED HOME IN SOUGHT OUT SOUTHGATE VILLAGE GREEN* Recently reduced and move-in ready, this charming villa offers an exceptional opportunity in one of the area's most sought-after 55+ communities. The home features a brand-new kitchen equipped with all modern appliances, fresh new carpeting in halwway and bedrooms, and stylish laminate flooring throughout living areas. A Bright and airy open floor plan complemented by freshly painted interiors and partially updated bathrooms. Residents enjoy convenient access to nearby shopping, parks, and scenic walkways in a relaxing and peaceful ambiance.. Pets welcome (under 20 lbs., subject to approval).
Listing is courtesy of: Y GROUP REALTY (800-386-2830)
Listing Agent: Nancy Yialouris (727-252-3631)
3960 LAKESIDE RD #156, SARASOTA, FL 34232
$224,90034 Days on yellowkey MLS ID: A4693592
REDUCED by $5,000 (2.2%) on 06/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1540 Built: 1973 Tax: $3,218 (2025)Community: Glen Oaks Ridge Villas 2Spa: NoVilla
Taxes:$3,218
Remarks: GLEN OAKS RIDGE...an Active 55+ FRENCH PROVINCIAL VILLA COMMUNITY for you! WAIT TILL YOU SEE THE DIRECT LAKE FRONT VIEWS of this 1550 Square Foot villa where you can see the lake from the large living room, Large dining room, kitchen, Florida room, Family room AND foyer! That is right...become mesmerized all day long watching the sun bounce off of your very own lake right outside your door! Come check out this 2 bedroom, 2 bath villa with large common area rooms, a Florida room that is air conditioned, kitchen with updated cabinetry, quartz counters, lighting AND a huge laundry/utility/storage room to top things off. Plenty of parking with your own one car carport and a driveway for a second car and plenty of overflow parking. Location, location, location...is where you are...walk to Bobby Jones golf course, only 3 miles to UTC AND downtown Sarasota...just a sprint from there to St. Armand's and Lido Beach! Freshly painted. Come buy this million dollar view for only $224,900!
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Scotty Ledford (941-400-7360)
5023 VILLAGE GARDENS DR #29, SARASOTA, FL 34234
$230,00099 Days on yellowkey MLS ID: A4686540
REDUCED by $9,000 (3.8%) on 05/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 966 Built: 1981Monthly Fee: $530 Tax: $1,942 (2025)Community: Village Gardens Ph 1Spa: NoVilla
Taxes:$1,942
Elementary School: Emma E. Booker Elementary
Remarks: Move-in ready and not impacted by recent storms, according to the owner. In the desirable Village Gardens community, this beautifully updated home is set within a lush, park-like environment with mature tree canopy and exceptional recreational amenities. Residents enjoy access to a heated pool, pickleball and tennis courts, and an active clubhouse. Ideally just north of downtown Sarasota and minutes from the University Parkway corridor, providing convenient access to Sarasota-Bradenton International Airport, UTC Mall, Interstate 75, and renowned cultural destinations including Ringling Museum of Art & Design, Asolo Theatre, Sarasota Ballet, Ringling College of Art & Design and USF. This rare Palm model features a screened-in Florida room, making it one of the larger floor plans in the community. The home was extensively updated in 2023 with new electrical, renovated baths, an updated kitchen, new flooring, baseboards and fresh interior paint, creating a modern and inviting interior. Additional improvements include a paver patio added in 2025, ideal for outdoor relaxation. Inside, the home offers a welcoming foyer entry, a spacious great room with vaulted ceilings and clerestory windows. The kitchen has been renovated with beautiful cabinets, countertops and backsplash. The primary suite includes a walk-in shower, and direct access to the Florida room. The second bedroom has plenty of room and the guest bath includes a tub for soaking. An interior utility room offers additional storage along with a washer and dryer. Additional highlights include roof replaced in 2014 and air conditioner approximately 6–8 years old The HOA covers exterior maintenance and the roof, providing low-maintenance living in one of Sarasota’s charming and convenient communities. A rare opportunity to enjoy easy Florida living in a beautifully maintained neighborhood so move right in!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Jaci Krawtschenko (941-284-3789)
3412 TALLYWOOD CIR #7018, SARASOTA, FL 34237
$284,5005 Days on yellowkey MLS ID: A4697416
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1668 Built: 1983 Tax: $1,351 (2025)Community: Tallywood Ph 1 & 2Spa: NoVilla
Taxes:$1,351
Remarks: TALLYWOOD-A 55+ CANOPY TREE SHADE Villa community close to The Orioles ball park, Bobby Jones Golf Course, Downtown Sarasota, Lido/St. Armand's and UTC! This is the largest floorplan available at the Villas in Tallywood with just under 1700 square feet! The MAIN LEVEL has a PRIMARY bedroom suite, guest bedroom/bathroom, CATHEDRAL CEILINGS in the living room/dining room, LARGE KITCHEN AND there is a LOFT/3rd bedroom upstairs with LOADS OF STORAGE. Updates include new HURRICANE WIND RATED WINDOWS AND SLIDERS THROUGHOUT, hot water tank is 3 years old, most appliances are 3-6 years old. There is a transferrable home warranty that conveys with the home till the end of the year 2026. You have a beautiful lanai plus plenty of open parking PLUS your own carport with more storage! Tallywood boasts a large Olympic size pool, clubhouse with gym, library, community kitchen for events, shuffleboard, etc. Priced right @ $284,500. Don't let this one slip away!
