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    Active
    Single Family Residence

    9725 CHESTNUT RIDGE DRIVE

    WINDERMERE, FL, 34786·ISLEWORTH

    MLS# O6370294

    $5,975,000

    7

    Beds

    5

    5 Full · 2 Half

    8,000

    Sq Ft

    Description

    Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed. The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes. Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility. Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings. Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance. It is a residence restored with intention, where discretion, craftsmanship, and comfort converge. Private showings are easily accommodated, including same-day requests. Some photos (4 rooms on the second floor) have been virtually staged.

    Property Overview

    StatusActive
    TypeSingle Family Residence
    Year Built1999
    CityWINDERMERE
    Area34786 - WINDERMERE
    SubdivisionISLEWORTH
    StateFL
    CountyOrange
    List Date01/02/2026
    MLS#O6370294
    List Price$5,975,000

    Bedrooms & Bathrooms

    Bedrooms7
    Bathrooms6
    Full Bathrooms5
    Half Bathrooms2

    Structure

    Garage Capacity3
    ParkingDriveway, Garage Faces Side
    Construction MaterialsBlock, Stucco
    RoofTile
    Foundation DetailsSlab
    FlooringTile, Travertine, Wood
    Private PoolYes
    Patio & PorchCovered, Enclosed, Rear Porch, Screened

    Size & Lot

    Living Area8,000 sqft
    Lot Size24,349 sqft
    Acres0.56
    Lot DescriptionLandscaped, Near Golf Course, Paved
    Water FrontYes

    Utilities

    HeatingCentral
    CoolingCentral Air, Zoned
    WaterPublic
    SewerSeptic Tank

    Additional Features

    Interior FeaturesBuilt-in Features, Ceiling Fans(s), Elevator, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar
    Exterior FeaturesFire Pit, French Doors, Outdoor Kitchen
    AppliancesBar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, 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

    9725 CHESTNUT RIDGE 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$29,046.23 (2024)

    HOA, Community & Pets

    HOA & Recurring Fees

    AssociationDan O'Connell
    HOA Fee$3,129 / quarterly
    Fee Includes
    Guard - 24 Hour
    Pool
    Maintenance Grounds
    Management
    Security
    Amenities
    Clubhouse
    Elevators
    Fitness Center
    Gated
    Golf Course
    Maintenance
    Park
    Pickleball Court(s)
    Playground
    Pool
    Racquetball
    Recreation Facilities
    Sauna
    Security
    Spa/Hot Tub
    Storage
    Tennis Court(s)

    Community Features

    Buyer Approval Required
    Clubhouse
    Fitness Center
    Gated Community - Guard
    Golf Carts OK
    Golf
    No Truck/RV/Motorcycle Parking
    Playground
    Pool
    Racquetball
    Restaurant
    Tennis Court(s)
    Water Features
    Private Boat Ramp,Water Access,Waterfront

    Pet Policy

    Pets AllowedYes

    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 DOUGLAS ELLIMAN · Dianna Desboyaux

    Frequently Asked Questions

    What is the asking price for 9725 CHESTNUT RIDGE DRIVE?

    The listing price for 9725 CHESTNUT RIDGE DRIVE is $5,975,000.

    How many bedrooms and bathrooms does 9725 CHESTNUT RIDGE DRIVE have?

    This property features 7 bedrooms and 5 full bathrooms plus 2 half bath(s).

    What is the square footage of 9725 CHESTNUT RIDGE DRIVE?

    The living area is approximately 8,000 square feet.

    What community is 9725 CHESTNUT RIDGE 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 9725 CHESTNUT RIDGE DRIVE built?

    This property was built in 1999.

    What schools are near 9725 CHESTNUT RIDGE 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 9725 CHESTNUT RIDGE 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 2026-08-22. 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.