9724 Chestnut Ridge Drive

Sold 7/25/25
Sold 7/25/25
Gallery Image 1
Last Sold Price
$4,330,000
5 beds5,557 sqft$779/sqft
9724 Chestnut Ridge Dr, Windermere, FL 34786

Description

Motivated Seller - Experience refined lakefront living in this exceptional estate, ideally located within the renowned Isleworth Golf & Country Club. Set along the shores of Lake Bessie on a beautifully landscaped 0.56-acre lot, the home spans 5,557 square feet of luxurious living space. A NEW METAL ROOF in 2024 adds both modern appeal and long-term durability, enhancing the home’s overall value and aesthetic. Grand mahogany French doors welcome you into an expansive formal living room, where large...Motivated Seller - Experience refined lakefront living in this exceptional estate, ideally located within the renowned Isleworth Golf & Country Club. Set along the shores of Lake Bessie on a beautifully landscaped 0.56-acre lot, the home spans 5,557 square feet of luxurious living space. A NEW METAL ROOF in 2024 adds both modern appeal and long-term durability, enhancing the home’s overall value and aesthetic. Grand mahogany French doors welcome you into an expansive formal living room, where large picture windows perfectly frame the breathtaking lake vistas. Adjacent, the elegant formal dining room connects to a gourmet kitchen featuring smooth granite countertops, a center island with a professional-grade range and contemporary hood, stainless steel appliances, and travertine flooring. A cozy breakfast nook and inviting family room—both with stunning lake views—complete the heart of the home. Wine enthusiasts will appreciate the custom wine cellar, adorned with a reclaimed Old World wooden door and capacity for over 500 bottles. This space seamlessly connects to a richly appointed home office and trophy room, each featuring bespoke wooden built-ins. The primary suite offers a tranquil sitting area overlooking the lake, along with a luxurious en-suite bath that includes dual vanities, a garden tub, and a walk-in shower. Upstairs, three additional bedrooms accompany a home theater with soundproof walls, a built-in wet bar, and intricate wood detailing, creating the ultimate cinematic experience. Outdoors, a spacious lanai with a summer kitchen overlooks an elevated terrace, pool, and spa, perfect for entertaining or relaxing while enjoying spectacular sunsets and nightly fireworks from nearby theme parks. This rare lakefront gem blends timeless elegance with a prime location, offering an unparalleled lifestyle in one of Central Florida’s most exclusive communities.
LISTING CLOSED: 07/25/2025 12:00 AM

  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 9724 Chestnut Ridge Drive

Status
Sold
MLS #
O6310606
Days on Market
37
Taxes
$38,334 / year
HOA Fees
$3,129 / quarter
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential / Single Family Residence
Year Built
1990
Lot Size
0.56 AC / 24,255 SF
County
Orange County
Architectural Style
Custom, Mediterranean
Subdivision Name
ISLEWORTH
Township
23
Garage Spaces
6
View
Pool, Water
Waterfront
Yes
Water View
Lake
Furnished
Unfurnished
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Location

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

Sold By ISLEWORTH REALTY LLC, Michelle Corbin

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Building Information for 9724 Chestnut Ridge Drive

Stories-Year Built1990Building Size-Lot Size0.56 AC / 24,255 SF

Payment Calculator

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$26,246 per month

30 year fixed, 6.55% Interest

Principal and Interest

$22,009

Property Taxes

$3,195

HOA Dues

$1,043

The Payment Calculator is for illustrative purposes only.

