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$3,250,000
1 Day On Site

9743 CHESTNUT RIDGE DRIVE
WINDERMERE, FL 34786

For Sale|Single Family Residence|Active
5
Beds
7
Total Baths
6
Full Baths
1
Partial Bath
6,328
SqFt
$514
/SqFt
1987
Built
Subdivision:
ISLEWORTH
County:
Orange
Call Now: (407) 721-5225
Is this the listing for you? We can help make it yours.
(407) 721-5225
9743 CHESTNUT RIDGE DRIVE9743 CHESTNUT RIDGE DRIVE9743 CHESTNUT RIDGE DRIVE9743 CHESTNUT RIDGE DRIVE
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Monthly Payment (Est.)

$14,828
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2025 Information is deemed reliable but not guaranteed.

Nestled at the end of a quiet cul-de-sac on 1.15 acres within the renowned Isleworth Golf & Country Club, this exceptional residence offers refined luxury, thoughtful design, and exceptional grounds designed for outdoor enjoyment all year round. Featuring five bedrooms, six full bathrooms, and a powder room, the home spans more than 6,300 square feet, with lovely architectural style and beautifully appointed interiors. The stunning great room is a true centerpiece, featuring soaring cathedral ceilings, exposed wood beams, and abundant natural light. Formal living and dining rooms provide ideal spaces for entertaining, while the chef’s kitchen boasts granite countertops, white cabinetry, and high-end Bosch and Sub-Zero appliances. The primary suite is a serene retreat, featuring a luxurious en-suite bath and direct access to the pergola and pool for seamless indoor-outdoor living. Upstairs, a versatile bonus room offers flexible space for a yoga studio, home gym, game room or creative retreat, complemented by a stylish loft office perfect for work-from-home needs. Step outside to discover the expansive backyard complete with modern pool is surrounded by low-maintenance artificial turf, expansive lanai spaces for alfresco dining, and multiple seating areas ideal for gatherings or quiet relaxation—all framed by a vast, fenced yard. This extraordinary home offers both comfort and sophistication in a community renowned for its golf, amenities, and lifestyle. A rare opportunity to live luxuriously in a premier setting.

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Listing Snapshot
Price 
$3,250,000
Days On Site 
1 Day
Bedrooms 
5
Inside Area (SqFt) 
6,328 sqft
Total Baths 
7
Full Baths 
6
Partial Baths 
1
Lot Size 
1.15 Acres
Year Built 
1987
MLS® Number 
O6314871
Status 
Active
Property Tax 
$22,676
HOA/Condo/Coop Fees 
$1,043 monthly
Sq Ft Source 
Builder
Friends & Family
Recent Activity
21 hours agoListing updated with changes from the MLS®
yesterdayListing first seen on site
General Features
Acres 
1.15
Attached Garage 
Yes
Direction Faces 
South
Foundation 
Slab
Garage 
Yes
Garage Spaces 
4
Parking 
Garage Faces SideAttached
Pets 
Breed Restrictions
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
SqFt Total 
7162
Stories 
Two
Utilities 
Cable AvailableNatural Gas AvailableCable ConnectedElectricity ConnectedNatural Gas Connected
Water Source 
Public
Zoning 
P-D
Interior Features
Appliances 
Bar FridgeDishwasherDisposalDryerFreezerMicrowaveRefrigeratorWasherWine Refrigerator
Cooling 
Central Air
Fireplace 
Yes
Fireplace Features 
Family Room
Flooring 
TileWood
Heating 
CentralElectric
Interior 
Built-in FeaturesHigh CeilingsVaulted Ceiling(s)Walk-In Closet(s)Wet Bar
Laundry Features 
InsideLaundry Room
Window Features 
Window CoveringsENERGY STAR Qualified WindowsWindow Treatments
Bathroom 1 
Level - First
Bedroom 2 
Level - First
Bedroom 3 
Level - First
Bedroom 4 
Level - First
Great Room 
Level - First
Gym 
Level - Second
Kitchen 
Level - First
Living Room 
Level - First
Master Bedroom 
Level - First
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Exterior Features
Construction Details 
Concrete
Exterior 
Awning(s)Lighting
Lot Features 
Landscaped
Pool Features 
In GroundPrivate
Private Pool 
Yes
Roof 
Tile
View 
Pool
Waterfront Features 
Lake Privileges
Waterview 
Pool
Windows/Doors 
Window CoveringsENERGY STAR Qualified WindowsWindow Treatments
Community Features
Association Dues 
3129
Financing Terms Available 
CashConventional
HOA Fee Frequency 
Quarterly
MLS Area 
34786 - Windermere
Roads 
Paved
Township 
23
Schools
School District
Unknown
Elementary School
Windermere Elem
Middle School
Chain of Lakes Middle
High School
Olympia High
Listing courtesy of ISLEWORTH REALTY LLC 4079612979

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Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2025, Stellar MLS.
Last checked: 2025-06-06 04:07 AM EDT

Neighborhood & Commute
Source: Walkscore
Community information and market data Powered by ATTOM Data Solutions. Copyright ©2019 ATTOM Data Solutions. Information is deemed reliable but not guaranteed.
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