5050 Isleworth Country Club DriveWindermere, FL 34786Price: $3,390,000

  • Price: $3,390,000
  • Est. Mortgage of $/month
  • 170 Days on Market
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$
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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Jun 25, 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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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 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
Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence was renovated in 2020 featuring a new tile roof, fresh paint inside and out, all bathrooms updated and a fully renovated kitchen. Spanning over 3,300 square feet, the 4-bedroom, 4.5-bath is nestled in the heart of Windermere, Florida. The foyer with groin ceiling is light and bright as natural light floods into the home from the glass entryway. Arched details abound in the entrance and this staple in Mediterranean design is carried throughout the estate. Two steps down into the sunken formal living room, the gas fireplace is the centerpiece featuring an artistic stone slab above the hearth and framed by wall-to-wall stacked stone. Completing the space are four large arched windows, two arched doors providing access to the back garden and a built-in dry bar. Situated between the family room and formal living room, and serviced by the nearby kitchen, the formal dining room offers the same illumination of natural sunlight from two large arched windows. The kitchen features new KitchenAid stainless steel appliances, a NXR Pro gas range and built-in 40 bottle Euro Cave wine fridge. The custom cabinetry provides ample storage and tastefully pairs in a dark grey-brown tone with the white tile backsplash, multi-tonal grey to white tile range hood and marble counters with soft neutral veins. The custom cabinetry continues seamlessly into the family room with built-in entertainment center. Down the hall from the kitchen and family room are the guest rooms. The first features an ensuite bathroom and the other two bedrooms are serviced by the hall bath with dual sinks. The hall bath also provides access to the patio and serves as the pool bath. Situated on the opposite end of the home, we find the primary suite, powder bath off the foyer and a flex room. The primary is airy and bright with arched windows, stacked stone fireplace and a dazzling chandelier. The suite features two separate bathrooms - one with walk-in shower and the second with free-standing soaking tub. The walk-in closet offers a warm cedar wood ceiling and custom built-ins. The flex room proposes many uses whether it be an office, nursery, gym, den or library. This stunning property offers a seamless blend of indoor-outdoor living boasting a covered patio with fireplace, open-air pool with spa and views of the fairway. Rounding out the estate is a welcoming circular driveway that extends to the rear motor court with two-car garage plus golf cart parking. Whether hosting or unwinding, this home elevates every moment.
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, Sliding Doors, 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 DescriptionPrivate, On Golf Course, In County, Paved, Landscaped
  • 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 Listed01/10/2026
  • 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 Timestamp2026-01-10T05:16:59
  • Vegetation Mature Landscaping, Oak Trees
  • View Golf Course
  • View Count1

Basic Information

  • List Price$3,390,000
  • ListingContractDate2026-01-03
  • MLS NumberO6372348
  • Mls Status Active
  • OriginalListPrice3975000
  • PublicSurveyRange28
  • StatusACT

Rooms

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

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
  • RoofTile, Concrete
  • 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

Tax Information

  • Association Fee $3,129
  • Association Fee Frequency Quarterly
  • Fees$12,516
  • MFR Association Fee Requirement Required
  • Monthly HOA Amount $1,043
  • Tax Year 2025
  • Taxes$28,793
  • Total Monthly Fees $1,043

Basic Information

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

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
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 June 28, 2026 10:31 PM 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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