Location: Sarasota
Do Not Show Listings
5867 HELICON PL, SARASOTA, FL 34238
$404,00050 Days on yellowkey MLS ID: A4689669
REDUCED by $17,000 (4.0%) on 05/06/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1534 Built: 2002Monthly Fee: $476 Tax: $3,252 (2025)Community: VillagewalkVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,252
Elementary School: Ashton Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: MAKE AN OFFER! This beautiful water view home with two bedrooms and two baths has been lovingly cared for and is loaded with updates. Beautiful 20" ceramic tile in every room, updated kitchen with pot sink, granite counters with rounded edges for counter seating, updated cabinets with pull out shelving and new doors, newer appliances and glass entry door. Faux Fireplace in Living area to warm your heart. The home has had a recent 4 pt inspection, dryer vents have been cleaned, A/C serviced recently, garage springs replaced by Precision Garage Doors, new shower door in master bath and so much more. Clear hurricane shutters allow light to brighten the home with secure protection. Dome solar light in 2nd bedroom for added natural light. Freshly painted throughout. Brinks Safe in Laundry Room. Village Walk is a wonderful unique community, built hurricane safe with poured concrete walls and foundations. Every home in Village Walk is considered to be a Single Family Home, roofs are tied down to the structures, the Florida Building Codes are considered to be above average. Inspectors, roofers and Insurance agents that are familiar with Village Walk will share this information with you. Village Walk is in Flood Zone X, an area that is determined to have little chance of flooding. FEMA updated, 8/2/24. Flood Zone provided by Sarasota County Tax reports. Evacuation zone D, flood insurance is not mandatory, but flood insurance is available. Village Walk power lines are underground with a Sarasota Fire Department just down Honore. Seldom losing power. Amenities include 24 hour guarded gate, geo-thermal heated and cooled lap & lagoon pools, six Har-Tru Tennis courts, Pickle ball, Bocce' ball and Basketball courts, State of the Art fitness Center, Miles of walking and bike paths, over 500 acres of lakes and preserves. There are over 50 activity groups who meet daily, weekly, or monthly. Plus there is a full service Cafe with full service Bar, Gas Station, Barber shop/Hair Salon, and Gift Shop. A special NOTE is that Village Walk did not lose power during the hurricanes and there was No flooding. What a Fantastic Place to Call HOME!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kim Klee (941-400-8922)
5915 TIDEWOOD AVE #4, SARASOTA, FL 34231
$299,900165 Days on yellowkey MLS ID: A4675716
REDUCED by $20,100 (6.3%) on 05/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1155 Built: 1973 Tax: $1,857 (2025)Community: Baywood Colony Sec 1Villa
Taxes:$1,857
Elementary School: Phillippi Shores Elementary
Remarks: One or more photo(s) has been 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)
39 STRATHMORE BLVD, SARASOTA, FL 34233
$140,00010 Days on yellowkey MLS ID: N6144447
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1195 Built: 1968Monthly Fee: $274 Tax: $2,427 (2025)Community: Strathmore VillaVilla
Taxes:$2,427
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. This 2-bedroom, 2-bath villa with a covered carport offers an incredible opportunity to enjoy the best of Sarasota living in the sought-after 55+ community of Strathmore Villa. Featuring a spacious and functional floor plan, this residence provides comfortable, low-maintenance living with plenty of room to relax and entertain. Residents of Strathmore Villa enjoy a wealth of amenities, including a heated community pool, clubhouse, and shuffleboard courts, all set within a beautifully landscaped, pet-friendly community. The