9725 CHESTNUT RIDGE DRIVE Windermere, FL $ 29,000
9725 CHESTNUT RIDGE DRIVE
$ 29,000
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9725 CHESTNUT RIDGE DRIVE

Windermere, FL, 34786
$ 29,000
Bedrooms7 Baths5.2 Sq 8,000
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Property for Rent in Windermere, FL

for $29,000 with 7 bedrooms and 5 full baths, 2 half baths. This 8,000 square foot property was built in 1999 on a lot size of 0.56.

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.

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Rental Active

Price

$ 29,000

Bedrooms

7

Full Bath

5

Half Bath

2

Taxes

$ 0

Style

Single Family Residence

Lot Size

0.56

Year Built

1999

Town/City

Windermere

County/Region

Orange

MLS | Web ID

O6436860

Features
General
Sewer Septic Tank
Heating Central
Cooling Central Air Zoned
Utilities Electricity Connected Water Connected
Appliances Bar Fridge Built-In Oven Dishwasher Disposal Dryer Exhaust Fan Freezer Ice Maker Microwave Range Range Hood Refrigerator Washer
Garage Spaces 3
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)
Pets Allowed Yes
Year Built 1999
Tenant Pays Cleaning Fee Re-Key Fee
View Garden Pool Water
Levels Three Or More
Property Subtype Single Family Residence
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)
County Orange
New Construction false
Property Type Residential Lease
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
Spa Features Heated In Ground
Elementary School Windermere Elem
Middle/Junior High School Chain of Lakes Middle
Ok to Lease 24 Months
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6436860
Availability Date 2026-09-01
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Lease Amount Frequency Monthly
Water View Pond
Water Access Type Lake - Chain of Lakes Pond
Minimum Lease 8-12 Months
Water Access Y/N true
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
DockY/N false
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Interior
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
Furnished Y/N Unfurnished
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
Total Baths 7
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Exterior
Exterior Amenities Fire Pit French Doors Outdoor Kitchen
Parking Features Driveway Garage Faces Side
Lot Features Landscaped Near Golf Course
Water Source Public
Lot Size Area 24349
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
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* Excluded Features
List By
diannadesboyaux@gmail.com

Email

Nearby
0 Elementary School
0 Middle School
Olympia High High School High School
Pricing History
Date Price Price Change Description
8/26/2026 $29,000 Listed Price

Map


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9725 CHESTNUT RIDGE DRIVE, Windermere, FL, 34786 is a Property for Rent at $29,000 with 8,000 sqft and a lot size of 0.56. 9725 CHESTNUT RIDGE DRIVE has 7 bedrooms, 5.2 baths, and was built in 1999. The property's zip code is 34786 which is in Windermere, FL