5199 Latrobe Drive

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Active

$5,300,000

6 beds7 baths4,665 sqft$1,136/sqft

5199 Latrobe Dr, Windermere, FL 34786

Est: $31,267/moGet pre-approved

Single FamilyProperty Type

0.52 acresLot Size

1993Year Built

$1,136/sq ftPrice per sq ft

$3,672 / quarterHOA Fees

4 carsParking Spaces

Description

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,...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.

92 days on Market

Listed by: Monica Lochmandy 407.230.6888 mlochmandy@isleworth.com Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
Listed by: Michelle Corbin 407.491.2690 michelle.corbin@isleworth.com Brokerage DRE #1050525 • ISLEWORTH REALTY LLC

Last updated: 07/23/2026 01:32 PM • Source: MFRMLS, MLS#: O6409961

Location

Listing Courtesy of ISLEWORTH REALTY LLC, Monica Lochmandy; ISLEWORTH REALTY LLC, Michelle Corbin

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$31,267 per month

30 year fixed, 6.55% Interest

Principal and Interest

$26,939

Property Taxes

$3,103

HOA Dues

$1,224

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Property Information for 5199 Latrobe Drive

Property Details

Taxes: $37,241 / year
MLS Type: Residential / Single Family Residence
County: Orange County
Architectural Style: Traditional
Subdivision Name: ISLEWORTH
Township: 23
Garage Spaces: 4
View: Golf Course, Water
Waterfront: No
Furnished: Unfurnished

Building Information

Stories: 1
Year Built: 1993
Lot Size: 0.52 AC / 22,749 SF

Summary

Location and General Information

Building Area Source: Public Records
Building Area Total: 6622.0

Building Area Units: Square Feet
Community Features: Community Boat Ramp, Water Access, Buyer Approval Required, Community Mailbox, Gated Community - Guard, Golf Carts OK, Golf, Park
Direction Faces: Southeast
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.
Elementary School: Windermere Elem
Middle Or Junior School: Chain of Lakes Middle
High School: Olympia High
Floor Number: 1
Mls Major Change Type: New Listing
Major Change Type: New Listing
Listing Service: Full Service
Road Frontage Type: Street Paved
Senior Community: No
Unit Number: No
Street Number: 5199
Street Name: LATROBE DR
State: FL
City: WINDERMERE

Parking

Attached Garage: Yes
Carport: No

Garage: Yes
Parking Features: Driveway, Split Garage

Taxes and HOA Information

Association Approval Required: Yes
Association Fee Includes: 24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security

Association Fee Requirement: Required
Association Name: Dan O’Connell
Association Phone: 407-909-2071
Association: Yes
CDD: No
Pet Restrictions: Per Orange County breed restrictions, number limits and leash laws.
Tax Block: 3
Tax Book Number: 16-118
Tax Legal Description: ISLEWORTH 16/118 LOT 315
Tax Lot: 315
Tax Year: 2025

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Virtual Tour URL Unbranded: https://player.vimeo.com/video/1191725218?h=cecd1e93ef&badge=0&autopause=0&player_id=0&app_id=58479

Property

Lot Information

Additional Parcels: No
Additional Water Information: The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a private, community boat ramp for our residents eager to enjoy these great waters.

Lot Features: Landscaped, On Golf Course
Parcel Number: 162328389903150
Total Acreage: 1/2 to less than 1
Water Access: Lake - Chain of Lakes
Water Access: Yes
Water Extras: No
Zoning: P-D
Living Area: 4665

Property and Assessments

Year Built Numeric: 1993
Amenities Additional Fees: Club amenities are available to Club members only. Residents of the community are not required to join the Isleworth Golf & Country Club.

Association Amenities: Cable TV, Fence Restrictions, Gated, Playground, Security, Vehicle Restrictions
Flood Zone Code: X
Homestead: No
New Construction: No
Public Survey Range: 28
Public Survey Section: 16
Dock YN: No

Utilities

Sewer: Septic Tank
Utilities: Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Street Lights, Water Connected

Water Source: Public

Interior and Exterior Features

Exterior Features

Construction Materials: Block, Concrete, Stucco
Exterior Features: French Doors, Irrigation System, Rain Gutters

