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5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - photo 1

$3,189,000

5050 ISLEWORTH COUNTRY CLUB DRIVE

WINDERMERE, FL 34786

Estimated payment $20,372/month

includes HOA $3,672/mo · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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4Beds
5Baths
3,365Sq Ft
$948Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

HOA $3,672/mo
Private Pool
Fireplace
Garage
Built in 1987
22,514 sqft Lot

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.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:4
  • •Bathrooms:5 (4 full, 1 half)
  • •Full bathrooms:4
  • •Half bathrooms:1

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:3,365 sqft
  • •Total interior livable area:3,365 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:22,514 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1987

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Price history

DateEventPrice
2026-09-04T00:00:00.000ZListed for sale$3,189,000$948/sqft

Listing Agent

Toni Cafferty

COMPASS FLORIDA LLC

Brokerage Phone: 407-203-9441

Source: Stellar MLS · MLS #O6438618

Data Powered by Home Junction, Inc.

Nearby

Schools

CHAIN OF LAKES MIDDLE

High · 0.8 mi

OLYMPIA HIGH

High · 0.9 mi

CENTRAL FLORIDA POLYTECHNIC ACADEMY

Elementary · 1.3 mi

Supermarkets

Publix

0.5 mi

Walmart Neighborhood Market

0.8 mi

Walmart Grocery Pickup

0.8 mi

Dining

Sakura Ramen Orlando

0.6 mi

Healthy D'Lite

0.6 mi

The Grove

0.6 mi

Parks

Johnson Park

0.7 mi

Lake Street Park

0.9 mi

Central Park

1.0 mi

Beaches

Conrad Beach

5.7 mi

West Beach

5.8 mi

East Beach

5.8 mi

Nearby amenity locations include data © OpenStreetMap contributors.