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About this home
9725 Chestnut Ridge Dr is a 1999-built home in Isleworth, Windermere. Inside you'll find 7 bedrooms, 7 bathrooms, and 8,000 square feet of living space. Listed at $5,975,000 (about $747/sqft), 285 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $3,129 quarterly.
Virtually Staged. 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. Some photos have been virtually staged. Private showings are easily accommodated, including same-day requests.
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The essentials
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Details
Districts can re-zone, so verify directly with the district before relying on these.
Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.
Price history
Neighborhood
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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA includes any condo dues reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.
Quick answers.
Price
$5,975,000
$747 per sq ft
Beds and baths
7 beds, 7 baths
Size
8,000 sq ft
Time on market
285 days
Year built
1999
Monthly payment
About $37,613/mo
That is 20% down on a 30-year fixed at 6.8%, plus the home's $29,046 annual tax bill, insurance, and the $3,129/qtr HOA fee.
HOA fee
$3,129/qtr
Managed by Dan O'Connell.
Flood zone
Zone X
That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.
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