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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
Bedrooms & Bathrooms
Structure
Size & Lot
Utilities
Additional Features
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
HOA, Community & Pets
HOA & Recurring Fees
Community Features
Pet Policy
Pet policies are subject to HOA/condo association rules. Verify current restrictions before purchase.
Ask About This Property
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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.
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