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9731 Chestnut Ridge Drive Windermere, FL 34786

4 Beds
4 Baths
4,877 Sqft
23,624 Sqft lot
0.54 Acre lot
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$3,400,000 Est. $12,520 / mo.*
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Status: Active
Property Type: Single Family Residence
Year Built: 1986
Neighborhood: Isleworth
Days on Website: 5

Courtesy of ISLEWORTH REALTY LLC

Description

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.

Open House

Property Details and Features

  • Living Area Meters: 453.09
  • Room Count: 10
  • Building Area Total: 6151
  • Building Area Units: Square Feet
  • Construction Materials: "Block", "Stucco"
  • Direction Faces: Northeast
  • Levels: "Two"
  • Living Area: 4877
  • Stories Total: 2
  • Year Built: 1986
  • Total Annual Fees: $12,516
  • Total Monthly Fees: $1,043
  • Water Access: Lake - Chain of Lakes
  • Association Email: dan.occonnell@isleworth.com
  • Association Fee Requirement: Required
  • Association Approval Required YN: 1
  • Monthly HOA Amount: $1,043
  • Association Fee Frequency: Quarterly
  • Association Fee Includes: "Guard - 24 Hour", "Cable TV", "Escrow Reserves Fund", "Internet", "Maintenance Grounds", "Maintenance", "Security"
  • Association Fee: $3129
  • Association Name: Dan O'Connell
  • Association Phone: 407-909-2071
  • Available For Lease
  • Minimum Lease: No Minimum
  • Calculated List Price By Calculated Sq Ft: $697
  • Lot Size Square Meters: 2195
  • Total Acreage: 1/2 to less than 1
  • Features: "Landscaped", "Near Golf Course", "Paved"
  • 0.54 acres
  • 23624 square feet
  • View: "Pool"
  • Pet Restrictions: Per Orange County breed restrictions, number limits and leash laws.
  • Pets Allowed: "Breed Restrictions"
  • 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.
  • Utilities: "BB/HS Internet Available", "Cable Connected", "Electricity Connected", "Natural Gas Connected", "Water Connected"
  • Water Source: "Public"
  • Road Surface: "Paved"
  • 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"
  • Other Equipment: "Irrigation Equipment"
  • 4 full bathrooms
  • Bedrooms Total: 4
  • Community Features: "Community Mailbox", "Gated Community - No Guard", "Golf Carts OK", "Golf", "Playground", "Street Lights"
  • Cooling: "Central Air", "Zoned"
  • Exterior Features: "Balcony", "Outdoor Grill", "Rain Gutters"
  • Flooring: "Marble", "Travertine"
  • Foundation Details: "Block", "Slab"
  • Attached Garage Yn: t
  • Garage Spaces: 2
  • Heating: "Central", "Electric", "Natural Gas"
  • Interior Features: "Cathedral Ceiling(s)", "Ceiling Fans(s)", "Kitchen/Family Room Combo", "Primary Downstairs", "Stone Counters", "Thermostat", "Walk-In Closet(s)"
  • Laundry Features: "Laundry Room"
  • County or Parish: Orange
  • Subdivision: ISLEWORTH
  • Township: 23
  • Parking Features: "Circular Driveway", "Golf Cart Garage"
  • Pool Features: "Heated", "In Ground", "Lighting", "Self Cleaning"
  • Spa Features: "Heated", "In Ground"
  • Zoning: P-D
  • Roof: "Tile"
  • Elementary School: Windermere Elem
  • Middle Or Junior School: Chain of Lakes Middle
  • High School: Olympia High
  • Sewer: "Septic Tank"

Location

$3,400,000 - 9731 Chestnut Ridge Drive, Windermere, FL 34786
9731 Chestnut Ridge Drive Windermere, FL 34786
County or Parish: Orange

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This content last updated on August 21, 2025 1:21PM. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.