prime location just off Bee Ridge Road places you minutes from shopping, dining, healthcare facilities, and everyday conveniences, while the world-famous Siesta Key Beach is only a short drive away. Whether you're looking for a year-round residence, seasonal retreat, or investment in the Florida lifestyle, this villa represents exceptional value. With its desirable location, community amenities, and affordable ownership opportunity, this is one of the best buys in Sarasota's active adult market. Don't miss your chance to own a piece of paradise and enjoy the comfort, convenience, and vibrant lifestyle that Strathmore Villa has to offer. This property is subject to a 3-Day First Look Period. Seller will negotiate offers after the period expires.The seller does not accept blind offers or escalation clauses.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Christina Burns (941-451-9247)
2121 PUEBLO CIR #V6, SARASOTA, FL 34231
$179,90027 Days on yellowkey MLS ID: A4692375
1 Days Off yellowkey (back on 5/27/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1972 Tax: $2,132 (2025)Community: Woodside Village WestSpa: NoVilla
Taxes:$2,132
Elementary School: Gulf Gate Elementary
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. VALUE PRICED! Immaculate & Updated Villa in the "Gulf Gate Area" that you will be proud to call home! Many updates, including the following: Tile Roof 2025*2.5 Ton, 15.2 Seer2 Air Conditioner 2024*Updated Kitchen Cabinetry, Granite Tops 2022*Dishwasher, Microwave, Range & Refrigerator 2022*Bath Vanities & Tops replaced 2022*Porcelain Tile throughout 2018*Washer & Dryer 2018*Interior freshly painted 2018*Lighting 2018*Plumbing redone overhead by association 2018. Don't miss showing this one ... the QUALITY speaks for itself. There is also a laundry closet off of the kitchen and the washer & dryer are included in the sale. There is a patio in the back of the villa where you can relax and have a cup of coffee while you enjoy the beautiful Florida weather! This villa has an assigned parking space and there is plenty of guest parking. The primary bedroom suite offers a walk-in-closet. This wonderful South Sarasota location is prime & only minutes to our World Famous Siesta Key Beaches! Gulf Gate Shopping and Fine Restaurants are nearby, as well as the Gulf Gate Library, several fitness centers, Legacy Trail, Costco & More. Cultural downtown Sarasota & the UTC Mall are only 20 minutes away. Come home to your affordable villa and enjoy the Heated Community Pool which will be waiting for you and your friendly neighbors! Enforced deed restrictions protect your privacy and investment! You must own 1 year prior to renting and the minimum leasing period is 2 months. You'll love this 55+ community & this Villa is priced to sell. The quarterly fees are reasonable and the fees include Cable TV*Sewer/Water Maintenance*Trash*Pest Control*Pool & More. H-U-R-R-Y on this Beauty before it's gone. Available for immediate occupancy (once aplication by association is approved!) EZ Show.
Listing is courtesy of: DEBBIE HERING REALTY & ASSOC. (941-320-1070)
Listing Agent: Debbie Hering (941-320-1070)
5521 CHANTECLAIRE #21, SARASOTA, FL 34235
$329,00092 Days on yellowkey MLS ID: A4684320
REDUCED by $10,500 (3.1%) on 05/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 1985 Tax: $3,913 (2025)Community: ChanteclaireVilla
Taxes:$3,913
