5050 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL $ 3,189,000
5050 ISLEWORTH COUNTRY CLUB DRIVE
$ 3,189,000
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5050 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL, 34786
$ 3,189,000
Bedrooms4 Baths4.1 Sq 3,365

Monthly Estimate*

$ 20,136

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Single Family Home for sale in Windermere, FL

for $3,189,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,365 square foot home was built in 1987 on a lot size of 0.52.

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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Single Family Active

Price

$ 3,189,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 28,793

Style

Single Family Residence

Lot Size

0.52

Year Built

1987

Town/City

Windermere

County/Region

Orange

MLS | Web ID

O6438618

Features
General
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 Y
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Interior
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
Total Baths 5
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Exterior
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
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* Excluded Features
List By
Compass Florida Llc

Broker

toni.cafferty@compass.com

Email

Affordability Calculator

$22,535
Per Month
89%
11%
0%
Monthly Principal & Interest
$20,136
Monthly Property Taxes
$2,399
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Olympia High High School High School
Pricing History
DatePricePrice ChangeDescription
9/4/2026$3,189,000 Listed Price

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5050 ISLEWORTH COUNTRY CLUB DRIVE, Windermere, FL, 34786 is a Single Family Home for sale at $3,189,000 with 3,365 sqft and a lot size of 0.52. 5050 ISLEWORTH COUNTRY CLUB DRIVE has 4 bedrooms, 4.1 baths, and was built in 1987. The property's zip code is 34786 which is in Windermere, FL