5092 Isleworth Country Club Drive, Windermere, FL 34786

Windermere
Local realty services provided by:ERA Advantage Realty, Inc.
5092 Isleworth Country Club Drive,Windermere, FL 34786
$8,500,000
  • 4 Beds
  • 5 Baths
  • 7,100 sq. ft.
  • Single family
  • Active
Listed by: michelle corbin, monica lochmandy
Office: isleworth realty llc.
MLS#:O6446272
Source:MFRMLS

Price summary

  • Price:$8,500,000
  • Price per sq. ft.:$823.72
  • Monthly HOA dues:$1,224

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...

Contact an agent

contact an agent

Yes, I would like more information. Please use and/or share my information with an ERA®  affiliated agent to contact me about my real estate needs. By clicking Send message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an ERA®  affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE® , CENTURY 21® , Coldwell Banker® , Corcoran® , Sotheby's International Realty® ). I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:1995
  • Subdivision & Development:ISLEWORTH
  • Listing ID #:O6446272
  • Added:1 day(s) ago
  • Updated:October 02, 2026 at 04:18 PM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:5
  • Full bathrooms:5
  • Flooring:Brick, Carpet, Marble, Travertine, Wood
  • Dining Description:Eat In Kitchen
  • Kitchen Description:Bar Fridge, Built-In Oven, Convection Oven, Dishwasher, Disposal, Eat-in Kitchen, Exhaust Fan, Freezer, Ice Maker, Kitchen/Family Room Combo, Microwave, Range, Range Hood, Refrigerator, Solid Wood Cabinets, Stone Counters, Water Filtration System, Wet Bar, Wine Refrigerator
  • Bedroom Description:High Ceilings, Primary Bedroom Main Floor, Walk-In Closet(s)
  • Living area:7,100 sq. ft.

Heating and cooling

  • Cooling:Central Air, Zoned
  • Heating:Central, Zoned
  • Central air:Yes

Structure and exterior

  • Roof:Tile
  • Year built:1995
  • Building area:7,100 sq. ft.
  • Lot area:0.93 Acres
  • Lot Features:Landscaped, On Golf Course, Oversized, Paved, Private
  • Architectural Style:Mediterranean
  • Construction Materials:Block, Stucco
  • Exterior Features:Balcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
  • Foundation Description:Slab
  • Levels:2 Story

Schools

  • High school:Olympia High
  • Middle school:Chain of Lakes Middle
  • Elementary school:Windermere Elem

Utilities

  • Water:Public
  • Sewer:Septic Tank

Finances and disclosures

  • Price:$8,500,000
  • Price per sq. ft.:$823.72
  • Tax amount:$57,071 (2026)

Features and amenities

  • Appliances:Bar Fridge, Built-in Oven, Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Irrigation Equipment, Microwave, Range, Range Hood, Refrigerator, Washer, Water Filtration System, Wine Refrigerator
  • Laundry features:Dryer, Laundry Room, Washer
  • Amenities:Built-In Features, Cable Connected, Cable TV, Cathedral Ceiling(s), Ceiling Fans(s), Central Vaccum, Crown Molding, Eat-in Kitchen, Fire Hydrant, Gated, High Ceilings, Irrigation Equipment, Kitchen/Family Room Combo, Maintenance, Natural Gas Connected, Optional Additional Fees, Playground, Primary Bedroom Main Floor, Security, Solid Wood Cabinets, Stone Counters, Underground Utilities, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
  • Pool features:In Ground, Private Pool
  • Smart home:Yes

Parking

  • Parking description:Attached Garage, Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
  • Garage:Yes
  • Garage spaces:4
MLS LogoThe information being provided by Stellar Mls is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Stellar Mls. ERA Advantage Realty, Inc. is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of ERA Advantage Realty, Inc., a broker participant of Stellar Mls. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Stellar Mls and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Properties in listings may have been sold or may no longer be available. Copyright 2026 Stellar Mls. All rights reserved.

New listings near 5092 Isleworth Country Club Drive