Elementary School: Gocio Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: WELCOME HOME TO AN AMAZING OPPORTUNITY to live in one of Sarasota's most established Golf and Country Club communities in this wonderful 3 BEDROOM, 2 BATH Bright and Spacious Villa nestled in the well- established Villas of Chanteclaire in The Meadows Golf and Country Club. This villa offers the new buyer exciting opportunities to creatively update the current floor---a wonderful opportunity to your personal taste or simply just enjoy the decor 'as is'. Enjoy discovering the best use the tiled sunroom, lined with windows overlooking the garden area! The Villas' Roof is less than two years old. NO CCD Fee. Enjoy many miles of trail to walk, hike or bike. Fun for all to choose from. Located a short drive to University Town Center and the commercial surrounding areas designed for shopping, entertainment, and recreational pastimes of your choosing. So much fun close by. Year-round entertainment indoors and outside for local residents and for visitors alike. Oh, and do experience the NEW World Class Mote Marine Seaquarium.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Jackie Woods (941-356-4093)
3252 WESTFORD LN #122, SARASOTA, FL 34231
$260,00053 Days on yellowkey MLS ID: A4688937
0 Days Off yellowkey (back on 5/24/2026)
REDUCED by $5,000 (1.9%) on 05/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1131 Built: 1972Monthly Fee: $175 Tax: $1,670 (2025)Community: Gulf Gate Garden Homes EVilla
Taxes:$1,670
Remarks: Under contract-accepting backup offers. Welcome to 3252 Westford Lane — LOW $175 monthly HOA in Gulf Gate Gardens Homes in Sarasota, Florida! (Kitchen photos virtually staged with alternate wall color) A wonderful opportunity in one of Sarasota’s most desirable Gulf Gate neighborhoods, this 2 bedroom, 2 bath villa presents comfortable Florida living with a functional layout and peaceful greenbelt view from your private patio and bonus room. Inside, 1,131 sq ft of space, this one story home showcases a floor plan that flows effortlessly from room to room with generous living spaces for everyday living or seasonal stays. Inside, you’ll find comfortable living spaces and ample indoor storage — perfect for modern convenience. The home features plenty of closet/cabinet/pantry space, a clean layout, and excellent natural light throughout. There is also a carport and large indoor utility/laundry room. For the chef in the family the kitchen offers stainless steel appliances, a kitchen island for ease everyday or entertaining. Enjoy a greenbelt view in a peaceful community setting. Low maintenance fees making this residence ideal for first time buyers, downsizers, or snowbirds seeking a low upkeep Sarasota home. Well maintained property features include: Roof 2017, (2) exterior doors (side and rear) w/ blinds between glass, impact glass 2017, A/C 2020, Exterior painted 2022, Exterior motion light 2026 new, All outlets and rocker switches 2017, All wood blinds and woven window treatments, All Door hardware inside and out 2017, Guest Bathroom toilet 2019, Shut off valve at water heater 2019, Garbage Disposal 2019, Stainless Appliances: Whirlpool Range 2026, Refrigerator 2026, Bosch Dishwasher like new, Whirlpool Microwave like new. Air conditioner has been consistently maintained and new UV light installed 2026 and carbon filtration system added in 2026 ($2k). All interior has been painted (walls and ceilings), Great Room/Dining/Florida Room low maintenance solid surface stained concrete. Carpet and upgraded pad in bedrooms (pad has the waterproof barrier on top between pad and carpet 2017. Storage room new cabinetry and plumbed for utility sink. Exterior- all re-landscaped, Exterior patio wood look deck tiles and metal privacy trellis 2026, All interior and exterior lights 2021, Private Mailbox. Location & Community Highlights: Prime Gulf Gate Gardens location with easy access to Gulf Gate Village, Legacy Trail, YMCA/Potter Park, Costco; close to dining, shopping, and services. High walkability score. Minutes from the world famous Siesta Key Beach and nearby cultural hotspots. • Low monthly HOA that covers grounds maintenance and irrigation. From its quiet greenbelt setting to its proximity to beaches, trails, and conveniences, this home offers the best of Gulf Gate living in Sarasota.