2809 SWIFTON DR #4, SARASOTA, FL 34231
$249,90015 Days on yellowkey MLS ID: A4695978
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 934 Built: 1971 Tax: $2,532 (2025)Community: Swifton Villas Sec AVilla
Taxes:$2,532
Remarks: Fabulous Value! This UPDATED, END-UNIT, ground floor, single-story 2 BEDROOM / 2 BATHROOM condo is perfectly situated in a desirable 55+ community. Being sold TURN-KEY FURNISHED, you can move right in and start enjoying the Florida lifestyle! Major upgrades include a wonderful kitchen complete with soft-close cabinets with pull-out shelves. You will love the bonus Florida Room! It is the perfect space for relaxing, reading or entertaining. Brand NEW full-size WASHER & DRYER. A carport adds convenience right outside your front door. Enjoy LOW CONDO FEES (only $385/mo) that INCLUDE WATER, SEWER, TRASH, BASIC CABLE, EXTERIOR MAINTENANCE AND ROOF, making carefree living a reality. Community amenities include a beautiful, heated pool and a welcoming clubhouse with an active social calendar. Located just 3 miles from Siesta Key, and easy access to shopping, dining, and more. Whether you're looking for a full-time residence or a winter retreat in the sunshine, this condo checks all the boxes. Book your showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-486-8686)
Listing Agent: Susan Honsberger (941-549-9749)
5440 RIVERBLUFF CIR #87, SARASOTA, FL 34231
$219,00028 Days on yellowkey MLS ID: A4695042
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 864 Built: 1971Monthly Fee: $622 Tax: $2,033 (2025)Community: Strathmore Riverside ISpa: YesVilla
Taxes:$2,033
Remarks: Fully renovated and move-in ready, this charming 1-bedroom, 1-bathroom standalone villa in the highly sought-after 55+ Strathmore Riverside Villas community is the Florida lifestyle opportunity you have been waiting for. Whether you are pursuing the snowbird dream or making the permanent move to paradise, this turnkey gem is ready for you right now. Fresh 2025 upgrades include a brand new kitchen, new flooring throughout, and new plumbing — no projects, no headaches, just move in and start living. The bright open-concept layout offers comfortable and easy living with an in-unit washer and dryer, covered carport, and attached storage room. The community is where the magic happens. Start your morning with a swim in the large heated pool maintained at a year-round 85 degrees, spend your afternoon on the fishing dock, and end your day watching the sun set over Phillippi Creek. Boating enthusiasts will love the community marina with direct access to the Intracoastal Waterway and the Gulf of Mexico — boat slips available through the association. Additional amenities include a clubhouse, fitness room, shuffleboard courts, billiards, library, and two saunas. HOA fee includes cable TV, water, sewer, exterior building and grounds maintenance, building insurance, escrow reserves, and onsite management. Conveniently located near Publix, Detwiler's Farm Market, Sarasota Memorial Hospital, Phillippi Farmhouse Market, and just minutes to world-famous Siesta Key Beach. At this price with these upgrades in this community, this one will not last long. Schedule your showing today.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Evona Poplawski (941-228-9455)
5103 GREENCROFT RD, SARASOTA, FL 34235
$295,000650 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
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)
3915 SCHWALBE DR #128, SARASOTA, FL 34235
$222,000845 Days on yellowkey MLS ID: A4601517
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1195 Built: 1964Monthly Fee: $450 Tax: $1,979 (2023)Community: Strathmore Villa Sec 10Villa
Taxes:$1,979
Remarks: Virtually Staged. This beautifully upgraded 2-bedroom, 2-bathroom villa offers the perfect blend of comfort, convenience, and Florida living. Located between University Parkway and Downtown Sarasota, you’ll enjoy easy access to shopping, golf courses, Gulf beaches, Sarasota/Bradenton International Airport, Lakewood Ranch, and vibrant Downtown Sarasota. The villa is situated in a peaceful, 55+ community, making it the ideal spot for those looking for a relaxed and maintenance-free lifestyle. Whether you're seeking a seasonal retreat or a full-time residence, this home offers the perfect "lock and go" solution. Inside, you'll find spacious living areas and upgraded finishes throughout. The community features a beautiful pool for you to enjoy the Florida sunshine, while maintenance-free living allows you to focus on enjoying everything Sarasota has to offer. This villa offers a rare opportunity to own a beautifully updated home in one of Sarasota's most desirable locations. Don’t miss your chance—schedule your showing today!
