5199 Latrobe Dr

Windermere, FL 34786

$5,494,000
Price
5
Beds
4,665 Sq. Ft.
$1,178 / Sq. Ft.
4,665
Sq. Ft.
$1,178
per Sq. Ft.
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Description

One or more photo(s) has been virtually staged. Nestled in the exclusive and coveted gated community of Isleworth, this fully remodeled, turn-key golf estate is positioned along Isleworth’s famed championship golf course. This remarkable golf-front property reveals a stylish and modern retreat you are sure to fall in love with. Spanning more than 6,600 square feet of indoor living and outdoor covered space, the estate blends warmth, elegance and comfort with contemporary fixtures and chic new lighting...One or more photo(s) has been virtually staged. Nestled in the exclusive and coveted gated community of Isleworth, this fully remodeled, turn-key golf estate is positioned along Isleworth’s famed championship golf course. This remarkable golf-front property reveals a stylish and modern retreat you are sure to fall in love with. Spanning more than 6,600 square feet of indoor living and outdoor covered space, the estate blends warmth, elegance and comfort with contemporary fixtures and chic new lighting set against beautiful outdoor living and views of Isleworth’s 4th fairway. No space has been overlooked, from the ideally located gourmet kitchen to the well appointed laundry room. This home boast generously sized bedrooms designed for various floorplans such as six bedrooms, five bedrooms and an office, or four bedrooms with office and gym. It was purposely designed to allow the owner to pursue whatever lifestyle fits their needs. Accompanying the bedrooms and flex spaces are six full baths and one half bath; each crafted with exquisite attention to detail. The estate kitchen includes contemporary white cabinetry, stainless steel appliances and gorgeous quartz countertops. The kitchen overlooks the sizable family room and casual dining area which offers direct access to the sprawling screened lanai and pool area. A sophisticated master suite awaits, showcasing beautiful porcelain plank floors, walk-in shower, cozy free standing bathtub and a large walk-in closet. Completing the interior, this meticulously maintained home offers up to five additional bedroom suites, a laundry room, half powder bathroom, full pool bathroom and a 4-car garage, providing unparalleled flexibility to accommodate your every need. Venture outside to discover your private sanctuary—a stunning outdoor oasis perfect for hosting lavish events or enjoying tranquil moments surrounded by lush landscaping and sweeping views. The new refreshing saltwater pool and spa have been completely enclosed in a new, one-of-a-kind lanai with new pool deck, allowing for enjoyment of the pool at all times of the year from dawn to dusk. This estate features a four-car garage tailored for the car enthusiast and plenty of driveway space for more parking. Exquisite landscaping surrounds the home, from the brick paver motor court to the fenced backyard with a spectacular golf course view. From the well designed interiors to the manicured exteriors, this estate represents the pinnacle of refined living. Its distinctive lot combines spaciousness, privacy, and stunning vistas to create a one-of-a-kind retreat.

Property Details for 5199 Latrobe Drive

Architectural Style
Traditional
Subdivision Name
ISLEWORTH
Township
23
Garage Spaces
4
View
Golf Course
Waterfront
No
LISTING UPDATED: 10/17/2025 09:49 AM

Property Details for 5199 Latrobe Drive

StatusActive
MLS #O6315618
Days on Market202
Taxes$36,055 / year
HOA Fees$12,516 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1993
Lot Size0.52 AC / 22,749 SF
CountyOrange County

Location

Listing Courtesy of COLDWELL BANKER RESIDENTIAL RE, Shane Croft; COLDWELL BANKER RESIDENTIAL RE, Tracy Croft
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Building Information for 5199 Latrobe Drive

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

Payment Calculator

$31,195 per month

30 year fixed, 6.28% Interest

Principal and Interest

$27,148

Property Taxes

$3,005

HOA Dues

$1,043

The Payment Calculator is for illustrative purposes only.

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, Private Boat Ramp, Waterfront, Association Recreation - Owned, Golf Carts OK, Golf, Playground, Special Community Restrictions
  • Direction Faces: Southeast
  • Directions: From Conroy Windermere to front entrance of Isleworth, first left on Latrobe, home on the 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
  • Street Suffix: DRIVE
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
Taxes and HOA Information
  • Association Approval Required: Yes
  • Association Fee Includes: 24-Hour Guard, Cable TV, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security
  • Association Fee Requirement: Required
  • Association Name: Isleworth Community Association
  • 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: 2024
Virtual Tour
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: On Golf Course
  • Parcel Number: 162328389903150
  • Total Acreage: 1/2 to less than 1
  • Water Access: Lake - Chain of Lakes
  • Water Access: Yes
  • Water Body Name: LAKE BUTLER CHAIN OF LAKES
  • Water Extras: Boat Ramp - Private, Skiing Allowed
  • Water Extras: Yes
  • Water: Boat Ramp - Private, Skiing Allowed
  • 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, Gated, Optional Additional Fees, Playground, Security
  • Flood Zone Code: X
  • Homestead: No
  • New Construction: No
  • Public Survey Range: 28
  • Public Survey Section: 16
Utilities
  • Sewer: Septic Tank
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sprinkler Meter, Street Lights
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Stucco
  • Exterior Features: French Doors, Irrigation System, Outdoor Grill
  • Foundation Details: Slab
  • Levels: One
  • Pool Features: Gunite, Heated, In Ground, Screen Enclosure
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Tile
  • Spa Features: Heated, In Ground
  • Spa: Yes
  • Vegetation: Mature Landscaping, Trees/Landscaped
  • Waterfront Features: Waterfront
  • Waterfront Feet Total: 0
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 6
  • Appliances: Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Ice Maker, Microwave, Refrigerator
  • Cooling: Central Air, Zoned
  • Fireplace Features: Family Room
  • Fireplace: Yes
  • Flooring: Ceramic Tile
  • Heating: Central, Electric, Zoned
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Dry Bar, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
  • Laundry Features: Laundry Room
  • 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: Yes

Property History for 5199 Latrobe Drive

DateEvent & SourcePriceAppreciation
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—
DateEvent & SourcePrice
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, Compass 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
Olympia High School
Public - 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

Olympia High School
Public9 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 June 5, 2025 by COLDWELL BANKER RESIDENTIAL RE, it's currently listed at $5,494,000. It has been on the market for a total of 202 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 5-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 makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of COLDWELL BANKER RESIDENTIAL RE, Shane Croft; COLDWELL BANKER RESIDENTIAL RE, Tracy Croft

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: 10/17/2025 09:49 AM