USAFLLongboat KeyWinding Oaks14-3427 Winding Oaks Dr

14-3427 Winding Oaks Dr, LONGBOAT KEY, FL

Condo

For Sale

Listed price in listed location currency (USD).

$1,150,000

332

MLS® A4686623

Key Facts
Description
Rooms
Map

Key Facts

Type Condominium

Levels Residential

Size 2555 sqft

Garage Yes

Maintenance Fees

Taxes $13,850

Days Active 3

Approx. Age 1988

Avg. Price Per Sqft $450

MLS® Number A4686623

Property Address: 14-3427 Winding Oaks Dr, LONGBOAT KEY, FL, 34228-4129

Average square foot calculated using Size range provided by listing agent.

Description

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.

MLS® NumberA4686623

Locker

Ensuite LaundryNo

Balcony

Furnished

Laundry LevelInside, Laundry Room

Exposure

Exterior

GarageYes

Approx. Age1988

Stories1

Pets

Included in Maintenance Fee

Heat

Hydro

Water

Building Insurance

Condo Taxes

Cable TV

Central Air

Parking Maintenance

Utilities

Heat

A/C

Heating Fuel

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

Mar 23, 2026List Date

$1,150,000List Price

Jan 29, 2025End Date

$1,195,000Sold Price

Sold

Dec 30, 2024List Date

$1,195,000List Price

Home Estimate Zoopraisal®

This property is estimated to sell between: $1,150,000 and $2,053,000.

Similar properties in this area sold on average for: $1,751,875

Expected to sell in 20 days. Similar properties sold in 23 days. This home has been on Zoocasa for 3 days.

The estimated sale price does not take into account many variables such as recent renovations, type of appliances, school district etc. To get a more accurate estimate please contact agent.

Commute

Commute

Starting Address

Destination Address

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