Listing is courtesy of: THE SUNSHINE STATE COMPANY (941-263-2613)
Listing Agent: Kasey Truman, P.A. (941-842-0661)
5649 WESTWIND LN, SARASOTA, FL 34231
$294,00043 Days on yellowkey MLS ID: A4693241
REDUCED by $5,000 (1.7%) on 06/06/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1169 Built: 1980Monthly Fee: $560 Tax: $2,641 (2025)Community: Villa GardensVilla
Taxes:$2,641
Remarks: Welcome to your hidden gem in the heart of Sarasota! This charming Westwind Lane home invites you in with a bright, open layout and tasteful updates that make it feel warm and move-in ready from day one. Step outside to your own private space—perfect for unwinding after a long day or hosting friends and family while enjoying the Florida lifestyle. Just minutes from Siesta Key and close to great shopping, dining, and daily conveniences, the location truly speaks for itself. It’s the kind of place you dream about when you think of living in Sarasota. Come see it for yourself—schedule your private showing today before it’s gone!
Listing Agent: Marina Paige (941-263-9545)
5723 DEER HOLLOW TRL, SARASOTA, FL 34232
$285,00030 Days on yellowkey MLS ID: TB8511154
REDUCED by $14,000 (4.7%) on 06/15/2026
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 721 Built: 1985Monthly Fee: $45 Tax: $1,776 (2025)Community: Deer HollowVilla
Taxes:$1,776
Remarks: Location, location, location! Welcome to this 2 bedroom, 1 bathroom villa ideally situated in the heart of Sarasota with quick access to I-75, making commuting and exploring the area incredibly convenient. This move in ready home has already had the major updates completed for peace of mind, including a new roof in 2022 with a 10 year warranty, hurricane grade windows, slider, and front door installed in 2023, new AC in 2024, and replaced exterior siding. Enjoy low HOA fees of just $335 annually while taking advantage of community amenities including a playground and peaceful preserve walking paths. Whether you’re looking for a primary residence or a seasonal getaway this villa offers comfort, convenience, and value all in one. Perfectly positioned near the vibrant UTC area, this home is just minutes from Nathan Benderson Park, The Mall at University Town Center, top rated dining, shopping, Sarasota-Bradenton International Airport, Downtown Sarasota, and the world famous beaches of Siesta Key and Lido Key. Schedule your showing today!
Listing is courtesy of: PEOPLE'S TRUST REALTY (727-946-0904)
Listing Agent: Ali Kochno (813-766-7143)
462 OAK HILL CIR #5, SARASOTA, FL 34232
$234,900287 Days on yellowkey MLS ID: A4664046
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1254 Built: 1985Monthly Fee: $520 Tax: $1,196 (2024)Community: Village Oaks Sec DVilla
Taxes:$1,196
Tax Year: 2024
Remarks: Welcome to 462 Oak Hill Cir! This 2-bedroom, 2-bath home with a spacious two-car garage offers comfort, function, and the chance to put your personal touch on a well-located property in Sarasota. The home features an open layout, abundant natural light, and a split-bedroom design that balances privacy and convenience. Step outside and enjoy the community’s tranquil setting, while being just minutes from University Town Center shopping, Benderson Park, golf courses, and the cultural attractions of downtown Sarasota. World-famous Siesta Key and Lido beaches are also a short drive away, making this an ideal home base for enjoying all the area has available. Curious? Don’t wait to see this home in person—it’s a property that needs to be experienced, not just viewed online. No sight-unseen offers will be entertained. Schedule your private showing today and explore the possibilities!
Listing is courtesy of: KONA REALTY (941-718-8293)
Listing Agent: Dan Ivanov (941-544-0475)
4637 WILLOW WOOD CIR #44, SARASOTA, FL 34241
$299,000375 Days on yellowkey MLS ID: A4655394
0 Days Off yellowkey (back on 6/19/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1679 Built: 1982 Tax: $2,219 (2024)Community: Hammocks Iii,Bent TreeVilla
Taxes:$2,219
Elementary School: Lakeview Elementary
High School: Sarasota High
Remarks: Under contract-accepting backup offers. UNDER $300,000 Freshly Painted & updated 3BR/2BA Villa in Bent Tree Hammocks III – No Age Restrictions Tucked away on a quiet dead-end street, this spacious 3-bedroom, 2-bath villa offers privacy and a peaceful, park-like setting. The split floor plan includes formal living and dining rooms, an eat-in kitchen with in-unit laundry, and a 2-car attached garage. Enjoy indoor-outdoor living with a screened lanai that opens to an additional open patio—ideal for morning coffee or casual entertaining. Bent Tree Hammocks III is a well-kept, sought-after community just two miles east of I-75, putting shopping, dining, golf courses, and Sarasota’s beaches within easy reach. Priced below market for a quick sale and easy to show. Seller will consider offers. A great opportunity to own in a desirable community with no age restrictions.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Lisa Bouck, Pa (941-374-0165)
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