9724 Chestnut Ridge Drive
Description
- Listed by: Carey Sheffield 407.961.2979 she@careysheffield.com Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
- Listed by: Michelle Corbin 407.491.2690 michelle.corbin@isleworth.com Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
Recent comparable sales
Median sold price
$3,900,000
Avg days on market
61
Sale-to-list ratio
92.4%
Windermere, FL
9 comparable properties found
$3,900,000
Sold 08/20/26
- 5
- Bedrooms
- 7
- Bathrooms
- 5,695
- Square Feet
- 0.26
- Acres
$3,750,000
Sold 03/28/25
- 5
- Bedrooms
- 6
- Bathrooms
- 5,802
- Square Feet
- 1.99
- Acres
$4,100,000
Sold 08/13/25
- 5
- Bedrooms
- 7
- Bathrooms
- 6,196
- Square Feet
- 1.09
- Acres
$4,029,999
Sold 04/10/26
- 5
- Bedrooms
- 7
- Bathrooms
- 5,895
- Square Feet
- 2.16
- Acres
$3,250,000
Sold 09/26/25
- 5
- Bedrooms
- 7
- Bathrooms
- 6,328
- Square Feet
- 1.15
- Acres
$4,850,000
Sold 06/12/26
- 5
- Bedrooms
- 7
- Bathrooms
- 6,188
- Square Feet
- 1.16
- Acres
$3,200,000
Sold 06/03/25
- 5
- Bedrooms
- 7
- Bathrooms
- 5,218
- Square Feet
- 0.51
- Acres
$1,770,000
Sold 11/14/24
- 5
- Bedrooms
- 6
- Bathrooms
- 5,478
- Square Feet
- 1.21
- Acres
$4,125,000
Sold 09/05/25
- 5
- Bedrooms
- 6
- Bathrooms
- 4,783
- Square Feet
- 0.58
- Acres
Location
Sold By ISLEWORTH REALTY LLC, Michelle Corbin
Payment Calculator
$26,246 per month
30 year fixed, 6.55% Interest
$22,009
$3,195
$1,043
Know your buying power with a preapproval and custom rate in minutes
1Property Information for 9724 Chestnut Ridge Drive
- Taxes: $38,334 / year
- MLS Type: Residential / Single Family Residence
- 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
- Year Built: 1990
- Lot Size: 0.56 AC / 24,255 SF
- 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
- Attached Garage: Yes
- Carport: No
- Garage: Yes
- Parking Features: Circular Driveway, Golf Cart Garage, Golf Cart Parking, Ground Level
- 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
- 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
- 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
- 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
- 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
- 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
- Minimum Lease Period: 0
- Pets Allowed: Breed Restrictions
Property History for 9724 Chestnut Ridge Drive
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| 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 | — | |
| May 20, 2025 | Listed (Active) MFRMLS #O6310606 | $4,800,000 | — |
| May 9, 2019 | Expired MFRMLS #O5706286 | $2,975,000 | — |
| May 10, 2018 | Listed (Active) MFRMLS #O5706286 | $3,075,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 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 | — |
| 05/20/2025 | Listed (Active) MFRMLS #O6310606 | $4,800,000 |
| 05/09/2019 | Expired MFRMLS #O5706286 | $2,975,000 |
| 05/10/2018 | Listed (Active) MFRMLS #O5706286 | $3,075,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 9724 Chestnut Ridge Drive
Schools near 9724 Chestnut Ridge Drive
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Charter - | K to 8 | |||
| Public - | 6 to 8 | |||
| 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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- Square Feet
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Nearby home values
| Address | Sold price | Beds | Baths | Sqft | Lot (Sqft) |
|---|---|---|---|---|---|
This home: 9724 Chestnut Ridge Drive, Windermere, FL 34786 | $4,330,000 | 5 | 6 | 5,557 | 24,255 |
$3,500,000 | 5 | 5 | 5,164 | 28,154 | |
$7,120,000 | 4 | 8 | 11,079 | 102,890 | |
$2,350,000 | 3 | 4 | 3,494 | 21,787 | |
$3,250,000 | 5 | 7 | 6,328 | 49,984 | |
$100 | 5 | 5.5 | 5,323 | 25,008 | |
– | – | – | – | 85,384 | |
$1,290,000 | 5 | 7 | 6,028 | 80,865 | |
$100 | 5 | 3.5 | 5,441 | 22,576 | |
$73,953 | – | – | 1,197 | 1,697,824 | |
– | 7 | 11 | 14,002 | 175,790 | |
$1,500,000 | 3 | 5 | 5,309 | 22,919 | |
$5,344 | – | – | – | 232,209 | |
$2,400,000 | 3 | 4 | 4,554 | 21,830 | |
– | 4 | 3 | 3,561 | 53,071 | |
$1,600,000 | 5 | 5 | 4,833 | 22,936 |
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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
