5050 Isleworth Country Club Drive

WINDERMERE, FL
$ 3,189,000 Beds 4 Baths 4.5 Sq 3,365
Monthly Estimate* How much can I afford?

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.

Active

  • Price
  • $ 3,189,000
  • City
  • WINDERMERE
  • Bedrooms
  • 4
  • Full Bathrooms
  • 4
  • County
  • Orange
  • Half Bathrooms
  • 1
  • Area
  • Windermere
  • Lot Size
  • 0.52 Acres
  • Zip
  • 34786
  • Sqr Footage
  • 3,365
  • Year Built
  • 1987
  • Taxes
  • $ 28793
  • Style
  • Single Family Residence
  • MLS#
  • O6438618
Listed By: COMPASS FLORIDA LLC with 407-203-9441. - 407-203-9441
Data Source: Stellar MLS

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 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

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Apollo Beach, FL office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
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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.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

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

Price History

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

Property vs Zip Code Average in 34786

Price
AVG $2.49M
$3.19M
Taxes
AVG $23,922
$28,793
Year Built
AVG 2004
1987

In The Neighborhood

Areas That We Cover

5050 Isleworth Country Club Drive WINDERMERE, FL is a Single Family Home for sale at $3189000 with 3365 sqft and a lot size of 0.52 Acres Acre(s). 5050 Isleworth Country Club Drive WINDERMERE has 4 bedrooms, 4 baths and was built in 1987. The property's zip code is 34786 which is in WINDERMERE, FL

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: 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.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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