Location: Sarasota
Do Not Show Listings
5099 FLAG ST, SARASOTA, FL 34232
$499,000137 Days on yellowkey MLS ID: A4680473
2 Days Off yellowkey (back on 6/15/2026)
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,291
Elementary School: Wilkinson Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. 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)
10233 LAKE WALES CIR, SARASOTA, FL 34241
$559,75011 Days on yellowkey MLS ID: A4693223
REDUCED by $5,200 (0.9%) on 06/11/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1634 Built: 2024Monthly Fee: $244 Tax: $4,837 (2025)Community: Grand Park Ph ISpa: NoVilla
Taxes:$4,837
Elementary School: Lakeview Elementary
High School: Riverview High
Middle School: Sarasota Middle
Remarks: Rare Neal Homes Villa presents a unique opportunity to own a piece of luxury nestled in the exclusive Sold-out gated Villa Community of Grand Park, Sarasota. Everything is done for you. With low HOA fees & Fantastic Community Amenities. This beautiful villa boasts tons of beautiful upgrades and high-end fixtures. Starting with solid concrete block construction, full tile roof, whole-house natural gas generator, updated hurricane impact windows and upgraded triple pocket sliders. The two spacious bedrooms plus office/den with French doors includes upgraded tiled floors that extend throughout the entire home. A custom tray ceiling in the great room features stained wood 12-foot ceiling beams, a solid high end wood ceiling fan, upgraded 8-foot doors throughout, and elegant high-end designer lighting and ceiling fans. A custom built-in bar with a wine refrigerator adds a touch of elegance, while stylish architectural brick wall, wainscotting, and walnut wood wall features highlight the luxurious finishes expected in this level of home. Plantation shutters were added on every window as well as a custom honeycomb cellular shade on the triple sliders, custom his and hers closets with 8-foot glass barn doors provide organized storage in the primary. The well-appointed kitchen features shaker soft-close cabinets, two 36-inch upgraded glass door cabinets, and two sets of triple-stack pot drawers. The seamless quartz countertops highlight a beautiful center island with a large stainless steel single bowl sink. New stainless-steel appliances, including an upgraded slide-in gas range with air fryer and upgraded counter-depth refrigerator are included. There is a large walk-in pantry with an upgraded 8-foot glass door providing additional storage space that completes the kitchen area. The guest bedroom includes a new (never used) queen size Murphy bed. The laundry room includes a new washer and gas dryer with added cabinet storage, laundry sink and upgraded faucet. Relax on your extended brick paver lanai while enjoying the protected conservation and nature views. Observe wildlife such as deer and cranes roaming within this park-like setting. The professionally landscaped property includes micro drip irrigation to all plants and trees, and high-end landscape and path lighting that illuminates the exterior surroundings. The front brick paver driveway leads to an upgraded screened porch, while the oversized two-car garage boasts high ceilings & epoxy floors. The garage features include high-end diamond plate storage cabinets, a workstation, and two 4ft x 8ft overhead storage racks. This eliminates the need for any attic storage. Additionally, there is a new upgraded top-of-the-line whole house Kinetico Water filtration and water softener system. Grand Park is a nature-focused, resort-style Maintenance free community with plenty of open space with miles of conservation walking & biking trails. You love strolling around the lakes and discovering the abundance of nature sharing this beautifully planned community. Amenities include an active clubhouse with full-time social director, resort-style tropical pools, full fitness center, pickleball and tennis courts, and two dog parks all a short walk from your new home. Easy access to shopping, dining, nearby beach's including the #1 beach in America Siesta key beach. And you're a short ride to downtown Sarasota's comedy clubs, cultural events and active downtown entertainment. The only thing missing is you
Listing is courtesy of: COACH SANTONI (813-784-1188)
Listing Agent: Coach Santoni (813-784-1188)
5609 EVERGREEN DR #28, SARASOTA, FL 34233
$270,000275 Days on yellowkey MLS ID: A4665113
0 Days Off yellowkey (back on 5/23/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1601 Built: 1980Monthly Fee: $471 Tax: $1,849 (2024)Community: Center Gate Village 4Villa
Taxes:$1,849
