3427 WINDING OAKS DRIVE UNIT 14

For sale Days on market 36

$1,150,000

$450/sq ft

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Overview

Bedroom

Bath

Year Built

1988

Garage

Sqft

2555

Property Type

Condominium

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.

Property Details

MLS#

A4686623

Garage

Total Floor in Bldg

Address

3427 WINDING OAKS

City

LONGBOAT KEY

State/county

Zip/Postal Code

34228

Area

Winding Oaks

Country

United States

HOA

Yes

Assoc Fee

$--

Assoc Fee Pd

Quarterly

Tax Amount

$13,849

Maint Fee

$--

Tax Year

2025

Built-In Oven

Cooktop

Dishwasher

Dryer

Electric Water Heater

Microwave

Refrigerator

Washer

Wine Refrigerator

Golf Course

Water

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