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5074 Isleworth Country Club DriveWindermere, FL, 34786

5beds
7baths
7,099sqft
Single Family Residence
Built in 1988
$1,224 Monthly HOA Fee
$7,250,000
For sale
$7,595,000−$345,000 (5%)Reduced May 21, 2026
Price per sqft
$1,021
Days on market
267
Listed Jan 14, 2026
MLS #O6373191Updated Oct 7, 2026

About this property

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.

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Property details

Property type
Single Family Residence
Street address
5074 Isleworth Country Club Drive
City
Windermere
State
FL
ZIP code
34786
Year built
1988
New construction
No
Faces
East
Rooms
11
Building stories
1
Living area
7,099 sqft
Total building area
9,236 sqft
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 12:01 AM EDT

Price & sale history

Asking price reduced by $345,000 (4.5%) since first listed.

EventPrice
Price reducedMLS #O6373191$7,250,000Change: −4.5%−$345,000
Listed for saleMLS #O6373191$7,595,000
SoldMLS #O5452725$1,050,000
Listed for saleMLS #O5452725$1,250,000
History may be incomplete.
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