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. This approximately 1,600 square foot house offers two bedrooms and two bathrooms. The property features a pool for year-round enjoyment. Crown molding throughout the home adds an elegant touch. The roof is new, providing peace of mind. The air conditioning system is newer, ensuring comfortable climate control. The hot water heater is also new, guaranteeing a reliable supply of hot water. The location of this home is a desirable attribute. Ceramic tile flooring and new carpet create a welcoming ambiance. The kitchen has been updated with modern appliances and finishes. The bathroom has also been updated with a fresh, contemporary design. The homeowners association fees are low, making this an affordable option.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Tom Palazzo (404-734-5735)
4464 CALLE SERENA, SARASOTA, FL 34238
$429,000305 Days on yellowkey MLS ID: A4662305
1 Days Off yellowkey (back on 6/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2833 Built: 1988Monthly Fee: $833 Tax: $6,505 (2023)Community: Prestancia/Villa PalmerasVilla
Taxes:$6,505
Elementary School: Gulf Gate Elementary
Tax Year: 2023
Remarks: Some photos have been virtually staged. Idyllically located in Villa Palmeras at Prestancia, this spacious 2,833 sf maintenance-free villa offers soaring ceilings, skylights, and expansive windows that fill the home with natural light. A gated courtyard entry welcomes you into the open floor plan featuring a large living/dining area, eat-in kitchen with abundant cabinetry, and an enclosed 12x40 Florida room with golf and water views. The owner’s suite boasts a sitting area, walk-in closet, and spacious bath with soaking tub and separate shower. Guest bedrooms are privately situated on opposite sides of the home for comfort and privacy. Additional highlights include two new A/C units (2020), breezeway to garage, and flexible third bedroom/den with French doors. Villa Palmeras residents enjoy two heated community pools, lush landscaping, and 24/7 guard-gated security. Optional membership is available at TPC Prestancia Golf Club with two 18-hole courses, dining, and social activities. Ideally located near shopping, dining, Legacy Trail, and Siesta Key beaches.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
8085 SCARLETBUSH DR, SARASOTA, FL 34240
$497,99051 Days on yellowkey MLS ID: A4691768
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1530 Built: 2026Monthly Fee: $245 Tax: $971 (2025)Community: Windward At Lakewood Ranch Phase 2Spa: NoVilla
Taxes:$971
Elementary School: Tatum Ridge Elementary
High School: Booker High
Middle School: McIntosh Middle
Remarks: The Tidewater 2 by Neal Communities is a thoughtfully designed twin villa offering two bedrooms, two baths, a spacious den, and an open-concept living area. The extended covered lanai at the rear of the home showcases desirable south-facing water views, creating a relaxing outdoor retreat. The primary suite features two closets and an en-suite bath with dual vanities, a walk-in shower, and a private water closet. A well-appointed guest bedroom includes its own walk-in closet and convenient access to a full secondary bath. Interior upgrades include tile flooring throughout the main living areas, quartz countertops, shaker-style cabinetry, and a gas range for added style and functionality.
Listing is courtesy of: NEAL COMMUNITIES REALTY, INC. (941-328-1111)
Listing Agent: John Neal (941-313-8575)
5723 DEER HOLLOW TRL, SARASOTA, FL 34232
$285,00025 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
Elementary School: Gocio Elementary
Middle School: Booker Middle
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)
5023 VILLAGE GARDENS DR #29, SARASOTA, FL 34234
$230,00094 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)
2717 RIVERBLUFF PL #V49, SARASOTA, FL 34231
$270,000120 Days on yellowkey MLS ID: A4681632
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1480 Built: 1971Monthly Fee: $725 Tax: $2,787 (2025)Community: Strathmore Riverside IVilla
Taxes:$2,787
Elementary School: Phillippi Shores Elementary
Remarks: Mrs. Clean Lives Here! Absolutely Charming 2 bed/2bath end-unit Villa! Stunning kitchen that gently flows into dining room area Thw Dining room area opens into large living room with another large family room area creating LOTS of living space A bonus room with the ability to make this your own game room, office space, or just your own oasis! Crown molding in living and dining room with gorgeous wood flooring. Separate storage and laundry room for your convenience Plenty of Guest parking and carport near your front door. This lovely community has a Clubhouse, community pool, fitness, activity calendars, and a Marina ( annual fee is approximatley $1344- annually ). Close to fabulous restaurnants and shops, Detweilers Famers Market and the South bridge to world famous Siesta Key! Freshly Painted within this last year! Active Community with clubhouse facility, community Pool and marina (CHECK)! This is a stunning villa with an exceptional location, just minutes to Siesta Key, shopping and fine dining! If you are looking to live the Sarasota lifestyle come checkjk on this breathtaking villa TODAY!!
