5199 LATROBE DR, Windermere, FL 34786
Property image
Property image
FOR SALE
3D VIEW
0.52 ACRES

$5,300,000

  • 6 Beds
  • 6.5 Baths
  • 4,665 sqft (on 0.52 acres)

5199 LATROBE DR, Windermere, FL 34786

Est. Mortgage $38,717/mo*
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Home Highlights

Single-Family Home
Built in 1993
0.52 acre lot
$1,136/sqft
4 Car Garage
HOA $1,224/mo

Local Information

  • Map ViewExplore the area around 5199 LATROBE DR.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 15 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

Home Details for 5199 LATROBE DR

Interior Features

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

Exterior Features

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

Days on Market

Cumulative Days on Market: 57Days on Market: 107

Property Information

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

Price & Status

Price
List Price: $5,300,000Price Per Sqft: $1,136

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: WINDERMERECommunity: ISLEWORTH
School Information
Elementary School: Windermere ElemJr High / Middle School: Chain of Lakes MiddleHigh School: Olympia High

Agent Information

Listing Agent
Listing ID: O6409961

Building

Building Area
Building Area: 6622 Square Feet

Community

Community Features: Community Boat Ramp, Water Access, Buyer Approval Required, Community Mailbox, Gated Community - Guard, Golf Carts OK, Golf, ParkNot Senior Community

HOA

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

Lot Information

Lot Area: 0.52 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

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

Additional Information

HOA Amenities: Cable TV,Fence Restrictions,Gated,Playground,Security,Vehicle Restrictions

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windermere

At least 271 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

  • 80 % 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.
  • Anjalique Creative Concepts
    "We’ve lived in this area for 5 years and absolutely love it! The people in the community are always friendly, welcoming and supportive of one another. All the surrounding neighborhoods are well maintained and there are always organized activities in the community that makes it fun to meet new residents moving in."
    0
    Flag
  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
    Flag
  • Valentina
    "Trick or treating is big but it’s more about small groups of neighbors doing things together rather than large activities in the entire neighborhood."
    0
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  • Juliana Daurio
    "I moved to Windermere in 2004. When my kids were 3 and 4. This feels like home since then. Now that my kids are gone I see no need to move. I have many nice neighbors and enjoy everything that this area has to offer. "
    0
    Flag
  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
    Flag
  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
    Flag
  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
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  • Datylberman
    "I work at home so I’m not versed in the commute anywhere.many people in Windermere work at hone also.friends who work downtown are happy with their commute."
    0
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  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
    Flag
  • Garrett Hendrickson
    "Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
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  • Ngandhi62
    "Great areas to walk dogs and great puppy parks. Very close convenient veterinarians and pet supply stores. There are also many pet owners in area, therefore a nice social community is created."
    5
    Flag
  • Sean H.
    "It is a very pet friendly neighborhood. And has many fenced in dog areas and 90% of people are respectful enough to clean up after their dogs."
    3
    Flag
  • Limegreenlilo
    "Quiet & neighbors look out for one another. We have a FB page for residents to help each other out. I have been a resident ten years and love living here. HOA is good and they keep everything nice."
    0
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  • Carylpalmerini17
    "Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
    3
    Flag
  • Carylpalmerini17
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
    3
    Flag
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
    1
    Flag
  • Msldancer
    "See lots of dogs in the area, most are very social. But I do not like that some owners do not put their dogs on leashes, they also then get mad when you come by even though you’re dog is leashes as it should be."
    2
    Flag
  • Mckenziejl
    "They would like the many trails and dog parks. Most of the neighborhoods are not gated or man guarded, so you can easily move in and out of them. Each neighborhood is unique and wherher you're going for walk with or without you pet, the time would be enjoyable."
    0
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  • Jessica
    "30min or less to get to any of the central Florida locations. Some locations can even see fireworks. Traffic can be a little heavy during the am/pm rush but nothing super crazy."
    2
    Flag
  • Stephanie F.
    "Easy to get to Disney. I work on Disney property. High traffic during rush hour times. Very quick during non peak rush hour times. "
    1
    Flag
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
    0
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  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
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  • David M.
    "I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
    0
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  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
    2
    Flag
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
    1
    Flag
  • Dasom.jang
    "It’s a nice and safe area to live in. There isn’t much going on, but there are food truck nights once a month, and farmer’s market on every Saturday in Winter Garden. "
    0
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  • John F.
    "I have lived in Windermere for 20 years. Very safe and good clean people. The cops are very responsive and people are rich and have class "
    0
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  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
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  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
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  • Evelyn T.
    "It’s a small oasis away from the hustle and bustle of such a vacation heavy town. I love getting to feel like I’m actually away from work and in a calm space but still be a 20 minute commute."
    1
    Flag
  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
    0
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  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
    1
    Flag
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
    0
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  • Loypippin
    "It’s a safe area but growing too quickly. Too many new houses and schools getting crowded. The schools are great, but need to be built faster to keep up. "
    1
    Flag
  • Beverly B.
    "It is very safe well lighted small community with many families with and without children. Everyone is friendly and keep their properties in great shape"
    0
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  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
    1
    Flag
  • Princess J.
    "Great place to live, and I feel safe in this area. I moved to this area when I moved to Florida and it was the best decision. "
    1
    Flag
  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
    0
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Market trends in Windermere

