To schedule a showing of 9731 Chestnut Ridge Drive, Windermere, Florida, Call David Shippey at 863-521-4517 TODAY!
$3,400,000 | 4 beds | 4 full baths | N/A half baths | 4,877 sqft
Windermere, FL 34786
- 4Beds
- 4.00Total Baths
- 4 Full, 0 HalfBaths
- 4,877SqFt
- 1986Year Built
- 0.54Acres
- MLS# O6336655
- Residential
- SingleFamilyResidence
- Active
- Approx Time on Market10 months, 1 day
- Area34786 - Windermere
- CountyOrange
- Subdivision Isleworth
Overview
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 homes 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.
Agriculture / Farm
Association Fees / Info
Community Features: BoatFacilities, CommunityMailbox, Golf, GolfCartsOk, Playground, WaterAccess, Gated, StreetLights
Pets Allowed: BreedRestrictions
Hoa Frequency Rate: 3672
Association: Yes
Association Amenities: Playground, Security, CableTv
Hoa Fees Frequency: Quarterly
Association Fee Includes: CableTv, Internet, MaintenanceGrounds, MaintenanceStructure, ReserveFund, Security
Bathroom Info
Total Baths: 4.00
Fullbaths: 4
Building Info
Roof: Tile
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Pool Features: Heated, InGround, PoolSweep
Patio: Balcony
Pool Private: Yes
Exterior Features: Balcony, SprinklerIrrigation, OutdoorGrill, RainGutters
Fees / Restrictions
Financial
Original Price: $3,400,000
Garage / Parking
Parking Features: CircularDriveway, GolfCartGarage
Attached Garage: Yes
Garage: Yes
Green / Env Info
Interior Features
Floors: Marble, Travertine
Levels: Two
Spa: Yes
Laundry Features: LaundryRoom
Interior Features: CeilingFans, CathedralCeilings, KitchenFamilyRoomCombo, MainLevelPrimary, StoneCounters, WalkInClosets
Appliances: BarFridge, BuiltInOven, Dryer, Dishwasher, ExhaustFan, Disposal, GasWaterHeater, IceMaker, Microwave, Range, Refrigerator, RangeHood, WaterSoftener, TrashCompactor, WaterPurifier, Washer
Spa Features: Heated, InGround
Lot Info
Direction Remarks: 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.
Lot Size Units: Acres
Lot Size Acres: 0.54
Lot Sqft: 23,624
Lot Desc: NearGolfCourse, Landscaped
Misc
Other
Special Conditions: None
Security Features: SecuritySystem, SmokeDetectors, SecurityLights, GatedCommunity
Other Rooms Info
Property Info
Section: 16
Class Type: SingleFamilyResidence
Property Sub Type: SingleFamilyResidence
Construction Materials: Block, Stucco
Stories: 2
Total Stories: 2
Foundation: Block, Slab
Human Modified: Yes
Room Info
Total Rooms: 10
Sqft Info
Sqft: 4,877
Bulding Area Sqft: 6,151
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,024
Tax Lot: 7
Tax Legal Description: ISLEWORTH 16/118 LOT 7
Tax Block: 3899
Tax Annual Amount: 19866.86
Tax Book Number: 16-118
Unit Info
Utilities / Hvac
Heating: Central, Electric, NaturalGas
Water Source: Public
Sewer: SepticTank
Cool System: CentralAir, Zoned, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: CableConnected, ElectricityConnected, NaturalGasConnected, HighSpeedInternetAvailable, WaterConnected
Waterfront / Water
View: Yes
Water Body Name: LAKE BUTLER CHAIN OF LAKES
View: Pool
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.This listing courtesy of Isleworth Realty Llc
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MLS IDX data last updated on 06-18-2026 2:09 PM EST.
If you have any questions on 9731 Chestnut Ridge Drive, Windermere, Florida, please call David Shippey at 863-521-4517.
MLS# O6336655 located at 9731 Chestnut Ridge Drive, Windermere, Florida is brought to you by David Shippey REALTOR®
9731 Chestnut Ridge Drive, Windermere, Florida has 4 Beds, 4 Full Bath, and 0 Half Bath.
The MLS Number for 9731 Chestnut Ridge Drive, Windermere, Florida is O6336655.
The price for 9731 Chestnut Ridge Drive, Windermere, Florida is $3,400,000.
The status of 9731 Chestnut Ridge Drive, Windermere, Florida is Active.
The subdivision of 9731 Chestnut Ridge Drive, Windermere, Florida is Isleworth.
The home located at 9731 Chestnut Ridge Drive, Windermere, Florida was built in 2026.