3427 Winding Oaks Drive #14, Longboat Key, FL 34228
Local realty services provided by:ERA ONETEAM REALTY
Listed by: carolyn donnelly, pa
Office: coldwell banker realty
MLS#:A4686623
Source:MFRMLS
Price summary
- Price:$1,150,000
- Price per sq. ft.:$351.68
About this home
Under contract-accepting backup offers. Privately tucked away within the private Winding Oaks community on Longboat Key, this beautifully updated three-bedroom villa offers an easy, elevated way to enjoy Sarasota's coastal lifestyle. Overlooking the Harbourside Golf Course, the home captures peaceful water views and the scenic 5th hole, creating a backdrop that feels both open and serene. Designed for effortless living, this turnkey furnished residence blends the comfort of a single-family home with the simplicity of maintenance-free ownership-ideal for seasonal stays or extended escapes. Inside, an airy open layout, soaring ceilings, and wide-plank tile floors create a light, welcoming feel, while floor-to-ceiling sliders connect seamlessly to the outdoor living spaces. The kitchen is both stylish and functional, featuring Italian white-lacquer cabinetry, stone countertops, and premium appliances-perfect for casual evenings at home or hosting friends. The living room centers around a custom gas fireplace and flows naturally to a spacious screened lanai, where you can unwind with long water views and soft coastal breezes. The home features many new furnishings and many recent updates. A private courtyard with a heated pool adds another layer of relaxation, offering a quiet place to start the day or wind down after time on the water, golf course or tennis courts. The primary suite is a calm retreat of its own, with tranquil water views, a spa-like bath, and a generous walk-in closet. Two additional en-suite bedrooms provide flexibility for visiting guests or a comfortable home office. Ownership includes access to the Bay Isles Beach Club, where days can be spent on pristine Gulf-front sands with thoughtfully appointed amenities. Within Winding Oaks, residents enjoy a recently refreshed community pool, walking paths, and a secure, gated setting. Optional golf, tennis and social memberships are available at the Longboat Key Club. Just minutes from dining and shopping on world-renowned St. Armands Circle and the cultural amenities of downtown Sarasota, this retreat makes it easy to step into the best of the area-while always having a peaceful place to return to. Simple, sophisticated, and distinctly Longboat Key....
Contact an agent
Home facts
- Year built:1988
- Listing ID #:A4686623
- Added:47 day(s) ago
- Updated:May 10, 2026 at 07:46 AM
Rooms and interior
- Bedrooms:3
- Total bathrooms:3
- Full bathrooms:3
- Flooring:Luxury Vinyl, Tile
- Dining Description:Eat In Kitchen, Living Room/Dining Room Combo
- Kitchen Description:Built-In Oven, Cooktop, Dishwasher, Eat-in Kitchen, Microwave, Refrigerator, Solid Surface Counters, Stone Counters, Wine Refrigerator
- Bedroom Description:High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Walk-In Closet(s)
- Living area:2,555 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central, Electric, Natural Gas
- Central air:Yes
Structure and exterior
- Roof:Tile
- Year built:1988
- Building area:2,555 sq. ft.
- Architectural Style:Coastal
- Construction Materials:Hardi Plank Type
- Exterior Features:Awning(s), Covered Porch/Patio, Deck, Front Porch, Lighting, Patio, Rear Porch, Screened
- Foundation Description:Slab
- Levels:1 Story
Schools
- Elementary school:Southside Elementary
Utilities
- Water:Public, Water Connected
- Sewer:Public Sewer, Sewer Connected
Finances and disclosures
- Price:$1,150,000
- Price per sq. ft.:$351.68
- Tax amount:$13,850 (2025)
Features and amenities
- Appliances:Built-in Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Irrigation Equipment, Microwave, Refrigerator, Washer, Wine Refrigerator
- Laundry features:Dryer, Inside, Laundry Room, Washer
- Amenities:Built-In Features, Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Irrigation Equipment, Living Room/Dining Room Combo, Maintenance, Natural Gas Available, Open Floorplan, Pool, Primary Bedroom Main Floor, Solid Surface Counters, Spa/Hot Tub, Split Bedroom, Stone Counters, Tennis Court(s), Thermostat, Underground Utilities, Walk-In Closet(s), Window Treatments
- Pool features:Gunite, Heated, In Ground, Pool, Private Pool
Parking
- Parking description:Attached Garage, Deeded, Driveway, Garage Door Opener
- Garage:Yes
- Garage spaces:2
New listings near 3427 Winding Oaks Drive #14
- New
$5,600,000Active0.71 Acres6441 Gulfside Road, LONGBOAT KEY, FL 34228
MLS# A4692771Listed by: DEVELOPERS REALTY LBK, INC - New
$2,250,000Active3 beds 3 baths2,192 sq. ft.581 Yardarm Lane, LONGBOAT KEY, FL 34228
MLS# A4689437Listed by: COLDWELL BANKER REALTY - New
$3,850,000Active3 beds 3 baths2,650 sq. ft.1241 Gulf Of Mexico Drive #506, LONGBOAT KEY, FL 34228
MLS# A4689658Listed by: LPT REALTY, LLC - New
$1,899,000Active4 beds 3 baths3,009 sq. ft.3040 Gulf Of Mexico Drive #3, LONGBOAT KEY, FL 34228
MLS# A4692587Listed by: PREMIER SOTHEBY'S INTERNATIONAL REALTY - New
$670,000Active2 beds 2 baths1,260 sq. ft.843 Bayport Way #843, LONGBOAT KEY, FL 34228
MLS# TB8505224Listed by: HOME SOLD REALTY LLC - New
$599,000Active2 beds 2 baths1,192 sq. ft.1930 Harbourside Drive #122, LONGBOAT KEY, FL 34228
MLS# A4692494Listed by: COLDWELL BANKER REALTY - New
$2,900,000Active3 beds 4 baths3,045 sq. ft.524 Hornblower Lane, LONGBOAT KEY, FL 34228
MLS# A4692210Listed by: DOUGLAS ELLIMAN
$830,000Pending3 beds 2 baths1,704 sq. ft.541 De Narvaez Drive, LONGBOAT KEY, FL 34228
MLS# A4691592Listed by: MICHAEL SAUNDERS & COMPANY- New
$425,000Active1 beds 1 baths936 sq. ft.6700 Gulf Of Mexico Drive #143, LONGBOAT KEY, FL 34228
MLS# A4692139Listed by: DALTON WADE INC - New
$675,000Active2 beds 2 baths1,362 sq. ft.3330 Gulf Of Mexico Drive #107D, LONGBOAT KEY, FL 34228
MLS# A4692214Listed by: CENTURY 21 BEGGINS ENTERPRISES