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.
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Beds
5
Baths
6
Stories
2
Lot width
—
Lot depth
—
Lot size
1.86 Acres
Year renovated
1995
Sq. Ft.
5,402
Year built
1990
Style
Single Family Residential
County
Orange County
APN
282316389900150
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
P-D
Planned Development District
To provide for planned residential communities, containing a variety of residential structures and diversity of building arrangements, with complementary and compatible commercial or industrial uses or both; planned commercial centers with complementary and compatible residential or industrial uses or both; planned tourist commercial centers with complementary and compatible uses which may include tourist attractions, theme parks, residential and light storage; or planned industrial parks with complementary and compatible residential or commercial uses or both; and public and quasipublic facilities developed in accordance with an approved development plan; To allow diversification of uses, structures, and open spaces in a manner compatible with existing and permitted land uses on abutting properties; To reduce improvement and energy costs through a more efficient use of land design and smaller networks of utilities and streets than is possible through application of other zoning districts and subdivision requirements; To ensure that development will occur according to limitations of use, design, density, coverage and phasing stipulated on an approved development plan; To preserve the natural amenities and environmental assets of the land by encouraging the preservation and improvement of scenic and functional open areas; To encourage an increase in the amount and use of open space areas by permitting a more economical and concentrated use of building areas than would be possible through conventional zoning districts; To provide maximum opportunity for application of innovative concepts of site planning in the creation of aesthetically pleasing living, shopping and working environments on properties of adequate size, shape and location; The P-D district is a flexible zoning district which is intended to provide an appropriate balance between the intensity of development and the ability to provide adequate capacity within the support services and facilities.
Appliances: Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
Flooring: Carpet, Tile, Travertine, Wood
Building Elevator YN: 0
Exterior
Building Information
Construction Materials: Block, Stucco
Roof: Metal
Exterior Features
Patio And Porch Features: Patio, Rear Porch, Screened
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Public, Underground Utilities
Additional Water Information: The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a private, community boat ramp for our residents eager to enjoy these great waters.
Location
Multi-Family Financial Information
Total Annual Fees: $12,516
Total Monthly Fees: $1,043
Multi-Unit Information
Unit Number YN: 0
Furnished: Unfurnished
HOA Information
Association Name: Dan O'Connell
Has HOA
MFR_Association2YN: 0
Association Fee Requirement: Required
Association Approval Required Y/N: 1
Monthly HOA Amount: 1043.00
Association Amenities: Cable TV, Gated, Maintenance, Playground, Security
Middle Or Junior High School: Chain of Lakes Middle
High School: Olympia High
Location Information
Directions: I-4 to Conroy Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive.Turn right on Latrobe, turn right on Chestnut Ridge Drive. Estate will be on the Left.
Community Information
Community Features: Community Mailbox, Golf Carts OK, Golf, Playground, Street Lights
Pets Allowed: Breed Restrictions
Public facts
Beds: 5
Baths: 6.0
Sq. Ft.: 5,402
Stories: 2.0
Lot Size: 1.86 acres
Style: Single Family Residential
Year Built: 1990
Year Renovated: 1995
County: Orange County
APN: 282316389900150
Home facts updated by county records on Aug 17, 2026
Other
Miscellaneous Information
Third Party YN: 1
Listing Information
Attribution Contact: 407-909-9000
Previous Status: Pending
Backups Requested YN: 0
Listing Date Information
Days to Contract: 49
Status Contractual Search Date: 2025-07-25
Listing Price Information
Calculated List Price By Calculated Sq Ft: 863.78
Green Information
Green Verification Count: 0
Direction Faces: Northeast
Home Information
Living Area: 5557
Living Area Units: Square Feet
Living Area Source: Public Records
Living Area Meters: 516.26
Building Area Total: 8162
Building Area Units: Square Feet
Building Area Source: Public Records
Foundation Details: Block, Slab
Levels: Two
Around this home
Schools
Windermere Elementary School
Public PreK-5 • Assigned • 1.7mi
10/10
Chain Of Lakes Middle School
Public 6-8 • Assigned • 1.1mi
3/10
Olympia High School
Public 9-12 • Assigned • 1.1mi
5/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
8/10 Heat Factor
6 days above 108° expected this year, 20 days in 30 years
9/10 Wind Factor
99% chance of strong winds in next 30 years
1/10 Air Factor
0 unhealthy days expected this year, 0 days in 30 years
Provided by First Street
Historical weather
Windermere, FL • 34786
Average low and high temperatures (°F)
68
48
75
54
81
60
84
65
90
72
91
74
92
76
91
76
89
75
83
69
78
60
73
55
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
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Nov
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Sun exposure
In this area, properties receive around 8.6 hours in
June and 6.7 hours in December, placing it above the
U.S. average for solar exposure.
8.6 hrs
6.7 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$4.59M – $5.56M
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