Single Family Residence at 9725 CHESTNUT RIDGE DR, WINDERMERE
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Photo Virtually staged - 9725 CHESTNUT RIDGE DR, WINDERMERE
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Virtually Staged - 9725 CHESTNUT RIDGE DR, WINDERMERE
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Virtually Staged - 9725 CHESTNUT RIDGE DR, WINDERMERE
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Virtually Staged - 9725 CHESTNUT RIDGE DR, WINDERMERE
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Virtually Staged - 9725 CHESTNUT RIDGE DR, WINDERMERE
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Virtually Staged - 9725 CHESTNUT RIDGE DR, WINDERMERE
Primary Bathroom/ First Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
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Primary Bathroom/ First Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Primary bedroom closet - 9725 CHESTNUT RIDGE DR, WINDERMERE
Primary bedroom / First Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Primary Bedroom closet - 9725 CHESTNUT RIDGE DR, WINDERMERE
Primary Bedroom / First Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
Bedroom 2 / suite/ 1st Floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
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Office - 9725 CHESTNUT RIDGE DR, WINDERMERE
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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
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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
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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
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Bedroom 6 /second floor - 9725 CHESTNUT RIDGE DR, WINDERMERE
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Bedroom 7 /second floor / Flex room - 9725 CHESTNUT RIDGE DR, WINDERMERE
Photo Virtually staged - 9725 CHESTNUT RIDGE DR, WINDERMERE
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Photo virtually staged - 9725 CHESTNUT RIDGE DR, WINDERMERE
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81 photos

$29,000

9725 CHESTNUT RIDGE DR
WINDERMERE, FL 34786
Listed by Dianna Desboyaux · DOUGLAS ELLIMAN
Bedrooms
7
Bathrooms
6
Living area
8,000 sqft
Year built
1999

About this home

A rare opportunity to lease a beautifully renovated residence within Isleworth, offering exceptional space, privacy, comfort, and an elevated Central Florida lifestyle. Newly renovated and exceptionally private, this sophisticated Isleworth residence offers approximately 8,000 square feet of beautifully designed living space, combining refined luxury with the comfort and functionality of an exceptional home. Rich walnut cabinetry and custom wood detailing bring warmth and character throughout, while elegant living spaces, a fireplace, and wine cellar create an inviting setting for both everyday living and entertaining. At the heart of the home, the impressive chef’s kitchen features Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, steam oven, dual dishwashers, and a discreet hidden pantry. Two separate laundry areas add convenience for a residence of this scale. The flexible floor plan includes six bedrooms, a dedicated office, and a bonus room with a closet that may serve as an additional bedroom, guest suite, fitness room, or private retreat. Five full and two half baths are beautifully finished with a calm, contemporary aesthetic, while an elevator provides effortless access between levels. Outdoors, complete privacy and peaceful pond views create a wonderful sense of retreat. A gas-heated pool and spa, expansive outdoor living areas, and summer kitchen provide an ideal setting for relaxing, dining, and entertaining year-round. The residence also features four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors. Some photos have been virtually staged. Private showings are easily accommodated, including same-day requests.

Highlights

WaterfrontPrivate poolFireplace

Property details

MLS #
MFRO6436860
Property type
Single Family Residence
Subdivision
ISLEWORTH
Status
Active
Days on market
22
On market date
August 26, 2026
Stories
N/A
Total bathrooms
6
Garage spaces
3
Parking spaces
N/A
Lot size
0.56 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

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

Walkability

Blended score for WINDERMERE's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

64
Walkable
out of 100
EPA National Walkability Index
10.0 / 20 -- Below average walkable
Google Places amenity density
85 / 100
Restaurants & cafes19
Grocery stores3
Parks5
Schools9
Transit stops0
Pharmacies5

Mortgage calculator

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

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Adjust tax / insurance estimates
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$
/mo
Est. monthly payment
$325/mo
$5,800 down
$23,200 loan
Principal & interest$150
Property tax (est.)$24
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 22 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.