To schedule a showing of 9725 Chestnut Ridge Drive, Windermere, Florida, Call David Shippey at 863-521-4517 TODAY!
$6,000,000 | 7 beds | 5 full baths | 2 half baths | 8,000 sqft
Windermere, FL 34786
- 7Beds
- 7.00Total Baths
- 5 Full, 2 HalfBaths
- 8,000SqFt
- 1999Year Built
- 0.56Acres
- MLS# O6370294
- Residential
- SingleFamilyResidence
- Active
- Approx Time on Market5 months, 15 days
- Area34786 - Windermere
- CountyOrange
- Subdivision Isleworth
Overview
Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence.Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed.The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes.Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility.Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings.Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance.It is a residence restored with intention, where discretion, craftsmanship, and comfort converge.Private showings are easily accommodated, including same-day requests. Some photos (4 rooms on the second floor) have been virtually staged.
Agriculture / Farm
Association Fees / Info
Community Features: BoatFacilities, Clubhouse, Fitness, Golf, GolfCartsOk, Playground, Pool, Restaurant, Racquetball, TennisCourts, Waterfront, WaterAccess, Gated
Pets Allowed: Yes
Hoa Frequency Rate: 3129
Association: Yes
Association Amenities: Clubhouse, Elevators, FitnessCenter, GolfCourse, MaintenanceGrounds, Gated, Playground, Pickleball, Park, Pool, RecreationFacilities, Racquetball, Sauna, SpaHotTub, Security, Storage, TennisCourts
Hoa Fees Frequency: Quarterly
Association Fee Includes: AssociationManagement, MaintenanceGrounds, Pools, Security
Bathroom Info
Total Baths: 7.00
Fullbaths: 5
Building Info
Window Features: EnergyStarQualifiedWindows, Skylights
Roof: Tile
Building Area Source: Builder
Buyer Compensation
Exterior Features
Pool Features: Heated, Indoor, InGround, Lap, OutsideBathAccess, ScreenEnclosure, Tile, Association, Community
Patio: RearPorch, Covered, Enclosed, Screened
Pool Private: Yes
Exterior Features: FrenchPatioDoors, FirePit, OutdoorKitchen
Fees / Restrictions
Financial
Original Price: $6,950,000
Garage / Parking
Parking Features: Driveway, GarageFacesSide
Attached Garage: Yes
Garage: Yes
Green / Env Info
Interior Features
Fireplace Desc: Gas, LivingRoom, PrimaryBedroom
Fireplace: Yes
Floors: PorcelainTile, Travertine, Wood
Levels: ThreeOrMore
Spa: Yes
Laundry Features: LaundryRoom
Interior Features: WetBar, BuiltInFeatures, CeilingFans, Elevator, HighCeilings, KitchenFamilyRoomCombo, LivingDiningRoom, MainLevelPrimary, OpenFloorplan, StoneCounters, SplitBedrooms, Skylights, WalkInClosets, SeparateFormalLivingRoom
Appliances: BarFridge, BuiltInOven, Dryer, Dishwasher, ExhaustFan, Freezer, Disposal, IceMaker, Microwave, Range, Refrigerator, RangeHood, Washer
Spa Features: Heated, InGround
Lot Info
Direction Remarks: I-4 to Conroy Windermere Road west to Isleworth Golf and Country Club which will be on the left, turn right onto Latrobe Drive and next right onto Chestnut Ridge Drive, the home will be situated on the right.
Lot Size Units: Acres
Lot Size Acres: 0.56
Lot Sqft: 24,349
Vegetation: PartiallyWooded
Lot Desc: NearGolfCourse, BuyerApprovalRequired, Landscaped
Misc
Other
Special Conditions: None
Security Features: SmokeDetectors, GatedWithGuard, GatedCommunity
Other Rooms Info
Property Info
Section: 16
Class Type: SingleFamilyResidence
Property Sub Type: SingleFamilyResidence
Construction Materials: Block, Stucco
Total Stories: 2
Foundation: Slab
Human Modified: Yes
Room Info
Total Rooms: 5
Sqft Info
Sqft: 8,000
Bulding Area Sqft: 11,952
Living Area Units: SquareFeet
Living Area Source: Builder
Tax Info
Tax Year: 2,024
Tax Lot: 6
Tax Legal Description: ISLEWORTH 16/118 LOT 6 & BEG NW COR OF SAID LOT 6 TH S 63 DEG E 85 FT N 76 DEG E39.14 FT N 63 DEG W 113.43 FT S 30 DEGW 25.29 FT TO POB & BEG AT WLY MOST COROF LOT 4 TH N33-00-00E ALONG WLY LINE OFLOT 4 10.06 FT TH N63-04-56W 133.88 FTTH S30-16-40W 1 0.02 FT TO NELY LINE OF LANDS DESC IN 5925/4062 TH S63-04-56E 133.40 FT TO POB
Tax Block: 00
Tax Annual Amount: 29046.23
Tax Book Number: 16-118
Unit Info
Utilities / Hvac
Heating: Central
Water Source: Public
Sewer: SepticTank
Cool System: CentralAir, Zoned, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: ElectricityConnected, WaterConnected
Waterfront / Water
Waterfront: Yes
Waterfront Features: Pond
View: Yes
View: Garden, Pond, Pool, Water
Directions
I-4 to Conroy Windermere Road west to Isleworth Golf and Country Club which will be on the left, turn right onto Latrobe Drive and next right onto Chestnut Ridge Drive, the home will be situated on the right.This listing courtesy of Douglas Elliman
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MLS IDX data last updated on 06-17-2026 8:19 AM EST.
If you have any questions on 9725 Chestnut Ridge Drive, Windermere, Florida, please call David Shippey at 863-521-4517.
MLS# O6370294 located at 9725 Chestnut Ridge Drive, Windermere, Florida is brought to you by David Shippey REALTOR®
9725 Chestnut Ridge Drive, Windermere, Florida has 7 Beds, 5 Full Bath, and 2 Half Bath.
The MLS Number for 9725 Chestnut Ridge Drive, Windermere, Florida is O6370294.
The price for 9725 Chestnut Ridge Drive, Windermere, Florida is $6,000,000.
The status of 9725 Chestnut Ridge Drive, Windermere, Florida is Active.
The subdivision of 9725 Chestnut Ridge Drive, Windermere, Florida is Isleworth.
The home located at 9725 Chestnut Ridge Drive, Windermere, Florida was built in 2026.