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3435 WINDING OAKS DRIVE LONGBOAT KEY FL 34228

$1,150,000
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3435 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4680403 3435 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4680403 3435 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4680403 3435 WINDING OAKS DRIVE, LONGBOAT KEY, FL 34228 - MLS#MFRA4680403

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 3435 Winding Oaks Dr #18

2 Bedrooms
2/1 Bathrooms
2 Car Garage
3,270 Square Feet
2,555SF Living Area
Pool:
No
Water: None
Year Built 1988
Listed For 5 Days

Don't miss this condo for sale in Bay Isles! Own your own slice of tropical paradise on longboat key with this beautiful two bedroom two and on half bath villa in the exclusive winding oaks community located behind the gates of Bay Isles association. Sweeping views of the longboat key club harbourside golf course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. meticulously maintained, impact windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles beach club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. conveniently located mid key, one mile from publix and cvs and a short drive to the restaurants and shops of st armandÂ’s and downtown sarasota.

This luxury condo was built in 1988 and features 2 bedrooms, and 2 full bathrooms plus 1 half bath. 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 does not have a private swimming pool.

Directions to this property are as follows: Gulf Of Mexico Dr To Bay Isle Parkway. Check In At Guard Gate And Receive Pass. Left On Harbourside Drive Stay In Left Lane Use Pass To Continue Through Manual Gate. Take Right On Winding Oaks Drive Villa Is 9th On The Right Hand Side.

Please contact your ZFC agent for more information about MLS# MFRA4680403 or any other condos for sale in Longboat Key or elsewhere in the Sarasota County area.

Features & Amenities

Appliances

Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer

Other Equipment

Private Entrance, Private Yard

Cooling

Central Air, Humidity Control

Heating

Central, Electric

Flooring

Carpet, Tile, Vinyl, Wood

Parking

Garage Door Opener

Lot Size

602945

View

Golf Course, Water view

Construction Materials

Hardi Plank Type

Security Features

Gated Community, Security Gate, Security System, Security System Leased, Smoke Detector(s)

Interior Features

Ceiling Fans(s), Eat-in Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Tray Ceiling(s)

Furnished

Furnished

Exterior Features

Awning(s), Courtyard, Garden, Lighting, Private Entrance, Private Yard, Sliding Doors

Patio And Porch Features

Patio, Rear Porch, Screened

Roof

Tile

Window Features

Blinds, Window Treatments

Utilities

B B/H S Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected

Laundry

Inside, Laundry Room

Fencing

Masonry

Fireplace

Living Room

Zoning

M U C1

Year Built

1988

Pets Allowed

Dogs O K, Size Limit, Yes

Annual Real Estate Taxes

$8,565 (2025)

Legal Description

Unit 18 Winding Oaks

Property Type

Condominium

Other Association Fee

$922 /Annually

Association Fee Includes

Guard -24 Hour, Cable T V, Common Area Taxes, Pool, Escrow Reserves Fund, Fidelity Bond, Maintenance Structure, Maintenance Grounds, Recreational Facilities, Trash

Association Amenities

Pool, Vehicle Restrictions

Community Features

Association Recreation -Owned, Buyer Approval Required, Deed Restrictions, Gated Community -Guard, Pool

Direction Faces

Southwest

MLS Number

MFRA4680403

Universal Property Id

U S-12115-N-0004121018-S-18

Days On Market

5

Community Name

Winding Oaks

Property Manager

Neil Fleet 941-383-3200

3435 Winding Oaks Dr Price Calculator

Get Mortgage Quote For This Condo

The payment calculator figures for 3435 Winding Oaks Dr #18 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 $8,565 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 3435 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
1928 HARBOURSIDE DR #1404 $Log in to view 2 2/0 3,385SF Fairway Bay 1 06/13/2025
3060 GRAND BAY BLVD #124 $Log in to view 2 2/1 3,148SF Grand Bay 1 03/18/2025
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
1922 HARBOURSIDE DR #1102 $Log in to view 2 2/1 2,606SF Fairway Bay 1 04/07/2025
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
1591 GULF OF MEXICO DR #617 $Log in to view 2 3/1 3,618SF St Regis 11/17/2025

MLS# MFRA4680403 Listing History

01/28/2026 Listed for sale by MICHAEL SAUNDERS & COMPANY with MLS# MFRA4680403 with a list price of $1,150,000.
This listing of 3435 Winding Oaks Dr Longboat Key FL 34228 was last updated on 2026-03-03 18:12:08. Listing courtesy of MICHAEL SAUNDERS & COMPANY.
MLS

Map of 3435 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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