Date
Details
Price
Change
Source
10/03/2025
Listed
$4,900,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/47
$4,900,000
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Property Description
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 property's 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 Florida's finest communities.
Full Property Details
Full Property Details for 5036 Latrobe Dr
General
- Price: $4,900,000
- HOA FEE: $1,043/month
- HOA FEE FREQ.: Quarterly
- Taxes: $17,326 (2024)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6346003
- Updated: 10/7/2025
- Added to Site: 105 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 8
- Interior Features: Built-in Features, Central Vacuum, High Ceilings, Primary Bedroom Main Floor, Walk-In Closet(s), Wet Bar
- Fireplace: Yes
- Fireplace(s): Living Room
- Appliances: 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
- Flooring: Marble, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 4
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Cable TV, Playground
- Pool: Yes
- Private Pool: Yes
- Pool Description: Deck, In Ground, Lighting
- Security/Safety: Security System
Exterior
- Exterior Features: Balcony, French Doors, Irrigation System, Lighting
- Deck/Patio: Enclosed
- Porch/Patio/Deck: Enclosed
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
Location
- Area: 34786 - Windermere
- County: Orange
- Development Name: 34786 - Windermere
- Subdivision: ISLEWORTH
- Driving Directions: I-4 to Conroy Windermere Road west to Isleworth subdivision. Turn Right on Latrobe and home is on the Right.
- Direction Faces: East
School Information
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
Community
- Community Name: 34786 - Windermere
- Community Features: Private Boat Ramp, Water Access, Community Mailbox, Deed Restrictions, Gated Community - Guard, Golf Carts OK, Golf, Playground
- Optional Amenities: Cable TV, Playground
- Association: Yes
- Assoc. Name: Dan O’Connell
- Assoc. Fees Include: 24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Security
- Pet Restrictions: Per Orange County breed restrictions, number limits and leash laws.
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Central, Electric, Natural Gas
Utilities
- Sewer: Septic Tank
- Water District: LAKE BESSIE
- Water: Public
- Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Street Lights
Structural Information
- Architectural Info: Traditional
- Architectural Style: Traditional
- Exterior Const.: Block, Stucco
- Roof: Tile
- Stories/Levels: Two
- Square Feet: 5,548
- Sq. Ft. Source: Owner
- Year Built: 1990
Lot Features
- Property View: Water
- Lot Size (Acres): 0.69
- Lot Size (Sq. Ft.): 29,911
- Lot Size: 29911
- Street/Road Desc.: Paved
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Lake
- Water Extras: Yes
- Water Front Name: LAKE BESSIE
- Water Front Desc.: Lake Front
Financial Considerations
- Association Fee: $3,129
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $17,326
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: ISLEWORTH 16/118 LOT 22
- Flood Zone Info: AE
- APN: 162328389900220
- Property ID: 162328389900220
Listed by Isleworth Realty Llc
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Listing agents
— 5036 Latrobe Dr —
Isleworth Realty Llc
Isleworth Realty Llc
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 5036 Latrobe Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Windermere Elementary School 11125 Park Avenue, Windermere, FL 34786 | K-5 | 1.8 mi |
Chain Of Lakes Middle School 8700 Conroy Windermere Road, Orlando, FL 32835 | 6-8 | 1.1 mi |
Olympia High School 4301 South Apopka Vineland Road, Orlando, FL 32835 | 9-12 | 1.1 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5036 Latrobe Dr
Tax History
Tax History for 5036 Latrobe Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$17,326
—
$1,109,293
3%
2024
$17,326
7%
$1,078,030
3%
2023
$16,159
4%
$1,046,631
6%
2021
$15,501
-1%
$986,550
-3%
2022
$15,689
1%
$1,016,147
4%
2021
$15,501
1%
$972,929
2%
2019
$15,274
1%
$951,055
2%
2018
$15,167
1%
$933,322
2%
2017
$15,002
—
$914,125
2%
2016
$14,979
-2%
$895,323
1%
2015
$15,244
-1%
$889,099
1%
2014
$15,397
2%
$882,043
1%
2013
$15,091
—
$869,008
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 5036 Latrobe Dr
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Sold by Stockworth Realty Group
5036 Latrobe Drive, Windermere, FL 34786 (MLS# O6346003) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 5036 Latrobe Drive is currently listed for $4,900,000 and was received on October 03, 2025. Want to learn more about 5036 Latrobe Drive? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.