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$3,400,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 4,877 Sq. Ft.
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Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home's thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.

Full Property Details for 9731 Chestnut Ridge Dr

General

  • Price: $3,400,000
  • HOA FEE: $1,043/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $19,866 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6336655
  • Updated: 8/16/2025
  • Added to Site: 152 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 10
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Kitchen and Family Room Combination, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Trash Compactor, Washer, Water Filtration System, Water Purifier, Water Softener
  • Flooring: Marble, Travertine

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Cable TV, Playground, Security
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated, In Ground, Lighting, Self Cleaning
  • Spa Description: Heated, In Ground
  • Security/Safety: Gated Community, Security Lights, Security System, Smoke Detector(s)

Exterior

  • Exterior Features: Balcony, Irrigation System, Outdoor Grill, Rain Gutters

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Circular Driveway, Golf Cart Garage

Location

  • Area: 34786 - Windermere
  • County: Orange
  • Development Name: 34786 - Windermere
  • Subdivision: ISLEWORTH
  • Driving 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.
  • Direction Faces: Northeast

School Information

  • Elementary School: Windermere Elem
  • Middle School: Chain of Lakes Middle
  • High School: Olympia High

Community

  • Community Name: 34786 - Windermere
  • Community Features: Community Boat Ramp, Water Access, Community Mailbox, Gated Community - No Guard, Golf Carts OK, Golf, Playground
  • Optional Amenities: Cable TV, Playground, Security
  • Association: Yes
  • Assoc. Name: Dan O'Connell
  • Assoc. Fees Include: 24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Security
  • Pet Restrictions: Per Orange County breed restrictions, number limits and leash laws.

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Central, Electric, Natural Gas

Utilities

  • Sewer: Septic Tank
  • Water District: LAKE BUTLER CHAIN OF LAKES
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Street Lights, Water Connected

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Tile
  • Stories/Levels: Two
  • Square Feet: 4,877
  • Sq. Ft. Source: Public Records
  • Year Built: 1986

Lot Features

  • Property View: Pool
  • Lot Size (Acres): 0.54
  • Lot Size (Sq. Ft.): 23,624
  • Lot Size: 23624
  • Frontage: Street Paved
  • Street/Road Desc.: Paved

Water Features

  • Water Access: Yes
  • Water Access Desc: Lake - Chain of Lakes
  • Water Front Name: LAKE BUTLER CHAIN OF LAKES

Financial Considerations

  • Association Fee: $3,129
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $19,866.86
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: ISLEWORTH 16/118 LOT 7
  • Flood Zone Info: X
  • APN: 162328389900070
  • Property ID: 162328389900070
  • Block/Lot/Section: 3899

Listed by Isleworth Realty Llc

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Listing agents

— 9731 Chestnut Ridge Dr —

  • Isleworth Realty Llc

  • Isleworth Realty Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 9731 Chestnut Ridge Dr

School District:Orange County School District
NameGradesDistance
Windermere Elementary School
11125 Park Avenue, Windermere, FL 34786
K-51.7 mi
Chain Of Lakes Middle School
8700 Conroy Windermere Road, Orlando, FL 32835
6-81.1 mi
Olympia High School
4301 South Apopka Vineland Road, Orlando, FL 32835
9-121.1 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 9731 Chestnut Ridge Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/16/2025
Listed
$3,400,000
172%
MLS
2/12/2010
Sold
$1,250,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 9731 Chestnut Ridge Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$19,867
—
$1,268,686
3%
2024
$19,867
7%
$1,232,931
3%
2023
$18,529
4%
$1,197,020
6%
2021
$17,784
-1%
$1,128,306
-3%
2022
$17,996
1%
$1,162,155
4%
2021
$17,784
1%
$1,112,728
2%
2019
$17,529
1%
$1,087,711
2%
2018
$17,407
1%
$1,067,430
2%
2017
$17,221
—
$1,045,475
2%
2016
$17,198
-2%
$1,023,972
1%
2015
$17,503
-1%
$1,016,854
1%
2014
$17,675
2%
$1,008,784
1%
2013
$17,324
—
$993,876
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Isleworth Realty Llc

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9731 Chestnut Ridge Drive, Windermere, FL 34786 (MLS# O6336655) is a Single Family property with 4 bedrooms and 4 full bathrooms. 9731 Chestnut Ridge Drive is currently listed for $3,400,000 and was received on August 16, 2025. Want to learn more about 9731 Chestnut Ridge Drive? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

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