5092 Isleworth Country Club DriveWindermere, FL 34786Sale Price: $4,000,000

  • Sale Price: $4,000,000
  • 530 Days Since Sale
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Federal 30-year interest rate: 6.5300000000000000000000000000000000000000% last updated on May 28, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $4,000,000Sale Price
  • 5Bedrooms
  • 4Full Bath
  • 1Half Baths
  • 6,115Square Feet

Listing Tools

This exquisite estate, built by Pelligrini Homes, sits along the front nine of Isleworth championship golf course and provides breathtaking views of Hole 6. Boasting 6,115 square feet of beautifully curated living space on an oversized lot, this home has been fully restored to the original esthetics from builder designs. Custom ceilings, travertine floors adorned with intricate tile inlays, and carefully crafted shell stone columns are just a few of the distinctive features that elevate this residence. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, complemented by a magnificent chandelier and a stately stone fireplace. The heart of the home lies within the chef's kitchen, where custom cabinets, professional-grade Wolf, Thermador, Bosch and Sub-Zero appliances, and granite countertops converge to create a culinary haven. A beautiful groin-vault ceiling adds to the allure while allowing direct access to both the casual dining nook and the formal dining room with a built-in bar for effortless entertaining. The family room, which has an open and airy layout, has a built-in media display and seamless access to the lanai. Retreat to the main-level owner's suite, where a cozy fireplace, dual closets, and a lavish bath await, featuring dual vanities, a walk-in shower, and a luxurious soaking tub enveloped by elegant stone columns. Additional interior highlights include a distinguished home office trimmed with knotty pine wood, a versatile bonus room, and a spacious laundry room outfitted with custom cabinetry. Upstairs, the remaining bedroom suites open onto a sprawling balcony, offering panoramic views of the golf course and the sparkling waters of Lake Bessie. Outside, a haven of relaxation awaits, complete with an open-air swimming pool, a private putting green, and ample deck space surrounded by meticulously maintained landscaping. The European-style lanai, with a graceful balustrade, provides the perfect setting for al fresco gatherings and captivating sunsets against the backdrop of the golf course. This estate epitomizes the ultimate in golf-front living with its unparalleled blend of luxury, convenience, and breathtaking surroundings.

Property Details of 5092 Isleworth Country Club Drive

Property Details

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Mortgage Calculator


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Est. Mortgage:
$/month over payments
Federal 30-year interest rate: 6.5300000000000000000000000000000000000000% last updated on May 28, 2026. * The above figures are estimates provided by Union Street Media using the FRED® API, and are not endorsed or certified by the Federal Reserve Bank of St. Louis. Check with your lender for actual interest rates.
Listed by Michelle Corbin of ISLEWORTH REALTY LLC (407-909-9000)

Listing Sold by ISLEWORTH REALTY LLC

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of May 30, 2026 5:34 PM EDT. 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. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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