5199 Latrobe Dr

Windermere, FL 34786

$5,300,000
Price
6
Beds
4,665 Sq. Ft.
$1,136 / Sq. Ft.
4,665
Sq. Ft.
$1,136
per Sq. Ft.
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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...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.
  1. Listed by Monica Lochmandy • Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
    P: (407)-230-6888 C: (407)-230-6888 mlochmandy@isleworth.com
  2. Listed by Michelle Corbin • Brokerage DRE #1050525 • ISLEWORTH REALTY LLC
    P: (407)-491-2690 C: (407)-491-2690 michelle.corbin@isleworth.com

Property Details for 5199 Latrobe Drive

Architectural Style
Traditional
Subdivision Name
ISLEWORTH
Township
23
Garage Spaces
4
View
Golf Course, Water
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 05/28/2026 04:08 PM

Property Details for 5199 Latrobe Drive

StatusActive
MLS #O6409961
Days on Market8
Taxes$37,241 / year
HOA Fees$3,672 / quarter
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1993
Lot Size0.52 AC / 22,749 SF
CountyOrange County
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Location

Listing Courtesy of ISLEWORTH REALTY LLC, Monica Lochmandy; ISLEWORTH REALTY LLC, Michelle Corbin
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Building Information for 5199 Latrobe Drive

Stories1Year Built1993Building Size-Lot Size0.52 AC / 22,749 SF

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$30,738 per month

30 year fixed, 6.36% Interest

Principal and Interest

$26,411

Property Taxes

$3,103

HOA Dues

$1,224

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Property Information for 5199 Latrobe Drive

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
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

DateEvent & SourcePriceAppreciation
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—
DateEvent & SourcePrice
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

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
Windermere Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Chain Of Lakes Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Windermere Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Chain Of Lakes Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

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 8 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 descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. 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: 05/28/2026 04:08 PM