Listing is courtesy of: KATHLEEN GOFF LICENSE R.E. BROKER (941-350-3902)
Listing Agent: Kathleen Goff (941-350-3902)
6308 MIDNIGHT PASS RD #6, SARASOTA, FL 34242
$995,000334 Days on yellowkey MLS ID: A4657483
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1965Monthly Fee: $1,005 Tax: $5,582 (2025)Community: Crescent ArmsSpa: NoVilla
Taxes:$5,582
High School: Sarasota High
Remarks: Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value. This thoughtfully updated residence blends custom coastal finishes with subtle Thai-inspired design, creating a warm, serene atmosphere throughout. The open-concept layout offers seamless flow between the kitchen, dining, and living areas ideal for both everyday living and entertaining. The gourmet kitchen features quartz countertops, stainless steel appliances, and generous workspace, all opening into a bright and inviting living area. Both bathrooms have been tastefully updated with spa-like finishes, including a walk-in shower and modern fixtures. Step outside to your private patio perfect for relaxing, grilling, or enjoying the tropical surroundings just moments from the beach. Crescent Arms offers exclusive private beach access to world-famous Siesta Key Beach, along with onsite management making this an excellent option for personal use, vacation rental income, or a combination of both. This property has a proven rental history with strong year-round bookings. Whether you’re searching for a coastal retreat, investment opportunity, or both, this villa delivers location, lifestyle, and value. Sold turnkey move right in or start generating income immediately.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
6300 MIDNIGHT PASS RD #21, SARASOTA, FL 34242
$869,000129 Days on yellowkey MLS ID: A4678951
0 Days Off yellowkey (back on 5/26/2026)
REDUCED by $30,000 (3.3%) on 05/26/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1253 Built: 1969 Tax: $5,276 (2025)Community: Crystal Sands 1Villa
Taxes:$5,276
Remarks: Under contract-accepting backup offers. Everything is brand new in this beautifully renovated, turnkey furnished two bedroom, two bath end-unit villa offering an exceptional Siesta Key beach lifestyle just steps from the Gulf. The desirable split floor plan features spacious bedrooms, generous closets, and an open-concept living area filled with natural light, enhanced by a sun-lit Florida room. The updated kitchen is thoughtfully designed with granite countertops, a coordinating backsplash, soft-close cabinetry, and new stainless steel appliances. The primary suite offers a wall-to-wall closet, transom window, and sliding glass doors opening to the Florida room. Additional highlights include luxury vinyl plank flooring, all-new furnishings, and an attached one-car garage with washer and dryer plus ample storage for beach gear. Whether enjoyed as a private coastal retreat or a lock-and-leave rental opportunity, this residence truly offers the best of both worlds. Crystal Sands is a well-managed, financially stable beachfront community that has remained highly desirable since 1969 due to consistent upkeep and thoughtful renovations. The condominium comprises a collection of one, two, and three bedroom villas along with a Gulf-front high-rise tower, all set within beautifully maintained grounds. Residents and guests enjoy private beach access with umbrellas and loungers, two heated swimming pools, a clubhouse, on-site rental management, and night security, all just moments from Siesta Key’s renowned dining and shopping.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Bev Murray (941-724-4995)
4034 WILSHIRE CIR E #154, SARASOTA, FL 34238
$409,00010 Days on yellowkey MLS ID: A4693402
1 Days Off yellowkey (back on 5/26/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1990 Built: 1989 Tax: $1,845 (2025)Community: Lakeshore VillageVilla
Taxes:$1,845
Remarks: Under contract-accepting backup offers. MUST SEE THIS REMODEL! Located in the highly desirable Lakeshore Village community in Sarasota, this beautifully remodeled 3-bedroom, 2-bath attached villa with a 2-car garage offers nearly 2,000 square feet of stylish, move-in-ready living just minutes from Siesta Key Beach, shopping, dining, I-75, and everything Sarasota has to offer. From the moment you step inside, you’ll appreciate the light, bright open floor plan with vaulted ceilings, luxury vinyl plank flooring throughout, fresh interior paint, updated lighting, and designer touches at every turn. The spacious great room is ideal for entertaining and features a custom built-in wine and beverage station, creating the perfect gathering space for family and friends. The remodeled kitchen is both beautiful and functional, showcasing custom cabinetry, quartz countertops, decorative tile backsplash, stainless steel appliances, and updated fixtures designed for everyday living with effortless style. The primary suite offers a true retreat with a fully redesigned bath featuring double vanities, a private water closet, large linen storage, and an expansive walk-in shower with dual shower heads and decorative tile accents. Bedroom 3, accented by stylish barn doors, is currently used as a den/home office, while Bedroom 2 provides flexible space for guests, hobbies, or a private retreat. Step onto the enclosed Florida room and enjoy lush tropical landscaping and a peaceful backyard setting — the perfect spot for morning coffee, relaxing with a book, or simply enjoying Florida living year-round. Located in Flood Zone X, where flood insurance is not required, this home also offers exceptional maintenance-free living. Monthly condominium fees include CABLE, INTERNET, lawn care, pest control, exterior maintenance, exterior painting, roof reserves, and irrigation of common areas. Residents of Lakeshore Village enjoy an active lifestyle with access to a heated and chilled community pool, tennis and pickleball courts, clubhouse, billiards room, library, community kitchen, and a full calendar of social activities and neighborhood events. Beautifully updated, impeccably maintained, and perfectly located — this Sarasota villa is truly move-in ready and sure to impress.
