$5,300,000
5199 Latrobe Dr
Windermere, FL 34786
Property type
Year built
Lot size
Price / sq ft
HOA dues
Day on market
Garage spaces
Flood zone
About this home
Set within the gates of renowned Isleworth, this beautifully reimagined golf-front estate presents an exceptional opportunity to experience refined Central Florida living at its finest. Perfectly positioned along Isleworth’s celebrated championship golf course, the residence captures sweeping views of the fourth fairway while offering the privacy, comfort, and sophistication synonymous with the community’s distinguished lifestyle.Thoughtfully renovated and impeccably maintained, the home encompasses more than 6,600 square feet of combined indoor living and covered outdoor space, where contemporary finishes, designer lighting, and warm architectural details create an atmosphere that is both elegant and inviting. Every space has been intentionally curated—from the centrally located gourmet kitchen to the well-appointed utility spaces, resulting in a residence designed for effortless everyday living and elevated entertaining alike.The flexible floor plan offers exceptional versatility to suit a variety of lifestyles, accommodating configurations of up to six bedrooms, or alternatively a combination of bedrooms, office space, fitness room, or additional gathering areas. Six full baths and one half bath are finished with timeless materials and meticulous attention to detail throughout.At the heart of the home, the designer kitchen features sleek white cabinetry, quartz countertops, stainless steel appliances, and seamless connectivity to the expansive family room and casual dining area. Large glass openings invite natural light indoors while providing direct access to the screened lanai and resort-style pool environment beyond.The private primary suite serves as a luxurious retreat, highlighted by porcelain plank flooring, a spa-inspired bath with freestanding soaking tub and walk-in shower, and an oversized custom walk-in closet. Additional guest suites provide comfort and flexibility for family and visitors, while the home’s four-car garage and expansive motor court offer abundant space for automobile enthusiasts and guests alike.Outdoors, the estate transforms into a true private sanctuary. A newly redesigned saltwater pool and spa are enclosed within a custom lanai structure and complemented by an expansive new pool deck, creating a year-round setting for relaxation and entertaining. Lush landscaping, a fenced rear lawn, and panoramic golf course vistas further enhance the sense of serenity and exclusivity.Blending timeless elegance with modern livability, this exceptional Isleworth residence offers a rare combination of spacious design, privacy, and premier golf-front surroundings within one of the finest golf club communities in the world.
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 history1 days on market
- Status: ActiveMay 27, 2026
- Listed$5,300,000May 27, 2026
- Price increased$5,300,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 1
- Subdivision
- Isleworth
- County
- Orange
- Year built
- 1993
- Living area
- 4,665 sq ft
- Price/sq ft
- $1,136
- Building area
- 6,622 sq ft (Public Records)
- Lot size
- 22,749 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- X
- Garage
- 4 spaces
- Pool
- Private pool
- Annual taxes
- $37,241 (2025)
- Parcel #
- 16-23-28-3899-03-150
- Zoning
- P-D
- MLS #
- O6409961
Interior Details
- Bedrooms
- 6
- Full bathrooms
- 6
- Half bathrooms
- 1
- Flooring
- Ceramic Tile
- Appliances
- Built-In Oven, Dishwasher, Disposal, Exhaust Fan, Microwave, Refrigerator
- Interior features
- Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)
- Laundry
- Electric Dryer Hookup, In Kitchen, Laundry Room, Washer Hookup
- Stories / Levels
- One
- Direction faces
- Southeast
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric, Zoned
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 4
- Attached garage
- Yes
- Parking features
- Driveway, Garage
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
- 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
- French Doors, Rain Gutters
- Construction materials
- Block, Concrete, Stucco
- Roof
- Concrete, Tile
- Foundation
- Slab
- Pool
- Private pool
- Water access
- Yes
- Road surface
- Asphalt
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Water 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 1 | First | |
| Bedroom 2 | First | |
| Bedroom 3 | First | |
| Bedroom 4 | First | |
| Bedroom 5 | First | |
| Family Room | First | |
| Kitchen | First | |
| Living Room | First | |
| Dining Room | First |
Listing Details
- Listing date
- 2026-05-25
- On market date
- 2026-05-27
- Original list price
- $5,300,000
- Occupant type
- Vacant
- MLS area
- 34786 - Windermere
- Listing AOR
- Orlando Regional
- Status changed
- 2026-05-27
- Tax legal description
- ISLEWORTH 16/118 LOT 315
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
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 Left or Right. Have drivers license or passport ready to for guard gate for entry.
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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 May 28, 2026 at 4:03 PM 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.
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