5050 Isleworth Country Club Drive, Windermere, FL 34786

Windermere
Local realty services provided by:Better Homes and Gardens Real Estate Executive Real Estate
5050 Isleworth Country Club Drive,Windermere, FL 34786
$3,189,000
  • 4 Beds
  • 5 Baths
  • 3,365 sq. ft.
  • Single family
  • Active
Listed by: toni cafferty
Office: compass florida llc.
MLS#:O6438618
Source:MFRMLS

Price summary

  • Price:$3,189,000
  • Price per sq. ft.:$658.48
  • Monthly HOA dues:$1,224

About this home

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...

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Home facts

  • Year built:1987
  • Subdivision & Development:ISLEWORTH
  • Listing ID #:O6438618
  • Added:69 day(s) ago
  • Updated:November 12, 2026 at 08:23 PM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:5
  • Full bathrooms:4
  • Half bathrooms:1
  • Flooring:Tile
  • Dining Description:Eat In Kitchen, Formal Dining Room
  • Kitchen Description:Dishwasher, Disposal, Eat-in Kitchen, Kitchen/Family Room Combo, Microwave, Range, Range Hood, Refrigerator, Solid Wood Cabinets, Stone Counters, Water Softener, Wine Refrigerator
  • Bedroom Description:High Ceilings, Primary Bedroom Main Floor, Walk-In Closet(s)
  • Basement Description:Block
  • Living area:3,365 sq. ft.

Heating and cooling

  • Cooling:Central Air, Zoned
  • Heating:Central, Electric, Zoned
  • Central air:Yes

Structure and exterior

  • Roof:Concrete, Tile
  • Year built:1987
  • Building area:3,365 sq. ft.
  • Lot area:0.52 Acres
  • Lot Features:Landscaped, On Golf Course, Paved, Private
  • Construction Materials:Block, Stucco
  • Exterior Features:Covered Porch/Patio, Lighting, Rain Gutters, Rear Porch, Sprinkler Metered
  • Foundation Description:Block
  • Levels:1 Story

Schools

  • High school:Olympia High
  • Middle school:Chain of Lakes Middle
  • Elementary school:Windermere Elem

Utilities

  • Water:Public, Water Connected
  • Sewer:Public, Septic Tank

Finances and disclosures

  • Price:$3,189,000
  • Price per sq. ft.:$658.48
  • Tax amount:$28,793 (2025)

Features and amenities

  • Appliances:Dishwasher, Disposal, Dryer, Gas Water Heater, Irrigation Equipment, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
  • Laundry features:Dryer, Inside, Laundry Room, Washer
  • Amenities:BB/HS Internet Available, Basketball Court, Built-In Features, Cable Available, Cable TV, Central Vaccum, Eat-in Kitchen, Fence Restrictions, Gated, High Ceilings, Irrigation Equipment, Kitchen/Family Room Combo, Natural Gas Connected, Optional Additional Fees, Phone Available, Playground, Primary Bedroom Main Floor, Security, Solid Wood Cabinets, Stone Counters, Underground Utilities, Vehicle Restrictions, Walk-In Closet(s), Window Treatments
  • Pool features:Gunite, Private Pool, Tile

Parking

  • Parking description:Attached Garage, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
  • Garage:Yes
  • Garage spaces:2
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