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    Active
    Single Family Residence

    5138 FAIRWAY OAKS DR

    WINDERMERE, FL, 34786·ISLEWORTH

    MLS# O6401757

    $4,999,500

    4

    Beds

    5

    Baths

    4,330

    Sq Ft

    Description

    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.

    Property Overview

    StatusActive
    TypeSingle Family Residence
    Year Built1994
    CityWINDERMERE
    Area34786 - WINDERMERE
    SubdivisionISLEWORTH
    StateFL
    CountyOrange
    List Date04/25/2026
    MLS#O6401757
    List Price$4,999,500

    Bedrooms & Bathrooms

    Bedrooms4
    Bathrooms5
    Full Bathrooms5
    Half Bathrooms0

    Structure

    StyleTraditional
    Garage Capacity3
    ParkingCircular Driveway, Garage Door Opener, Garage Faces Side
    Construction MaterialsBlock, Stucco
    RoofTile
    Foundation DetailsSlab
    FlooringTile
    Private PoolYes
    Patio & PorchCovered, Rear Porch

    Size & Lot

    Living Area4,330 sqft
    Lot Size21,939 sqft
    Acres0.50
    Lot DescriptionLandscaped, On Golf Course, Oversized Lot
    Water FrontNo

    Utilities

    HeatingElectric, Natural Gas
    CoolingCentral Air, Zoned
    WaterPublic
    SewerSeptic Tank

    Additional Features

    Interior FeaturesBuilt-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)
    Exterior FeaturesFrench Doors, Lighting, Rain Gutters
    AppliancesBar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator

    Contact Agent

    Holiday Realty LLC

    Central Florida Real Estate Experts

    (800) 936-1754

    Our team typically responds within 1 hour during business hours.

    Neighborhood

    About ISLEWORTH

    5138 FAIRWAY OAKS DR is located in the ISLEWORTH community in WINDERMERE, FL. Part of Orange County.

    The ISLEWORTH neighborhood offers convenient access to local schools, shopping, dining, parks, and major commute routes.

    HOA & Tax Information

    Annual Property Tax$19,599.37 (2025)

    HOA, Community & Pets

    HOA & Recurring Fees

    AssociationDan O’Connell
    HOA Fee$3,672 / quarterly
    Fee Includes
    Guard - 24 Hour
    Cable TV
    Escrow Reserves Fund
    Internet
    Maintenance Grounds
    Private Road
    Security
    Amenities
    Cable TV
    Gated
    Playground
    Security

    Community Features

    Buyer Approval Required
    Community Mailbox
    Gated Community - Guard
    Golf Carts OK
    Playground
    Street Lights
    Water Features
    Community Boat Ramp,Water Access

    Pet Policy

    Pets AllowedBreed Restrictions

    Pet policies are subject to HOA/condo association rules. Verify current restrictions before purchase.

    Ask About This Property

    Ask a question about this home and get quick, listing-based help from Holiday Realty.

    Answers are generated from listing data and may be incomplete — please verify details with a Holiday Realty agent.

    Listing courtesy of ISLEWORTH REALTY LLC · Monica Lochmandy

    Frequently Asked Questions

    What is the asking price for 5138 FAIRWAY OAKS DR?

    The listing price for 5138 FAIRWAY OAKS DR is $4,999,500.

    How many bedrooms and bathrooms does 5138 FAIRWAY OAKS DR have?

    This property features 4 bedrooms and 5 full bathrooms.

    What is the square footage of 5138 FAIRWAY OAKS DR?

    The living area is approximately 4,330 square feet.

    What community is 5138 FAIRWAY OAKS DR located in?

    This property is located in the ISLEWORTH community in WINDERMERE, FL. The neighborhood offers convenient access to local schools, shopping, dining, and parks.

    When was 5138 FAIRWAY OAKS DR built?

    This property was built in 1994.

    What schools are near 5138 FAIRWAY OAKS DR?

    WINDERMERE is served by the Orange County Public Schools district. Contact us for details on nearby elementary, middle, and high schools, including ratings and enrollment information.

    How do I schedule a showing for 5138 FAIRWAY OAKS DR?

    You can schedule a private showing by clicking "Schedule a Showing" on this page or calling us at (800) 936-1754.

    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 2026-08-14. All data is obtained from various sources and may not have been verified by broker or MLS GRID.

    IDX information is provided exclusively for consumers' personal noncommercial use.

    © 2026 Stellar MLS. All rights reserved.