$4,900,000
5036 Latrobe Drive
Windermere, FL 34786
Listing updated: June 29, 2026 at 10:59 AM ET
Listing courtesy of Isleworth Realty Llc · Monica Lochmandy · MLS #O6346003 · Pending · 407-909-9000Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
Under contract-accepting backup offers. 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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history175 days on market
- Status: PendingMar 28, 2026
- Listed$4,900,000Oct 3, 2025
- Price increased$4,900,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Pending
- Days on market
- 175
- Subdivision
- Isleworth
- County
- Orange
- Year built
- 1990
- Living area
- 5,548 sq ft
- Price/sq ft
- $883
- Building area
- 30,056 sq ft (Owner)
- Lot size
- 29,911 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- AE (12095C0385F)
- Garage
- 3 spaces
- Pool
- Private pool
- Annual taxes
- $17,326 (2024)
- Parcel #
- 16-23-28-3899-00-220
- Zoning
- P-D
- MLS #
- O6346003
Ask about this home
Have a question? Ask the broker directly.
Ryan Solberg answers personally — no call center, no spam. Your question goes straight to him.
Interior Details
- Bedrooms
- 5
- Full bathrooms
- 4
- Half bathrooms
- 1
- Flooring
- Marble, Tile, Wood
- 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
- Interior features
- Built-in Features, Central Vaccum, High Ceilings, Primary Bedroom Main Floor, Walk-In Closet(s), Wet Bar
- Laundry
- Inside, Laundry Room
- Stories / Levels
- Two
- Direction faces
- East
- Fireplace
- Yes
- In-law suite
- Yes
Heating & Cooling
- Heating
- Central, Electric, Natural Gas
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 3
- Attached garage
- Yes
HOA & Financial
- HOA fee
- $3,672 / Quarterly
- Monthly HOA
- $1,224/mo
- Total monthly fees
- $1,224/mo
- Total annual fees
- $14,688
- HOA name
- Dan O’Connell
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Per Isleworth Community Association (ICA)
- Approval process
- Per Isleworth Community Association (ICA)
Exterior & Construction
- Exterior features
- Balcony, French Doors, Lighting
- Construction materials
- Block, Stucco
- Roof
- Tile
- Foundation
- Slab
- Pool
- Private pool
- Waterfront
- Yes
- Water access
- Yes
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected
Community
- Pets allowed
- Breed Restrictions
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | |
| Bedroom 2 | First | |
| Dining Room | First | |
| Kitchen | First | |
| Great Room | First | |
| Bedroom 3 | Basement | |
| Bedroom 4 | Basement | |
| Bedroom 5 | Basement |
Listing Details
- Listing date
- 2025-07-29
- On market date
- 2025-10-03
- Original list price
- $4,900,000
- Occupant type
- Vacant
- MLS area
- 34786 - Windermere
- Listing AOR
- Orlando Regional
- Status changed
- 2026-03-28
- Tax legal description
- ISLEWORTH 16/118 LOT 22
Flood risk
FEMA Special Flood Hazard Area (1% annual-chance / “100-year” floodplain). Flood insurance is generally required by mortgage lenders.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
I-4 to Conroy Windermere Road west to Isleworth subdivision. Turn Right on Latrobe and home is on the Right.
More homes like this
$2,999,000
5073 Latrobe Dr
Windermere, FL 34786
4 bd · 6 ba · 4,706 sqft
Isleworth
MLS ID #O6414325, ISLEWORTH REALTY LLC.
Listing provided by Stellar MLS
$3,200,000
4819 Alexandra Garden Ct
Windermere, FL 34786
4 bd · 5 ba · 3,745 sqft
Isleworth
MLS ID #O6330108, ISLEWORTH REALTY LLC.
Listing provided by Stellar MLS
$3,299,000
5145 Latrobe Dr
Windermere, FL 34786
4 bd · 5 ba · 4,512 sqft
Isleworth
MLS ID #O6382287, SOUTHERN REALTY GROUP LLC.
Listing provided by Stellar MLS
$3,299,999
5001 Latrobe Dr
Windermere, FL 34786
5 bd · 5 ba · 4,417 sqft
Isleworth
MLS ID #O6389183, Q BOUTIQUE SPECIALTY REALTY INC.
Listing provided by Stellar MLS
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 29, 2026 at 10:59 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA