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9731 Chestnut Ridge Drive

Windermere, FL 34786
  • $3,400,000
  • STATUS: Active
  • ON SITE: 204 Days
  • MLS #: O6336655
UPDATED: 161 min ago
$3,400,000
  • 4
    BEDS
  • 0.54
    ACRES
  • 4
    BATHS
  • 0
    1/2 BATHS
  • 4,877
    SQFT
  • $697
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1986
County:
Area:

School Information

Elementary School:
Middle School:
High School:

Description

Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.

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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-03-08T23:43:18.983.
www.floridasuncoasthouses.com/homes/166980641
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9731 Chestnut Ridge Drive Windermere, FL 34786

  • Price: $3,400,000
  • Status: Active
  • On Site: 204 Days
  • Updated: 161 min ago
  • MLS #: O6336655
4
Beds
4
Baths
0
½ Baths
0.54
Acres
4,877
SQFT
$697
$/SQFT
1986
Built
Neighborhood:
Isleworth
County:
Orange
Area:
Windermere
Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High
Property Description
Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.
Exterior Features

Additional Water Information The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a privatecommunity boat ramp for our residents eager to enjoy these great waters. Attached Garage Yn Yes Carport Yn No Construction Materials BlockStucco Covered Spaces 2 Direction Faces Northeast Exterior Features BalconyIrrigation SystemOutdoor GrillRain Gutters Foundation Details BlockSlab Lot Features LandscapedNear Golf Course Open Parking YN Yes Parking Features Circular DrivewayGolf Cart Garage Pool Features HeatedIn GroundLightingSelf Cleaning Pool Private Yn Yes Road Frontage Type Street Paved Road Surface Type Paved Roof Tile Spa Features HeatedIn Ground View Pool Water Access Lake - Chain of Lakes Water Access Yn Yes Water Body Name LAKE BUTLER CHAIN OF LAKES Water Extras Yn No Water View Yn No Waterfront Feet Total 0 Waterfront Yn No

Interior Features

Appliances Bar FridgeBuilt-In OvenDishwasherDisposalDryerExhaust FanGas Water HeaterIce MakerMicrowaveRangeRange HoodRefrigeratorTrash CompactorWasherWater Filtration SystemWater PurifierWater Softener Building Area Total 6151 Cooling Central AirZoned Cooling YN Yes Fireplace Yn No Flooring MarbleTravertine Heating CentralElectricNatural Gas Heating YN Yes Interior Features Cathedral Ceiling(s)Ceiling Fan(s)Kitchen/Family Room ComboPrimary Bedroom Main FloorStone CountersThermostatWalk-In Closet(s) Laundry Features Laundry Room Levels Two Rooms Primary Bathroom Bedroom 3 (Built-in Closet) Primary Bedroom (Dual Closets) Bedroom 4 (Built-in Closet) Bedroom 2 (Built-in Closet) Office Kitchen Dining Room Family Room Living Room Sewer Septic Tank Stories Total 2 Water Source Public

Property Features

Additional Lease Restrictions Per Isleworth Community Association (ICA) Amenities Additional Fees Club amenities are available to Club members only. Residents of the community are not required to join the Isleworth Golf & Country Club. Approval Process Per Isleworth Community Association (ICA) Association Amenities Cable TVPlaygroundSecurity Association Approval Required Yn Yes Association Fee 3672 Association Fee Frequency Quarterly Association Fee Includes 24-Hour GuardCable TVEscrow Reserves FundInternetMaintenance GroundsMaintenance RepairsSecurity Association Fee Monthly Amount 1224 Association Fee Requirement Required Association Yn Yes Cdd Yn No Community Features Community Boat RampWater AccessCommunity MailboxGated Community - No GuardGolf Carts OKGolfPlayground Down Payment Resource No Flood Zone Code X Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Listing Terms CashConventional Minimum Lease No Minimum New Construction Yn No Ownership Fee Simple Pet Restrictions Per Orange County breed restrictionsnumber limits and leash laws. Pets Allowed Breed Restrictions Property Sub Type Single Family Residence Realtor Info As-IsAssoc approval requiredNo Sign Security Features Gated CommunitySecurity LightsSecurity SystemSmoke Detector(s) Senior Community Yn No Special Listing Conditions None Tax Annual Amount 19866.86 Total Annual Fees 14688 Total Monthly Fees 1224 Utilities BB/HS Internet AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedStreet LightsWater Connected Yrs Of Owner Prior To Leasing Re No Zoning P-D


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of ISLEWORTH REALTY LLC: 407-909-9000.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-03-08T23:43:18.983.
 
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