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$814K
$92.5KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$292
$18MoM
Available listings
274
22MoM

Home Value

Trulia Estimate
$4.8M
Since last month
Decreased$37K (-0.8%)
Since last year
Decreased$194K (-3.9%)
Since last sale
Increased$2M (+86.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +120% in the last 10 years
MonthEstimated value
2026
August 2026$4.8M
August 2026$4.8M
July 2026$4.84M
June 2026$4.89M
May 2026$5.15M
April 2026$5M
March 2026$4.98M
February 2026$4.96M
January 2026$4.95M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5157 LATROBE DRIVE, Windermere, FL
0.15
Single-Family Home
$4,400,000
12/30/25
6
8.5
5,721
5067 LATROBE DRIVE, Windermere, FL
0.37
Single-Family Home
$2,750,000
10/31/25
5
7
6,219
4806 ALEXANDRA GARDEN CT, Windermere, FL
0.34
Single-Family Home
$3,900,000
08/20/26
5
6
5,695
5036 LATROBE DRIVE, Windermere, FL
0.42
Single-Family Home
$4,350,000
07/15/26
5
4.5
5,548
5104 ISLEWORTH COUNTRY CLUB DRIVE, Windermere, FL
0.16
Single-Family Home
$5,000,000
05/31/26
4
6
9,636
9213 FOXHALL COURT, Orlando, FL
0.51
Single-Family Home
$3,250,000
10/20/25
5
6.5
6,700
1003 DOWN RESERVE COURT, Windermere, FL
0.56
Single-Family Home
$4,500,000
03/11/26
6
7
6,816
9743 CHESTNUT RIDGE DRIVE, Windermere, FL
0.54
Single-Family Home
$3,250,000
09/26/25
5
6.5
6,328
5138 FAIRWAY OAKS DRIVE, Windermere, FL
0.78
Single-Family Home
$2,500,000
09/24/25
4
4.5
4,330
1009 DOWN RESERVE COURT, Windermere, FL
0.63
Single-Family Home
$3,100,000
09/05/26
5
7
7,940

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5181 LATROBE DRIVE, Windermere, FL 34786
0.07
$2,825,700
4
5
3,645
Off Market
9433 PALM TREE DRIVE, Windermere, FL 34786
0.08
$539,900
3
2
1,819
For Sale
9426 PALM TREE DRIVE, Windermere, FL 34786
0.12
$655,000
4
2
2,063
Recently Sold
5174 VARDON DRIVE, Windermere, FL 34786
0.12
$5,134,000
6
8
10,701
Off Market
9473 PALM TREE DRIVE, Windermere, FL 34786
0.12
$709,300
3
2
2,084
Off Market
5157 LATROBE DRIVE, Windermere, FL 34786
0.15
$4,400,000
6
8.5
5,721
Recently Sold
9375 WOODBREEZE BOULEVARD, Windermere, FL 34786
0.14
$473,200
3
2
1,492
Off Market
9385 PALM TREE DRIVE, Windermere, FL 34786
0.15
$537,800
3
2
1,489
Off Market
5104 ISLEWORTH COUNTRY CLUB DRIVE, Windermere, FL 34786
0.16
$5,000,000
4
6
9,636
Recently Sold
9481 PALM TREE DRIVE, Windermere, FL 34786
0.14
$545,500
3
2
1,492
Off Market
5092 ISLEWORTH COUNTRY CLUB DRIVE, Windermere, FL 34786
0.16
$4,648,000
5
4.5
6,115
Off Market

Price and Tax history

DateEventPrice
May 27, 2026
Source: Stellar MLS #O6409961
Listed For Sale
$5,300,000
Dec 31, 2025
Source: Stellar MLS #O6315618
ListingRemoved
$5,494,000
Jun 5, 2025
Source: Stellar MLS #O6315618
Listed For Sale
$5,494,000
Aug 5, 2022
Source: N/A
Sold
$2,575,000
Jun 9, 2022
Source: Stellar MLS #O6030513
Pending
$2,650,000

LGBTQ Local Legal Protections

Monica Lochmandy, ISLEWORTH REALTY LLC, (407) 909-9000
Agent Phone: (407) 230-6888

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Frequently asked questions about 5199 LATROBE DR

  • What is the estimated monthly payment for 5199 LATROBE DR?
    Based on a $5,300,000 list price with 20% down at today's rates, the estimated monthly payment for 5199 LATROBE DR in Windermere, FL is approximately $38,069 (about $28,586 principal & interest, $9,408 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 5199 LATROBE DR compare to homes in Windermere?
    5199 LATROBE DR in Windermere, FL is listed at $5,300,000, about 551% above the $814K median sale price in Windermere.
  • What do residents say about Windermere?
    Residents describe Windermere, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Windermere, FL.
  • What are the closest schools to 5199 LATROBE DR?
    The closest schools to 5199 LATROBE DR in Windermere, FL are Chain Of Lakes Middle School (rated 3/10), Olympia High School (rated 5/10), Windermere Elementary School (Pre-K, rated 10/10).
  • Does 5199 LATROBE DR have air conditioning?
    Yes, 5199 LATROBE DR in Windermere, FL has air conditioning.
  • Does 5199 LATROBE DR have a pool?
    Yes, 5199 LATROBE DR in Windermere, FL has a pool.
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.