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$3,600,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 5,972 Sq. Ft.
  • Updated 1 day ago
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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. .

Full Property Details for 5237 Isleworth Country Club Dr

General

  • Price: $3,600,000
  • HOA FEE: $1,224/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $45,808 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6427447
  • Updated: 7/30/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 6
  • Interior Features: Built-in Features, Primary Bedroom Main Floor, Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Living Room
  • Appliances: Built-In Oven, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Carpet, Marble, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 5

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside

Additional Information

  • Shared Amenities: Cable TV, Gated, Playground
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground
  • Spa: Yes
  • Spa Description: In Ground

Exterior

  • Exterior Features: Irrigation System

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3

Location

  • Area: 34786 - Windermere
  • County: Orange
  • Development Name: 34786 - Windermere
  • Subdivision: ISLEWORTH
  • Driving Directions: I-4 to Conroy Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive. Estate will be on the Left or Right.
  • Direction Faces: Northwest

School Information

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

Community

  • Community Name: 34786 - Windermere
  • Community Features: Lake, Private Boat Ramp, Water Access, Waterfront, Community Mailbox, Deed Restrictions, Gated Community - Guard, Golf, Playground
  • Optional Amenities: Cable TV, Gated, Playground
  • Association: Yes
  • Assoc. Name: Dan O'Connell
  • Assoc. Fees Include: 24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Repairs, Private Road, Security
  • Number of Pets: 2
  • Pet Restrictions: Per Orange County breed restrictions, number limits and leash laws.

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Central, Zoned

Utilities

  • Sewer: Septic Tank
  • Water District: BUTLER CHAIN OF LAKES - LAKE CHASE
  • Water: Well
  • Utility Description: Cable Connected, Electricity Connected, Public

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Tile
  • Stories/Levels: Two
  • Square Feet: 5,972
  • Sq. Ft. Source: Public Records
  • Year Built: 1989

Lot Features

  • Property View: Golf Course, Water
  • Lot Size (Acres): 0.51
  • Lot Size (Sq. Ft.): 22,076
  • Lot Size: 22076
  • Street/Road Desc.: Paved

Water Features

  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake - Chain of Lakes
  • Water Front Name: BUTLER CHAIN OF LAKES - LAKE CHASE
  • Water Front Desc.: Lake, Waterfront

Financial Considerations

  • Association Fee: $3,672
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $45,808.14
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: ISLEWORTH 16/118 LOT 232
  • Flood Zone Info: AE
  • APN: 162328389902320
  • Property ID: 162328389902320
  • Block/Lot/Section: 2

Listed by Isleworth Realty Llc

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Listing agents

— 5237 Isleworth Country Club Dr —

  • Isleworth Realty Llc

  • Isleworth Realty Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5237 Isleworth Country Club Dr

School District:Orange County School District
NameGradesDistance
Windermere Elementary School
11125 Park Avenue, Windermere, FL 34786
K-52.2 mi
Chain Of Lakes Middle School
8700 Conroy Windermere Road, Orlando, FL 32835
6-81.4 mi
Olympia High School
4301 South Apopka Vineland Road, Orlando, FL 32835
9-121.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5237 Isleworth Country Club Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/30/2026
Listed
$3,600,000
20%
MLS
1/31/2023
Sold
$3,000,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5237 Isleworth Country Club Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$45,808
—
$2,743,490
-1%
2025
$45,808
7%
$2,770,580
7%
2024
$42,719
-4%
$2,585,849
-13%
2023
$44,543
23%
$2,973,589
33%
2021
$36,304
-7%
$2,238,763
-9%
2022
$38,956
7%
$2,448,719
9%
2021
$36,304
-3%
$2,251,439
-1%
2019
$37,585
1%
$2,264,116
2%
2018
$37,392
1%
$2,224,892
2%
2017
$37,152
12%
$2,186,597
13%
2016
$33,036
-2%
$1,942,003
1%
2015
$33,624
-1%
$1,928,503
1%
2014
$33,926
1%
$1,913,197
1%
2013
$33,561
—
$1,901,852
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Isleworth Realty Llc

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5237 Isleworth Country Club Drive, Windermere, FL 34786 (MLS# O6427447) is a Single Family property with 5 bedrooms and 5 full bathrooms. 5237 Isleworth Country Club Drive is currently listed for $3,600,000 and was received on July 30, 2026. Want to learn more about 5237 Isleworth Country Club Drive? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

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