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5138 FAIRWAY OAKS DR WINDERMERE FL 34786

$5,500,000
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5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786 - MLS#MFRO6401757 5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786 - MLS#MFRO6401757 5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786 - MLS#MFRO6401757 5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786 - MLS#MFRO6401757

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 5138 Fairway Oaks Dr

4 Bedrooms
5 Bathrooms
3 Car Garage
5,911 Square Feet
4,330SF Living Area
Pool:
Yes
Water: None
Year Built 1994
Listed For 10 Days

Don't miss this home for sale in Isleworth! Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth golf & country club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.the outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of lake brenda - also known as hourglass pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the butler chain of lakes, with access to world-class golf, dining, and amenities, all just moments from central florida’s premier shopping, dining, and entertainment destinations.

This luxury single family home was built in 1994 and features 4 bedrooms, and 5 full bathrooms. This home for sale is 5,911 square feet, with 4,330 sq ft being air conditioned living space. The home has a 3 car garage and has a private swimming pool.

Directions to this property are as follows: From Apopka Vineland Road To West On Conroy Windermere To Left Into Isleworth (isleworth Country Club Drive) To Right On Fairway Oaks.

Please contact your ZFC agent for more information about MLS# MFRO6401757 or any other homes for sale in Windermere or elsewhere in the Orange County area.

Features & Amenities

Appliances

Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator

Architecture

Traditional

Cooling

Central Air, Zoned

Heating

Electric, Natural Gas

Flooring

Tile

Parking

Circular Driveway, Garage Door Opener, Garage Faces Side

Lot Size

21939

View

Golf Course, Water view

Construction Materials

Block, Stucco

Security Features

Gated Community, Security Gate

Interior Features

Built-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s)

Furnished

Furnished

Exterior Features

French Doors, Lighting, Rain Gutters

Lot Features

Landscaped, On Golf Course, Oversized Lot

Patio And Porch Features

Covered, Rear Porch

Pool Features

Deck, Heated, In Ground

Roof

Tile

Utilities

Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Water Connected

Water Body Name

L A K E B R E N D A A K A H O U R G L A S S P O N D

Laundry

Corridor Access, Inside, Laundry Room

Fencing

Other

Fireplace

Family Room

Spa Features

Heated, In Ground

Zoning

P-D

Year Built

1994

Pets Allowed

Breed Restrictions

Annual Real Estate Taxes

$19,599 (2025)

Legal Description

Isleworth 16/118 Lot 108

Property Type

Single Family Home

HOA Fees

$3,672 /Quarterly

Association Fee Includes

Guard -24 Hour, Cable T V, Escrow Reserves Fund, Internet, Maintenance Grounds, Private Road, Security

Association Amenities

Cable T V, Gated, Playground, Security

Community Features

Buyer Approval Required, Community Mailbox, Gated Community -Guard, Golf Carts O K, Playground, Street Lights

Direction Faces

Northeast

MLS Number

MFRO6401757

Universal Property Id

U S-12095-N-162328389901080-R-N

Days On Market

10

Community Name

Isleworth

Property Manager

Dan O’ Connell 407-909-2071

5138 Fairway Oaks Dr Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 5138 Fairway Oaks Dr 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 home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $19,599 but will likely change when this home sells. These estimations are calculated from a list price of $5,500,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 5138 Fairway Oaks Dr

Address Sale Price Bed Bth Size Location Sale Date
No comps found for this property

MLS# MFRO6401757 Listing History

04/23/2026 Listed for sale by ISLEWORTH REALTY LLC with MLS# MFRO6401757 with a list price of $5,500,000.

Orange County Schools

Elementary School

High School

This listing of 5138 Fairway Oaks Dr Windermere FL 34786 was last updated on 2026-05-05 15:12:10. Listing courtesy of ISLEWORTH REALTY LLC.
MLS

Map of 5138 Fairway Oaks Dr Windermere FL 34786

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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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