USAFLWindermereIsleworth5050 Isleworth Country Club Dr
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$3,189,000

For Sale

2 days ago

5050 Isleworth Country Club Dr, Windermere, FL

House

MLS® O6438618

4 Bed

5 Bath

3365 sqft

2 Parking

  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 3365 sqft
Garage Yes
Taxes $28,793
Days Active 2
Lot Size 0.52 Acres
Approx. Age 1987
Avg. Price Per Sqft $947
MLS® Number O6438618

Property Address: 5050 Isleworth Country Club Dr, WINDERMERE, FL, 34786-8920

Average square foot calculated using Size range provided by listing agent.

Description

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.
MLS® NumberO6438618
Laundry LevelEnsuite
Central VacNo
FireplaceYes
Acreage
Exterior
GarageYes
Approx. Age1987
Basement
DrivewayCircular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
Garage Spaces
HeatCentral, Electric, Zoned
A/CCentral Air, Zoned

Extras

Rooms

Change to metres

Family Room:First Floor13 × 23 ft
Bedroom 2:First Floor12 × 11 ft
Bathroom 1:First Floor5 × 7 ft
Laundry:First Floor6 × 12 ft
Dining Room:First Floor12 × 16 ft
Bathroom 4:First Floor6 × 13 ft
Living Room:First Floor19 × 17 ft
Kitchen:First Floor13 × 23 ft
Other:First Floor20 × 20 ft
Den:First Floor16 × 7 ft
Bedroom 3:First Floor13 × 11 ft
Other:First FloorNot available
Bedroom 4:First Floor12 × 12 ft

Price History

-End Date
Not Sold YetSold Price

For Sale

Sep 4, 2026List Date
$3,189,000List Price

Home Appraisal

This property is estimated to sell between: $2,875,000 and $3,346,000.
Similar properties in this area sold on average for: $2,875,000
Expected to sell in 97 days. Similar properties sold in 99 days. This home has been on eXp Realty for 2 days.

The estimated sale price does not take into account many variables such as recent renovations, type of appliances, school district etc. To get a more accurate estimate please contact agent.

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5050 Isleworth Country Club Dr, Windermere, FL

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