For Sale
Photo 1 of Single family home for sale at 5237 Isleworth Country Clb Dr, Windermere, FL 34786 | MLS# O6427447 | Listing updated on 2026-10-28
Photo 2 of Single family home for sale at 5237 Isleworth Country Clb Dr, Windermere, FL 34786 | MLS# O6427447 | Listing updated on 2026-10-28
2
Beds Icon

Street View

$3,600,000

Monthly Est:$17,919

  • Beds Icon5 Beds
  • Beds Icon
    5 Baths
  • Beds Icon5,972sqft

5237 Isleworth Country Clb Dr, Windermere, FL 34786

$17,919/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 1989

  • $1,224/mo HOA

  • 22,076 sqft lot

  • $603/sq.ft

Description

Located along the 2nd tee of Isleworth's renowned championship golf course, this beautiful golf-front estate offers an exceptional location within the gates. The five-bedroom home features offers a spacious and open floor plan of more than 5,900 square feet overlooking the serene golf and water vistas. .

  • Houzeo last checked: 2 hours ago
  • Listing updated: October 28, 2026 at 10:52 am
  • Listing Provided by: Monica Lochmandy (407) 230-6888 , Sarah Longwell | ISLEWORTH REALTY LLC (407) 909-9000
  • Source: Stellar MLS-FL | MLS#: O6427447 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Orange County

  • City

    Windermere

  • Neighborhood

    --

  • Year Built

    1989

  • HOA Fees

    $1224/mo

  • Finished Area

    5,972 sqft

  • Lot Size

    22,076 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6427447

  • MLS Status

    Active

  • Days on Market

    89

  • 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.

Security Gate Security Gate

Security Guard Security Guard

Internet Internet

Maintenance Maintenance

Cable TV Cable TV

Park Playground Park Playground

Escrow Reserves Fund Escrow Reserves Fund

Private Road Private Road

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: 5

    Bathrooms: 5

Interior

  • Sewer

    Septic Tank

  • Heating

    Central, Zoned

  • Cooling

    Central Air, Zoned

  • Interior Features

    Built In Features, Primary Bedroom Main Floor, Walk In Closet(s)

  • Appliances

    Built In Oven, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer

  • Flooring

    Carpet, Marble, Wood

Construction

  • Year Built

    Year Built: 1989

  • Home type

    Single Family Residence

  • Foundation Details

    Block, Slab

  • Construction Materials

    Block, Stucco

  • Roof

    Tile

Utilities & Energy

  • Pool Features

    In Ground

  • Association Amenities

    Cable Tv, Gated, Playground

  • Fireplace Features

    Living Room

  • Laundry Features

    Inside

  • Utilities

    Cable Connected, Electricity Connected, Public

  • Water Source

    Well

Other Features

  • Community Features

    Community Mailbox, Deed Restrictions, Gated Community Guard, Golf, Playground

  • Subdivision Name

    Isleworth

Price History

DateEventPrice

10/27/2026

Source: mls_logoStellar MLS-FL #MFRO6427447

Listed for Sale

$3,600,000

$603/sqft

07/30/2026

Source: mls_logoStellar MLS-FL #MFRO6427447

Contingent (Active Under Contract)

$3,600,000 +44900.00%

$603/sqft

09/20/2016

Source: mls_logoStellar MLS-FL #MFRO5442667

Price Decreased

$8,000 -33.33%

$1/sqft

09/20/2016

Source: mls_logoStellar MLS-FL #MFRO5442667

Sold

$12,000

$2/sqft

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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