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Marcia Morse (941-374-0442)
5647 MONTE ROSSO RD, SARASOTA, FL 34243
$295,90048 Days on yellowkey MLS ID: A4692218
REDUCED by $2,000 (0.7%) on 06/08/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1115 Built: 1994Monthly Fee: $332 Tax: $2,714 (2025)Community: Riviera Club Village At Longwood Run Ph 02Spa: NoVilla
Taxes:$2,714
Remarks: Price Reduction!! Welcome to this 1,658 sq ft single-family home offering 2 bedrooms, 2 full bathrooms, a 2-car garage and a Florida room. This move-in-ready Villa has 1,115 sq ft of heated living space and a rare courtyard for outdoor living and gardening. The new roof (2020), new water heater (2022), new Central AC (2023), new ductwork, new electrical wiring, and security cameras are some of the upgrades for a stress-free living. You will love the skylight-filled living space with cathedral ceilings, which cuts down the electricity bill. A sliding door leads to the Florida room in the rear. Both bedrooms have wood-looking laminate floors. Granite counters and an eating space in the kitchen add to the ease of living. Other features include new ceiling fans and modern lighting. The all-ages Riviera Club Village is a highly sought-after community with low HOA fees and NO CDD. Trash charges are part of the property tax. The monthly HOA fee ($331.67) is comparatively low considering that it covers the maintenance and repairs of the roof, driveway, sidewalks, gutters, exterior painting, landscaping, tree trimming and street lights. This area was not affected by any of the recent hurricanes. The Longwood Park Community Center, owned and maintained by Sarasota County, is just around the corner and offers plenty of recreation facilities and amenities for all ages. Therein are playgrounds and rides, a gymnasium, indoor rooms for meetings and celebrations, Pickleball courts, Tennis courts, a Basketball court, a Baseball field, and dog-walks. For a healthier lifestyle, you can become a member of Sarasota's well-known Palm-Aire Country Club across the University Pkwy, which has one of the best swimming pools, spa, and recreation facilities like tennis, pickleball, 18-hole Golf Club, etc. For beach-lovers, the world-famous Siesta Key Beach is about 13 miles away, and it is only 10 miles to the idyllic Lido Key Beach. Living near several breathtaking blue keys, busy marinas, and extensive waterways of Sarasota is a dream come true. Think of yet another attraction, the European-styled St. Armands Circle, famous for high-end outdoor shopping, galleries, restaurants and a central park with circus-themed statues. Just behind the Riviera Club Village sits the reputed Foundations Christian Montessori Academy for K-12 graders. It takes barely 5-8 minutes to the sprawling University Town Center (UTC) Mall, Sarasota's upscale shopping and dining destination. Located close to the Sarasota-Bradenton International Airport, downtown Sarasota, the University of South Florida, New Florida State College, Ringling College of Art, and the Ringling Museum of Art, this place is one of the best locations to enjoy Florida's endless summer. Come and make it yours, and don’t miss this rare opportunity!
