9743 Chestnut Ridge Dr

Windermere, FL 34786

$3,250,000
Last Sold Price
5
Beds
6,328 Sq. Ft.
$514 / Sq. Ft.
6,328
Sq. Ft.
$514
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Closed 9/26/25
Closed 9/26/25
front view of a house with a yard

Description

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,...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.
  1. Listed by Carey Sheffield • Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
    P: (407)-961-2979 C: (407)-961-2979 she@careysheffield.com
  2. Listed by Michelle Corbin • Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
    P: (407)-491-2690 C: (407)-491-2690 michelle.corbin@isleworth.com

Property Details for 9743 Chestnut Ridge Drive

Subdivision Name
ISLEWORTH
Township
23
Garage Spaces
4
View
Pool
Waterfront
No
LISTING UPDATED: 09/26/2025 12:43 PM

Property Details for 9743 Chestnut Ridge Drive

StatusClosed
MLS #O6314871
Days on Market6
Taxes$22,676 / year
HOA Fees$12,516 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1987
Lot Size1.15 AC / 49,984 SF
CountyOrange County
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Location

Listing Courtesy of ISLEWORTH REALTY LLC, Carey Sheffield; ISLEWORTH REALTY LLC, Michelle Corbin

Sold By STOCKWORTH REALTY GROUP, Rob Rahter

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Building Information for 9743 Chestnut Ridge Drive

Stories-Year Built1987Building Size-Lot Size1.15 AC / 49,984 SF

Payment Calculator

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$19,298 per month

30 year fixed, 6.46% Interest

Principal and Interest

$16,365

Property Taxes

$1,890

HOA Dues

$1,043

The Payment Calculator is for illustrative purposes only.

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Property Information for 9743 Chestnut Ridge Drive

Summary
Location and General Information
  • Building Area Source: Builder
  • Building Area Total: 7162.0
  • Building Area Units: Square Feet
  • Direction Faces: South
  • Directions: 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.
  • Elementary School: Windermere Elem
  • Middle Or Junior School: Chain of Lakes Middle
  • High School: Olympia High
  • Mls Major Change Type: Sold
  • Major Change Type: Closed
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 9743
  • Street Name: CHESTNUT RIDGE
  • Street Suffix: DRIVE
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Garage Faces Side
Taxes and HOA Information
  • Association Approval Required: Yes
  • Association Fee Requirement: Required
  • Association Name: Dan O’Connell
  • Association Phone: 407-909-2071
  • Association: Yes
  • CDD: No
  • Pet Restrictions: Per Orange County Breed restrictions, number limits and leash laws.
  • Tax Block: 00
  • Tax Book Number: 16-118
  • Tax Legal Description: ISLEWORTH 16/118 LOT 8
  • Tax Lot: 8
  • Tax Year: 2024
Property
Lot Information
  • Additional Parcels: No
  • Additional Water Information: The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a private, community boat ramp for our residents eager to enjoy these great waters.
  • Lot Features: Landscaped, Oversized Lot
  • Parcel Number: 162328389900080
  • Total Acreage: 1 to less than 2
  • Water Access: Lake - Chain of Lakes
  • Water Access: Yes
  • Water Body Name: LAKE BUTLER CHAIN OF LAKES
  • Water Extras: No
  • Zoning: P-D
  • Living Area: 6328
Property and Assessments
  • Year Built Numeric: 1987
  • Flood Zone Code: X
  • Flood Zone Date: 09-25-2009
  • Flood Zone Panel: 12095C0385F
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 28
  • Public Survey Section: 16
  • Dock YN: No
Utilities
  • Sewer: Septic Tank
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Concrete
  • Exterior Features: Awning(s), Irrigation System, Lighting
  • Foundation Details: Slab
  • Levels: Two
  • Pool Features: In Ground
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Tile
  • Spa: No
  • Waterfront Feet Total: 0
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 6
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Freezer, Microwave, Refrigerator, Washer, Wine Refrigerator
  • Cooling: Central Air
  • Fireplace Features: Family Room, Master Bedroom
  • Fireplace: Yes
  • Flooring: Tile, Hardwood
  • Heating: Central, Electric
  • Interior Features: Built-in Features, Ceiling Fan(s), High Ceilings, Primary Bedroom Main Floor, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
  • Laundry Features: Inside, Laundry Room
  • Living Area Source: Builder
  • Living Area Units: Square Feet
  • Room Count: 9.0
  • Water View: No
  • Window Features: ENERGY STAR Qualified Windows, Window Treatments
  • Bathrooms Half: 1
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Breed Restrictions

Property History for 9743 Chestnut Ridge Drive

DateEvent & SourcePriceAppreciation
Sep 26, 2025

Sold

MFRMLS #O6314871

$3,250,000—
Sep 23, 2025

Sold (Public Record)

Public Record #1914118399

$3,250,000

+4.8% / yr

Jun 10, 2025

Pending

MFRMLS #O6314871

—
Jun 4, 2025

Listed (Active)

MFRMLS #O6314871

$3,250,000—
Jun 15, 2004

Sold (Public Record)

Public Record #136827040

$1,200,000

+12.8% / yr

Jun 14, 2004

Sold

MFRMLS #O4523456

$1,200,000—
Jun 11, 2004

Pending

MFRMLS #O4523456

—
Dec 10, 2003

Listed (Active)

MFRMLS #O4523456

$1,195,000—
Jul 18, 2001

Sold (Public Record)

Public Record #76306183

$845,000—
DateEvent & SourcePrice
09/26/2025

Sold

MFRMLS #O6314871

$3,250,000
09/23/2025

Sold (Public Record)

Public Record #1914118399

$3,250,000

+4.8% / yr

06/10/2025

Pending

MFRMLS #O6314871

—
06/04/2025

Listed (Active)

MFRMLS #O6314871

$3,250,000
06/15/2004

Sold (Public Record)

Public Record #136827040

$1,200,000

+12.8% / yr

06/14/2004

Sold

MFRMLS #O4523456

$1,200,000
06/11/2004

Pending

MFRMLS #O4523456

—
12/10/2003

Listed (Active)

MFRMLS #O4523456

$1,195,000
07/18/2001

Sold (Public Record)

Public Record #76306183

$845,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 9743 Chestnut Ridge Drive

Taxable ValueLand-Additions-Total-
Tax Record2024$22,676 ($1,890 / month)
Home Facts
Beds5Total Finished SqFt4,979 SqFtAbove Grade Finished SqFt4,979 SqFtStories2Lot Size49,985 SqFtStyleSingle Family ResidenceYear Built1987Year Renovated2000ZoningP-DCountyORANGEAPN16-23-28-3899-00-080Fireplace TypeHas Fireplace

Schools near 9743 Chestnut Ridge Drive

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Windermere Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Chain Of Lakes Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Windermere Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Chain Of Lakes Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of ISLEWORTH REALTY LLC, Carey Sheffield; ISLEWORTH REALTY LLC, Michelle Corbin

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 09/26/2025 12:43 PM