Waterfront - Golf Course - Primary on Main
Address
9725 Chestnut Ridge Drive, WINDERMERE, FL
Price
$ 5,975,000
Property Attributes
- MLS#O6370294
- TypeSingle Family
- Listing Status Active
- CountyOrange
- CityWINDERMERE
- AreaWindermere
- NeighborhoodISLEWORTH
- Zip34786
- StyleSingle Family Residence
- Year Built1999
- Taxes$ 29046
- Price$ 5,975,000
- Bedrooms7
- Full Bathrooms5
- Half Bathrooms2
- Sqr Footage8000
- Lot Size0.56 Acres
Data Source:
Stellar MLS
Property Description
Virtually Staged. 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. Some photos have been virtually staged. Private showings are easily accommodated, including same-day requests.
| Elementary School | Middle School | High School |
|---|---|---|
| Windermere Elem Elementary School | Chain of Lakes Middle Middle School | Olympia High High School |
| Price History | |
|---|---|
| 1/2/2026 | Listed $6,950,000 |
| 4/15/2026 | 12$6,150,000 |
| 5/2/2026 | 2$6,000,000 |
| 8/22/2026 | Listed $5,975,000 |
General Features
| Sewer | Septic Tank |
|---|---|
| Heating | Central |
| Cooling | Central Air,Zoned |
| Utilities | Electricity Connected,Water Connected |
| Roof | Tile |
| Appliances | Bar Fridge,Built-In Oven,Dishwasher,Disposal,Dryer,Exhaust Fan,Freezer,Ice Maker,Microwave,Range,Range Hood,Refrigerator,Washer |
| Zoning | P-D |
| HOA Fee | 3129 |
| Garage Spaces | 3 |
| Association Fee Includes | 24-Hour Guard,Community Pool,Maintenance Grounds,Manager,Pool Maintenance,Security |
| Patio/Porch Features | Covered,Enclosed,Rear Porch,Screened |
| Pool Features | Heated,In Ground,Indoor,Lap,Outside Bath Access,Screen Enclosure,Tile |
| Security Features | Gated Community,Smoke Detector(s) |
| Construction Materials | Block,Stucco |
| Pets Allowed | Yes |
| Year Built | 1999 |
| View | Garden,Pool,Water |
| Levels | Three Or More |
| Property Subtype | Single Family Residence |
| Tax Year | 2024 |
| Ownership | Fee Simple |
| Waterfront Features | Waterfront,Pond |
| Community Features | Private Boat Ramp,Water Access,Waterfront,Buyer Approval Required,Clubhouse,Fitness Center,Gated Community - Guard,Golf Carts OK,Golf,No Truck/RV/Motorcycle Parking,Playground,Pool,Racquetball,Restaurant,Tennis Court(s) |
| Assoc Fee Paid Per | Quarterly |
| County | Orange |
| New Construction | false |
| Property Type | Residential |
| Association Amenities | Clubhouse,Elevator(s),Fitness Center,Gated,Golf Course,Maintenance,Park,Pickleball Court(s),Playground,Pool,Racquetball,Recreation Facilities,Sauna,Security,Spa/Hot Tub,Storage,Tennis Court(s) |
| Attached Garage | true |
| Subdivision Name | ISLEWORTH |
| Facing Direction | West |
| Garage Y/N | true |
| Total Rooms | 5 |
| Full Baths | 5 |
| Status | Active |
| 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. |
| High School | Olympia High |
| City | WINDERMERE |
| Association Name | Dan O'Connell |
| Senior Community Y/N | false |
| MLS Area | 34786 - Windermere |
| Lot Size Units | Square Feet |
| Lot Size Square Feet | 24349 |
| Carport Y/N | false |
| Listing Terms | Cash,Conventional |
| Spa Features | Heated,In Ground |
| Elementary School | Windermere Elem |
| Land Lease Y/N | false |
| Tax Annual Amount | 29046.23 |
| Middle/Junior High School | Chain of Lakes Middle |
| Additional Parcels Y/N | false |
| Lease Considered Y/N | true |
| Virtual Tour | https://www.propertypanorama.com/instaview/stellar/O6370294 |
| Building Area Units | Square Feet |
| Living Area Units | Square Feet |
| Standard Status | Active |
| Occupancy Type | Vacant |
| Tax Lot | 6 |
| 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 |
| Water View | Pond |
| Water Access Type | Lake - Chain of Lakes,Pond |
| Minimum Lease | 8-12 Months |
| Water Access Y/N | true |
| Monthly HOA Amount | 1043 |
| Additional Rooms | Den/Library/Office,Family Room,Formal Living Room Separate,Interior In-Law Suite w/Private Entry,Media Room |
| Water View Y/N | true |
| Flood Zone Code | X |
| In Law Suite YN | false |
| Flood Zone Code X | Yes |
Interior Features
| Interior Amenities | Built-in Features,Ceiling Fan(s),Elevator,High Ceilings,Kitchen/Family Room Combo,Living Room/Dining Room Combo,Open Floorplan,Primary Bedroom Main Floor,Skylight(s),Split Bedroom,Stone Counters,Thermostat,Walk-In Closet(s),Wet Bar |
|---|---|
| Flooring | Porcelain Tile,Travertine,Hardwood |
| Fireplace Features | Gas,Living Room,Master Bedroom |
| Total Stories | 2 |
| Air Conditioning Y/N | true |
| Heating Y/N | true |
| Window Features | ENERGY STAR Qualified Windows |
| Fireplace Y/N | true |
| Half Baths | 2 |
| Laundry Features | Laundry Room |
| Total Bedrooms | 7 |
| LivingAreaSource | Builder |
| Total Baths | 7 |
Exterior Features
| Exterior Amenities | Fire Pit,French Doors,Outdoor Kitchen |
|---|---|
| Vegetation | Mature Landscaping,Trees/Landscaped |
| Parking Features | Driveway,Garage Faces Side |
| Lot Features | Landscaped,Near Golf Course |
| Water Source | Public |
| Lot Size Area | 24349 |
| Foundation Details | Slab |
| Spa | true |
| Building Area Total | 11952 |
| Lot Size Acres | 0.56 |
| Road Surface Type | Paved,Asphalt |
| Private Pool | true |
| Waterfront Y/N | true |
| Covered Spaces | 3 |
| Road Frontage Type | Street Paved |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 34786
Price
Taxes
Year Built
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Updated on September 28, 2026 4:05 PM UTC
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© 2026 Greater Alabama MLS. 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. IDX content is not guaranteed accurate by the MLS or Numen Realty Advisors. Data last updated: September 28, 2026 3:54 PM UTC
All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating
