Waterfront - Golf Course - Primary on Main

Address

5050 Isleworth Country Club Drive, WINDERMERE, FL

Listing Type

Active

Price

$ 3,189,000

Property Attributes

MLS#O6438618
TypeSingle Family
Listing Status Active
CountyOrange
CityWINDERMERE
AreaWindermere
NeighborhoodISLEWORTH
Zip34786
StyleSingle Family Residence
Year Built1987
Taxes$ 28793
Price$ 3,189,000
Bedrooms4
Full Bathrooms4
Half Bathrooms1
Sqr Footage3365
Lot Size0.52 Acres

Data Source:

Stellar MLS

Property Description

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.

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

Price History
9/4/2026	Listed $3,189,000

General Features

Sewer	Septic Tank
Heating	Central,Electric,Zoned
Cooling	Central Air,Zoned
Utilities	BB/HS Internet Available,Cable Available,Electricity Connected,Natural Gas Connected,Phone Available,Public,Sprinkler Meter,Street Lights,Underground Utilities,Water Connected
Possession	Close Of Escrow
Roof	Concrete,Tile
Appliances	Dishwasher,Disposal,Dryer,Gas Water Heater,Microwave,Range,Range Hood,Refrigerator,Tankless Water Heater,Washer,Water Softener,Wine Refrigerator
Zoning	P-D
HOA Fee	3672
Garage Spaces	2
Association Fee Includes	24-Hour Guard,Cable TV,Escrow Reserves Fund,Maintenance Grounds,Maintenance Repairs,Private Road,Security
Patio/Porch Features	Covered,Rear Porch
Pool Features	Gunite,Tile
Security Features	Gated Community
Construction Materials	Block,Stucco
Pets Allowed	Breed Restrictions,Cats OK,Dogs OK,Yes
Year Built	1987
View	Golf Course
Levels	One
Property Subtype	Single Family Residence
Tax Year	2025
Ownership	Fee Simple
Waterfront Features	Lake,Waterfront
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)
Assoc Fee Paid Per	Quarterly
County	Orange
New Construction	false
Property Type	Residential
Association Amenities	Basketball Court,Cable TV,Fence Restrictions,Gated,Optional Additional Fees,Playground,Security,Vehicle Restrictions
Attached Garage	true
Subdivision Name	ISLEWORTH
Facing Direction	Southeast
Garage Y/N	true
Total Rooms	13
Full Baths	4
Status	Active
Directions	I-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right.
High School	Olympia High
City	WINDERMERE
Association Name	Dan O'Connell
Senior Community Y/N	false
MLS Area	34786 - Windermere
Lot Size Units	Square Feet
Lot Size Square Feet	22514
Carport Y/N	false
Listing Terms	Cash,Conventional
Spa Features	In Ground
Elementary School	Windermere Elem
Property Attached Y/N	false
Land Lease Y/N	false
Tax Annual Amount	28793
Middle/Junior High School	Chain of Lakes Middle
Additional Parcels Y/N	false
Lease Considered Y/N	true
Building Area Units	Square Feet
Living Area Units	Square Feet
Standard Status	Active
Occupancy Type	Owner
Tax Lot	41
Legal Description	ISLEWORTH 16/118 LOT 41
Minimum Lease	7 Months
Water Access Y/N	false
Monthly HOA Amount	1224
Additional Rooms	Den/Library/Office,Formal Dining Room Separate,Formal Living Room Separate
Water View Y/N	false
Flood Zone Code	X
In Law Suite YN	false
Flood Zone Code X	Yes

Interior Features

Interior Amenities	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
Flooring	Porcelain Tile
Furnished Y/N	Negotiable
Fireplace Features	Living Room,Outside,Master Bedroom
Air Conditioning Y/N	true
Heating Y/N	true
Window Features	Blinds,Drapes,Rods,Shades,Tinted Windows
Fireplace Y/N	true
Half Baths	1
Laundry Features	Inside,Laundry Room
Total Bedrooms	4
LivingAreaSource	Public Records
Total Baths	5

Exterior Features

Exterior Amenities	Irrigation System,Lighting,Rain Gutters,Sliding Doors,Sprinkler Metered
Vegetation	Mature Landscaping,Oak Trees
Fencing	Fenced
Parking Features	Circular Driveway,Driveway,Garage Door Opener,Garage Faces Rear,Golf Cart Parking,Oversized
Lot Features	In County,Landscaped,On Golf Course
Water Source	Public
Lot Size Area	22514
Foundation Details	Block
Spa	true
Building Area Total	4843
Lot Dimensions	190 x 151 x 128 x 145
Lot Size Acres	0.52
Road Surface Type	Paved,Asphalt
Private Pool	true
Waterfront Y/N	false
Covered Spaces	2
Road Frontage Type	Street Paved,Private Road
Road Responsibility	Private Maintained Road