There are multiple listings for this address:
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.
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.
Property Details
Price:
$5,975,000
MLS #:
O6370294
Status:
Active
Beds:
7
Baths:
6
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Jan 2, 2026
Finished Sq Ft:
8,000
Total Sq Ft:
11,952
Lot Size:
24,349 sqft / 0.56 acres (approx)
Year Built:
1999
See this Listing
Schools
Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High
Interior
Appliances
Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
Bathrooms
5 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air, Zoned
Flooring
Porcelain Tile, Travertine, Hardwood
Heating
Central
Interior Features
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
Laundry Features
Laundry Room
Levels
Three Or More
Exterior
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 YN
1
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)
Covered Spaces
3
Direction Faces
West
Exterior Features
Fire Pit, French Doors, Outdoor Kitchen
Garage Spaces
3
Lot Features
Landscaped, Near Golf Course
Open Parking YN
1
Parking Features
Driveway, Garage Faces Side
Patio And Porch Features
Covered, Enclosed, Rear Porch, Screened
Security Features
Gated Community, Smoke Detector(s)
Spa Features
Heated, In Ground
View
Garden, Pool, Water
Waterfront Features
Waterfront, Pond
Window Features
ENERGY STAR Qualified Windows
Financial
HOA Name
Dan O’Connell
HOA Phone
407-909-2071
Map
Community
- Address9725 CHESTNUT RIDGE DRIVE WINDERMERE FL
- SubdivisionISLEWORTH
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Market Summary
Current real estate data for Single Family in WINDERMERE as of Aug 29, 2026
248
Single Family Listed
117
Avg DOM
460
Avg $ / SqFt
$2,334,742
Avg List Price
Property Summary
- Located in the ISLEWORTH subdivision, 9725 CHESTNUT RIDGE DRIVE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $5,975,000 and features 7 beds, 6 baths, and has approximately 8,000 square feet of living space, and was originally constructed in 1999. The current price per square foot is $747. The average price per square foot for Single Family listings in WINDERMERE is $460. The average listing price for Single Family in WINDERMERE is $2,334,742. To schedule a showing of MLS#o6370294 at 9725 CHESTNUT RIDGE DRIVE in WINDERMERE, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
Similar Listings Nearby
Courtesy of DOUGLAS ELLIMAN. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 9725 CHESTNUT RIDGE DRIVE
WINDERMERE, FL
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.
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.
Property Details
Price:
$29,000
MLS #:
O6436860
Status:
Active
Beds:
7
Baths:
6
Type:
Rental
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Aug 26, 2026
Finished Sq Ft:
8,000
Total Sq Ft:
11,952
Lot Size:
24,349 sqft / 0.56 acres (approx)
Year Built:
1999
See this Listing
Schools
Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High
Interior
Appliances
Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
Bathrooms
5 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air, Zoned
Flooring
Porcelain Tile, Travertine, Hardwood
Heating
Central
Interior Features
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
Laundry Features
Laundry Room
Levels
Three Or More
Exterior
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 YN
1
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)
Covered Spaces
3
Direction Faces
West
Exterior Features
Fire Pit, French Doors, Outdoor Kitchen
Garage Spaces
3
Lot Features
Landscaped, Near Golf Course
Open Parking YN
1
Parking Features
Driveway, Garage Faces Side
Patio And Porch Features
Covered, Enclosed, Rear Porch, Screened
Security Features
Gated Community, Smoke Detector(s)
Spa Features
Heated, In Ground
View
Garden, Pool, Water
Waterfront Features
Waterfront, Pond
Window Features
ENERGY STAR Qualified Windows
Financial
HOA Name
Dan O’Connell
HOA Phone
407-909-2071
Map
Community
- Address9725 CHESTNUT RIDGE DRIVE WINDERMERE FL
- SubdivisionISLEWORTH
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Market Summary
Current real estate data for Rental in WINDERMERE as of Aug 29, 2026
248
Rental Listed
117
Avg DOM
460
Avg $ / SqFt
$2,334,742
Avg List Price
Property Summary
- Located in the ISLEWORTH subdivision, 9725 CHESTNUT RIDGE DRIVE WINDERMERE FL is a Rental for sale in WINDERMERE, FL, 34786. It is listed for $29,000 To schedule a showing of MLS#o6436860 at 9725 CHESTNUT RIDGE DRIVE in WINDERMERE, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.