Listing is courtesy of: NEXTHOME IN THE SUN (941-706-1717)
Listing Agent: George Raju (507-722-6331)
4504 CITATION LN #C, SARASOTA, FL 34233
$289,00084 Days on yellowkey MLS ID: A4686138
REDUCED by $10,900 (3.6%) on 06/08/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1385 Built: 1991Monthly Fee: $650 Tax: $2,900 (2025)Community: Calumet At Centergate 1Villa
Taxes:$2,900
Elementary School: Ashton Elementary
Remarks: LUXURY PLUS LIFESTYLE RETREAT VILLA - Beautiful interior finishes and positioned on a premium corner lot in an intimate maintenance-free enclave community of only 66 homes. This elegant yet warm and inviting villa offers 2 bedrooms plus a den, 2.5 baths, and an oversized 2-car garage with two new garage door openers (2024). The home is thoughtfully updated with new appliances (2025), new A/C (2024), plush carpeting (2023), new window screens (2024), and finished with deluxe window shades. The floor plan has spacious rooms and an abundance of storage closets and garage storage space as well. A vaulted, screened lanai creates seamless indoor-outdoor living, filled with natural light throughout the day, while a cozy fireplace in the living room adds warmth and charm — creating a true Florida sanctuary. The main level includes a private primary suite, a versatile office/den, and a convenient half bath. The beautifully designed slate-gray kitchen opens to the expansive dining and living areas, ideal for both everyday living and entertaining. Upstairs, a second bedroom with en suite bath and walk-in closet provides comfort and privacy for guests. Just steps away, enjoy the community’s heated pool overlooking a tranquil pond, a clubhouse with full kitchen, and a fitness room. Ideally located with easy access to I-75 and just minutes from shopping, dining, parks, The Legacy Trail, Home Depot, hospitals and award-winning Siesta Beach! The HOA COVERS ROOF MAINTENANCE AND EXTERIOR PAINTING, along with weekly landscaping services including mowing, edging, and trimming. It also includes hedge and tree trimming, irrigation and sprinkler systems, outdoor pest control, and leaf removal. Residents have access to the community center, which features a meeting room, kitchen, restrooms, fitness center, and pool, as well as private use of clubhouse facilities. ADDITIONAL SERVICES include pool maintenance, mailbox upkeep, street lighting, and maintenance of all common areas such as the lake, entrance, signage, community spaces, visitor parking, exterior walls, and landscaping. VERY EASY TO SHOW AS WELL!
Listing Agent: Kathryn Cooper, Pa (941-320-8075)
5176 CEDAR HAMMOCK LN, SARASOTA, FL 34232
$319,9008 Days on yellowkey MLS ID: A4696717
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1246 Built: 1984Monthly Fee: $33 Tax: $2,077 (2025)Community: Cedar HammockSpa: NoVilla
Taxes:$2,077
Remarks: Virtually Staged. Welcome to this beautifully updated 2-bedroom, 2-bathroom home in the highly desirable Cedar Hammock community - offering exceptional value and move-in ready comfort. Step inside to an open, light-filled layout featuring newer luxury vinyl plank flooring, updated ceilings, recently painted inside and out, creating a clean, modern feel throughout. The kitchen has been tastefully upgraded with white shaker-style cabinetry, and stainless-steel appliances, making it both stylish and functional for everyday living. The lanai has been converted to a bonus room providing additional living space for your enjoyment. You will be able to enjoy the cool Florida winter evenings in front of your stone-faced wood burning fireplace in the great room. The bathrooms have been tastefully updated providing a clean and modern feeling. The Home provides flexible living space perfect for relaxing or entertaining. A one-car garage and inviting outdoor space with a fenced yard adds to the home’s overall appeal. Major systems are in solid condition, including a newer roof and HVAC system, providing added peace of mind. Located in a quiet neighborhood with ultra-low HOA fees, this home is just minutes from shopping, dining, downtown Sarasota, and world-famous Gulf beaches. Don’t miss this opportunity. Homes in Cedar Hammock rarely come available in this condition and price range. Schedule your showing today.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Dave Clapp (941-376-1443)
5475 CHANTECLAIRE #58, SARASOTA, FL 34235
$525,00010 Days on yellowkey MLS ID: A4695707
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 1985 Tax: $5,106 (2025)Community: ChanteclaireVilla
Taxes:$5,106
