by Global Lifestyle Properties

See Home Value
Lake Butler 34786 Isleworth
9743 CHESTNUT RIDGE DRIVE
$3,250,000
● House - Off Market

9743 CHESTNUT RIDGE DRIVE

WINDERMERE, FL 34786
bedrooms
5 Beds
bathrooms
6 Baths, 1 Half Bath
square feet
6,328 Ft²
$20,977
Est. Monthly
$3,129
HOA / Fees
-0.38%
Cap Rate

About This Property

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.
Unit Size
6,328 Ft²
Days on Market
114 days
Land Size
1.15 acres
Price per sqft
$514
Property Type
House
Property Taxes
$1,890
HOA Dues
$3,129
Year Built
1987

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Last updated: 2 years ago (Stellar MLS #O6314871)

Price History

Date / Event Date Event Price
Sep 26, 2025 Sold
Sold
Jun 11, 2025 In contract -
In contract
May 21, 2025 Listed by ISLEWORTH REALTY LLC $3,250,000
Listed by ISLEWORTH REALTY LLC
Jun 15, 2004 Sold
Sold
Jul 18, 2001 Sold
Sold

Property Highlights

Garage
Air Conditioning
Fireplace

Building Info

Overview

    General

  • Year Built: 1987
  • Effective Year Built: 2000
  • Building Count: 1
  • Bedroom Count: 5
  • Bathroom Count: 6
  • Full Bathrooms: 6
  • Partial Bathrooms: 6
  • Building Condition: 3
  • Building Quality: 9
  • Construction Type: 0
  • Building Style: 0
  • Exterior Walls Type: 11
  • Interior Walls Type: 14
  • Roof Shape Type: 7
  • Roof Cover Type: 4
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 15
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 933
  • Parking Space Count: 4
  • Patio Type: 59
  • Porch Type: 126
  • Pool Type: 8

    Dimensions

  • Lot Size Square Feet: 49,985
  • Total Building Area: 7,162
  • Gross Building Area: 7,162
  • Building Area: 4,917
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 1
  • Heating: 4
  • Heated Square Feet: 4,917
  • Heating Fuel Type: 3

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: ISLEWORTH
  • Land Acres: 0000001147
  • Standard Land Use Code: 1001
  • County Land Use Code: 0104
  • State Land Use Code: 001
  • Legal Description 1: ISLEWORTH 16/118 LOT 8

Neighborhood

  • School District Name: Orange County School District
  • School Tax School District: 0332
  • Census Tract: 014809

Zoning

  • Zoning: P-D

Geography

  • Assessors Map Reference: 72B
  • Subdivision Tract Number: 3899
  • Parcel: 16-23-28-3899-00-080
  • Lot: 8
  • Meridian: SEC 16 TWN 23S RNG 28E
  • Municipality: UN-INCORPORATED
  • Latitude: 28.4931
  • Longitude: -81.5231

    Address

  • Full Address: 9743 Chestnut Ridge Dr
  • Address - House Number: 9743
  • Address - Street Name: Chestnut Ridge
  • Address - Suffix Type: Dr
  • State: FL
  • City Name: Windermere
  • Carrier Code: R010
  • 4-Digit Zip Code: 8945
  • Zip Code: 34786

Valuation

    Tax

  • Total Area: 5,697
  • Tax Year: 2023
  • Tax Amount: $2,114,945
  • Tax Rate Code Area: 75-ORG

    Appraisal Valuation

  • Standard Deviation: 0.123
  • Valuation Date: Jan 03, 2024
  • Confidence Score: 86
  • Final Value: 2,265,641
  • High Value: 2,544,503
  • Low Value: 1,986,779

    Market Valuation

  • Market Total Value: $1,987,939
  • Market Land Value: $750,000
  • Market Improvement Value: $1,237,939

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $1,363,267

    Exemptions

  • Homeowner Exemption: Yes

    Sales

  • Current Sale Contract Date: Jun 14, 2004
  • Current Sale Recording Date: Jun 15, 2004
  • Current Sale Price:
  • Current Sale Document Type: 71
  • Current Sale Input Document Number: 20040377843
  • Previous Sale Recording Date: Jul 18, 2001
  • Previous Sale Amount: $845,000
  • Previous Sale Document Type: 27

    Financing

  • First Mortgage Financing Type: ADJ
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Isleworth


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Frequently Asked Questions

When was property at 9743 Chestnut Ridge Drive built and last sold?
The property at 9743 Chestnut Ridge Drive was built in 1987 and last sold on Jun 14, 2004 for $1,200,000.
How much is this home worth?
The estimated value of the home located at 9743 Chestnut Ridge Drive is $0.
What are some comparable homes to 9743 Chestnut Ridge Drive?
There are currently no comparable homes to 9743 Chestnut Ridge Drive.