Date
Details
Price
Change
Source
8/26/2026
Listed
$29,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
A rare opportunity to lease a beautifully renovated residence within Isleworth, offering exceptional space, privacy, comfort, and an elevated Central Florida lifestyle. Newly renovated and exceptionally private, this sophisticated Isleworth residence offers approximately 8,000 square feet of beautifully designed living space, combining refined luxury with the comfort and functionality of an exceptional home. Rich walnut cabinetry and custom wood detailing bring warmth and character throughout, while elegant living spaces, a fireplace, and wine cellar create an inviting setting for both everyday living and entertaining. At the heart of the home, the impressive chef's kitchen features Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, steam oven, dual dishwashers, and a discreet hidden pantry. Two separate laundry areas add convenience for a residence of this scale. The flexible floor plan includes six bedrooms, a dedicated office, and a bonus room with a closet that may serve as an additional bedroom, guest suite, fitness room, or private retreat. Five full and two half baths are beautifully finished with a calm, contemporary aesthetic, while an elevator provides effortless access between levels. Outdoors, complete privacy and peaceful pond views create a wonderful sense of retreat. A gas-heated pool and spa, expansive outdoor living areas, and summer kitchen provide an ideal setting for relaxing, dining, and entertaining year-round. The residence also features four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors. Private showings are easily accommodated, including same-day requests.
Full Property Details
Full Property Details for 9725 Chestnut Ridge Dr
General
- Rent: $29,000
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6436860
- Updated: 8/27/2026
- Added to Site: 1 day(s) ago
Rental Information
- Lease/Rent Term: 24 Months
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 5
- Interior Features: Built-in Features, Ceiling Fan(s), Elevator, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Skylight(s), Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar
- Fireplace: Yes
- Fireplace(s): Gas, Living Room, Master Bedroom
- Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Porcelain Tile, Travertine, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 7
- Full Bathrooms: 5
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 7
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared 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)
- Pool: Yes
- Private Pool: Yes
- Pool Description: Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile
- Spa: Yes
- Spa Description: Heated, In Ground
- Security/Safety: Gated Community, Smoke Detector(s)
Exterior
- Exterior Features: Fire Pit, French Doors, Outdoor Kitchen
- Deck/Patio: Covered, Enclosed, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Enclosed, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Driveway, Garage Faces Side
Location
- Area: 34786 - Windermere
- County: Orange
- Development Name: 34786 - Windermere
- Subdivision: ISLEWORTH
- Driving 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.
- Direction Faces: West
School Information
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
Community
- Community Name: 34786 - Windermere
- 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)
- Optional Amenities: Clubhouse, Elevator(s), Fitness Center, Gated, Golf Course, Maintenance, Park, Pickleball Court(s), Playgrou
- Association: Yes
- Assoc. Name: Dan O'Connell
- Pet Restrictions: Please call the association
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Central
Utilities
- Sewer: Septic Tank
- Water: Public
- Utility Description: Electricity Connected, Water Connected
Structural Information
- Windows: ENERGY STAR Qualified Windows
- Stories/Levels: Three Or More
- Square Feet: 8,000
- Sq. Ft. Source: Builder
- Year Built: 1999
Lot Features
- Property View: Garden, Pool, Water
- Lot Size (Acres): 0.56
- Lot Size (Sq. Ft.): 24,349
- Lot Size: 24349
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Lake - Chain of Lakes, Pond
- Water Front Desc.: Waterfront, Pond
Financial Considerations
- Lease Price: $29,000
- Assoc Fee Desc.: Required
- Application Fee: $500
- Security Deposit: $29,000
Disclosures and Reports
- Flood Zone Info: X
- APN: 162328389900060
- Property ID: 162328389900060
Listed by Douglas Elliman
Schools
Schools serving 9725 Chestnut Ridge Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Windermere Elementary School 11125 Park Avenue, Windermere, FL 34786 | K-5 | 1.7 mi |
Chain Of Lakes Middle School 8700 Conroy Windermere Road, Orlando, FL 32835 | 6-8 | 1.1 mi |
Olympia High School 4301 South Apopka Vineland Road, Orlando, FL 32835 | 9-12 | 1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 9725 Chestnut Ridge Dr
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- Townhouse
- Active
- Updated 16 hours ago
- 3Beds
- 3Total Baths
- 1,567Sq. Ft.
Listed by Miguel Anastacio (407) 487-2421
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,451Sq. Ft.
Listed by Homevest Realty
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 2Total Baths
- 1,140Sq. Ft.
Listed by Wilson Management Group
- Condo
- Active
- Updated 1 day ago
- 2Beds
- 2Total Baths
- 1,031Sq. Ft.
Listed by Re/Max 200 Realty
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- Townhouse
- Active
- Updated 5 days ago
- 3Beds
- 3Total Baths
- 1,423Sq. Ft.
Listed by The Apartment Brothers Llc
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,327Sq. Ft.
Listed by Sims Realty Llc
- Condo
- Active
- Updated 6 days ago
- 2Beds
- 2Total Baths
- 1,127Sq. Ft.
Listed by Century 21 Carioti
- Single Family
- Active
- Updated 6 days ago
- 4Beds
- 2Total Baths
- 2,479Sq. Ft.
Listed by Rp Investment Realty Llc
9725 Chestnut Ridge Drive, Windermere, FL 34786 (MLS# O6436860) is a Single Family property with 7 bedrooms, 5 full bathrooms and 2 partial bathrooms. 9725 Chestnut Ridge Drive is currently listed for rent at $29,000 and was received on August 26, 2026. Want to learn more about 9725 Chestnut Ridge Drive? Do you have questions about finding other real estate for sale or rent in Windermere? You can browse all Windermere rentals or contact a Coldwell Banker agent to request more information.