Remarks: One of a kind! Welcome to this beautifully updated villa on the 14th fairway of the Meadows Golf Course. Enjoy stunning golf course views from the builder’s choice lot in Chanteclaire. Fully updated in 2023, the interior features luxury vinyl flooring, crown molding and abundant natural light. The open kitchen boasts stainless-steel appliances, Malibu quartz countertops, a new tile backsplash and Oxford Maple soft-close cabinetry with direct access to the grilling patio. Perfect for entertaining, the living room includes new custom cabinetry, a matching quartz countertop and a built-in wine fridge. The spacious primary suite serves as a true retreat, complete with a custom walk-in closet and a sliding door that opens to peaceful nature views. The present owners have added extensive premium updates for ultimate comfort and peace of mind. The home features full-height, custom PGT hurricane-rated windows and doors throughout, powered aluminum hurricane shutters and plantation shutters in the dining room and bedrooms. Mechanical and structural upgrades include a high-efficiency Trane variable-speed HVAC unit and a new shingle roof installed in 2025 with 71 additional joist clips for enhanced wind protection. This property sits at a 33-foot elevation in Flood Zone X, making it the perfect choice for a secure, lock-and-leave Florida lifestyle. Outside, a quiet cul-de-sac location, paver driveway and charming courtyard welcome you home. Mature shade trees, colorful sunsets and a daily parade of local birds frame the golf course views. The villa is also just a short distance from two heated community pools. The comprehensive HOA fee covers exterior insurance, maintenance-free yard care, irrigation, pest control, exterior cleaning and painting, roof maintenance, dryer vent cleaning, neighborhood pools and basic cable. Set within the 1,600 park-like acres of The Meadows, this resort-style community offers an active social calendar, 14 miles of scenic trails, championship golf courses, a junior Olympic pool, pickleball, Har-Tru tennis and a fitness center. You are just 15 minutes from downtown Sarasota, Bradenton, Lakewood Ranch and Sarasota International Airport and mere minutes from Whole Foods, Trader Joe’s, Nathan Benderson Park, the Legacy Trail and premier dining at University Town Center. Experience worry-free Florida living at its finest!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Fernando Viteri, Pa (941-400-7676)
4391 WOODMANS CHART #155, SARASOTA, FL 34235
$349,00031 Days on yellowkey MLS ID: A4694064
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1535 Built: 1977 Tax: $3,452 (2025)Community: Woodmans ChartVilla
Taxes:$3,452
Remarks: Nestled in the highly sought after community of Woodmans Chart, this 2 bedroom/2 bath villa combines architectural character, abundant natural light, and a resort style lifestyle just 15 minutes from downtown Sarasota and about 30 minutes from world-renown Siesta Key Beach. Soaring vaulted ceilings with striking wood beams create warmth and charm throughout most of the home, while recent interior paint and new plank-style tile flooring add a fresh, modern touch. The spacious living area also has a sun room adjoining it with a large skylight that basks the area in light, and creates a bright and welcoming gathering space. A spacious primary suite features a row of French doors that open to the main living area, enhancing the home's airy, open feeling. What was most likely once an open atrium has been thoughtfully enclosed to create a stunning sunroom featuring three skylights set into the vaulted ceiling. Bathed in natural light and surrounded by two walls of French doors, this inviting space would make an exceptional art studio, reading room, or extra sleeping area for guests. The entire rear of the home is designed to bring the outdoors in, with walls of glass featuring dual four-paneled sliding glass doors and a large picture window overlooking the expansive 35-foot screened lanai-perfect for entertaining, relaxing, or enjoying peaceful garden views. Just off the dining room, a door leads to a private outdoor patio finished with charming brick pavers-an ideal setting for relaxing outdoors in complete privacy, enjoying morning coffee, or soaking up the Florida sunshine. From the patio, you have direct access to the spacious two-car garage, offering both convenience and ample storage. Residents of Woodmans Chart enjoy access to two community pools as well as a private tennis court tucked away among mature trees and lush landscaping, adding to the peaceful, resort-style that makes The Meadows such a sought-after community. The 1600 acres of The Meadows offers 14 miles of scenic trails and optional memberships to a fitness center, tennis and pickleball courts, a Junior Olympic pool, and golf. Everyday conveniences are close at hand, with easy access to premium shopping, dining, and entertainment including The Fresh Market, Whole Foods, UTC Mall, the new Mote Marine Laboratory & Aquarium, and the popular Waterside district in Lakewood Ranch. This central location places the very best of the Sarasota lifestyle right at your doorstep. There is a One Time $1000.00 Capital Improvement fee at Closing.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Stacy Liljeberg (941-544-6103)
