5036 Latrobe Drive, Windermere, FL 34786
For Sale $4,900,000
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Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests with custom French entry doors that flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas. A richly appointed library adds warmth and refinement, while two en-suite bedrooms complete this floor, including the primary suite. With its oversized windows capturing endless lake vistas, a large sitting area, exterior balcony, and an en-suite bath featuring dual vanities, a soaking tub, and walk-in shower, the primary suite is a sanctuary of light and serenity. On the lower level, the estate offers two expansive bonus areas joined by a well-equipped kitchenette. Ideal for gaming, entertaining, or working from home, both spaces connect effortlessly to the sun-drenched pool terrace—seamlessly integrating indoor luxury and outdoor living. A stunning mature oak tree anchors the propertys beautiful lakefront grounds, stretching gracefully toward the water’s edge—a signature of the property’s natural beauty. Beyond the oak tree, Lake Bessie shimmers in full view, offering a breathtaking backdrop to the estate. A rare combination of elegance, versatility, and iconic setting, this residence presents a lifestyle within one of Central Floridas finest communities.
Built-in Features
Central Vaccum
High Ceilings
Primary Bedroom Main Floor
Walk-In Closet(s)
Wet Bar
Cable TV
Playground
Taxes: $17,326.00
Tax Year: 2024
HOA Fee 1: $3,129.00
HOA Frequency 1: Quarterly
Condo Fee Frequency: Quarterly
Balcony
French Doors
Lighting
Bar Fridge
Built-In Oven
Convection Oven
Dishwasher
Disposal
Dryer
Freezer
Gas Water Heater
Ice Maker
Microwave
Range Hood
Refrigerator
Tankless Water Heater
Washer
Wine Refrigerator
Water
Lake Front
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
MLS Area: 34786 - Windermere
Price per Square Feet: $883.20
Water: Public
Lot Desc.: Landscaped, Near Golf Course
Construction: Block, Stucco
Date Listed: 2025-10-03 16:22:25
Pool: Yes
Pool Type: Deck, In Ground, Lighting
Private Spa: No
Garage Spaces: 3
Flooring: Marble, Tile, Wood
Roof: Tile
Heating: Central, Electric, Natural Gas
Cooling: Central Air, Zoned
Pets: Breed Restrictions
Sewer: Septic Tank
Amenities: Cable Tv, Playground
Listing Courtesy Of: Isleworth Realty Llc
mlochmandy@isleworth.com
Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests with custom French entry doors that flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas. A richly appointed library adds warmth and refinement, while two en-suite bedrooms complete this floor, including the primary suite. With its oversized windows capturing endless lake vistas, a large sitting area, exterior balcony, and an en-suite bath featuring dual vanities, a soaking tub, and walk-in shower, the primary suite is a sanctuary of light and serenity. On the lower level, the estate offers two expansive bonus areas joined by a well-equipped kitchenette. Ideal for gaming, entertaining, or working from home, both spaces connect effortlessly to the sun-drenched pool terrace—seamlessly integrating indoor luxury and outdoor living. A stunning mature oak tree anchors the propertys beautiful lakefront grounds, stretching gracefully toward the water’s edge—a signature of the property’s natural beauty. Beyond the oak tree, Lake Bessie shimmers in full view, offering a breathtaking backdrop to the estate. A rare combination of elegance, versatility, and iconic setting, this residence presents a lifestyle within one of Central Floridas finest communities.
Property Details
Price: $4,900,000
Sq Ft: 5,548
($883 per sqft)
Bedrooms: 5
Bathrooms: 4
Partial Baths: 1
City: Windermere
County: Orange
Type: Single Family Reside
Development: Isleworth
Acres: 0.69
Year Built: 1990
Listing Number: O6346003
Status Code: A-Active
Taxes: $17,326.00
Tax Year: 2024
Garage:
3
Pets Allowed: Breed Restrictions
Interior Features:
Built-in Features
Central Vaccum
High Ceilings
Primary Bedroom Main Floor
Walk-In Closet(s)
Wet Bar
Amenities:
Cable TV
Playground
Financial Information:
Taxes: $17,326.00
Tax Year: 2024
HOA Fee 1: $3,129.00
HOA Frequency 1: Quarterly
Condo Fee Frequency: Quarterly
Exterior Features:
Balcony
French Doors
Lighting
Equipment:
Bar Fridge
Built-In Oven
Convection Oven
Dishwasher
Disposal
Dryer
Freezer
Gas Water Heater
Ice Maker
Microwave
Range Hood
Refrigerator
Tankless Water Heater
Washer
Wine Refrigerator
View:
Water
Waterfront Description:
Lake Front
School Information:
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
Additional Information:
MLS Area: 34786 - Windermere
Price per Square Feet: $883.20
Water: Public
Lot Desc.: Landscaped, Near Golf Course
Construction: Block, Stucco
Date Listed: 2025-10-03 16:22:25
Pool: Yes
Pool Type: Deck, In Ground, Lighting
Private Spa: No
Garage Spaces: 3
Flooring: Marble, Tile, Wood
Roof: Tile
Heating: Central, Electric, Natural Gas
Cooling: Central Air, Zoned
Pets: Breed Restrictions
Sewer: Septic Tank
Amenities: Cable Tv, Playground
Map of 5036 Latrobe Drive, Windermere, FL 34786
Listing Courtesy Of: Isleworth Realty Llc
mlochmandy@isleworth.com