Listing is courtesy of: RE/MAX PALM (941-929-9090)
Listing Agent: Maggie Nasser (941-780-1006)
3416 W CHELMSFORD CT #2, SARASOTA, FL 34235
$420,000509 Days on yellowkey MLS ID: A4634668
3 Days Off yellowkey (back on 5/26/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1513 Built: 1990 Tax: $4,165 (2023)Community: The MeadowsVilla
Taxes:$4,165
Tax Year: 2023
Remarks: This beautiful villa sits at the end of a dead-end street, a few steps from the community pool and has stunning lake and golf course views. As you enter the walkway you are greeted by a gated entry gaining access to the front loggia that is accented with pavers and leads to your private entrance. The grand foyer is large and is the perfect space to display your art or family heirlooms. The kitchen has been professionally updated with stunning finishes and features high-end appliances. There is an office or den off the kitchen through dual pocket tiffany doors. The guest bedroom is spacious and provides a view to the front lanai. The living room and dining room provide for gracious living and entertaining allowing expansive views of the golf course and lake. Golf views are also from the primary suite with its large bathroom and walk-in closet. This home features high ceilings throughout, extensive levels of crown moldings, elegant features and finishes and is perfect for year-round living or as a wonderful getaway home for seasonal or frequent visitors.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: David Dangelo (941-587-7268)
5021 BARRINGTON CIR #302, SARASOTA, FL 34234
$160,000230 Days on yellowkey MLS ID: A4663516
REDUCED by $15,000 (8.6%) on 05/26/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1078 Built: 1982Monthly Fee: $599 Tax: $2,471 (2024)Community: Barrington WoodsVilla
Taxes:$2,471
Elementary School: Emma E. Booker Elementary
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. Embrace the ultimate Sarasota lifestyle in this beautifully maintained 2-bedroom, 2-bathroom villa, perfectly situated in a secure fenced community and featuring elegant, vaulted ceilings and two private screened lanais for enjoying the beautiful Florida weather. This property offers a low-maintenance, resort-style experience with a fantastic community pool and a dedicated carport for convenient parking. The villa's outstanding location provides quick access to both necessities and leisure: it's just minutes from Sarasota-Bradenton International Airport (SRQ), a short drive to the famous Gulf beaches, and centrally located near esteemed institutions like New College and the Ringling School of Art and Design. It's an ideal retreat for anyone seeking the perfect blend of security, comfort, and immediate proximity to Downtown Sarasota's rich scene of arts and culture.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kelly Oatsvall (941-447-7256)
3541 WILKINSON WOODS DR #40, SARASOTA, FL 34231
$289,900195 Days on yellowkey MLS ID: A4672490
REDUCED by $5,000 (1.7%) on 04/20/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1548 Built: 1980 Tax: $3,658 (2025)Community: Wilkinson WoodsVilla
Taxes:$3,658
Elementary School: Wilkinson Elementary
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Skip the renovation stress and discover an UNBEATABLE VALUE in this updated 2-bedroom, 2-bath attached villa, offering IMPACT WINDOWS, New A/C (2026) and NEWER APPLIANCES. Bathed in natural light, this home features elegant QUARTZ COUNTERTOPS throughout, designer LED-illuminated mirrors, and sleek, durable laminate flooring. Beyond the stylish interior lies a charming paver patio—a relaxing retreat for morning coffee or sunset breezes. Located in an enclave that feels like a hidden secret in South Sarasota, you are minutes from Siesta Key’s white sands, casual and world-class dining, entertainment...but miles from the stress of a fixer-upper. Experience just how effortless Florida living can be by taking this stylish, move-in-ready villa off your screen and scheduling your in-person tour today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Elisa Gersman (941-735-0595)
5354 MYRTLE WOOD #50, SARASOTA, FL 34235
$247,000139 Days on yellowkey MLS ID: A4677059
REDUCED by $8,900 (3.5%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1064 Built: 1981Monthly Fee: $592 Tax: $2,906 (2024)Community: SomersetSpa: NoVilla
Taxes:$2,906