4937 CHASE OAKS DR, SARASOTA, FL 34241
$365,00042 Days on yellowkey MLS ID: A4692927
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1572 Built: 1997Monthly Fee: $370 Tax: $2,373 (2025)Community: Heritage Oaks Golf & Country ClubVilla
Taxes:$2,373
Remarks: Not just another lovely home on a street, this "Buttonwood" Club Home, former builder's model, is ready for the opportunity to make it your own. With classic design and fully furnished, the home is waiting for the right touch. The kitchen is spacious and conveniently designed, with granite countertops. The Breakfast Nook has a buffet server with overhead lighting and extra cabinet space. Washer/dryer laundry room is in a separate utility room, conveniently adjacent to the kitchen. The den has a built-in entertainment center and an integrated desk/computer work space. The Primary bedroom is more spacious due to the optional bay window which overlooks the water and the golf course. The en-suite bath has double sinks, a step-in shower and an enormous walk-in closet. Situated on a semi private street, in proximity to the tennis courts, Pro Shop, Jr. Olympic pool and spa, and the main clubhouse with the 19th Hole, dining rooms and meeting rooms. Through the breezeway takes you to the newly renovated fitness center, complete with first class fitness equipment and a full-time director and specialty adjunct instructors. All conveniently located and accessible to your new home. In fact, one of the neighborhood pools is located in the other direction and about the same distance. Heritage Oaks Golf and Country Club is a bundled community (all owners are members of the club and enjoy access to the amenities) situated on 550 acres, five miles of walking trails, four neighborhood pools, gated with a 24-hour guard on duty. Sarasota is "The Arts Capital of Florida, and as such, has many cultural and artistic venues: restaurants, world class beaches, Selby Gardens, Mote Marine St. Armand's Circle and the three convenient airports. Come and enjoy the Heritage Oaks Lifestyle in Sunny Sarasota.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: R Glen Ridgeway (941-302-2376)
4601 LAS BRISAS LN, SARASOTA, FL 34238
$625,00051 Days on yellowkey MLS ID: A4690192
REDUCED by $20,000 (3.1%) on 05/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2428 Built: 1988Monthly Fee: $800 Tax: $5,706 (2025)Community: Prestancia/Villa D'esteVilla
Taxes:$5,706
Remarks: Tucked within the charming Villa d’Este enclave of TPC Prestancia, this beautifully updated villa welcomes you with a relaxed coastal feel and an easy sense of home from the moment you step inside. Natural light fills the space, enhanced by soaring ceilings and an open layout that allows each room to flow comfortably into the next. The kitchen sits at the heart of it all, where quartz countertops are paired with a soft aqua subway tile backsplash—adding just the right touch of color and personality while keeping a clean, coastal look. The primary suite is set apart for privacy, creating a quiet retreat, while the guest bedrooms are located on the opposite side of the home—ideal for hosting family or friends. Each bedroom is generously sized and bright, offering comfortable, airy spaces throughout. Step outside to a cozy lanai, perfect for a quiet morning coffee, then continue to the additional outdoor seating area just beyond—an inviting spot to relax, gather, or enjoy Sarasota’s year-round sunshine. Practical updates add to the home’s appeal, including a new roof, fascia, skylights and gutters completed within the past year. The property is sold furnished for your convenience. Whether you’re here full-time or seasonally, the ease of living stands out. The community takes care of the exterior of the villa and of the landscaping, so you can simply enjoy your time without the upkeep. TPC Prestancia community provides 24/7 gated security and is recognized as an Audubon Certified Sanctuary, with 565 acres of mature trees, wildlife, and walking paths. Fine dining, shopping is only minutes away! Located only 4 miles from world-renowned Siesta Key Beach, this home offers you piece of mind in the most upscaled golf community in Palmer Ranch, Sarasota. TPC Prestancia social, sports (tennis, brand new pickleball courts, gym in construction) and golf memberships are available and optional. This is a rare opportunity to own a turnkey villa, move in condition that combines space, thoughtful updates in one of the best locations in Sarasota. Schedule your private showing today (Floorplan and 3D tour available)!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Pascale Durand (973-727-9784)
1732 KESTRAL PARK WAY S #43, SARASOTA, FL 34231
$534,00071 Days on yellowkey MLS ID: A4686630
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1368 Built: 1982Monthly Fee: $167 Tax: $5,360 (2025)Community: The LandingsVilla
Taxes:$5,360
Remarks: THIS RARELY AVAILABLE and highly sought-after Landings Carriage Home, nestled within mature landscaping and offering verdant vistas from every room, is ready for its next owner. This residence lives like a single-family home, featuring a charming living area with a wood-burning fireplace, custom mantle, glass-topped shelf divider, and LVT plank flooring. Abundant windows fill the home with natural light, while plantation shutters provide privacy and character. The surrounding landscaping includes hibiscus, palms, ferns, and flowering trees, supported by an irrigation system, creating a peaceful garden setting. A paver driveway and walkway enhance the welcoming curb appeal. The split floor plan offers privacy, with a spacious primary suite featuring a dressing-room-style closet. The updated primary bathroom includes a walk-in shower with travertine, stone vanity top, high ceilings, and mirrored and tiled accents. The suite also features a ceiling fan and access to a private patio. The guest bedroom offers two closets and a full patio door for natural light. The second bathroom includes a granite-top vanity and tub/shower combination. The dining area is highlighted by a coastal-style glass bead chandelier. A glass-enclosed lanai provides flexible space for an office, den, or guest area. The kitchen features newer stainless steel appliances, granite countertops, a breakfast area, and a patio door leading to a private walled courtyard with a ceramic tiled fountain—ideal for relaxing or outdoor dining. Residents of The Landings enjoy scenic nature trails leading to Roberts Bay, along with a private fishing gazebo and kayak launch. Conveniently located between the Siesta Key bridges and approximately seven miles to downtown Sarasota. THIS IS THE LOCATION!! New additional gutters (2025), new TPO lanai roof (2026), new barrel tile roof (2022 association maintained), tankless hot water heater, new GE stacked full size washer and dryer with wifi capability (2021), new stainless steel Kitchen Aid appliances (2023), new garbage disposal (2024), new wifi controlled thermostat (2022), newer A/C system, create a home for you to easily move right into. Landscaping and building exterior maintenance are included in the monthly fees, so you are free to take advantage of the ideal Landings location—strategically developed as one of Sarasota’s premier gated communities with optional Racquet Club membership with 8 Har-Tru tennis courts, pro shop, fitness center, meeting rooms, pool and spa. The Landings has a lush well maintained nature trail that leads to Roberts Bay with a private fishing gazebo and rental space to park your kayak. Midway between the two Siesta Key bridges and approximately 7 miles from downtown—this is THE LOCATION.”
Listing Agent: Heather Chase (941-320-3121)
1141 MERLE WAY #14, SARASOTA, FL 34232
$210,000141 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)
4439 DEER TRAIL BLVD, SARASOTA, FL 34238
$479,999157 Days on yellowkey MLS ID: A4677582
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1939 Built: 1992Monthly Fee: $282 Tax: $4,835 (2025)Community: Villas At Deer CreekVilla
Taxes:$4,835
Remarks: Just reduced $30,000 and Seller offering a $30,000 credit at closing. Seller is highly motivated. Mesmerizing scenic lake views from this sought after Deer Creek Villa home located in the heart of Palmer Ranch. This Villa home offers close to 2,000 sq ft with enclosed Lanai with sliding doors to enjoy the warm breezes. Spacious rooms sizes, vaulted ceilings and lots of light in this 2-bedroom, 2-bath floor plan with large den/office. Lovely living room, dining room & white cabinetry kitchen with granite counters & decorative tile backsplash. Separate laundry room with cabinetry. Large Primary Suite with high ceilings & walk-in closet. The Primary Bath with granite double vanity, soaking tub & tiled shower. Split double bedroom & bath. The den/office could be a 3rd bedroom or exercise room. Deer Creek is one of the more established gated communities that offers residents gorgeous tree lined street, lush tropical flora & tranquil lakes. Deer Creek is a gated community with 24 hr. security that is low maintenance with a wonderful Community Pool & great social activities for all residents to enjoy. Close to everything in Sarasota, including top-rated schools, world-class golf courses, 8 miles to Downtown Sarasota, including Marie Selby Gardens. Shopping, all within 1 mile. Costco, Target, Sprouts, Starbucks, Kohls, the soon to be re-developed Sarasota Square Mall and a new Trader Joe's opening in Spring. The famous Legacy Trail is just a short distance away. Easy to schedule a showing.
