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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.
| DAYS ON MARKET | 52 | LAST UPDATED | 4/16/2026 |
|---|---|---|---|
| TRACT | WINDING OAKS | YEAR BUILT | 1988 |
| COMMUNITY | 34228 - Longboat Key | GARAGE SPACES | 2.0 |
| COUNTY | Sarasota | STATUS | Pending |
| PROPERTY TYPE(S) | Condo/Townhouse/Co-Op |
| Elementary School | Southside Elementary |
|---|
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| AMENITIES | Insurance, Maintenance Grounds, Maintenance Structure, Pest Control, Security |
| APPLIANCES | Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Wine Refrigerator |
| AREA | 34228 - Longboat Key |
| CONSTRUCTION | HardiPlank Type |
| EXTERIOR | Awning(s), Lighting |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Central, Electric, Natural Gas |
| INTERIOR | Built-in Features, Eat-in Kitchen, High Ceilings, Open Floorplan, Stone Counters, Walk-In Closet(s) |
| LOT DESCRIPTION | Waterfront |
| PARKING | Deeded, Driveway, Garage Door Opener, Attached |
| POOL | Yes |
| POOL DESCRIPTION | Gunite, Heated, In Ground, Private |
| SEWER | Public Sewer |
| STORIES | 1 |
| STYLE | Coastal |
| SUBDIVISION | WINDING OAKS |
| TAXES | 13849.79 |
| UTILITIES | Electricity Connected, Natural Gas Available, Sewer Connected, Underground Utilities, Water Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Lake, Pond, Water, Golf Course |
| WATER | Public |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | Lake Privileges, Lake Front, Pond |
MORTGAGE CALCULATOR
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Listing provided by Carolyn Donnelly, PA, COLDWELL BANKER REALTY, 941-383-6411
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 5/14/26 5:14 AM PDT.
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