$3,400,000
9731 Chestnut Ridge Drive
Windermere, FL 34786
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history235 days on market
- Status: ActiveAug 16, 2025
- Listed$3,400,000Aug 16, 2025
- Price increased$3,400,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 235
- Subdivision
- Isleworth
- County
- Orange
- Year built
- 1986
- Living area
- 4,877 sq ft
- Price/sq ft
- $697
- Building area
- 6,151 sq ft (Public Records)
- Lot size
- 23,624 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- X (12095C0385F)
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $19,867 (2024)
- Parcel #
- 16-23-28-3899-00-070
- Zoning
- P-D
- MLS #
- O6336655
Interior Details
- Bedrooms
- 4
- Full bathrooms
- 4
- Flooring
- Marble, Travertine
- 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
- Interior features
- Cathedral Ceiling(s), Ceiling Fans(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
- Laundry
- Laundry Room
- Stories / Levels
- Two
- Direction faces
- Northeast
Heating & Cooling
- Heating
- Central, Electric, Natural Gas
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Circular Driveway, Golf Cart Garage
HOA & Financial
- HOA fee
- $3,672 / Quarterly
- Monthly HOA
- $1,224/mo
- Total monthly fees
- $1,224/mo
- Total annual fees
- $14,688
- HOA name
- Dan O'Connell
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- No Minimum
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Per Isleworth Community Association (ICA)
- Approval process
- Per Isleworth Community Association (ICA)
Exterior & Construction
- Exterior features
- Balcony, Outdoor Grill, Rain Gutters
- Construction materials
- Block, Stucco
- Roof
- Tile
- Foundation
- Block, Slab
- Pool
- Private pool
- Water access
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Water Connected
Community
- Pets allowed
- Breed Restrictions
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | Second | |
| Primary Bathroom | Second | |
| Bedroom 2 | First | |
| Bedroom 3 | First | |
| Bedroom 4 | First | |
| Office | Second | |
| Kitchen | Second | |
| Dining Room | Second | |
| Living Room | Second | |
| Family Room | Second |
Listing Details
- Listing date
- 2025-07-30
- On market date
- 2025-08-16
- Original list price
- $3,400,000
- Occupant type
- Owner
- MLS area
- 34786 - Windermere
- Listing AOR
- Orlando Regional
- Status changed
- 2025-08-16
- Tax legal description
- ISLEWORTH 16/118 LOT 7
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of April 8, 2026 at 9:19 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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