5050 Isleworth Country Club Drive, Windermere, FL 34786
$3,189,000 - For Sale
Property Details
Price: $3,189,000
Sq Ft: 3,365
($948 per sqft)
Bedrooms: 4
Bathrooms: 4
Partial Baths: 1
City:Windermere
County:Orange
Type:Single Family
Development:Isleworth
Subdivision:Isleworth
Acres:0.5200
Year Built:1987
Listing Number:O6438618
Status Code:A-Active
Taxes:$28,793.00
Tax Year: 2025
Garage: 2
/ Y
Furnishings: Negotiable
Pets Allowed: Breed Restrictions, Cats OK, Dogs OK, Yes
Total Recurring Fees: $1,224
Total Recurring Fee Frequency: 0.00
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Equipment:
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
Exterior Features:
Lighting
Rain Gutters
Sprinkler Metered
View:
Golf Course
Amenities:
Basketball Court
Cable TV
Fence Restrictions
Gated
Optional Additional Fees
Playground
Security
Vehicle Restrictions
Financial Information:
Taxes: $28,793.00
Tax Year: 2025
Association Fee: $3,672.00
Association Fee Frequency: Quarterly
Room Dimensions:
Laundry: Inside, Laundry Room
School Information:
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
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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 Area: 34786 - Windermere
Total Square Footage: 4,843
Price per Square Feet: $947.70
Water: Public
Construction: Block, Stucco
Date Listed: 2026-09-04 00:00:00
Pool: Y
Pool Description: Gunite, Tile
Private Spa: Y
Furnished: Negotiable
Windows: Blinds, Drapes, Rods, Shades, Tinted Windows
Parking: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Tile
Roof: Concrete, Tile
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Fireplace: Y
Security: Gated Community
Laundry: Inside, Laundry Room
Pets: Breed Restrictions, Cats Ok, Dogs Ok, Yes
Sewer: Septic Tank
Lot Desc.: In County, Landscaped, On Golf Course, Paved, Private
Parcel ID: 16-23-28-3899-0
Amenities: Basketball Court, Cable Tv, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions
Listing Courtesy Of: Compass Florida Llc
toni.cafferty@compass.com
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.
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Additional Information:
MLS Area: 34786 - Windermere
Total Square Footage: 4,843
Price per Square Feet: $947.70
Water: Public
Construction: Block, Stucco
Date Listed: 2026-09-04 00:00:00
Pool: Y
Pool Description: Gunite, Tile
Private Spa: Y
Furnished: Negotiable
Windows: Blinds, Drapes, Rods, Shades, Tinted Windows
Parking: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Tile
Roof: Concrete, Tile
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Fireplace: Y
Security: Gated Community
Laundry: Inside, Laundry Room
Pets: Breed Restrictions, Cats Ok, Dogs Ok, Yes
Sewer: Septic Tank
Lot Desc.: In County, Landscaped, On Golf Course, Paved, Private
Parcel ID: 16-23-28-3899-0
Amenities: Basketball Court, Cable Tv, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions
Map of 5050 Isleworth Country Club Drive, Windermere, FL 34786
Listing Courtesy Of: Compass Florida Llc
toni.cafferty@compass.com
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Location
1201 6th Ave W. Suite 300
Bradenton, FL, 34205
Contact
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