5199 Latrobe Dr , Windermere, FL 34786
$5,300,000
- 6
- beds
- 6 full · 1 half
- baths
- 4,665
- sqft
- 1993
- year built
$5,300,000
5199 Latrobe Dr , Windermere, FL 34786
- 6
- beds
- 6 full · 1 half
- baths
- 4,665
- sqft
- 1993
- year built
- Status:
- Active
- MLS #:
- O6409961
- Neighborhood:
- ISLEWORTH
- County:
- Orange
- Listed By:
- Monica Lochmandy - ISLEWORTH REALTY LLC
- Agent Phone:
- (407) 230-6888
- Agent Email:
- mlochmandy@isleworth.com
Sponsoring Broker: Derek Eisenberg, Continental Real Estate Group, Inc
Virtually Staged. 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.
Highlights
- Residential
- Single Family Residence
- Built in 1993
- 0.52 Acre Lot
- $3,672/qtr HOA
- 4 Car Garage
- 167 days on Market
-
- Bedrooms
- 6
-
- Bathrooms
- 6 full · 1 half
-
- Year Built
- 1993
-
- Stories
- 1.0
-
- Architectural Style
- Traditional
-
- Construction Materials
- Stucco, Block, Concrete
-
- Foundation
- Slab
-
- Garage Spaces
- 4.0
-
- Parking Features
- Driveway, Attached, Garage
-
- Living Area
- 4665.0
-
- Interior Features
- Walk-In Closet(s), Stone Counters
-
- Appliances
- Dishwasher, Microwave, Refrigerator, Disposal, Exhaust Fan
-
- Flooring
- Ceramic Tile
-
- Furnished
- Unfurnished
-
- Exterior Features
- Rain Gutters
-
- Patio And Porch
- Deck
-
- Pool Features
- Gunite, Heated, In Ground, Private, Screen Enclosure
-
- Security Features
- Gated Community, Security Gate
-
- Cooling
- Central Air, Zoned
-
- Heating
- Electric, Zoned, Central
-
- Acres
- 0.52
-
- Lot Features
- On Golf Course, Landscaped, Paved
-
- Water Front Features
- Lake Privileges
-
- View
- Golf Course, Water
-
- Utilities
- Cable Available, Natural Gas Available, Cable Connected, Natural Gas Connected, Electricity Connected, Water Connected
-
- Water
- Public
-
- Area
- 34786 - Windermere
-
- County
- Orange
-
- City
- Windermere
-
- Neighborhood
- ISLEWORTH
-
- Zip Code
- 34786
-
- High School
- Olympia High
-
- Middle School
- Chain of Lakes Middle
-
- Elementary School
- Windermere Elem
-
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Estimated Value
$2,865,907
Estimated Sales Price Range:
$2,521,998 - $3,209,815
Source: Constellation Data Labs
Price History
| 05/27/2026 | Listed | $5,300,000 |
| Source: Stellar MLS #O6409961 | ||
| 06/05/2025 | Off Market | — |
| Source: Stellar MLS #O6315618 | ||
| 06/02/2022 | Off Market | — |
| Source: Stellar MLS #O6030513 | ||
| 10/04/2018 | Off Market | — |
| Source: Stellar MLS #O5737878 | ||
| 03/15/2007 | Off Market | — |
| Source: Stellar MLS #O4757403 | ||
| 07/26/2004 | Off Market | — |
| Source: Stellar MLS #O4571322 | ||
Source: MLS Data
Deed History
| 08/05/2022 | Warranty Deed | $2,575,000 |
| 02/20/2019 | Warranty Deed | $1,500,000 |
| 03/21/2008 | Correction Release | $0 |
| 08/21/2007 | Warranty Deed | $2,600,000 |
| 10/05/2004 | Warranty Deed | $1,700,000 |
| 02/09/2004 | Warranty Deed | $850,000 |
| 08/03/2000 | Warranty Deed | $1,120,000 |
| 10/03/1995 | Warranty Deed | $750,000 |
| 08/09/1993 | Warranty Deed | $663,300 |
Source: Public records via Constellation Data Labs
Mortgage History
| 02/20/2019 | ARM (Adjustable Rate Mortgage as of August, 2009) | $1,050,000 |
| 07/26/2013 | ARM (Adjustable Rate Mortgage as of August, 2009) | $1,351,200 |
| 08/21/2007 | Unknown | $1,580,000 |
| 09/27/2005 | Credit Line (Revolving) | $500,000 |
| 10/05/2004 | Unknown | $1,190,000 |
| 02/25/2004 | Credit Line (Revolving) | $160,000 |
| 02/09/2004 | Unknown | $680,000 |
| 09/25/2001 | New Conventional | $799,500 |
| 08/03/2000 | New Conventional | $784,000 |
| 08/09/1993 | $530,600 |
Source: Public records via Constellation Data Labs
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There are currently 34 properties available in Windermere, with 5 under contract to close soon. Properties in the city have an average sale price of $2,915,592 and typically spend 124 days on the market before being sold.
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Source: ez Home Search, MLS Data
Frequently Asked Questions
How do I schedule a tour of 5199 Latrobe Dr?
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How do I get more information about 5199 Latrobe Dr?
Click Ask a Question to talk with our team. You already know it is a 6 bed, 6 bath, listed for $5,300,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Windermere, and can even get you in to see the property quickly.
How do I get a virtual tour of 5199 Latrobe Dr?
Yes! A virtual tour is available for 5199 Latrobe Dr. Click here to view the full walkthrough and explore every room at your own pace. If you would like a guided virtual showing or have questions along the way, we can connect you with our local expert to walk you through it live.
How much is the monthly mortgage payment for 5199 Latrobe Dr?
With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 5199 Latrobe Dr at around $33,264. This includes estimated property taxes and insurance.
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How do I get pre-approved to buy 5199 Latrobe Dr?
Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.
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Can I negotiate the asking price for 5199 Latrobe Dr?
In most cases, yes. Whether 5199 Latrobe Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Windermere's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.
How do I make an offer on 5199 Latrobe Dr?
We can handle that for you. Our preferred local agent specializes in residentials in Windermere and can guide you through every step of the offer process.
You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.
What is the price per square foot for this home?
This home is listed at $5,300,000 with 4,665 sqft of space—that comes out to approximately $1,136 per square foot.
How long has this property been on the market?
5199 Latrobe Dr was listed on May 27, 2026, which means it's been on the market for 167 days.
Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.
When was this house built?
This home was built in 1993, making it approximately 33 years old.
What is the lot size of this property?
5199 Latrobe Dr sits on a 0.52-acre lot, which is 22,651 square feet.
What schools are assigned to this property?
Based on MLS info, this home is zoned for:
- Elementary: Windermere Elem
- Middle: Chain of Lakes Middle
- High: Olympia High
Want to see how these schools compare? Check out our Orange County School Guide to see ratings, reviews, and more for the schools in the area.
What are the property taxes for 5199 Latrobe Dr?
The most recent public record shows annual property taxes for 5199 Latrobe Dr were approximately $37,241. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.
Is there an HOA fee for this property, and what does it cover?
This home has an HOA fee of $3,672 paid quarterly.
This covers access to community features including: Playground, Gated, Cable TV, Security.
Is 5199 Latrobe Dr still available for sale?
Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.
Source: ez Home Search, MLS Data
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Listing information 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. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Stellar MLS. All rights reserved.
Last Updated: November 10, 2026 at 03:47PM | Source: Stellar MLS | MLS#: O6409961
