Single Family Residence at 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Single Family Residence at 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, photo 2 of 23
Single Family Residence at 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, photo 3 of 23
Single Family Residence at 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, photo 4 of 23
Single Family Residence at 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, photo 5 of 23
Single Family Residence at 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, photo 6 of 23
Single Family Residence at 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, photo 7 of 23
Single Family Residence at 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, photo 8 of 23
Primary Suite - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Dual Primary Bath - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Dual Primary Bath - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Ensuite - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Ensuite Bath - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Bedroom 3 - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Hall Bath - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Bedroom 4 - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Covered Patio - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Covered Patio - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Back Exterior - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Aerial with views of Lake Bessie - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Waterfront Tennis Center - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Driving Range - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
Waterfront Clubhouse - 5050 ISLEWORTH COUNTRY CLUB DR, WINDERMERE
23 photos

$3,189,000

5050 ISLEWORTH COUNTRY CLUB DR
WINDERMERE, FL 34786
Listed by Toni Cafferty · COMPASS FLORIDA LLC
Bedrooms
4
Bathrooms
4.5
Living area
3,365 sqft
Year built
1987

About this home

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

Highlights

Private poolFireplace

Property details

MLS #
MFRO6438618
Property type
Single Family Residence
Subdivision
ISLEWORTH
Status
Active
Days on market
1
On market date
September 4, 2026
Stories
N/A
Total bathrooms
4.5
Garage spaces
2
Parking spaces
N/A
Lot size
0.52 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

ElementaryCharter
CENTRAL FLORIDA POLYTECHNIC ACADEMY
1.31 mi away · Grades 0-8
Nearest school -- attendance-zone data not available here
Not yet rated
Local Score not yet available for this school
Enrollment
0
District
ORANGE
Middle
CHAIN OF LAKES MIDDLE
0.83 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,108
Student:teacher ratio
20.1:1
District
ORANGE
High
OLYMPIA HIGH
0.94 mi away · Grades 8-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,878
Student:teacher ratio
24.8:1
District
ORANGE

Walkability

Blended score for WINDERMERE's center: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

64
Walkable
out of 100
EPA National Walkability Index
10.0 / 20 -- Below average walkable
Nearby-amenity density
85 / 100
Restaurants & cafes19
Grocery stores3
Parks5
Schools9
Transit stops0
Pharmacies5

Mortgage calculator

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Est. monthly payment
$19,355/mo
$637,800 down
$2,551,200 loan
Principal & interest$16,547
Property tax (est.)$2,658
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 19 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.