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3427 WINDING OAKS DRIVE LONGBOAT KEY FL 34228

$1,150,000
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3427 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4686623 3427 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4686623 3427 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4686623 3427 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4686623

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 3427 Winding Oaks Dr #14

3 Bedrooms
3 Bathrooms
2 Car Garage
3,270 Square Feet
2,555SF Living Area
Pool:
Yes
Water
Year Built 1988
Listed For 0 Days

Don't miss this condo for sale in Bay Isles! 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. Both the living room and lanai feature brand new furnishings. 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.

This luxury condo was built in 1988 and features 3 bedrooms, and 3 full bathrooms. This condo for sale is 3,270 square feet, with 2,555 sq ft being air conditioned living space. The condo2 assigned parking garage spots and has a private swimming pool.

Directions to this property are as follows: North On Gulf Of Mexico Drive To The Light At Bay Isles Parkway. Turn Right Into Bay Isles, Go To Gatehouse, Continue On Harbourside Drive To Winding Oaks On Right.

Please contact your ZFC agent for more information about MLS# MFRA4686623 or any other condos for sale in Longboat Key or elsewhere in the Sarasota County area.

Features & Amenities

Appliances

Built-In Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Wine Refrigerator

Other Equipment

Irrigation Equipment

Architecture

Coastal

Cooling

Central Air

Heating

Central, Electric

Flooring

Luxury Vinyl, Tile

Parking

Deeded, Driveway, Garage Door Opener

View

Golf Course, Water view

Construction Materials

Hardi Plank Type

Security Features

Gated Community

Interior Features

Built-in Features, Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments

Furnished

Turnkey

Exterior Features

Awning(s), Lighting, Sliding Doors

Property Condition

Completed

Patio And Porch Features

Covered, Deck, Front Porch, Patio, Rear Porch, Screened

Pool Features

Gunite, Heated, In Ground

Roof

Tile

Window Features

Blinds, Shades, Window Treatments

Utilities

Electricity Connected, Sewer Connected, Underground Utilities, Water Connected

Waterfront Features

Lake Front, Pond

Laundry

Inside, Laundry Room

Fireplace

Gas, Living Room, Wood Burning

Zoning

M U C1

Year Built

1988

Pets Allowed

Cats O K, Dogs O K, Number Limit, Yes

Annual Real Estate Taxes

$13,850 (2025)

Legal Description

Unit 14 Winding Oaks

Property Type

Condominium

Other Association Fee

$2,040 /Annually

Association Fee Includes

Guard -24 Hour, Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Management, Pest Control, Private Road, Security

Association Amenities

Maintenance, Pool, Spa/Hot Tub, Tennis Court(s)

Community Features

Buyer Approval Required, Deed Restrictions, Gated Community -Guard, Golf, Pool, Sidewalks

Direction Faces

West

MLS Number

MFRA4686623

Universal Property Id

U S-12115-N-0004121014-S-14

Community Name

Winding Oaks

Property Manager

Winding Oaks/Neil Fleet 941-383-3200

3427 Winding Oaks Dr Price Calculator

Get Mortgage Quote For This Condo

The payment calculator figures for 3427 Winding Oaks Dr #14 should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this condo for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $13,850 but will likely change when this condo sells. These estimations are calculated from a list price of $1,150,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the condo characteristics and location.

Recent Condo Sales near 3427 Winding Oaks Dr

Address Sale Price Bed Bth Size Location Sale Date
3460 WINDING OAKS DR #38 $Log in to view 3 3/1 3,323SF Winding Oaks 04/30/2025
2161 GULF OF MEXICO DR #6 $Log in to view 3 3/0 4,024SF En Provence 11/14/2025
545 SANCTUARY DR #B-504 $Log in to view 3 3/1 3,940SF Longboat Key Club 03/31/2025
415 L AMBIANCE DR #C404 $Log in to view 3 3/1 3,770SF Longboat Key Club 05/27/2025
415 L AMBIANCE DR #C403 $Log in to view 3 3/1 3,770SF Longboat Key Club 02/03/2026
415 L AMBIANCE DR #C204 $Log in to view 3 3/1 3,770SF Longboat Key Club 03/16/2026
655 LONGBOAT CLUB RD #16B $Log in to view 3 3/1 3,683SF Longboat Key Club 01/06/2026
3040 GRAND BAY BLVD #216 $Log in to view 3 3/1 3,583SF Grand Bay 2 10/21/2025
1511 GULF OF MEXICO DR #302 $Log in to view 3 3/0 3,534SF Tencon Beach 02/03/2026
3030 GRAND BAY BLVD #381 $Log in to view 3 3/1 3,454SF Grand Bay 3 11/12/2025
435 L AMBIANCE DR #K506 $Log in to view 3 3/1 3,440SF Longboat Key Club 01/07/2026
3030 GRAND BAY BLVD #324 $Log in to view 3 3/0 3,314SF Grand Bay 12/31/2025

MLS# MFRA4686623 Listing History

03/23/2026 Listed for sale by COLDWELL BANKER REALTY with MLS# MFRA4686623 with a list price of $1,150,000.
This listing of 3427 Winding Oaks Dr Longboat Key FL 34228 was last updated on 2026-03-23 15:12:15. Listing courtesy of COLDWELL BANKER REALTY.
MLS

Map of 3427 Winding Oaks Dr Longboat Key FL 34228

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Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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