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3466 WINDING OAKS DRIVE LONGBOAT KEY FL 34228

$795,000
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3466 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4686581 3466 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4686581 3466 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4686581 3466 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4686581

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 3466 Winding Oaks Dr #35

2 Bedrooms
2 Bathrooms
2 Car Garage
2,568 Square Feet
2,039SF Living Area
Pool:
No
Water: None
Year Built 1988
Listed For 0 Days

Don't miss this condo for sale in Bay Isles! Located in one of the most sought-after villa communities on longboat key, this well-kept 2-bedroom, 2-bath home in winding oaks lives more like a single-family residence—without all the upkeep. Behind the gates of Bay Isles, it offers a great opportunity to enjoy a quiet, established neighborhood known for its natural beauty and relaxed feel. A paver driveway and walkway, surrounded by mature landscaping, lead you to the front door. Inside, high ceilings and warm wood floors immediately make the space feel open and inviting. The finishes are neutral and timeless, and the natural light really does the rest. Impact glass throughout adds both comfort and peace of mind. The main living area flows easily, with a striking corner of sliding glass doors that brings the outdoors in and opens to a spacious, screened, multi-level deck. It’s the kind of space you’ll actually use—whether that’s for entertaining, relaxing, or just enjoying the greenery around you. the kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. The breakfast bar connects seamlessly to the dining area and main living space, making it easy to stay connected. There’s also a separate family room that offers a more casual spot to unwind. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful water views. The bathroom is spacious, featuring dual vanities, a soaking tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding oaks is part of the Bay Isles harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities—including deeded beach access through the private Bay Isles beach club. It’s an easy, comfortable lifestyle in one of longboat key’s most desirable communities.

This lovely condo was built in 1988 and features 2 bedrooms, and 2 full bathrooms. This condo for sale is 2,568 square feet, with 2,039 sq ft being air conditioned living space. The condo2 assigned parking garage spots and does not have a private swimming pool.

Directions to this property are as follows: From St. Armands Circle - North To Gulf Of Mexico Dr, Turn Right At South Gate For Bay Isles (harbourside Dr), Turn Right To 2020 Harbourside Dr.

Please contact your ZFC agent for more information about MLS# MFRA4686581 or any other condos for sale in Longboat Key or elsewhere in the Sarasota County area.

Features & Amenities

Appliances

Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer

Other Equipment

Irrigation Equipment

Architecture

Other

Cooling

Central Air

Heating

Central, Electric

Flooring

Tile, Wood

Parking

Driveway, Garage Door Opener

Lot Size

602945

View

Water view

Construction Materials

Block, Stucco

Interior Features

Built-in Features, Ceiling Fans(s), Eat-in Kitchen, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Stone Counters, Thermostat, Window Treatments

Furnished

Negotiable

Exterior Features

Lighting, Sidewalk, Sliding Doors, Storage

Property Condition

Completed

Patio And Porch Features

Covered, Deck, Rear Porch

Pool Features

Heated, In Ground

Roof

Other

Utilities

Electricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected

Laundry

Laundry Room

Zoning

M U C1

Year Built

1988

Pets Allowed

Yes

Annual Real Estate Taxes

$4,919 (2025)

Legal Description

Unit 35 Winding Oaks

Property Type

Condominium

Other Association Fee

$1,379 /Annually

Association Fee Includes

Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Pest Control, Private Road, Sewer, Trash, Water

Association Amenities

Pool

Community Features

Deed Restrictions, Pool

Direction Faces

East

MLS Number

MFRA4686581

Universal Property Id

U S-12115-N-0004121035-S-35

Community Name

Winding Oaks

Property Manager

Fairway Bay Homeowners Association 941-383-2701

3466 Winding Oaks Dr Price Calculator

Get Mortgage Quote For This Condo

The payment calculator figures for 3466 Winding Oaks Dr #35 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 $4,919 but will likely change when this condo sells. These estimations are calculated from a list price of $795,000 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 3466 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
1591 GULF OF MEXICO DR #314 $Log in to view 2 2/1 3,127SF St Regis 03/13/2026
2013 HARBOUR LINKS DR #2013 $Log in to view 2 2/1 2,961SF Harbour Links 12/08/2025
2110 HARBOURSIDE DR #558 $Log in to view 2 2/1 2,874SF Fairway Bay 3 02/17/2026
340 GULF OF MEXICO DR #126 $Log in to view 2 2/1 2,674SF Tangerine Bay Club 03/02/2026
1904 HARBOURSIDE DR #202 $Log in to view 2 2/1 2,606SF Fairway Bay 1 02/27/2026
1928 HARBOURSIDE DR #1403 $Log in to view 2 2/1 2,606SF Fairway Bay 1 03/02/2026
360 GULF OF MEXICO DR #322 $Log in to view 2 2/1 2,584SF Tangerine Bay Club 03/06/2026
513 BAYPORT WAY #513 $Log in to view 2 2/0 2,504SF Bayport Beach And Tennis Club 02/18/2026
1211 GULF OF MEXICO DR #207 $Log in to view 2 2/0 2,036SF The Promenade 06/23/2025
1211 GULF OF MEXICO DR #108 $Log in to view 2 2/0 2,036SF The Promenade 04/30/2025
1211 GULF OF MEXICO DR #408 $Log in to view 2 2/0 2,017SF The Promenade 12/01/2025

MLS# MFRA4686581 Listing History

04/07/2026 Listed for sale by COLDWELL BANKER REALTY with MLS# MFRA4686581 with a list price of $795,000.
This listing of 3466 Winding Oaks Dr Longboat Key FL 34228 was last updated on 2026-04-07 10:12:10. Listing courtesy of COLDWELL BANKER REALTY.
MLS

Map of 3466 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

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