5050 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE FL 34786 | MLS #O6438618

5050 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL, 34786
$3,189,000
4 Beds
4.5 Baths
3,365 SqFt
0.52 Acres
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MLS #O6438618 image #0
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.

Property Details

Price:
$3,189,000
MLS #:
O6438618
Status:
Active
Beds:
4
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Sep 4, 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
In County, Landscaped, On Golf Course
Open Parking YN
1
Parking Features
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
Patio And Porch Features
Covered, Rear Porch
Roof
Concrete, Tile
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
$3,672
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 Sep 05, 2026
244
Single Family Listed
116
Avg DOM
463
Avg $ / SqFt
$2,307,744
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 $3,189,000 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 $948. The average price per square foot for Single Family listings in WINDERMERE is $463. The average listing price for Single Family in WINDERMERE is $2,307,744. To schedule a showing of MLS#o6438618 at 5050 ISLEWORTH COUNTRY CLUB DRIVE in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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5050 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL