5199 Latrobe Dr
Windermere, FL 34786
- 6 Beds
- 6.5 Baths
- 4,665 sqft (on 0.52 acres)
6 Beds
6.5 Baths
4,665 sqft
(on 0.52 acres)
Local Information
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Description
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.
Home Highlights
Parking
4 Car Garage
Outdoor
Deck, Pool
View
Golf Course, Water
HOA
$1,224/Monthly
Price/Sqft
$1,136
Listed
21 days ago
Home Details for 5199 Latrobe Dr
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Interior Details Number of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Dining Room, Family Room, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 6Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 4665 Square Feet |
Appliances & Utilities Utilities: Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Street Lights, Water ConnectedAppliances: Oven, Dishwasher, Disposal, Exhaust Fan, Microwave, RefrigeratorDishwasherDisposalLaundry: Electric Dryer Hookup,In Kitchen,Laundry Room,Washer HookupMicrowaveRefrigerator |
Heating & Cooling Heating: Central,Electric,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central |
Fireplace & Spa Fireplace: Living RoomSpa: Heated, In GroundHas a Fireplace |
Gas & Electric Has Electric on Property |
Windows, Doors, Floors & Walls Door: French DoorsFlooring: Ceramic Tile |
Levels, Entrance, & Accessibility Stories: 1Number of Stories: 1Levels: OneFloors: Ceramic Tile |
View Has a ViewView: Golf Course, Water |
Security Security: Gated Community, Security Gate |
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Exterior Home Features Roof: Concrete TilePatio / Porch: DeckExterior: Irrigation System, Rain GuttersFoundation: SlabHas a Private Pool |
Parking & Garage Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Driveway,Split Garage |
Pool Pool: Deck, Gunite, Heated, In Ground, Lighting, Screen EnclosurePool |
Frontage Waterfront: Lake PrivilegesRoad Surface Type: Paved, AsphaltNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
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Cumulative Days on Market: 1Days on Market: 21 |
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Year Built Year Built: 1993 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Traditional |
Building Construction Materials: Block, Concrete, StuccoNot a New ConstructionNo Additional Parcels |
Property Information Parcel Number: 162328389903150 |
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Price List Price: $5,300,000Price Per Sqft: $1,136 |
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MLS Status: Active |
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Direction & Address City: WINDERMERECommunity: ISLEWORTH |
School Information Elementary School: Windermere ElemJr High / Middle School: Chain of Lakes MiddleHigh School: Olympia High |
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Listing Agent Listing ID: O6409961 |
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Building Area Building Area: 6622 Square Feet |
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Community Features: Community Boat Ramp, Water Access, Buyer Approval Required, Community Mailbox, Gated Community - Guard, Golf Carts OK, Golf, ParkNot Senior Community |
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HOA Fee Includes: 24-Hour Guard, Cable TV, Reserve Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, SecurityHOA Name: Dan O’ConnellHOA Phone: 407-909-2071Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $1,224/Monthly |
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Lot Area: 0.52 acres |
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Special Conditions: None |
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Listing Terms: Cash, Conventional |
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Business Information Ownership: Fee Simple |
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Mls Number: O6409961Water View: WaterShowing Advance Notice: 24Showing AttendedShowing Requirements: 24 Hour Notice, Appointment Only, Call Before Showing, Call Listing Agent, Listing Agent Must Accompany, See RemarksUniversal Property Id: US-12095-N-162328389903150-R-N |
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HOA Amenities: Cable TV,Fence Restrictions,Gated,Playground,Security,Vehicle Restrictions |
Last check for updates: about 14 hours ago
Listing Provided by: Monica Lochmandy, (407) 230-6888
ISLEWORTH REALTY LLC, (407) 909-9000
Michelle Corbin, (407) 491-2690
ISLEWORTH REALTY LLC, (407) 909-9000
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6409961

Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Market trends in Windermere
Last updated May 2026
Avg. sale price
$672K
$26.67KMoM
Sale-to-List Price
97.5%
0.3%MoM
Price per sq ft
$262
$6MoM
Available listings
291
2MoM
Price History for 5199 Latrobe Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 05/27/2026 | $5,300,000 | Listed For Sale | Stellar MLS #O6409961 |
| 12/31/2025 | $5,494,000 | ListingRemoved | Stellar MLS #O6315618 |
| 06/05/2025 | $5,494,000 | Listed For Sale | Stellar MLS #O6315618 |
| 08/05/2022 | $2,575,000 | Sold | N/A |
| 06/09/2022 | $2,650,000 | Pending | Stellar MLS #O6030513 |
| 06/02/2022 | $2,650,000 | Listed For Sale | Stellar MLS #O6030513 |
| 02/20/2019 | $1,500,000 | Sold | N/A |
| 10/04/2018 | $1,695,000 | PriceChange | Agent Provided |
| 06/01/2018 | $1,775,000 | PriceChange | Agent Provided |
| 05/07/2018 | $1,898,000 | PriceChange | Agent Provided |
| 01/19/2018 | $1,899,000 | PriceChange | Agent Provided |
| 09/26/2017 | $1,999,000 | Listed For Sale | Agent Provided |
| 02/15/2017 | $1,995,000 | ListingRemoved | Agent Provided |
| 01/11/2017 | $1,995,000 | Listed For Sale | Agent Provided |
| 04/14/2016 | $1,995,000 | ListingRemoved | Agent Provided |
| 08/17/2015 | $1,995,000 | Listed For Sale | Agent Provided |
| 07/12/2014 | $1,990,000 | ListingRemoved | Agent Provided |
| 04/01/2014 | $1,990,000 | Listed For Sale | Agent Provided |
| 11/29/2011 | $2,395,000 | ListingRemoved | Agent Provided |
| 11/09/2011 | $2,395,000 | Listed For Sale | Agent Provided |
| 05/29/2011 | $2,495,000 | ListingRemoved | Agent Provided |
| 02/11/2011 | $2,495,000 | Listed For Sale | Agent Provided |
| 12/01/2010 | $2,495,000 | ListingRemoved | Agent Provided |
| 11/13/2010 | $2,495,000 | PriceChange | Agent Provided |
| 05/29/2010 | $2,795,000 | Listed For Sale | Agent Provided |
| 08/21/2007 | $2,600,000 | Sold | N/A |
| 10/05/2004 | $1,700,000 | Sold | N/A |
| 02/09/2004 | $850,000 | Sold | N/A |
| 08/03/2000 | $1,120,000 | Sold | N/A |
| 10/03/1995 | $750,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $36,356 |
| Assessment | $2,197,938 |
Home facts updated by county records
Comparable Sales for 5199 Latrobe Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.15 | Single-Family Home | $4,400,000 | 12/30/25 | 6 | 8.5 | 5,721 | |
0.37 | Single-Family Home | $2,750,000 | 10/31/25 | 5 | 7 | 6,219 | |
0.45 | Single-Family Home | $4,330,000 | 07/25/25 | 5 | 6 | 5,557 | |
0.12 | Single-Family Home | $5,200,000 | 07/29/25 | 6 | 8 | 10,701 | |
0.16 | Single-Family Home | $5,000,000 | 05/31/26 | 4 | 6 | 9,636 | |
0.51 | Single-Family Home | $3,250,000 | 10/20/25 | 5 | 6.5 | 6,700 | |
0.56 | Single-Family Home | $4,500,000 | 03/11/26 | 6 | 7 | 6,816 | |
0.54 | Single-Family Home | $3,250,000 | 09/26/25 | 5 | 6.5 | 6,328 | |
0.78 | Single-Family Home | $2,500,000 | 09/24/25 | 4 | 5 | 4,330 | |
0.42 | Single-Family Home | $2,950,000 | 02/20/26 | 3 | 3.5 | 4,089 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 5199 Latrobe Dr.
What Locals Say about Windermere
At least 270 Trulia users voted on each feature.
93 % Say it's dog friendly
92 % Say there are sidewalks
87 % Say car is needed
87 % Say parking is easy
81 % Say people would walk alone at night
80 % Say it's quiet
79 % Say there's holiday spirit
78 % Say kids play outside
75 % Say streets are well-lit
64 % Say yards are well-kept
60 % Say they plan to stay for at least 5 years
59 % Say it's walkable to grocery stores
56 % Say there's wildlife
55 % Say it's walkable to restaurants
54 % Say neighbors are friendly
40 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Monica Lochmandy, ISLEWORTH REALTY LLC, (407) 909-9000
Agent Phone: (407) 230-6888

5199 Latrobe Dr, Windermere, FL 34786 is a 6 bedroom, 7 bathroom, 4,665 sqft single-family home built in 1993. This property is currently available for sale and was listed by Stellar MLS on May 27, 2026. The MLS # for this home is MLS# O6409961.