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Property Information for 9724 Chestnut Ridge Drive

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 8162.0
  • Building Area Units: Square Feet
  • Community Features: Community Boat Ramp, Water Access, Community Mailbox, Gated Community - Guard, Golf Carts OK, Golf, Playground
  • Direction Faces: Northeast
  • 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 Left.
  • 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
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • Unit Number: No
  • Street Number: 9724
  • Street Name: CHESTNUT RIDGE DR
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Circular Driveway, Golf Cart Garage, Golf Cart Parking, Ground Level
Taxes and HOA Information
  • Association Approval Required: Yes
  • Association Fee Includes: 24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security
  • 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 15
  • Tax Lot: 15
  • 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, Near Golf Course
  • Parcel Number: 282316389900150
  • Total Acreage: 1/2 to less than 1
  • Water Access: Lake
  • Water Access: Yes
  • Water Body Name: LAKE BESSIE
  • Water Extras: Lift, Skiing Allowed
  • Water Extras: Yes
  • Water: Lift, Skiing Allowed
  • Zoning: P-D
  • Living Area: 5557
Property and Assessments
  • Year Built Numeric: 1990
  • Amenities Additional Fees: Club amenities are available to Club members only. Residents of the community are not required to join the Isleworth Golf & Country Club.
  • Association Amenities: Cable TV, Gated, Maintenance, Playground, Security
  • Building Elevator: No
  • Flood Zone Code: AE
  • Flood Zone Date: 09-25-2009
  • Homestead: Yes
  • New Construction: No
  • Property Attached: No
  • Public Survey Range: 28
  • Public Survey Section: 16
  • Dock YN: Yes
  • Dock Description: Lift
  • Dock Lift Capacity: 10000
  • Dock Dimensions: 400 SQFT
Utilities
  • Sewer: Septic Tank
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Public, Street Lights, Underground Utilities
  • Water Source: Canal/Lake For Irrigation, Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Stucco
  • Exterior Features: French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters
  • Fencing: Fenced
  • Foundation Details: Block, Slab
  • Levels: Two
  • Patio And Porch Features: Patio, Rear Porch, Screened
  • Pool Features: In Ground, Salt Water
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Metal
  • Spa Features: In Ground
  • Spa: Yes
  • Vegetation: Mature Landscaping, Oak Trees
  • Waterfront Features: Lake Front
  • Waterfront Feet Total: 100
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 6
  • Appliances: Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
  • Cooling: Central Air
  • Fireplace: No
  • Flooring: Carpet, Tile, Travertine, Hardwood
  • Heating: Central, Zoned
  • Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s), Wet Bar, Window Treatments
  • Laundry Features: Inside, Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 10.0
  • Water View: Yes
  • Bathrooms Half: 0
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Breed Restrictions

Property History for 9724 Chestnut Ridge Drive

DateEvent & SourcePriceAppreciation
Jul 25, 2025

Sold

MFRMLS #O6310606

$4,330,000—
Jul 18, 2025

Sold (Public Record)

Public Record #1906920704

$4,330,000—
Jun 26, 2025

Pending

MFRMLS #O6310606

—
DateEvent & SourcePrice
07/25/2025

Sold

MFRMLS #O6310606

$4,330,000
07/18/2025

Sold (Public Record)

Public Record #1906920704

$4,330,000
06/26/2025

Pending

MFRMLS #O6310606

—

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

Public Records for 9724 Chestnut Ridge Drive

Taxable ValueLand-Additions-Total-
Tax Record2024$38,334 ($3,195 / month)
Home Facts
Beds5Total Finished SqFt5,402 SqFtAbove Grade Finished SqFt5,402 SqFtStories2Lot Size81,210 SqFtStyleSingle Family ResidenceYear Built1990Year Renovated1995ZoningP-DCountyORANGEAPN16-23-28-3899-00-150Fireplace TypeHas Fireplace

Schools near 9724 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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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 9724 Chestnut Ridge Drive, Windermere, FL 34786
$4,330,000
5
5,557
24,255
9730 Chestnut Ridge Drive, Windermere, FL 34786
$3,500,000
5
5,164
28,154
9718 Chestnut Ridge Drive, Windermere, FL 34786
$7,120,000
4
11,079
102,890
9719 Chestnut Ridge Drive, Windermere, FL 34786
$2,350,000
3
3,494
21,787
9743 Chestnut Ridge Drive, Windermere, FL 34786
$3,250,000
5
6,328
49,984
5002 Mellon Court, Windermere, FL 34786
$100
5
5.5
5,323
25,008

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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: 07/25/2025 11:18 AM