
Listed by ISLEWORTH REALTY LLC
Status: Active
9731 Chestnut Ridge Dr
Windermere, FL 34786
$3,400,000
------/mo*
CalculateNestled 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.
Read more- Bedrooms
- 4
- Baths
- 4
- House Size
- 4,877 sqft
- Year Built
- 1986
- Lot Size
- 0.54 ac
Location
Market Insights
In the last 30 days, homes for sale in 34786, Windermere, FL were on the market for a median of 56 days and 2.22% of homes sold above list price.

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Get StartedInterior Information
- appliances
- Bar Fridge
- Dishwasher
- Disposal
- Dryer
- Exhaust Fan
- Gas Water Heater
- Ice Maker
- Microwave
- Range
- Range Hood
- Refrigerator
- Trash Compactor
- Washer
- Water Purifier
- Water Softener
- cooling
- Central Air
- Zoned
- features
- Cathedral Ceiling(s)
- Stone Counters
- Walk-in Closet(s)
- flooring
- Marble
- heating
- Central
- Electric
- Natural Gas
- laundry features
- Laundry Room
- view
- Pool
Exterior Information
- features
- Balcony
- Outdoor Grill
- Rain Gutters
- pool
- Heated
- In Ground
- Private
- road surface
- Paved
- roof
- Tile
Property Information
- community
- Gated
- Golf
- Playground
- Street Lights
- construction
- Block
- Stucco
- foundation
- Block
- Slab
- hoa fees
- $3,129.00
- Quarterly
- hoa includes
- Cable Tv
- Internet
- Maintenance Grounds
- Security
- lot
- Landscaped
- Near Golf Course
- Paved
- parking
- Circular Driveway
- Golf Cart Garage
- Attached
- security features
- Gated Community
- Security Lights
- Security System
- Smoke Detector(s)
- sewer
- Septic Tank
- subdivision name
- Isleworth
- utilities
- Cable Available
- Natural Gas Available
- Cable Connected
- Electricity Connected
- Natural Gas Connected
- Water Connected
- water source
- Public

- Listed By Monica Lochmandy
- (407) 909-9000
- ISLEWORTH REALTY LLC
- (407) 909-9000
- sales@isleworth.com
- MLS O6336655
Monthly Payments Calculator
Estimated Monthly Cost
$22,090
30 year fixed·6.9% interest rate
- Principal & Interest
- $17,914
- Property Taxes
- $2,833
- Home Insurance
- $300
- HOA Fees
- $1,043
*All calculations are estimates and provided for informational purposes only. Actual amounts may vary.