5050 Isleworth Country Club Drive, WINDERMERE, FL

$3,690,000

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4

Beds

5

Baths

3,365

Square feet

0.52

Acres

About 5050 Isleworth Country Club Drive

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.

Features of 5050 Isleworth Country Club Drive

MLS® # O6372348
Price $3,690,000
Bedrooms 4
Bathrooms 5.00
Full Baths 4
Half Baths 1
Square Footage 3,365
Acres 0.52
Year Built 1987
Type Residential
Sub-Type Single Family Residence
Status Active

Community Information

Address 5050 Isleworth Country Club Drive
Area Windermere
Subdivision ISLEWORTH
City WINDERMERE
County Orange
State FL
Zip Code 34786

Amenities

Amenities Basketball Court, Cable TV, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions
Parking Golf Cart Parking, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Oversized
# of Garages 2
View Golf Course
Is Waterfront No
Waterfront Lake, Waterfront
Has Pool Yes

Interior

Interior Features Built-in Features, Central Vacuum, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s), Window Treatments
Appliances Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
Heating Central, Electric, Zoned
Cooling Central Air, Zoned
Fireplace Yes
Fireplaces Living Room, Outside, Master Bedroom

Exterior

Exterior Features Irrigation System, Lighting, Rain Gutters, Sliding Doors, Sprinkler Metered
Lot Description On Golf Course, In County, Landscaped
Roof Tile, Concrete
Foundation Block

School Information

Elementary Windermere Elem
Middle Chain of Lakes Middle
High Olympia High

Additional Information

Date Listed January 10th, 2026
Days on Market 34
Zoning P-D
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeCOMPASS FLORIDA LLC

Listing Map

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