3427 WINDING OAKS DRIVE 14, Longboat Key, FL 34228

• 3 beds |
• 3 baths |
• 2,555 sqft

Property Description

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.

Listing Status:

Pending

Date Added:

March 23, 2026

Data Last Updated:

May 13, 2026 at 5:21AM

Listing Office:

COLDWELL BANKER REALTY : 941-383-6411

Listing Agent:

Carolyn Donnelly, PA : 941-350-9900

MLS ID:

A4686623

Interior

• General: Built-in FeaturesCeiling Fans(s)Eat-in KitchenHigh CeilingsLiving Room/Dining Room ComboOpen FloorplanPrimary Bedroom Main FloorSolid Surface CountersSplit BedroomStone CountersThermostatWalk-In Closet(s)Window Treatments
• Rooms: Inside Utility
• Appliances: Built-In OvenCooktopDishwasherDryerElectric Water HeaterMicrowaveRefrigeratorWasherWine Refrigerator
• Laundry: InsideLaundry Room
• Flooring: Luxury VinylTile
• A/C: Central Air
• Heating: CentralElectricNatural Gas
• Fireplace: GasLiving RoomWood BurningFireplace

Exterior

• General: Awning(s)LightingSliding Doors
• Style: Coastal
• Other Structures: Front PorchDeckRear PorchScreenedPatioCovered
• Pool: GuniteHeatedIn Ground
• Parking: DeededDrivewayGarage Door Opener

Construction

• Roofing: Tile
• Windows: BlindsShadesWindow Treatments
• General: HardiPlank TypeOneSlab

Location

• Road/Access: Paved
• HOA Amenities: MaintenancePoolSpa/Hot TubTennis Court(s)Guard - 24 HourPoolEscrow Reserves FundInsuranceMaintenance StructureMaintenance GroundsManagementPest ControlPrivate RoadSecurity2040.05Quarterly
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: MUC1UNIT 14 WINDING OAKS0004121014
• View: Golf CourseWater

Utilities

• Utilities: Electricity ConnectedNatural Gas AvailableSewer ConnectedUnderground UtilitiesWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple