5050 Isleworth Country Club DriveWindermere, FL 34786Price: $3,189,000

  • Price: $3,189,000
  • Est. Mortgage of $/month
  • 2 Days on Market
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$
%
$/month over payments
Federal 30-year interest rate: 6.71% last updated on Sep 3, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
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5050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 347865050 Isleworth Country Club Drive Windermere FL 34786
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  • 4Bedrooms
  • 0.52Acreage
  • 5Bathrooms
  • 1987Year Built
Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement-one with a walk-in shower and the other with a freestanding soaking tub-along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home's established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.
Listing Courtesy of COMPASS FLORIDA LLC

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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
    • Driveway
    • Garage Door Opener
    • Garage Faces Rear
    • Golf Cart Parking
    • Oversized

Location

  • Address5050 Isleworth Country Club Drive
  • AreaWindermere
  • CountyOrange
  • Exterior Features Lighting, Rain Gutters, Sprinkler Metered
  • StateFL
  • SubdivisionIsleworth
  • TownWindermere
  • Township 23
  • Zip34786

Property Information

  • Acreage0.52
  • Attached Garage YN Yes
  • Building Area Total 4,843
  • BuildingAreaUnitsSquare Feet
  • Fencing Fenced
  • LivingAreaUnitsSquare Feet
  • Lot DescriptionIn County, Landscaped, On Golf Course, Paved, Private
  • Lot Size Dimensions 190x151x128x145
  • Lot Size Square Feet 22,514
  • MFR Garage Dimensions 31x27
  • MFR Living Area Meters 312
  • MFR Lot Size Square Meters 2092
  • MFR Total Acreage 1/2 to less than 1
  • Square Feet3,365

Other

  • Building Area Source Public Records
  • Date Listed09/04/2026
  • MFR Additional Lease Restrictions Per Isleworth Community Association (ICA)
  • MFR Exist Lse Tenant YN No
  • MFR Flood Zone Code X
  • MFR Minimum Lease 7 Months
  • Status Change Timestamp2026-09-04T10:44:31
  • Vegetation Mature Landscaping, Oak Trees
  • View Golf Course
  • View Count2

Basic Information

  • List Price$3,189,000
  • ListingContractDate2026-08-28
  • MLS NumberO6438618
  • Mls Status Active
  • OriginalListPrice3189000
  • PublicSurveyRange28
  • StatusACT

Rooms

  • Bedrooms4
  • Full Bath4
  • Half Baths1
  • MFR Additional Rooms Den/Library/Office, Formal Dining Room Separate, Formal Living Room Separate

Property

  • ZoningP-D

Interior

  • Flooring Tile
  • Furnished Negotiable

Utilities

  • Cooling Central Air, Zoned
  • Heating Central, Electric, Zoned
  • Laundry Features Inside, Laundry Room
  • MFR Number Of Septics 1
  • Sewer Septic Tank
  • Utilities
    • BB/HS Internet Available
    • Cable Available
    • Electricity Connected
    • Natural Gas Connected
    • Phone Available
    • Public
    • Sprinkler Meter
    • Underground Utilities
    • Water Connected
  • Water Source Public

Water Body

  • MFR Water Access YN No
  • Pool Private YN Yes
  • Water ViewNo

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 2025
  • Taxes$28,793
  • Total Monthly Fees $1,224

Basic Information

  • Property SubTypeSingle Family Residence
  • Property TypeResidential

Building

  • Bathroom5
  • Construction Materials Block, Stucco
  • FireplaceLiving Room, Outside, Primary Bedroom
  • Fireplace YN Yes
  • Foundation Details Block
  • GarageYes
  • Garage Spaces2
  • Levels One
  • Patio And Porch Features Covered, Rear Porch
  • RoofConcrete, Tile
  • Rooms13
  • Window Features Blinds, Drapes, Rods, Shades, Tinted Windows
  • Year Built1987

Amenities

  • Appliances IncludedDishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
  • Association Amenities
    • Basketball Court
    • Cable TV
    • Fence Restrictions
    • Gated
    • Optional Additional Fees
    • Playground
    • Security
    • Vehicle Restrictions
  • Association Fee Includes
    • Cable TV
    • Escrow Reserves Fund
    • Guard - 24 Hour
    • Maintenance
    • Maintenance Grounds
    • Private Road
    • Security
  • Association YN Yes
  • Community Features
    • Association Recreation - Owned
    • Clubhouse
    • Community Mailbox
    • Fitness Center
    • Gated Community - Guard
    • Golf
    • Golf Carts OK
    • Irrigation-Reclaimed Water
    • Playground
    • Pool
    • Restaurant
    • Special Community Restrictions
    • Street Lights
    • Tennis Court(s)
  • MFR Amenities Additional Fees Membership to Isleworth Golf & Country Club offers amenities at a separate charge.
  • MFR Pet Restrictions Breed restrictions and leash laws per Orange County
  • Other AmenitiesFireplace, Garden, Pool, Golf, Tennis
  • Other Equipment Irrigation Equipment
  • PetsBreed Restrictions, Cats OK, Dogs OK, Yes
  • Pool Features Gunite, Tile
  • Security Features Gated Community
  • Spa Features In Ground
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 September 5, 2026 8:03 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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