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.
Property Details
Price:
$4,900,000
MLS #:
O6346003
Status:
Pending
Beds:
5
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Oct 3, 2025
Finished Sq Ft:
5,548
Total Sq Ft:
30,056
Lot Size:
29,911 sqft / 0.69 acres (approx)
Year Built:
1990
See this Listing
Schools
Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High
Interior
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
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Marble, Tile, Hardwood
Heating
Central, Electric, Natural Gas
Interior Features
Built-in Features, Central Vacuum, High Ceilings, Primary Bedroom Main Floor, Walk-In Closet(s), Wet Bar
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Architectural Style
Traditional
Association Amenities
Cable TV, Playground
Attached Garage YN
1
Community Features
Private Boat Ramp, Water Access, Community Mailbox, Deed Restrictions, Gated Community – Guard, Golf Carts OK, Golf, Playground
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
East
Exterior Features
Balcony, French Doors, Irrigation System, Lighting
Garage Spaces
3
Lot Features
Landscaped, Near Golf Course
Patio And Porch Features
Enclosed
Roof
Tile
Security Features
Security System
View
Water
Waterfront Features
Lake Front
Financial
HOA Fee
$3,672
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Security
HOA Name
Dan O’Connell
HOA Phone
407-909-2071
Tax Year
2024
Taxes
$17,326
Map
Community
- Address5036 LATROBE DRIVE WINDERMERE FL
- SubdivisionISLEWORTH
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ACREAGE AND UNREC
- ALADAR ON LAKE BUTLER
- ASHLIN FARK PH 2
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- BELLA VITA ESTATES
- BELLARIA
- BELMERE VILLAGE
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BELMERE VILLAGE G4 50 58
- BELMERE VILLAGE G5
- BELMERE VLG G2
- BUTLER BAY
- BUTLER RIDGE
- CARRINGTON
- CASA DEL LAGO REP
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- CREEKS RUN
- DAVIS SHORES
- DOWN ACRES ESTATES
- DOWN POINT SUB
- DOWNS COVE CAMP SITES
- EDEN ISLE
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE AT WINDERMERE LANDING
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTATES AT WINDERMERE
- FARMS
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- ISLEWORTH
- ISLEWORTH 01 AMD
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 01
- KEENES POINTE UNIT 03 46/104
- KEENES POINTE UNIT 2
- KEENES POINTE UNIT 7
- KEENES POINTE UNIT 9
- KEENES POINTE UT 04 SEC 31 48 82
- KEENES POINTE UT 06 50 95
- LAKE BURDEN
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #35 36
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CAWOOD ESTS REP
- LAKE CRESENT RESERVE
- LAKE CYPRESS COVE PH 02
- LAKE DAVIS RESERVE
- LAKE DOWN COVE
- LAKE DOWN ESTATES
- LAKE HANCOCK SHORES
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 02
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 04
- LAKE SAWYER SOUTH PH 3
- LAKES
- LAKES OF WINDERMERE PH 1
- LAKES OF WINDERMERE PH 2A
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE PH 3
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE VILLAGE TWNHMS
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE CONDO
- LAKESIDE/LKS/WINDERMERE PH 10
- LAKESIDE/LKS/WINDERMERE PH 4
- LEGADO
- MARINA BAY ESTATES
- MARSH SUB
- MERRICK LANDING
- METCALF PARK REP
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE
- OASIS COVE II/LAKESIDE VILLAGE PH
- OXFORD MOOR 47/30
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- PROVIDENCE PH 2
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PH 03 51 01
- RESERVE AT LAKE BUTLER
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND 45/120
- RESERVE AT LAKE BUTLER SOUND UNIT 02
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- RESERVE/BELMERE PH 04
- ROBERTS LANDING
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SHORES SUB
- SILVER WOODS
- SILVER WOODS PH 01
- SILVER WOODS PH 02
- SILVER WOODS PH 03A
- SILVER WOODS PH 04
- SILVER WOODS PH 3
- SOUTHBRIDGE VILLAGE
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT BEACH
- SUMMERPORT PH 02
- SUMMERPORT PH 03
- SUMMERPORT PH 04 C E F & G
- SUMMERPORT PH 05
- SUMMERPORT TRL
- SUNSET BAY
- TENNYSON PK/SUMMERPORT
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TUSCANY RIDGE 50 141
- VINEYARDS/HORIZON WEST PH 2A
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERSIDE
- WATERSTONE
- WATERSTONE A D E F G H J L
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WEST LAKE BUTLER ESTATES
- WEST POINT COMMONS
- WESTOVER CLUB
- WESTOVER CLUB PH 02 47/71
- WESTOVER CLUB PH 02 REP
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES / BELMERE PH 02
- WHITNEY ISLES AT BELMERE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WINDDERMERE POINTE
- WINDERMERE
- WINDERMERE DOWNS
- WINDERMERE GRANDE
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE ISLE-PH 2
- WINDERMERE LNDGS PH 02
- WINDERMERE RESERVE
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PHASE 1C 80/15 LOT 113
- WINDERMERE TRAILS PHASE 4A
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH IA
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
Market Summary
Current real estate data for Single Family in WINDERMERE as of Apr 27, 2026
290
Single Family Listed
97
Avg DOM
460
Avg $ / SqFt
$2,237,531
Avg List Price
Property Summary
- Located in the ISLEWORTH subdivision, 5036 LATROBE DRIVE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $4,900,000 and features 5 beds, 5 baths, and has approximately 5,548 square feet of living space, and was originally constructed in 1990. The current price per square foot is $883. The average price per square foot for Single Family listings in WINDERMERE is $460. The average listing price for Single Family in WINDERMERE is $2,237,531. To schedule a showing of MLS#o6346003 at 5036 LATROBE DRIVE in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of ISLEWORTH REALTY LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 5036 LATROBE DRIVE
WINDERMERE, FL

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