Remarks: NEW PRICE- Welcome to a move-in-ready villa offering effortless Florida living in one of the most sought-after enclaves within The Meadows—where tree-lined streets, mature landscaping, and an active outdoor lifestyle define the experience. Perfectly positioned on a quiet street just moments from community pools and miles of scenic trails, this residence delivers both privacy and immediate access to everything that makes The Meadows so desirable. Inside, vaulted ceilings and an open, light-filled layout create an inviting sense of space, while recent updates—including fresh interior paint and new flooring—provide a clean, modern feel with minimal effort required. The great room seamlessly opens through a full wall of sliding glass doors to a screened lanai surrounded by lush greenery—an ideal setting for morning coffee or a relaxed evening. The kitchen offers a functional and stylish workspace with stone countertops, stainless steel appliances, ample storage, and its own access to a private front lanai. The split-bedroom floor plan enhances comfort and flexibility, with a private primary suite tucked at the rear of the home featuring dual closets and a walk-in shower. A second bedroom with an ensuite bath at the front provides an ideal space for guests or a home office. A dedicated laundry area adds to the home’s practical design. Living in The Meadows means enjoying a 1,650-acre park-like community with over 14 miles of trails, 85 lakes, and optional memberships to golf, tennis, pickleball, a junior Olympic pool, and a fitness center. Just minutes from Nathan Benderson Park, the vibrant shopping and dining at University Town Center, downtown Sarasota, and the renowned beaches of Siesta Key and Lido Key, this villa offers the ideal balance of convenience, lifestyle, and value—whether as a full-time residence or seasonal retreat. Make an appointment to see this villa today.
Listing Agent: Andy Scherer (315-264-0944)
5723 DEER HOLLOW TRL, SARASOTA, FL 34232
$299,0007 Days on yellowkey MLS ID: TB8511154
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)
4316 CALLISTA LN, SARASOTA, FL 34243
$495,000178 Days on yellowkey MLS ID: A4674352
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1930 Built: 2005Monthly Fee: $243 Tax: $4,677 (2023)Community: Callista VillageVilla
Taxes:$4,677
Remarks: Experience modern living in this beautifully remodeled two-bedroom plus den home, perfectly situated in a prime location now available! The versatile den offers the perfect solution for a home office, guest room, or movie room. Nestled on a peaceful dead-end street for ultimate privacy and tranquility. Discover the ease of maintenance-free living allowing you to enjoy a relaxed lifestyle without the hassle of upkeep. Enjoy modern updates throughout, designed for comfort and style with natural light all throughout. Located in a highly desirable area near University Town Center that offers shopping, dining, and entertainment. Whether you're downsizing, retiring, or seeking a hassle-free lifestyle, this home is must-see. Don't miss this exceptional opportunity!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Samantha Jennen (941-321-6095)
2247 BISPHAM RD #50, SARASOTA, FL 34231
$239,00028 Days on yellowkey MLS ID: A4692145
1 Days Off yellowkey (back on 5/25/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1170 Built: 1974Monthly Fee: $700 Tax: $2,170 (2025)Community: Woodside Village EastVilla
Taxes:$2,170
Remarks: Under contract-accepting backup offers. Charming 2-bedroom, 2-bath villa in the highly desirable Gulf Gate area, just a few miles from the pristine sands of Siesta Key. This move-in ready, updated home features an open floor plan with cathedral ceilings and a bright, airy Florida room, creating a light and inviting living space. Enjoy the feel of a beach retreat without being in a flood zone. Furniture is available and included. The villa has been tastefully updated with quartz countertops in the kitchen, luxury vinyl flooring throughout, newer appliances, remodeled bathrooms, added can lighting, a new electrical panel, and HVAC replaced in 2022. Pavers have been added to create a charming front porch sitting area—perfect for relaxing outdoors. Additional highlights include covered parking and a shared circular drive that provides added guest parking convenience. Woodside Village East offers beautifully maintained grounds with mature landscaping and a community pool, all in a prime location close to beaches, shopping, dining, and entertainment.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Janice Melzer Langa (941-404-0802)