Foundation Details: Slab
Levels: One
Patio And Porch Features: Deck
Pool Features: Deck, Gunite, Heated, In Ground, Lighting, Screen Enclosure
Pool Private: Yes
Pool: Private
Pool Private: Yes
Roof: Concrete, Tile
Security Features: Gated Community, Security Gate
Spa Features: Heated, In Ground
Waterfront Feet Total: 0
Number Of Stories: 1

Interior Features

Bedrooms Total: 6
Bathrooms Full: 6

Appliances: Built-In Oven, Dishwasher, Disposal, Exhaust Fan, Microwave, Refrigerator
Cooling: Central Air, Zoned
Fireplace Features: Living Room
Fireplace: Yes
Flooring: Ceramic Tile
Heating: Central, Electric, Zoned
Interior Features: Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)
Laundry Features: Electric Dryer Hookup, In Kitchen, Laundry Room, Washer Hookup
Living Area Source: Public Records
Living Area Units: Square Feet
Room Count: 10.0
Water View: No
Bathrooms Half: 1

Rental

Rental Information

Minimum Lease Period: 0
Pets Allowed: Breed Restrictions

Property History for 5199 Latrobe Drive

Date	Event & Source	Price	Appreciation
May 27, 2026	Listed (Active) MFRMLS #O6409961	$5,300,000	—
Dec 30, 2025	Expired MFRMLS #O6315618	$5,494,000	—
Jun 5, 2025	Listed (Active) MFRMLS #O6315618	$5,494,000	—
Jul 14, 2022	Sold (Public Record) Public Record #1496851786	$2,575,000	+16.6% / yr
Jul 14, 2022	Sold MFRMLS #O6030513	$2,575,000	—
Jun 9, 2022	Pending MFRMLS #O6030513		—
Jun 2, 2022	Listed (Active) MFRMLS #O6030513	$2,650,000	—
Feb 19, 2019	Sold MFRMLS #O5737878	$1,500,000	—
Jan 9, 2019	Sold (Public Record) Public Record #639885038	$1,500,000	-4.7% / yr
Dec 8, 2018	Pending MFRMLS #O5737878		—
Oct 4, 2018	Listed (Active) MFRMLS #O5737878	$1,695,000	—
Sep 19, 2018	Withdrawn MFRMLS #O5536793	$1,775,000	—
Sep 20, 2017	Listed (Active) MFRMLS #O5536793	$1,999,000	—
Feb 14, 2017	Expired MFRMLS #O5386479	$1,995,000	—
Aug 14, 2015	Listed (Active) MFRMLS #O5386479	$1,995,000	—
Jul 11, 2014	Withdrawn MFRMLS #O5175883	$1,990,000	—
Aug 6, 2013	Listed (Active) MFRMLS #O5175883	$2,199,000	—
Apr 27, 2013	Expired MFRMLS #O4978366	$2,150,000	—
Apr 27, 2010	Listed (Active) MFRMLS #O4978366	$2,795,000	—
Aug 17, 2007	Sold (Public Record) Public Record #225052178	$2,600,000	+16.0% / yr
Aug 17, 2007	Sold MFRMLS #O4757403	$2,600,000	—
Jul 8, 2007	Pending MFRMLS #O4757403		—
Mar 15, 2007	Listed (Active) MFRMLS #O4757403	$3,125,000	—
Oct 5, 2004	Sold (Public Record) Public Record #144442676	$1,700,000	+188.4% / yr
Oct 1, 2004	Sold MFRMLS #O4571322	$1,700,000	—
Jul 27, 2004	Pending MFRMLS #O4571322		—
Jul 26, 2004	Listed (Active) MFRMLS #O4571322	$1,695,000	—
Feb 9, 2004	Sold (Public Record) Public Record #130197494	$850,000	—