Listing Agent: Betsy Campbell (203-554-8349)
5793 ITHACA WAY, SARASOTA, FL 34238
$439,0006 Days on yellowkey MLS ID: A4696958
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 2002Monthly Fee: $473 Tax: $4,942 (2025)Community: VillagewalkSpa: NoVilla
Taxes:$4,942
Remarks: New on the market is this rarely available extended Capri III Villa w/heated swimming pool! This villa has been well maintained and recently upgraded with double pane storm windows. The home was “Built Solid” by DiVosta Homes utilizing poured concrete and steel walls with a cement tile roof. Designed for full time or “lock n’ leave” seasonal owners you will enjoy virtual maintenance free living in VillageWalk. The split 2 bedroom, 2 bath floor plan offers privacy for you and your guests. Both bedroom suites offer walk-in closets w/modular organizers. The kitchen countertops and appliances have been upgraded as well. A recently installed efficient A.C. system will keep you cool for less. VillageWalk is one of Sarasota county's jewels. A true lifestyle community VillageWalk has a full time activities director, 2 heated pools, 6 HAR-TRU tennis courts, Pickleball and basketball courts plus a State-of-the-Art fitness Center and miles off walking trail's. The community TownCenter hosts a variety of activities daily activities incl. card games, club meetings, guest speakers, stretching and Pilates classes and much more. While there residents can get bite at the onsite Cafe' or visit to the gift shop or hair salon. There's even a gas station for convenience!! Schedule a showing today!
Listing is courtesy of: TOWN CENTER REALTY (941-929-9333)
Listing Agent: Scott Albert (941-929-9333)
119 WHISPERING SANDS CIR #V36, SARASOTA, FL 34242
$495,000301 Days on yellowkey MLS ID: A4656278
REDUCED by $30,000 (5.7%) on 06/14/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1160 Built: 1968Monthly Fee: $1,400 Tax: $6,617 (2024)Community: Whispering SandsVilla
Taxes:$6,617
Remarks: One or more photo(s) has been virtually staged. BEST PRICED VILLA IN WHISPERING SANDS! Don't miss this opportunity to own this lovely REMODELED VILLA just steps from the sand! This 2 bed/2 bath villa nestled in the premier GULF FRONT property of Whispering Sands is the perfect island getaway. Remodeled in 2025, this villa features all NEW vinyl plank flooring, paint, baseboards, trim, molding, and all interior doors. The bright NEW galley kitchen is a true highlight, offering stylish soft close cabinetry, granite countertops, stainless Whirlpool appliances, a side by side fridge with icemaker/dispenser, stainless farmhouse sink, and recessed and under-cabinet lighting. Both bathrooms have been refreshed with new granite counters, cabinets, vanities, and fixtures for a clean, contemporary feel. You’ll enjoy the ease of indoor-outdoor living with a tiled screened lanai – perfect for your morning coffee or evening relaxation. It could be further enclosed with windows or sliders and turned into a sunroom. This villa also features a nice skip trowel ceiling finish and plantation shutters. One car garage with NEW 2026 epoxy floor. NEW 2025 full sized Maytag WASHER & DRYER. NEW 2025 VILLA ROOF. 2025 HVAC system and 2025 water heater. Ideally located just around the corner from Whispering Sands’ two sparkling heated pools, clubhouse (currently in the beginning stages of being remodeled and which will include a fitness center and catering kitchen), NEW beachside Tiki Hut, shuffleboard, and 800' of your own private beach on the Gulf — perfect for enjoying Siesta Key’s world famous quartz sand and spectacular sunsets! When you're not luxuriating in the pool or going for a dip in the Gulf, step out of your front door and walk to shopping and dinner! Whispering Sands is situated right around the corner from the colorful boutiques and fine restaurants of Siesta Key Village. Embrace the island lifestyle! Whether as a year-round residence or a vacation retreat, this maintenance free Gulfside villa combines ease, style, comfort - and a great investment - in one of Siesta Key’s finest Gulf front properties.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
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