5237 ISLEWORTH COUNTRY CLUB DRIVE
    5237 ISLEWORTH COUNTRY CLUB DRIVE photo 2
    Active
    Single Family Residence

    5237 ISLEWORTH COUNTRY CLUB DRIVE

    WINDERMERE, FL, 34786·ISLEWORTH

    MLS# O6427447

    $3,600,000

    5

    Beds

    5

    Baths

    5,972

    Sq Ft

    Description

    Under contract-accepting backup offers. Located along the 2nd tee of Isleworth's renowned championship golf course, this beautiful golf-front estate offers an exceptional location within the gates. The five-bedroom home features offers a spacious and open floor plan of more than 5,900 square feet overlooking the serene golf and water vistas. .

    Property Overview

    StatusActive Under Contract
    TypeSingle Family Residence
    Year Built1989
    CityWINDERMERE
    Area34786 - WINDERMERE
    SubdivisionISLEWORTH
    StateFL
    CountyOrange
    List Date07/30/2026
    MLS#O6427447
    List Price$3,600,000

    Bedrooms & Bathrooms

    Bedrooms5
    Bathrooms5
    Full Bathrooms5
    Half Bathrooms0

    Structure

    Garage Capacity3
    Construction MaterialsBlock, Stucco
    RoofTile
    Foundation DetailsBlock, Slab
    FlooringCarpet, Marble, Wood
    Private PoolYes

    Size & Lot

    Living Area5,972 sqft
    Lot Size22,076 sqft
    Acres0.51
    Water FrontNo

    Utilities

    HeatingCentral, Zoned
    CoolingCentral Air, Zoned
    WaterWell
    SewerSeptic Tank

    Additional Features

    Interior FeaturesBuilt-in Features, Primary Bedroom Main Floor, Walk-In Closet(s)
    AppliancesBuilt-In Oven, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer

    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

    5237 ISLEWORTH COUNTRY CLUB DRIVE 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$45,808.14 (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
    Private Road
    Security
    Amenities
    Cable TV
    Gated
    Playground

    Community Features

    Community Mailbox
    Deed Restrictions
    Gated Community - Guard
    Golf
    Playground
    Water Features
    Lake,Private Boat Ramp,Water Access,Waterfront

    Pet Policy

    Pets AllowedBreed Restrictions, Yes
    Number Allowed2

    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 5237 ISLEWORTH COUNTRY CLUB DRIVE?

    The listing price for 5237 ISLEWORTH COUNTRY CLUB DRIVE is $3,600,000.

    How many bedrooms and bathrooms does 5237 ISLEWORTH COUNTRY CLUB DRIVE have?

    This property features 5 bedrooms and 5 full bathrooms.

    What is the square footage of 5237 ISLEWORTH COUNTRY CLUB DRIVE?

    The living area is approximately 5,972 square feet.

    What community is 5237 ISLEWORTH COUNTRY CLUB DRIVE 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 5237 ISLEWORTH COUNTRY CLUB DRIVE built?

    This property was built in 1989.

    What schools are near 5237 ISLEWORTH COUNTRY CLUB DRIVE?

    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 5237 ISLEWORTH COUNTRY CLUB DRIVE?

    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 2026-07-30. 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.