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Active - House for sale

5092 ISLEWORTH COUNTRY CLUB DRIVE, Windermere, FL

4 bds|5 bth|7,100 sqft

Facts & features

House Property type
44 days on Beycome
1995 Year built
$1,197 Price/Sqft.
4 car garage Parking
$3,672/qtr HOA
40,620 sqft Lot size

Why you’ll love it

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.

Translating description...

Listings courtesy of ISLEWORTH REALTY LLC as distributed by MLS GRID.

Listed by: Michelle Corbin • michelle.corbin@isleworth.com • ISLEWORTH REALTY LLC

Co-listed by: Monica Lochmandy • ISLEWORTH REALTY LLC

Source: Stellar MLS as distributed by MLS GRID, MLS#: O6446272 Stellar MLS as distributed by MLS GRID logo

Based on info available as of Nov 13, 2026 at 12:33 PM EST.

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Affordability

$5,525,000$11,475,000
1%20%
0%90%
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Estimated monthly payment

$48,961/mo

  • Mortgage$42,981
  • Property tax$4,756
  • HOA fee
  • Homeowners insurance
Due at closing$6,757,500
Down payment held in escrow$1,700,000
Closing costs$127,500
beycome credit Est.$170,000

Beycome estimates only. Actual amounts and terms vary by lender and location.

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Travel times

About Isleworth

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This local overview has been generated by Artur AI, for informational purposes only. Please verify all details independently before relying on it.

Flood & climate risk

FEMA Flood Zone X

Outside the high-risk Special Flood Hazard Area — flood insurance is usually optional but still worth considering.

More details

Source: FEMA National Flood Hazard Layer. Confirm on the FEMA Flood Map.

Disclaimer

Based on information submitted to the MLS GRID as of Nov 13, 2026 at 12:33pm EST. 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.

$8,500,000 Listed price

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$170,000 Credit back

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