Map

SoldSingle Family ResidenceSold

9724 Chestnut Ridge Dr

Windermere, FL 34786

$4,330,000

  • 5Beds
  • 6Baths6 full
  • 5,557Sq Ft
  • $779Per Sq Ft
  • 0.56Acres
  • 1990Built
Subdivision
Isleworth
County
Orange
MLS®
O6310606

Overview

Motivated Seller - Experience refined lakefront living in this exceptional estate, ideally located within the renowned Isleworth Golf & Country Club. Set along the shores of Lake Bessie on a beautifully landscaped 0.56-acre lot, the home spans 5,557 square feet of luxurious living space. A NEW METAL ROOF in 2024 adds both modern appeal and long-term durability, enhancing the home’s overall value and aesthetic. Grand mahogany French doors welcome you into an expansive formal living room, where large picture windows perfectly frame the breathtaking lake vistas. Adjacent, the elegant formal dining room connects to a gourmet kitchen featuring smooth granite countertops, a center island with a professional-grade range and contemporary hood, stainless steel appliances, and travertine flooring. A cozy breakfast nook and inviting family room—both with stunning lake views—complete the heart of the home. Wine enthusiasts will appreciate the custom wine cellar, adorned with a reclaimed Old World wooden door and capacity for over 500 bottles. This space seamlessly connects to a richly appointed home office and trophy room, each featuring bespoke wooden built-ins. The primary suite offers a tranquil sitting area overlooking the lake, along with a luxurious en-suite bath that includes dual vanities, a garden tub, and a walk-in shower. Upstairs, three additional bedrooms accompany a home theater with soundproof walls, a built-in wet bar, and intricate wood detailing, creating the ultimate cinematic experience. Outdoors, a spacious lanai with a summer kitchen overlooks an elevated terrace, pool, and spa, perfect for entertaining or relaxing while enjoying spectacular sunsets and nightly fireworks from nearby theme parks. This rare lakefront gem blends timeless elegance with a prime location, offering an unparalleled lifestyle in one of Central Florida’s most exclusive communities.

Listing Snapshot

Price
$4,330,000
Days On Site
N/A
Bedrooms
5
Inside Area (SqFt)
5,557 sqft
Total Baths
6
Full Baths
6
Partial Baths
0
Lot Size
0.56 Acres
Year Built
1990
MLS® Number
O6310606
Status
Sold
Property Tax
$38,334.25 (2024)
HOA/Condo/Coop Fees
$1,043 monthly
Sq Ft Source
Public Records

Property Details

General Features

16 items
Acres
0.56
Attached Garage
Yes
Direction Faces
Northeast
Foundation
Block, Slab
Garage
Yes
Garage Spaces
6
Levels
Two
Parking
Circular Driveway, Golf Cart Garage, Attached
Pets
Breed Restrictions
Property Sub Type
Single Family Residence
Sewer
Septic Tank
SqFt Total
8,162
Style
Custom, Mediterranean
Utilities
Cable Available, Natural Gas Available, Cable Connected, Electricity Connected, Natural Gas Connected, Underground Utilities
Water Source
Public
Zoning
P-D

Interior Features

18 items
Appliances
Bar Fridge, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
Cooling
Central Air
Flooring
Carpet, Tile, Wood
Furnished
Unfurnished
Heating
Central, Zoned
Interior
Crown Molding, Eat-in Kitchen, High Ceilings, Walk-In Closet(s), Wet Bar
Laundry Features
Inside, Laundry Room
Spa
Yes

Rooms

RoomDimensionsLevelFeatures
Bedroom 211x12FirstDescription - Room2
Bedroom 319x15SecondCeiling Fan(s), Stone Counters, Description - Room3
Bedroom 414x12SecondStone Counters, Description - Room4
Bedroom 512x23SecondDescription - Room8
Family Room16x23FirstCeiling Fan(s), Description - Room6
Great RoomFirst
KitchenFirst
Master Bedroom15x27FirstCeiling Fan(s), Double Vanity, Granite Counters, Description - Room1
Media Room20x22SecondBar, Granite Counters, Wet Bar, Description - Room5
OfficeFirstDescription - Room7

Exterior Features

14 items
Construction Details
Block, Stucco
Exterior
Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters, Dock
Fencing
Fenced
Lot Features
Landscaped, Near Golf Course, Paved, Waterfront
Patio And Porch
Patio, Rear Porch, Screened
Pool Features
In Ground, Salt Water, Private
Private Pool
Yes
Roof
Metal
Spa
Yes
Spa Features
In Ground
View
Lake, Water, Pool
Waterfront
Yes
Waterfront Features
Lake Privileges, Lake Front
Waterview
Lake, Water, Pool

Community Features

8 items
Association Amenities
Cable TV, Gated, Maintenance, Playground, Security
Association Fee
$3129.0
Association Fee Frequency
Quarterly
Community Features
Gated, Golf, Playground, Street Lights
MLS Area
34786 - Windermere
Township
23
Financing Terms Available
Cash, Conventional
Roads
Paved

Location

9724 Chestnut Ridge Dr, Windermere, FL 34786 · 34786 - Windermere

Neighborhood & Commute

ZIP Code 34786

Median household income
$127,371
Income per person
$64,053
Households
17,419
Average household size
2.82
Median age
38.9

Source: Walk Score.

Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.

Schools

Elementary School
Windermere Elem
Middle School
Chain of Lakes Middle
High School
Olympia High

Price & Status History

  1. Listing updated with changes from the MLS®
  2. Status changed to Closed

Friends & Family

Similar Homes

For sale in Windermere, single family residence, within 20% of this price.

Listing courtesy of ISLEWORTH REALTY LLC (407) 961-2979

Stellar MLS

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 2026, Stellar MLS.

Last checked: 2026-11-11 06:07 AM EST

Powered by Showcase IDX, a Constellation1 company

We use cookies to improve your experience and our marketing. Privacy Policy