Gabriella Massaro

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

$7,250,000.00
5074 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - 34786
5 beds
6.5 baths
7,099 sqft
$7,250,000.00
5074 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - 34786
Gabriella Massaro
$7,250,000.00
5 beds
6.5 baths
7,099 sqft
5074 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - 34786
For Sale
Photo 1
  • Built in 1988
  • 3 garage spaces
  • $1,021.27/sqft
  • Lot size: 23,455 sqft
  • 141 days on market

A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 7,000 square feet of refined living space, including a 2,400+ square-foot second-story addition designed by acclaimed architect Mark Nasrallah. Situated on over half an acre, the two-story home features 5 bedrooms, 6.5 bathrooms, and a seamless blend of timeless modern design and resort-style living. A striking 10-foot custom pivot door welcomes you into light-filled interiors, where elegant European porcelain tile and expansive open living spaces create a bright, elevated ambiance. Designed for both entertaining and everyday living, the main living areas flow effortlessly through expansive sliding glass doors to a stunning outdoor retreat, complete with a fully retractable screen enclosure. The chef’s kitchen serves as the centerpiece of the home, appointed with top-of-the-line appliances, custom European cabinetry, designer countertops, and an oversized island. A hidden chef’s pantry and temperature-controlled wine cellar enhance both functionality and style. The main-level primary suite offers a private, resort-inspired retreat, featuring a custom walk-in closet, a versatile bonus room ideal for fitness or wellness, and a dedicated in-home spa room. The spa-like primary bath includes a soaking tub, expansive walk-in shower, and a tropical outdoor shower, creating a tranquil escape. Upstairs, the newly constructed addition includes a secondary primary suite with a luxurious bath and walk-in closet, additional en-suite bedrooms, a spacious game room with access to a grand balcony overlooking panoramic golf course views, and a refined home theater. Outdoor living is equally impressive, featuring a sleek pool and heated spa, outdoor kitchen, wet bar, surround sound, and lush, manicured landscaping designed for privacy and enjoyment. Additional highlights include a fully integrated Crestron smart home system controlling lighting, audio, climate, and security, as well as a brand-new Generac generator for uninterrupted comfort. Fully remodeled and upgraded throughout, this residence presents a rare opportunity to own a like-new luxury estate in one of Central Florida’s most prominent communities.

  • Directions: Take Conroy Windermere road down to Isleworth - enter from the main entrance on Conroy. Take a left, continue to go straight, the property is on the right.
  • County: Orange
  • Geo subdivision: ISLEWORTH

Features

Financial

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Gabriella Massaro

Gabriella Massaro

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

See also

For Sale
6462 DEACON CIR, WINDERMERE, FL - 34786
$6,950,000.00
5 bds
5.0 ba
7,178 sqft
6462 DEACON CIR, WINDERMERE, FL - 34786
For Sale
9726 KILGORE ROAD, ORLANDO, FL - 32836
$6,800,000.00
5 bds
5.5 ba
10,010 sqft
9726 KILGORE ROAD, ORLANDO, FL - 32836
For Sale
9117 BAY POINT DRIVE, ORLANDO, FL - 32819
$6,995,000.00
5 bds
6.5 ba
6,365 sqft
9117 BAY POINT DRIVE, ORLANDO, FL - 32819
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6373191
Listing updated: June 1, 2026 at 12:17AM
Listing provided by: Armaan Memarpouri, MEM REALTY GROUP
Last checked 2 hours ago
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