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9743 CHESTNUT RIDGE DRIVE WINDERMERE FL 34786

$3,250,000
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Under Contract
9743 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786 - MLS#MFRO6314871 9743 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786 - MLS#MFRO6314871 9743 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786 - MLS#MFRO6314871 9743 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786 - MLS#MFRO6314871

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 9743 Chestnut Ridge Dr

5 Bedrooms
6/1 Bathrooms
4 Car Garage
7,162 Square Feet
6,328SF Living Area
Pool:
Yes
Water: None
Year Built 1987
Listed For 6 Days

Don't miss this home for sale in Isleworth! Nestled at the end of a quiet cul-de-sac on 1.15 acres within the renowned Isleworth golf & country club, this exceptional residence offers refined luxury, thoughtful design, and exceptional grounds designed for outdoor enjoyment all year round. Featuring five bedrooms, six full bathrooms, and a powder room, the home spans more than 6,300 square feet, with lovely architectural style and beautifully appointed interiors. The stunning great room is a true centerpiece, featuring soaring cathedral ceilings, exposed wood beams, and abundant natural light. Formal living and dining rooms provide ideal spaces for entertaining, while the chef’s kitchen boasts granite countertops, white cabinetry, and high-end bosch and sub-zero appliances. The primary suite is a serene retreat, featuring a luxurious en-suite bath and direct access to the pergola and pool for seamless indoor-outdoor living. Upstairs, a versatile bonus room offers flexible space for a yoga studio, home gym, game room or creative retreat, complemented by a stylish loft office perfect for work-from-home needs. Step outside to discover the expansive backyard complete with modern pool is surrounded by low-maintenance artificial turf, expansive lanai spaces for alfresco dining, and multiple seating areas ideal for gatherings or quiet relaxation—all framed by a vast, fenced yard. This extraordinary home offers both comfort and sophistication in a community renowned for its golf, amenities, and lifestyle. A rare opportunity to live luxuriously in a premier setting.

This luxury single family home was built in 1987 and features 5 bedrooms, and 6 full bathrooms plus 1 half bath. This home for sale is 7,162 square feet, with 6,328 sq ft being air conditioned living space. The home has a 4 car garage and has a private swimming pool.

Directions to this property are as follows: I-4 To Conroy Windermere Road West To Isleworth Subdivision. Stay Straight On Isleworth Country Club Drive.turn Right On Latrobe, Turn Right On Chestnut Ridge Drive. Estate Will Be On The Right.

Please contact your ZFC agent for more information about MLS# MFRO6314871 or any other homes for sale in Windermere or elsewhere in the Orange County area.

Features & Amenities

Appliances

Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Freezer, Microwave, Refrigerator, Washer, Wine Refrigerator

Other Equipment

Irrigation Equipment

Cooling

Central Air

Heating

Central, Electric

Flooring

Tile, Wood

Parking

Garage Faces Side

Lot Size

49984

View

Pool view

Construction Materials

Concrete

Interior Features

Built-in Features, Ceiling Fans(s), High Ceilings, Primary Bedroom Main Floor, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar

Exterior Features

Awning(s), Lighting

Lot Features

Landscaped, Oversized Lot

Pool Features

In Ground

Roof

Tile

Window Features

E N E R G Y S T A R Qualified Windows, Window Treatments

Utilities

B B/H S Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected

Water Body Name

L A K E B U T L E R C H A I N O F L A K E S

Laundry

Inside, Laundry Room

Fireplace

Family Room, Primary Bedroom

Zoning

P-D

Year Built

1987

Pets Allowed

Breed Restrictions

Annual Real Estate Taxes

$22,676 (2024)

Legal Description

Isleworth 16/118 Lot 8

Property Type

Single Family Home

HOA Fees

$3,129 /Quarterly

Direction Faces

South

MLS Number

MFRO6314871

Universal Property Id

U S-12095-N-162328389900080-R-N

Days On Market

6

Community Name

Isleworth

Property Manager

Dan O’ Connell 407-909-2071

9743 Chestnut Ridge Dr Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 9743 Chestnut Ridge Dr should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2024 which are $22,676 but will likely change when this home sells. These estimations are calculated from a list price of $3,250,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 9743 Chestnut Ridge Dr

Address Sale Price Bed Bth Size Location Sale Date
6216 Roseate Spoonbill $Log in to view 6 5/ 5,734SF Windermere Landing 01/15/2025

MLS# MFRO6314871 Listing History

05/21/2025 Listed for sale by ISLEWORTH REALTY LLC with MLS# MFRO6314871 with a list price of $3,250,000.

Orange County Schools

Elementary School

High School

This listing of 9743 Chestnut Ridge Dr Windermere FL 34786 was last updated on 2025-09-02 08:12:04. Listing courtesy of ISLEWORTH REALTY LLC.
MLS

Map of 9743 Chestnut Ridge Dr Windermere FL 34786

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Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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