5050 ISLEWORTH COUNTRY CLUB DRIVE, Windermere, Orange, Residential

5050 ISLEWORTH COUNTRY CLUB DRIVE

MLS# O643861832 days on marketUpdated September 5, 2026 10:47 am

$ 948 / sqft

$ 3,189,000

Overview

UpdatedSeptember 5, 2026 10:47 am
MLS #O6438618
Bedrooms4
Bathrooms4.5
Size3,365 ft²
Year Built1987
Garage2

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.

Address

Interior

  • AppliancesDishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
  • Bathrooms Full4
  • Bathrooms Half1
  • Bathrooms Total Integer5
  • Bedrooms Total4
  • CoolingCentral Air, Zoned
  • CoolingYes
  • Fireplace FeaturesLiving Room, Outside, Master Bedroom
  • FireplaceYes
  • FlooringPorcelain Tile
  • FurnishedNegotiable
  • HeatingCentral, Electric, Zoned
  • HeatingYes
  • Interior FeaturesBuilt-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
  • Laundry FeaturesInside, Laundry Room
  • LevelsOne
  • Living Area3,365
  • Living Area SourcePublic Records
  • Living Area UnitsSquare Feet
  • Rooms Total13
  • Security FeaturesGated Community
  • Spa FeaturesIn Ground
  • SpaYes
  • Window FeaturesBlinds, Drapes, Rods, Shades, Tinted Windows

Exterior

  • Attached GarageYes
  • Covered Spaces2
  • Direction FacesSoutheast
  • Exterior FeaturesIrrigation System, Lighting, Rain Gutters, Sliding Doors, Sprinkler Metered
  • FencingFenced
  • Garage Spaces2
  • GarageYes
  • Lot FeaturesIn County, Landscaped, On Golf Course
  • Lot Size Acres1
  • Lot Size Area22,514
  • Lot Size Dimensions190 x 151 x 128 x 145
  • Lot Size Square Feet22,514
  • Lot Size UnitsSquare Feet
  • Open ParkingYes
  • Parking FeaturesCircular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
  • Patio And Porch FeaturesCovered, Rear Porch
  • Pool FeaturesGunite, Tile
  • Road Frontage TypeStreet Paved, Private Road
  • Road Surface TypePaved, Asphalt
  • RoofConcrete, Tile
  • ViewGolf Course
  • Waterfront FeaturesLake, Waterfront

Structure

  • Building Area Total4,843
  • Construction MaterialsBlock, Stucco
  • Foundation DetailsBlock
  • Year Built1987

Utilities

  • SewerSeptic Tank
  • UtilitiesBB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Public, Sprinkler Meter, Street Lights, Underground Utilities, Water Connected
  • Water SourcePublic

Financial

  • Association AmenitiesBasketball Court, Cable TV, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions
  • Association Fee3,672
  • Association Fee FrequencyQuarterly
  • Association Fee Includes24-Hour Guard, Cable TV, Escrow Reserves Fund, Maintenance Grounds, Maintenance Repairs, Private Road, Security
  • AssociationYes
  • Parcel Number162328389900410
  • Pets AllowedBreed Restrictions, Cats OK, Dogs OK, Yes
  • Tax Annual Amount28,793
  • Tax Block00
  • Tax Book Number16/118
  • Tax Legal DescriptionISLEWORTH 16/118 LOT 41
  • Tax Lot41
  • Tax Year2025
  • ZoningP-D

Schools

  • Elementary SchoolWindermere Elem
  • High SchoolOlympia High
  • Middle Or Junior SchoolChain of Lakes Middle

Location

  • Community FeaturesCommunity 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)
  • CountryUnited States
  • County Or ParishOrange
  • DirectionsI-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right.
  • Latitude28
  • Longitude-82
  • MLS Area Major34786 - Windermere
  • Postal Code34786
  • Street NameISLEWORTH COUNTRY CLUB
  • Street Number5050
  • Street Number Numeric5,050
  • Street SuffixDRIVE
  • Subdivision NameISLEWORTH
  • Unparsed Address5050 ISLEWORTH COUNTRY CLUB DRIVE

Listing Info

  • List Price3,189,000
  • Contract Status Change DateSeptember 4, 2026
  • Cumulative Days On Market32
  • Days On Market32
  • Lease ConsideredYes
  • List Agent AOROrlando Regional
  • List Agent Emailtoni.cafferty@compass.com
  • List Agent Full NameToni Cafferty
  • List Agent Key27daf432d12391872b8dc7af95e3846c
  • List Agent MLS ID261215231
  • List Agent Preferred Phone904-449-2184
  • List Office MLS ID261020334
  • List Office NameCOMPASS FLORIDA LLC
  • List Office Phone407-203-9441
  • Listing Contract DateAugust 28, 2026
  • Listing IDO6438618
  • Listing Key73484cc0d9562bc40c378b673ccd7189
  • Listing TermsCash, Conventional
  • MLS StatusActive
  • Modification TimestampSeptember 5, 2026
  • On Market DateSeptember 4, 2026
  • Original Entry TimestampSeptember 4, 2026
  • Original List Price3,189,000
  • Originating System Keystellar
  • Originating System NameStellar MLS
  • OwnershipFee Simple
  • Photos Change TimestampSeptember 4, 2026
  • Photos Count23
  • Price Change TimestampSeptember 4, 2026
  • Source System Key804506826
  • Special Listing ConditionsNone
  • Status Change TimestampSeptember 4, 2026

Features & Amenities

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Meet your agent

TC

Toni Cafferty

Listing Agent · COMPASS FLORIDA LLC

BrokerageCOMPASS FLORIDA LLC
Agent MLS ID261215231
Office MLS ID261020334

Get in touch

Office · 407-203-9441

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Listing courtesy of COMPASS FLORIDA LLC

MLS# O6438618 · Listing agent Toni Cafferty · Phone 904-449-2184 · Data last updated September 5, 2026 10:47 am

TCToni Cafferty

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