Back to Search
5092 Isleworth Country Club Dr, Windermere, FL 34786
5092 Isleworth Country Club Dr, Windermere, FL 34786
5092 Isleworth Country Club Dr, Windermere, FL 34786
5092 Isleworth Country Club Dr, Windermere, FL 34786
5092 Isleworth Country Club Dr, Windermere, FL 34786
5092 Isleworth Country Club Dr, Windermere, FL 34786
5092 Isleworth Country Club Dr, Windermere, FL 34786

5092 Isleworth Country Club Dr Windermere, FL 34786

$8,500,000

ACTIVE
Beds
4
Baths
5
Sqft
7,100
Acres
0.93
Year
1995
Days on Site
18 Days
Property Type
Residential
Sub Type
Single Family Residence
Per Square Foot
$1,197
Date Listed
Oct 1, 2026

Description of 5092 Isleworth Country Club Dr, Windermere, FL 34786

Listing details for 5092 Isleworth Country Club Dr, Windermere, FL 34786 : Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.
Listing Updated : 10-02-2026 at 7:05 AM EDT
Listing Provided By

Michelle Corbin, 407-909-9000, ISLEWORTH REALTY LLC

Source

Stellar MLS as distributed by MLS GRID, MLS#: MFRO6446272

Property History

DateEventPrice
10/1/2026
Listed for sale
$8,500,000 +112.5%
$1,197/sqft
Source:Stellar MLS #MFRO6446272
12/17/2024
Sold
$4,000,000 -20%
$563/sqft
Source:Stellar MLS #MFRO6167834
11/21/2023
Listed for sale
$5,000,000 +88.7%
$704/sqft
Source:Stellar MLS #MFRO6167834
2/9/2015
Sold
$2,650,000 -15.9%
$373/sqft
Source:Stellar MLS #MFRO5188832
10/14/2013
Listed for sale
$3,150,000
$444/sqft
Source:Stellar MLS #MFRO5188832
Home Worth Check

Interested in 5092 Isleworth Country Club Dr, Windermere, FL 34786?

I agree to be contacted by Florida Realty Investments via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. For more information, please review our Privacy Policy.

Location of 5092 Isleworth Country Club Dr, Windermere, FL 34786

Streetview of 5092 Isleworth Country Club Dr, Windermere, FL 34786

Mortgage Calculator
Listing Price
Down Payment
Interest Rate

Schools Near 5092 Isleworth Country Club Dr, Windermere, FL 34786

Homes Similar to 5092 Isleworth Country Club Dr, Windermere, FL 34786

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
HomeWindermereIsleworth
What's your home worth?
Have a top local Realtor give you a FREE Comparative Market Analysis