113 WHISPERING SANDS DR #V47, SARASOTA, FL 34242
$615,00095 Days on yellowkey MLS ID: A4683156
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1344 Built: 1968Monthly Fee: $1,351 Tax: $5,993 (2025)Community: Whispering Sands Sec 5Villa
Taxes:$5,993
Remarks: One or more photo(s) has been virtually staged. NEW PRICE! Discover the ease of island living in this newly REMODELED 3BR/2BA villa with garage in the premier GULF FRONT property of Whispering Sands! As a rare freestanding villa, this residence offers the privacy of no shared walls and lives like a single family residence. Every detail has been thoughtfully curated, from the reimagined open galley kitchen with its sophisticated soft grey tones and granite countertops, stainless appliances, and soft close cabinetry and drawers – flowing seamlessly into the main living areas – to the beautifully updated bathrooms and elegant tile flooring. Textured ceilings and recessed lighting create a warm, contemporary ambience. The small private patio invites relaxed al fresco dining, while the rare 1-car garage—complete with an epoxy floor, full sized W/D hookup, and its own A/C system—adds exceptional convenience and storage. Behind the scenes, extensive upgrades provide total peace of mind. All windows and sliders are 2022 hurricane impact rated. The plumbing supply and drain lines in this villa were updated from cast iron to PVC in 2022. Further enhancing the home’s value are a NEW concrete tile villa roof and a 2023/2024 garage roof. 2022 HVAC system. Ideally located just steps from the clubhouse, 2 heated pools, and 800’ of Whispering Sands’ own PRIVATE beach on the Gulf, this residence also enjoys a prime setting next to the dining, shopping, and vibrant atmosphere of Siesta Key Village. Imagine starting your day with a morning dip in the Gulf followed by a peaceful stroll along the private shoreline. Spend the afternoon unwinding poolside or swimming invigorating laps in one of two heated pools. Stroll to the Village for a delicious, cozy supper and end the day gathered with friends as the Gulf sky ignites in breathtaking sunset color. Whether you’re seeking a full-time residence or the perfect coastal retreat, this move-in-ready villa offers the best of maintenance free, resort style living in an exceptional island location.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
5265 CHASE OAKS DR, SARASOTA, FL 34241
$329,90021 Days on yellowkey MLS ID: A4692750
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1564 Built: 2000Monthly Fee: $333 Tax: $2,432 (2025)Community: Club Homes 7Villa
Taxes:$2,432
Elementary School: Lakeview Elementary
Remarks: Welcome to one of the best values in the Sarasota–Manatee region, tucked behind the gates of the highly sought-after Heritage Oaks Golf & Country Club—a rare, debt-free golf community celebrated as much for its lifestyle and sense of community as its exceptional amenities. This Buttonwood model Club Home features 2 bedrooms and 2 full bathrooms. Also equipted with a hurricane shutter on the lanai for peace of mind! This move-in-ready residence offers a bright, efficient layout thoughtfully designed for comfortable everyday living. Luxury vinyl flooring welcomes you inside and leads to a spacious living area, while the screened lanai provides peaceful lake and golf course views—the perfect setting for morning coffee, afternoon tea, and daily entertainment from local wildlife and golfers passing by. Life at Heritage Oaks extends far beyond the golf course. Residents enjoy access to a fully private championship golf course with remarkably low entry fees, along with tennis, swimming pool, fitness facilities, fine and casual dining, and a vibrant social calendar. The recently renovated and expanded clubhouse serves as the heart of the community, bringing neighbors together for everything from casual gatherings to organized events. While Heritage Oaks has long been known as a premier seasonal destination, it also presents an outstanding opportunity for full-time living. With strong financial stability, exceptional amenities, and an unmatched lifestyle-to-price ratio, this home delivers first-class country club living, genuine community, and incredible value. At Heritage Oaks, the best part isn’t just the golf—it’s the people. Schedule your private tour today!
