5050 Isleworth Country Club Drive, Windermere, FL 34786
For Sale $3,975,000
Save Property
View Virtual Tour
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.
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
Basketball Court
Cable TV
Fence Restrictions
Gated
Optional Additional Fees
Playground
Security
Vehicle Restrictions
Taxes: $28,793.00
Tax Year: 2025
Association Fee: $3,129.00
Association Fee Frequency: Quarterly
Condo Fee Frequency: Quarterly
Lighting
Rain Gutters
Sliding Doors
Sprinkler Metered
Dishwasher
Disposal
Dryer
Gas Water Heater
Microwave
Range
Range Hood
Refrigerator
Tankless Water Heater
Washer
Water Softener
Wine Refrigerator
Golf Course
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
MLS Area: 34786 - Windermere
Price per Square Feet: $1,181.28
Water: Public
Lot Desc.: Private, On Golf Course, In County, Paved, Landscaped
Construction: Block, Stucco
Date Listed: 2026-01-10 04:50:29
Pool: Yes
Pool Type: Gunite, Tile
Private Spa: Yes
Furnished: Negotiable
Windows: Blinds, Drapes, Rods, Shades, Tinted Windows
Parking: Golf Cart Parking, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Oversized
Garage Spaces: 2
Flooring: Tile
Roof: Tile, Concrete
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Pets: Breed Restrictions, Cats Ok, Dogs Ok, Yes
Sewer: Septic Tank
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
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: $3,975,000
Sq Ft: 3,365
($1,181 per sqft)
Bedrooms: 4
Bathrooms: 4
Partial Baths: 1
City: Windermere
County: Orange
Type: Single Family Reside
Development: Isleworth
Acres: 0.52
Virtual Tour/Floorplan: View
Year Built: 1987
Listing Number: O6372348
Status Code: A-Active
Taxes: $28,793.00
Tax Year: 2025
Garage:
2
Furnishings: Negotiable
Pets Allowed: Breed Restrictions, Cats OK, Dogs OK, Yes
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
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: $3,129.00
Association Fee Frequency: Quarterly
Condo Fee Frequency: Quarterly
Exterior Features:
Lighting
Rain Gutters
Sliding Doors
Sprinkler Metered
Equipment:
Dishwasher
Disposal
Dryer
Gas Water Heater
Microwave
Range
Range Hood
Refrigerator
Tankless Water Heater
Washer
Water Softener
Wine Refrigerator
View:
Golf Course
School Information:
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
Additional Information:
MLS Area: 34786 - Windermere
Price per Square Feet: $1,181.28
Water: Public
Lot Desc.: Private, On Golf Course, In County, Paved, Landscaped
Construction: Block, Stucco
Date Listed: 2026-01-10 04:50:29
Pool: Yes
Pool Type: Gunite, Tile
Private Spa: Yes
Furnished: Negotiable
Windows: Blinds, Drapes, Rods, Shades, Tinted Windows
Parking: Golf Cart Parking, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Oversized
Garage Spaces: 2
Flooring: Tile
Roof: Tile, Concrete
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Pets: Breed Restrictions, Cats Ok, Dogs Ok, Yes
Sewer: Septic Tank
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