5243 Isleworth Country Club DriveWindermere, FL 34786Price: $5,100,000

  • Price: $5,100,000
  • Est. Mortgage of $/month
  • 218 Days on Market
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$/month over payments
Federal 30-year interest rate: 6.37% last updated on May 7, 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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5243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 347865243 Isleworth Country Club Drive Windermere FL 34786
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  • 4Bedrooms
  • 0.51Acreage
  • 6Bathrooms
  • 1992Year Built
Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense” remodel by McNally Construction and design by Debby Dearth of McNally Design using the highest quality materials combining the latest designs with timeless Mediterranean architecture. Enter to an impressive foyer and Great Room with soaring 20-foot ceilings above and basket weaved marble and wood flooring below, complemented by wood beams, stone gas fireplace with marble mantle, and shimmering chandeliers. An adjacent cocktail bar next to the dining room is fitted with Cristallo quartzite counters and a temperature-controlled wine cellar that can easily accommodate 700+ bottles of wine. The well-appointed chef's kitchen is fully equipped with a large center island, custom wood cabinetry, Italian dolomite counter tops, Sub Zero refrigerator, and a Wolf gas range with griddle. Family room and breakfast nook are perfectly sized for everyday entertaining with vaulted ceilings, reclaimed wood floors, and access to the pool patio and summer kitchen cabana. The dramatic first floor primary retreat features picturesque windows and a luxurious spa-like bath complete with chandelier, breakfast bar with Sub Zero fridge, dual vanities, garden tub, glass shower, and French doors to a walled outdoor space. The master closet provides access to a discrete room at the top of a spiral staircase that can be a gym, second study, or hidden Pilates room. Up the main staircase are three additional bedroom suites and a movie theater. An executive office is located on the first floor. Exterior living spaces feature a large covered lanai, heated saltwater pool, full pool bath, summer kitchen with stainless steel grill, sink, beverage refrigerator, custom-built stacked stone outdoor fireplace, and nearly 300 feet of golf frontage. Notable upgrades done in 2023 include a brand new tile roof, replacement of all custom doors and windows, remodeled kitchen, bathrooms with Kohler fixtures, door hardware, cocktail bar, flooring, Control 4 smart house features for lighting, electric shades, cameras, HVAC, pool equipment, garage doors, locks, built-in sound system, pool resurface, new pool heater, landscaping, complete interior and exterior paint, and exterior gray pavers. Home is built with concrete construction on both first and second floors. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.
Listing Courtesy of STOCKWORTH REALTY GROUP

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More Info

Location Information

  • Road Frontage DescriptionAsphalt

School Information

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

Parking

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

Basic Information

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

Property

  • ZoningP-D

Interior

  • Flooring Carpet, Marble, Tile, Wood
  • Furnished Unfurnished

Utilities

  • Cooling Central Air, Zoned
  • Heating Central, Electric, Zoned
  • Laundry Features Inside
  • MFR Number Of Septics 1
  • Sewer Septic Tank
  • Utilities Cable Connected, Natural Gas Connected, Underground Utilities, Water Connected
  • Water Source Public

Amenities

  • Appliances IncludedBar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
  • Association Amenities Gated, Park, Security
  • Association Fee Includes Guard - 24 Hour, Management, Private Road, Security
  • Association YN Yes
  • Community Features
    • Buyer Approval Required
    • Deed Restrictions
    • Gated Community - Guard
    • Golf
    • Golf Carts OK
    • Park
    • Street Lights
  • 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 Refer to ICA Documents
  • Other Amenities
    • Dock
    • Fireplace
    • Golf
    • Pool
    • Tennis
    • Water View
  • Other Equipment Irrigation Equipment
  • PetsYes
  • Pool Features Heated, In Ground, Salt Water
  • Security Features
    • Closed Circuit Camera(s)
    • Gated Community
    • Security System
    • Security System Owned
    • Smoke Detector(s)
    • Touchless Entry

Basic Information

  • List Price$5,100,000
  • ListingContractDate2025-10-09
  • MLS NumberO6348067
  • Mls Status Active
  • OriginalListPrice5325000
  • PostalCodePlus48900
  • PublicSurveyRange28
  • StatusACT

Rooms

  • Bedrooms4
  • Full Bath5
  • Half Baths1
  • MFR Additional Rooms Attic, Breakfast Room Separate, Den/Library/Office, Family Room, Great Room, Loft, Media Room, Storage Rooms

Building

  • Bathroom6
  • Construction Materials Block, Stucco
  • FireplaceGas, Living Room, Outside
  • Fireplace YN Yes
  • Foundation Details Slab
  • GarageYes
  • Garage Spaces3
  • Levels Two
  • Patio And Porch Features Covered, Porch, Rear Porch
  • Property StyleCustom, Mediterranean
  • RoofTile
  • Rooms11
  • Window Features Blinds, Insulated Windows, Shutters, Thermal Windows
  • Year Built1992

Water Body

  • MFR Water Access YN Yes
  • Pool Private YN Yes
  • Water AccessLake - Chain of Lakes
  • Water Body Name LAKE CHASE
  • Water ViewYes

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 2024
  • Taxes$50,194
  • Total Monthly Fees $1,224

Location

  • Address5243 Isleworth Country Club Drive
  • AreaWindermere
  • CountyOrange
  • Exterior Features French Doors, Lighting, Outdoor Kitchen, Storage
  • MFR Water View Lake - Chain of Lakes
  • StateFL
  • SubdivisionIsleworth
  • TownWindermere
  • Township 23
  • Zip34786

Property Information

  • Acreage0.51
  • Attached Garage YN Yes
  • Building Area Total 7,246
  • BuildingAreaUnitsSquare Feet
  • Fencing Fenced, Other
  • LivingAreaUnitsSquare Feet
  • Lot DescriptionIn County, Level, On Golf Course, Paved
  • Lot Size Square Feet 22,199
  • MFR Garage Dimensions 31x24
  • MFR Living Area Meters 596
  • MFR Lot Size Square Meters 2062
  • MFR Total Acreage 1/2 to less than 1
  • MFR Water Extras Boat Ramp - Private, Skiing Allowed
  • Other Structures Outdoor Kitchen
  • Square Feet6,424

Other

  • Building Area Source Public Records
  • Date Listed10/09/2025
  • MFR Additional Lease Restrictions Contact the Isleworth Community Association (ICA); Minimum 1 year lease required
  • MFR Exist Lse Tenant YN No
  • MFR Flood Zone Code X
  • MFR Flood Zone Date 2009-09-25
  • MFR Minimum Lease 1-2 Years
  • Status Change Timestamp2025-10-09T21:54:45
  • Vegetation Mature Landscaping, Oak Trees
  • View Golf Course, Water
  • View Count3
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 May 14, 2026 5:03 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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