Gabriella Massaro

Gabriella Massaro Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

$3,189,000.00
5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - 34786
4 beds
4.5 baths
3,365 sqft
$3,189,000.00
5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - 34786
Gabriella Massaro
$3,189,000.00
4 beds
4.5 baths
3,365 sqft
5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - 34786
For Sale
Photo 1
  • Built in 1987
  • 2 garage spaces
  • $947.70/sqft
  • Lot size: 22,514 sqft
  • 8 days on market

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.

  • Directions: I-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right.
  • County: Orange
  • Geo subdivision: ISLEWORTH

Nearby Schools

Windermere Elem

Chain of Lakes Middle

Olympia High

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

See also

For Sale
4243 ISABELLA CIRCLE, WINDERMERE, FL - 34786
$3,290,000.00
5 bds
6.0 ba
5,502 sqft
4243 ISABELLA CIRCLE, WINDERMERE, FL - 34786
For Sale
4301 DOWN POINT LANE, WINDERMERE, FL - 34786
$2,950,000.00
5 bds
4.0 ba
7,153 sqft
4301 DOWN POINT LANE, WINDERMERE, FL - 34786
For Sale
515 W 2ND AVENUE, WINDERMERE, FL - 34786
$3,300,000.00
4 bds
5.5 ba
3,966 sqft
515 W 2ND AVENUE, WINDERMERE, FL - 34786
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6438618
Listing updated: September 5, 2026 at 10:47AM
Listing provided by: Toni Cafferty, COMPASS FLORIDA LLC
Last checked 7 days ago
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