$3,189,000
Active

5050 ISLEWORTH COUNTRY CLUB DRIVE

WINDERMERE, FL 34786 — ISLEWORTH
4 Beds
5 Baths
3,365 sqft
0.52 acres
Built 1987
2-Car Garage

About This Property

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

Basics

Property Type
Residential
Property Subtype
Single Family Residence
MLS Number
O6438618
Year Built
1987
Levels
One
Additional Rooms
Den/Library/Office,Formal Dining Room Separate,Formal Living Room Separate
Direction Faces
Southeast
Occupant Type
Owner

Size & Structure

Living Area
3,365 sqft
Total Area
4,843 sqft
Lot Size
0.52 acres
Lot Sq Ft
22,514 sqft
Bedrooms
4
Full Baths
4
Half Baths
1
Garage Spaces
2

Interior

Flooring
Tile
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
Interior Features
Built-in Features, Central Vaccum, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s), Window Treatments
Laundry
Inside, Laundry Room
Windows
Blinds, Drapes, Rods, Shades, Tinted Windows
Fireplace
Yes — Living Room, Outside, Primary Bedroom
Furnished
Negotiable
A/C
Central Air, Zoned
Heating
Central, Electric, Zoned

Exterior & Lot

Exterior Features
Lighting, Rain Gutters, Sprinkler Metered
Construction
Block, Stucco
Roof
Concrete, Tile
Foundation
Block
Patio/Porch
Covered, Rear Porch
Fencing
Fenced
Lot Features
In County, Landscaped, On Golf Course, Paved, Private
View
Golf Course

Water & Pool

Pool
Yes — Gunite, Tile
Spa
Yes — In Ground

Community & HOA

HOA
Yes
HOA Fee
$3,672/Quarterly
HOA Amenities
Basketball Court, Cable TV, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions
Community Features
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), Street Lights
Pets Allowed
Breed Restrictions, Cats OK, Dogs OK, Yes
Security
Gated Community

Utilities & Systems

Water
Public
Sewer
Septic Tank
Utilities
BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Public, Sprinkler Meter, Underground Utilities, Water Connected
Cooling
Central Air, Zoned
Heating
Central, Electric, Zoned
Flood Zone
X
Parking
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized

Financial

List Price
$3,189,000
Annual Taxes
$28,793
Tax Year
2025
Listing Terms
Cash, Conventional
Special Conditions
None
Possession
Close Of Escrow

Schools

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

Location