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5050 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL, 34786
$3,390,000
4 Beds
4.5 Baths
3,365 SqFt
0.52 Acres
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MLS #O6372348 image #0
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.

Property Details

Price:
$3,390,000
MLS #:
O6372348
Status:
Active
Beds:
4
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Jan 10, 2026
Finished Sq Ft:
3,365
Total Sq Ft:
4,843
Lot Size:
22,514 sqft / 0.52 acres (approx)
Year Built:
1987
WaterfrontLakefrontPoolTennisPrimary Bedroom Main FloorCommunity GatedCommunity Club House34786 – Windermere34786windermereIsleworthWindermere ElemChain Of Lakes MiddleOlympia HighGolf CoursePer Isleworth Community Association (ica)7 MonthsPets Allowed

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Schools

Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High

Interior

Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Porcelain Tile
Heating
Central, Electric, Zoned
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
Laundry Features
Inside, Laundry Room
Levels
One

Exterior

Association Amenities
Basketball Court, Cable TV, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions
Attached Garage YN
1
Community Features
Community Boat Ramp, Lake, Water Access, Waterfront, Association Recreation – Owned, Clubhouse, Community Mailbox, Fitness Center, Gated Community – Guard, Golf Carts OK, Golf, Irrigation-Reclaimed Water, Playground, Pool, Restaurant, Special Community Restrictions, Tennis Court(s)
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
Southeast
Exterior Features
Irrigation System, Lighting, Rain Gutters, Sliding Doors, Sprinkler Metered
Fencing
Fenced
Garage Spaces
2
Lot Features
On Golf Course, In County, Landscaped
Open Parking YN
1
Parking Features
Golf Cart Parking, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Oversized
Patio And Porch Features
Covered, Rear Porch
Roof
Tile, Concrete
Security Features
Gated Community
Spa Features
In Ground
View
Golf Course
Waterfront Features
Lake, Waterfront
Window Features
Blinds, Drapes, Rods, Shades, Tinted Windows

Financial

HOA Fee
$3,129
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Maintenance Grounds, Maintenance Repairs, Private Road, Security
HOA Name
Dan O’Connell
HOA Phone
407-909-2071
Tax Year
2025
Taxes
$28,793

Map

Community

Subdivisions in WINDERMERE

Market Summary

Current real estate data for Single Family in WINDERMERE as of Apr 23, 2026
289
Single Family Listed
96
Avg DOM
458
Avg $ / SqFt
$2,232,275
Avg List Price

Property Summary

    Located in the ISLEWORTH subdivision, 5050 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $3,390,000 and features 4 beds, 5 baths, and has approximately 3,365 square feet of living space, and was originally constructed in 1987. The current price per square foot is $1,007. The average price per square foot for Single Family listings in WINDERMERE is $458. The average listing price for Single Family in WINDERMERE is $2,232,275. To schedule a showing of MLS#o6372348 at 5050 ISLEWORTH COUNTRY CLUB DRIVE in WINDERMERE, FL, contact your Preferred Real Estate Brokers agent at 4076987254.

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5050 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL