IDX

Listed by Michelle Corbin · Courtesy of ISLEWORTH REALTY LLC · Agent MLS ID# MFR261222137 · Deemed reliable but not guaranteed. · Listing updated: Oct 2, 2026 · 10:49 AM

5092 ISLEWORTH COUNTRY CLUB DR

Windermere, Orange, FL, 34786

Active

$8,500,000

$1197/sqft

4Beds
5Baths
7,100Sq Ft
1995Built
1Days on Market

About this home

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.

Facts & Features

MFRO6446272
$8,500,000
Active
4
5
5
0
7,100 sqft
0.9300
1995
Residential
Single Family Residence
Mediterranean

Community Information

5092 ISLEWORTH COUNTRY CLUB DR
Isleworth
Windermere
Orange
FL
34786
No

Amenities

Cable TV, Gated, Maintenance, Security, Playground, Optional Additional Fees
N/A
No
No
Yes

Interior

Ceiling Fans(s), High Ceilings, Vaulted Ceiling(s), Walk-In Closet(s), Eat-in Kitchen, Solid Wood Cabinets, Cathedral Ceiling(s), Kitchen/Family Room Combo, Stone Counters, Crown Molding, Window Treatments, Built-in Features, Primary Bedroom Main Floor, Central Vaccum, Wet Bar
Central, Zoned
Central Air, Zoned
Carpet, Wood, Marble, Brick, Travertine
Living Room, Primary Bedroom
N/A
Built-In Oven, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Washer, Electric Water Heater, Freezer, Range, Convection Oven, Range Hood, Exhaust Fan, Bar Fridge, Water Filtration System, Wine Refrigerator

Exterior

Rain Gutters, Lighting, Balcony, Outdoor Grill, Outdoor Shower
Block, Stucco
Slab
Tile
Fenced
Landscaped, Paved, Oversized Lot, On Golf Course, Private

School Information

Windermere Elem
Chain Of Lakes Middle
Olympia High

Additional Information

October 1, 2026
1
P-D
East
No

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This calculator provides estimates for informational purposes only and is not a loan offer, pre-approval, or commitment to lend. Actual rates, payments, and loan terms vary by lender and are subject to credit approval, income/asset verification, and market conditions. Property tax and homeowners insurance shown are estimates and may differ. PMI applies when the down payment is under 20%. For an official Loan Estimate, contact a licensed mortgage lender. ISLEWORTH REALTY LLC is a licensed real estate brokerage, not a mortgage lender. Equal Housing Opportunity.

1 day on market

Listing updated: Oct 2, 2026 · 10:49 AM

Listed by: Michelle Corbin · 407-491-2690—ISLEWORTH REALTY LLC · 407-909-9000

Updated from Real Estate Market Data

Location

Ahmed ElbatrawyAhmed ElbatrawyEmpire Network Realty

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