Date	Event & Source	Price
05/27/2026	Listed (Active) MFRMLS #O6409961	$5,300,000
12/30/2025	Expired MFRMLS #O6315618	$5,494,000
06/05/2025	Listed (Active) MFRMLS #O6315618	$5,494,000
07/14/2022	Sold (Public Record) Public Record #1496851786	$2,575,000 +16.6% / yr
07/14/2022	Sold MFRMLS #O6030513	$2,575,000
06/09/2022	Pending MFRMLS #O6030513	—
06/02/2022	Listed (Active) MFRMLS #O6030513	$2,650,000
02/19/2019	Sold MFRMLS #O5737878	$1,500,000
01/09/2019	Sold (Public Record) Public Record #639885038	$1,500,000 -4.7% / yr
12/08/2018	Pending MFRMLS #O5737878	—
10/04/2018	Listed (Active) MFRMLS #O5737878	$1,695,000
09/19/2018	Withdrawn MFRMLS #O5536793	$1,775,000
09/20/2017	Listed (Active) MFRMLS #O5536793	$1,999,000
02/14/2017	Expired MFRMLS #O5386479	$1,995,000
08/14/2015	Listed (Active) MFRMLS #O5386479	$1,995,000
07/11/2014	Withdrawn MFRMLS #O5175883	$1,990,000
08/06/2013	Listed (Active) MFRMLS #O5175883	$2,199,000
04/27/2013	Expired MFRMLS #O4978366	$2,150,000
04/27/2010	Listed (Active) MFRMLS #O4978366	$2,795,000
08/17/2007	Sold (Public Record) Public Record #225052178	$2,600,000 +16.0% / yr
08/17/2007	Sold MFRMLS #O4757403	$2,600,000
07/08/2007	Pending MFRMLS #O4757403	—
03/15/2007	Listed (Active) MFRMLS #O4757403	$3,125,000
10/05/2004	Sold (Public Record) Public Record #144442676	$1,700,000 +188.4% / yr
10/01/2004	Sold MFRMLS #O4571322	$1,700,000
07/27/2004	Pending MFRMLS #O4571322	—
07/26/2004	Listed (Active) MFRMLS #O4571322	$1,695,000
02/09/2004	Sold (Public Record) Public Record #130197494	$850,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 5199 Latrobe Drive

Taxable ValueLand$650,000Additions$1,597,850Total$2,247,850

Tax Record2024$36,356 ($3,030 / month)

Home Facts

Beds4Total Finished SqFt4,186 SqFtAbove Grade Finished SqFt4,186 SqFtStories1Lot Size22,749 SqFtStyleSingle Family ResidenceYear Built1993ZoningP-DCountyORANGEAPN16-23-28-3899-03-150Fireplace TypeHas Fireplace

Schools near 5199 Latrobe Drive

This home is within Orange County Public Schools.


Rating	School	Type	Grades	Distance
10/10	Windermere Elementary School	Public - Serves this home	PK to 5	2.1 mi
9/10	Cornerstone Academy Charter	Charter - Serves this home	K to 8	9.2 mi
3/10	Chain Of Lakes Middle School	Public - Serves this home	6 to 8	0.9 mi
6/10	Cornerstone Charter Academy High School	Charter - Serves this home	9 to 12	9.2 mi
5/10	Olympia High School	Public - Serves this home	9 to 12	1.0 mi
NR	Central Florida Polytechnic Academy	Charter - Nearby school	K to 8	1.0 mi
NR	Holy Family Catholic School	Private - Nearby school	PK to 8	0.7 mi


Rating	School	Distance
10/10	Windermere Elementary School PublicPK to 5 Serves this home	2.1 mi
9/10	Cornerstone Academy Charter CharterK to 8 Serves this home	9.2 mi
3/10	Chain Of Lakes Middle School Public6 to 8 Serves this home	0.9 mi
6/10	Cornerstone Charter Academy High School Charter9 to 12 Serves this home	9.2 mi
5/10	Olympia High School Public9 to 12 Serves this home	1.0 mi
NR	Central Florida Polytechnic Academy CharterK to 8 Nearby school	1.0 mi
NR	Holy Family Catholic School PrivatePK to 8 Nearby school	0.7 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 5199 Latrobe Drive, Windermere, FL 34786

5199 Latrobe Drive is a single family home for sale in Windermere, FL 34786. This property was listed for sale on May 27, 2026 by ISLEWORTH REALTY LLC, it's currently listed at $5,300,000. It has been on the market for a total of 92 days and was last sold on July 14, 2022. This listing's school district is Orange County Public Schools. Nearby schools include Windermere Elementary School, Cornerstone Academy Charter and Chain Of Lakes Middle School. 5199 Latrobe Drive is a 6-bed, 7-bath, 4,665 sqft single family home built in 1993.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of ISLEWORTH REALTY LLC, Monica Lochmandy; ISLEWORTH REALTY LLC, Michelle Corbin

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 07/23/2026 01:32 PM

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More information about 5199 Latrobe Drive, Windermere, FL 34786