For Sale
Single family home for sale at 5050 Isleworth Country Clb Dr, Windermere, FL 34786 | MLS# O6438618 | Listing updated on 2026-09-05
Photo 1 of Single family home for sale at 5050 Isleworth Country Clb Dr, Windermere, FL 34786 | MLS# O6438618 | Listing updated on 2026-09-05
Photo 2 of Single family home for sale at 5050 Isleworth Country Clb Dr, Windermere, FL 34786 | MLS# O6438618 | Listing updated on 2026-09-05
Photo 3 of Single family home for sale at 5050 Isleworth Country Clb Dr, Windermere, FL 34786 | MLS# O6438618 | Listing updated on 2026-09-05
Photo 4 of Single family home for sale at 5050 Isleworth Country Clb Dr, Windermere, FL 34786 | MLS# O6438618 | Listing updated on 2026-09-05
19+
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Street View

$3,189,000

Monthly Est:$15,873

  • Beds Icon4 Beds
  • Beds Icon
    5 Baths
  • Beds Icon3,365sqft

5050 Isleworth Country Clb Dr, Windermere, FL 34786

$15,873/moEst:

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  • Single Family Residence

  • Built in 1987

  • $1,224/mo HOA

  • 22,514 sqft lot

  • $948/sq.ft

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 fi
replace 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.

  • Houzeo last checked: 2 hours ago
  • Listing updated: September 5, 2026 at 10:48 am
  • Listing Provided by: Toni Cafferty (904) 449-2184 | COMPASS FLORIDA LLC (407) 203-9441
  • Source: Stellar MLS-FL | MLS#: O6438618 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Orange County

  • City

    Windermere

  • Neighborhood

    --

  • Year Built

    1987

  • HOA Fees

    $1224/mo

  • Finished Area

    3,365 sqft

  • Lot Size

    22,514 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6438618

  • MLS Status

    Active

  • Days on Market

    54

  • Cumulative Days on Market

    1

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Location

HOA Management

Dan O'Connell

HOA Fees

$3,672/ Quarterly

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Maintenance Maintenance

Security Gate Security Gate

Basket Ball Basket Ball

Cable TV Cable TV

Security Guard Security Guard

Park Playground Park Playground

Private Road Private Road

Escrow Reserves Fund Escrow Reserves Fund

Optional Additional Fees Optional Additional Fees

Vehicle Restrictions Vehicle Restrictions

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 5

  • Living Room

    Level: First

    Area: 323.00 Square Feet

    Dimensions: 19x17

  • Dining Room

    Level: First

    Area: 192.00 Square Feet

    Dimensions: 12x16

  • Kitchen

    Level: First

    Area: 299.00 Square Feet

    Dimensions: 13x23

  • Family Room

    Level: First

    Area: 299.00 Square Feet

    Dimensions: 13x23

  • Den

    Level: First

    Area: 112.00 Square Feet

    Dimensions: 16x7

  • Bathroom 1

    Level: First

    Area: 35.00 Square Feet

    Dimensions: 5x7

  • Primary Bedroom

    Level: First

    Area: 400.00 Square Feet

    Dimensions: 20x20

  • Primary Bathroom

    Level: First

  • Bedroom 2

    Level: First

    Area: 132.00 Square Feet

    Dimensions: 12x11

  • Bedroom 3

    Level: First

    Area: 143.00 Square Feet

    Dimensions: 13x11

  • Bathroom 4

    Level: First

    Area: 78.00 Square Feet

    Dimensions: 6x13

  • Bedroom 4

    Level: First

    Area: 144.00 Square Feet

    Dimensions: 12x12

  • Laundry

    Level: First

    Area: 72.00 Square Feet

    Dimensions: 6x12

Interior

  • Appliances

    Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator

  • Window Features

    Blinds, Drapes, Rods, Shades, Tinted Windows

  • Heating

    Central, Electric, Zoned

  • Flooring

    Tile

  • Exterior Features

    Lighting, Rain Gutters, Sprinkler Metered

  • Interior Features

    Built In Features, Central Vaccum, Eat In Kitchen, High Ceilings, Kitchen/family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk In Closet(s), Window Treatments

  • Cooling

    Central Air, Zoned

  • Sewer

    Septic Tank

Construction

  • Year Built

    Year Built: 1987

  • Home type

    Single Family Residence

  • Foundation Details

    Block

  • Roof

    Concrete, Tile

  • Construction Materials

    Block, Stucco

Utilities & Energy

  • Pool Features

    Gunite, Tile

  • Association Amenities

    Basketball Court, Cable Tv, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions

  • Water Source

    Public

  • Security Features

    Gated Community

  • Fireplace Features

    Living Room, Outside, Primary Bedroom

  • Parking Features

    Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized

  • Utilities

    Bb/hs Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Public, Sprinkler Meter, Underground Utilities, Water Connected

  • Laundry Features

    Inside, Laundry Room

Other Features

  • Subdivision Name

    Isleworth

  • Patio And Porch Features

    Covered, Rear Porch

  • Lot Features

    In County, Landscaped, On Golf Course, Paved, Private

  • Vegetation

    Mature Landscaping, Oak Trees

  • Community Features

    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), Street Lights

Price History

DateEventPrice

09/04/2026

Source: #MFRO6438618

Listed for Sale

$3,189,000 -5.93%

$948/sqft

07/05/2026

Source: mls_logoStellar MLS-FL #MFRO6372348

Listing Removed

$3,390,000

$1,007/sqft

02/25/2026

Source: mls_logoStellar MLS-FL #MFRO6372348

Price Decreased

$3,390,000 -8.13%

$1,007/sqft

01/24/2026

Source: mls_logoStellar MLS-FL #MFRO6372348

Price Decreased

$3,690,000 -7.17%

$1,097/sqft

01/10/2026

Source: mls_logoStellar MLS-FL #MFRO6372348

Price Increased

$3,975,000 +17.26%

$1,181/sqft

Show more

Nearby Homes

Based on information from Stellar MLS® through Oct 28, 2026, 02:15PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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