Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 2 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 3 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 4 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 5 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 6 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 7 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 8 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 9 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 10 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 11 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 12 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 13 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 14 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 15 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 16 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 17 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 18 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 19 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 20 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 21 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 22 of 64
Primary bedroom / First Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Primary Bedroom / First Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Primary Bathroom/ First Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Primary Bathroom/ First Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Primary bedroom closet - 9725 CHESTNUT RIDGE DR, WINDERMERE
Primary Bedroom closet - 9725 CHESTNUT RIDGE DR, WINDERMERE
Bedroom 2 / suite/ 1st Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 30 of 64
Office - 9725 CHESTNUT RIDGE DR, WINDERMERE
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 32 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 33 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 34 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 35 of 64
Bedroom 3 / 2nd Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Bedroom 3 / Second Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Bedroom 3 / second floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 39 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 40 of 64
Bedroom 4 / Second Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Bedroom 4 / Second Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Bedroom 4 / Second Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 44 of 64
Bedroom 5 / Second Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Bedroom 5 / Second Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Bedroom 5 / Second Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 48 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 49 of 64
Bedroom 6 /second floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 51 of 64
Bedroom 7 /second floor / Flex room - 9725 CHESTNUT RIDGE DR, WINDERMERE
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 53 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 54 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 55 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 56 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 57 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 58 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 59 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 60 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 61 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 62 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 63 of 64
Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE, photo 64 of 64
64 photos

$5,975,000

9725 CHESTNUT RIDGE DR
WINDERMERE, FL 34786
Listed by Dianna Desboyaux
Bedrooms
7
Bathrooms
5.2
Living area
8,000 sqft
Year built
1999

About this home

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.

Highlights

WaterfrontPrivate poolFireplace

Property details

MLS #
MFRO6370294
Property type
Single Family Residence
Subdivision
ISLEWORTH
Status
Active
Days on market
236
On market date
January 2, 2026
Stories
N/A
Total bathrooms
7
Garage spaces
3
Parking spaces
N/A
Lot size
0.56 acres
Loading map…

Nearby schools

Within 10 miles · public school directory data (NCES)

ElementaryCharter
CENTRAL FLORIDA POLYTECHNIC ACADEMY
1.49 mi away · Grades 0-8
Nearest school -- attendance-zone data not available here
Not yet rated
Local Score not yet available for this school
Enrollment
0
District
ORANGE
Middle
CHAIN OF LAKES MIDDLE
1.01 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,108
Student:teacher ratio
20.1:1
District
ORANGE
High
OLYMPIA HIGH
1.05 mi away · Grades 8-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,878
Student:teacher ratio
24.8:1
District
ORANGE

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$36,132/mo
$1,195,000 down
$4,780,000 loan
Principal & interest$31,003
Property tax (est.)$4,979
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 3 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.