5092 Isleworth Country Club DriveWindermere, FL 34786Price: $8,500,000

  • Price: $8,500,000
  • Est. Mortgage of $/month
  • 2 Days on Market
$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 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.
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5092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 347865092 Isleworth Country Club Drive Windermere FL 34786
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  • 4Bedrooms
  • 0.93Acreage
  • 5Bathrooms
  • 1995Year Built
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.
Listing Courtesy of ISLEWORTH REALTY LLC

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More Info

Location Information

  • Road Frontage DescriptionPaved

School Information

  • Elementary SchoolWindermere Elem
  • High SchoolOlympia High
  • Junior HighChain of Lakes Middle

Parking

  • Parking Features Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage

Location

  • Address5092 Isleworth Country Club Drive
  • AreaWindermere
  • CountyOrange
  • Exterior Features Balcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
  • MFR Water View Lake - Chain of Lakes
  • StateFL
  • SubdivisionIsleworth
  • TownWindermere
  • Township 23
  • Zip34786

Utilities

  • Cooling Central Air, Zoned
  • Heating Central, Zoned
  • Laundry Features Laundry Room
  • Sewer Septic Tank
  • Utilities Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Underground Utilities
  • Water Source Public

Water Body

  • MFR Additional Water Information The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a private, community boat ramp for our residents eager to enjoy these great waters.
  • MFR Water Access YN No
  • Pool Private YN Yes
  • Water Body Name BUTLER CHAIN OF LAKES
  • Water ViewYes

Other

  • Building Area Source Public Records
  • Date Listed10/01/2026
  • MFR Additional Lease Restrictions Per Isleworth Community Association (ICA)
  • MFR Exist Lse Tenant YN No
  • MFR Flood Zone Code X
  • MFR Minimum Lease 8-12 Months
  • Status Change Timestamp2026-10-01T14:56:20
  • Vegetation Mature Landscaping, Trees/Landscaped
  • View Garden, Golf Course, Trees/Woods, Water

Basic Information

  • List Price$8,500,000
  • ListingContractDate2026-10-01
  • MLS NumberO6446272
  • Mls Status Active
  • OriginalListPrice8500000
  • PublicSurveyRange28
  • StatusACT

Rooms

  • Bedrooms4
  • Full Bath5

Building

  • Bathroom5
  • Construction Materials Block, Stucco
  • FireplaceLiving Room, Primary Bedroom
  • Fireplace YN Yes
  • Foundation Details Slab
  • GarageYes
  • Garage Spaces4
  • Levels Two
  • Property StyleMediterranean
  • RoofTile
  • Rooms5
  • Window Features Drapes, Shutters, Window Treatments
  • Year Built1995

Amenities

  • Appliances IncludedBar Fridge, Built-In Oven, Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Water Filtration System, Wine Refrigerator
  • Association Amenities
    • Cable TV
    • Gated
    • Maintenance
    • Optional Additional Fees
    • Playground
    • Security
  • Association Fee Includes
    • Cable TV
    • Escrow Reserves Fund
    • Guard - 24 Hour
    • Internet
    • Maintenance
    • Maintenance Grounds
    • Private Road
    • Security
  • Association YN Yes
  • Community Features
    • Association Recreation - Owned
    • Community Mailbox
    • Fitness Center
    • Golf
    • Golf Carts OK
    • Playground
    • Pool
    • Street Lights
    • Tennis Court(s)
  • MFR Amenities Additional Fees Club amenities are available to Club members only. Residents of the community are not required to join the Isleworth Golf & Country Club.
  • MFR Pet Restrictions Per Orange County breed restrictions, number limits and leash laws.
  • Other AmenitiesFireplace, Pool, Golf, Tennis, Water View
  • Other Equipment Irrigation Equipment
  • PetsBreed Restrictions, Yes
  • Pool Features In Ground, Lighting
  • Security Features
    • Closed Circuit Camera(s)
    • Gated Community
    • Security Gate
    • Security Lights
    • Security System
    • Smoke Detector(s)
  • Spa Features Heated, In Ground

Tax Information

  • Association Fee $3,672
  • Association Fee Frequency Quarterly
  • Fees$14,688
  • MFR Association Fee Requirement Required
  • Monthly HOA Amount $1,224
  • Tax Year 2026
  • Taxes$57,070
  • Total Monthly Fees $1,224

Basic Information

  • Property SubTypeSingle Family Residence
  • Property TypeResidential
  • Virtual TourView Tour

Property

  • ZoningP-D

Interior

  • Flooring Brick, Carpet, Marble, Travertine, Wood
  • Furnished Negotiable

Property Information

  • Acreage0.93
  • Attached Garage YN Yes
  • Building Area Total 10,319
  • BuildingAreaUnitsSquare Feet
  • Fencing Fenced
  • LivingAreaUnitsSquare Feet
  • Lot DescriptionLandscaped, On Golf Course, Oversized Lot, Paved, Private
  • Lot Size Square Feet 40,620
  • MFR Living Area Meters 659
  • MFR Lot Size Square Meters 3774
  • MFR Total Acreage 1/2 to less than 1
  • Square Feet7,100
Fusilier Realty Group
Fusilier Realty Group
Office: 407-281-8455
10016 Wellness Way
Orlando, FL 32832

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of October 2, 2026 8:04 AM UTC. 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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