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$3,250,000

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 6 Full Baths
  • 1 Partial Bath
  • 6,328 Sq. Ft.
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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.

Full Property Details for 9743 Chestnut Ridge Dr

General

  • Sold For: $3,250,000
  • HOA FEE: $1,043/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $22,676 (2024)
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6314871
  • Added to Site: 225 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 9
  • Interior Features: Built-in Features, Ceiling Fan(s), High Ceilings, Primary Bedroom Main Floor, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
  • Fireplace: Yes
  • Fireplace(s): Family Room, Master Bedroom
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Freezer, Microwave, Refrigerator, Washer, Wine Refrigerator
  • Flooring: Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 6
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground

Exterior

  • Exterior Features: Awning(s), Irrigation System, Lighting

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 4
  • Covered Spaces: 4
  • Parking Features: Garage Faces Side

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: South

School Information

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

Community

  • Community Name: 34786 - Windermere
  • Association: Yes
  • Assoc. Name: Dan O’Connell
  • Pet Restrictions: Per Orange County Breed restrictions, number limits and leash laws.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

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

Structural Information

  • Exterior Const.: Concrete
  • Roof: Tile
  • Windows: ENERGY STAR Qualified Windows, Window Treatments
  • Stories/Levels: Two
  • Square Feet: 6,328
  • Sq. Ft. Source: Builder
  • Living Area: 6,328 Sq. Ft.
  • Year Built: 1987

Lot Features

  • Property View: Pool
  • Lot Size (Acres): 1.15
  • Lot Size (Sq. Ft.): 49,984
  • Lot Size: 1.1475
  • 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: $22,676
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: ISLEWORTH 16/118 LOT 8
  • Flood Zone Info: X
  • APN: 162328389900080
  • Property ID: 162328389900080

Listed by Isleworth Realty Llc
Sold by Stockworth Realty Group

Listing agents

— 9743 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

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 9743 Chestnut Ridge Dr

School District:Orange County School District
NameGradesDistance
Windermere Elementary School
11125 Park Avenue, Windermere, FL 34786
K-51.6 mi
Chain Of Lakes Middle School
8700 Conroy Windermere Road, Orlando, FL 32835
6-81.2 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 9743 Chestnut Ridge Dr

Date
Details
Price
Change
Source
9/26/2025
Sold
$3,250,000
—
MLS
6/04/2025
Listed
$3,250,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Isleworth Realty Llc
Sold by Stockworth Realty Group

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9743 Chestnut Ridge Drive, Windermere, FL 34786 (MLS# O6314871) is a Single Family property that was sold at $3,250,000 on September 26, 2025. Want to learn more about 9743 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.