Fúlvio K. Massaro

Fúlvio K. Massaro Investor, Founder & CEO

$14,250,000.00
5525 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL - 34786
5 beds
5.5 baths
9,511 sqft
$14,250,000.00
5525 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL - 34786
Fúlvio K. Massaro
$14,250,000.00
5 beds
5.5 baths
9,511 sqft
5525 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL - 34786
For Sale
Photo 1
  • Built in 1999
  • 6 garage spaces
  • $1,498.27/sqft
  • Lot size: 1.02 acres
  • 107 days on market

One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interior designs by Faith Fournet, the property has been fully transformed and thoughtfully curated over the last three years to deliver exceptional comfort, sophistication and panache at every turn. The two-story estate is set on a pristine 1.02-acre golf-front home site along Isleworth's famed championship golf course and from the moment you enter, you'll be captivated by the artistry in design and modern innovation. The interiors span more than 9,500 square feet living and 13,000 under roof, blending 5 bedrooms, 5.5 baths and an array of indoor and outdoor living areas with uncompromisingly luxurious finishes designed for effortless entertaining and quiet moments alike. At the heart of the home, the showstopping glass-enclosed wine room—temperature-controlled and with a 2,400-bottle capacity—is a collector's dream and the ultimate conversation piece. The primary suite is a sanctuary unto itself, featuring a magnificent two-story closet and dedicated dressing room with a bar. Indulge in true tranquility within the home’s private wellness suite, complete with exercise room, a rejuvenating steam room, dry sauna and invigorating cold plunge tub. Additional interior highlights include the grand kitchen with Cristallo quartzite lighted countertops; a fully custom lounge with full bar; an upper-level game room with bar; an oversized, air-conditioned garage accommodating up to 8 vehicles; two laundry rooms; and more. Outdoor spaces are equally impressive, with an expansive lanai and balcony, a custom swimming pool with fire pits, meticulously landscaped yard adorned with integrated lighting, sound and lush, native greenery and putting green —all overlooking panoramic views of Isleworth’s championship golf course. Whether hosting guests or enjoying a peaceful evening at home, this estate offers a rare opportunity to live a life of unmatched beauty, comfort, and distinction in one of Central Florida's most desirable enclaves.

  • Directions: West on Conroy Windermere RD, at traffic circle take 3rd exit onto Main Street. Turn right onto Chase Road. Turn right onto Isleworth Country Club Drive. House will be on your left.
  • County: Orange
  • Geo subdivision: ISLEWORTH

Nearby Schools

Windermere Elem

Chain of Lakes Middle

Olympia High

Features

Financial

Let's get in touch!

Fúlvio K. Massaro

Fúlvio K. Massaro

Investor, Founder & CEO

See also

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$13,500,000.00
5 bds
7 ba
6,872 sqft
10065 AUTUMN MIST LN, ORLANDO, FL - 32836
For Sale
9621 WINDY RIDGE, WINDERMERE, FL - 34786
$13,935,000.00
9 bds
13.0 ba
20,445 sqft
9621 WINDY RIDGE, WINDERMERE, FL - 34786
For Sale
9935 LAKE LOUISE, WINDERMERE, FL - 34786
$12,995,000.00
7 bds
8.5 ba
16,257 sqft
9935 LAKE LOUISE, WINDERMERE, FL - 34786
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6304800
Listing updated: July 22, 2025 at 7:19PM
Listing provided by: Monica Lochmandy - MLS #: 261067417, ISLEWORTH REALTY LLC - MLS #: 261013260
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