$8,500,000
 $45,630 est/mo Sourced by Back At You

5092 Isleworth Country Club Dr,WINDERMERE, FL 34786

WINDERMERE, FL 34786

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Description

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.

Details

MLS #O6446272
Listing TypeFor Sale
StyleHouse
HOA Dues$3,672
Sub-TypeFor-sale
StatusActive
Year1995
Days On Site29
Listing Provided ByISLEWORTH REALTY LLC | Michelle Corbin

Features

Bed(s)4
Bath(s) 5 Total
SQ Feet7,100
Garage4
PoolYes
Story(s)2
ZoningP-D
Acreage0.93
Property ViewGarden, Golf Course, Trees, Woods

Taxes

Property57070

Area Information

StateFL
CountyOrange
CityWINDERMERE
Zip Code34786
Area34786 Windermere
Community NameISLEWORTH
School DistrictOlympia High
Elementary SchoolWindermere Elem
High SchoolOlympia High
Listing VS Median (in ISLEWORTH)
Price:
$8,500,000
low | high
Med:
$4,100,000
100% of Average
sqft:
7,100
low | high
Med:
5,004
79.521126760563% of Average
$ / sqft:
$1,197
low | high
Med:
$819
81.560633845864% of Average
On site:
29
low | high
Med:
204
14.21568627451% of Average
Sourced by Back At You

Market Activity 34786

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 Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of October 30, 2026 at 4:33:32 AM PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

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Learn More About This Property

StateFL
CountyOrange
CityWINDERMERE
Zip Code34786
Area34786 Windermere
Community NameISLEWORTH
School DistrictOlympia High
Elementary SchoolWindermere Elem
High SchoolOlympia High
Listing VS Median (in ISLEWORTH)
Price:
$8,500,000
low | high
Med:
$4,100,000
100% of Average
sqft:
7,100
low | high
Med:
5,004
79.521126760563% of Average
$ / sqft:
$1,197
low | high
Med:
$819
81.560633845864% of Average
On site:
29
low | high
Med:
204
14.21568627451% of Average
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $6.375M - $10.625M
sqft: 5,000 - 8,500
Nearby Listings Property ImageNearby Listings Details
5074 ISLEWORTH COUNTRY CLUB DR Property Photo 1
$7,250,000
5074 Isleworth Country Club Dr
Windermere, FL 34786
Listing Updated: October 2, 2026 at 5:58:21 AM PDT