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9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL - photo 1

$5,975,000

9725 CHESTNUT RIDGE DRIVE

WINDERMERE, FL 34786

Estimated payment $33,917/month

includes HOA $3,129/mo · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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7Beds
7Baths
8,000Sq Ft
$747Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

HOA $3,129/mo
Private Pool
Fireplace
Garage
Built in 1999
24,349 sqft Lot

About This Home

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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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:7
  • •Bathrooms:7 (5 full, 2 half)
  • •Full bathrooms:5
  • •Half bathrooms:2

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:8,000 sqft
  • •Total interior livable area:8,000 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:24,349 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1999

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Price history

DateEventPrice
2026-01-02T00:00:00.000ZListed for sale$5,975,000$747/sqft

Listing Agent

Dianna Desboyaux

DOUGLAS ELLIMAN

Brokerage Phone: 561-655-8600

Source: Stellar MLS · MLS #O6370294

Data Powered by Home Junction, Inc.

Nearby

Schools

CHAIN OF LAKES MIDDLE

High · 1.0 mi

OLYMPIA HIGH

High · 1.1 mi

CENTRAL FLORIDA POLYTECHNIC ACADEMY

Elementary · 1.5 mi

Supermarkets

Publix

0.7 mi

Walmart Neighborhood Market

0.9 mi

Walmart Grocery Pickup

1.0 mi

Dining

Pizza 14

0.7 mi

Healthy D'Lite

0.7 mi

Sakura Ramen Orlando

0.7 mi

Parks

Johnson Park

0.5 mi

Lake Street Park

0.7 mi

Central Park

0.8 mi

Beaches

Conrad Beach

5.8 mi

West Beach

5.9 mi

East Beach

5.9 mi

Nearby amenity locations include data © OpenStreetMap contributors.