Listing is courtesy of: STERLING REALTY (941-379-5810)
Listing Agent: Greg Martin (941-315-3567)
5099 FLAG ST, SARASOTA, FL 34232
$499,000119 Days on yellowkey MLS ID: A4680473
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1647 Built: 2017Monthly Fee: $345 Tax: $5,291 (2025)Community: Enclave At Forest LakesVilla
Taxes:$5,291
Remarks: A beautiful, rare corner-unit, single-story residence in the gated Enclave at Forest Lakes, ideally located in the heart of Sarasota. This meticulously maintained home offers privacy, natural light, and an open layout designed for effortless living, all just minutes from Siesta Key Beach, downtown Sarasota, major highways, shopping, dining, and everyday conveniences. Featuring 2 bedrooms, a dedicated office/den with double French doors, and 2 bathrooms, the home showcases over $60,000 in builder upgrades. Interior highlights include 9-foot ceilings, 8-foot paneled doors, rich hardwood flooring throughout, and stylish tile in both bathrooms. The chef’s kitchen is a standout with light cabinetry, pull-out storage features, quartz countertops, a large island with a breakfast bar, stainless steel appliances, and a marble backsplash. The primary suite serves as a private retreat with a tray ceiling and a spa-like bath offering a walk-in shower, dual sinks, quartz counters, and ample storage. The great room opens to a full-width covered and screened lanai with remote-controlled fans and ceiling speakers, creating an ideal indoor-outdoor living space. Residents enjoy maintenance-free living with access to a heated resort-style pool, pavilion, dog park, and nearby Legacy Trail access. This corner-unit home combines luxury, privacy, and a central Sarasota location that puts beaches, culture, recreation, and shopping all within easy reach.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Ellen Wilson (704-651-6322)
2974 CAPTIVA GARDENS DR #17, SARASOTA, FL 34231
$269,90057 Days on yellowkey MLS ID: A4688730
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1206 Built: 1975 Tax: $1,511 (2025)Community: Captiva GardensSpa: NoVilla
Taxes:$1,511
Remarks: It's time for you to start enjoy living in Captiva Gardens, a small community located on 7 plus acres in the popular Gulf Gate area of Sarasota. This 2b/2b villa is a great unit and no noise from street traffic currently available in the community. The 1206 SF under air provides spacious living space with the fully applianced kitchen has ample storage with a pass through to the screened lanai and views of the private rear garden area. From the kitchen, you enter a "Extra" room. Visualize a formal dining room, a room for crafts or watching TV or maybe a home office. It's up to you! The living room allows for various furniture arrangements. You will be comfortable in the large ensuite master bedroom which has both a walk-in and double-door closet. Guests will enjoy the light and bright second bedroom and its easy access to the guest bath. The one car attached garage provides quick access to your home and conveniently includes the laundry with separate washer and dryer. This is a wonderful opportunity! Don't miss out. Call today for a personal tour of your new home.
Listing is courtesy of: SHORE TO SHORE R.E. (941-357-7076)
Listing Agent: Jim Claydon (941-504-3398)
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