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$635,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,575 Sq. Ft.
  • Updated 4 hours ago

Next open house:

Open House: 12:00 PM - 2:30 PM

Saturday 6/13 12:00 PM - 2:30 PM

6558 Helmsley Circle,Windermere, FL 34786

6558 Helmsley CircleWindermereFL34786

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  • Open House: 12:00 PM - 3:00 PM

    Sunday 6/14 12:00 PM - 3:00 PM

    6558 Helmsley Circle,Windermere, FL 34786
    6558 Helmsley CircleWindermereFL34786
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Immaculately maintained, move in ready, 4 bed, 3 bath family home in the highly sought after Preston Square community, an established Windermere community. The home feels warm and welcoming, but also luxurious with the 10ft ceilings, crown molding and plantation shutters. The kitchen features a dining area and boasts upgraded appliances, granite countertops and 42" cabinets. The primary bedroom is conveniently located on the first floor, a lovely refuge with tray ceiling, large walk in closet with built ins and en suite bathroom. The large upstairs bedroom, bathroom and bonus room would make a great teenager space, in law suite or entertainment area. Roof was replaced in 2022 and to save on high power bills, a complete, FULLY PAID, solar system installed in 2023!! Other upgrades include new interior paint and light fixtures in 2025, exterior painted in 2019 and a water purification system. For easy maintenance, the sod in the back yard has been replace with turf, is fully fenced and has a spacious screened patio - a serene, private place to relax with your favorite coffee or cocktail! Located in a top-rated school district and zoned for Windermere High School, this home combines luxury, convenience, and peace of mind in one of Central Florida's most desirable communities. square has a charming atmosphere and features its own community pool, park, playground and sport court, all located just minutes from shopping, dining, and theme parks. A short drive to historic Windermere Town with its weekly farmers market, monthly food carts, historic town hall and old school house. Don't miss the opportunity to live the Florida lifestyle in this gorgeous home located within a great school district!

Full Property Details for 6558 Helmsley Cir

General

  • Price: $635,000
  • HOA FEE: $129/month
  • Taxes: $4,553 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: S5151342
  • Updated: Today (6/11/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 9
  • Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Tray Ceiling(s), Walk-In Closet(s), Window Treatments
  • Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Solar Hot Water Owned, Washer, Water Filtration System
  • Furnishings: Unfurnished
  • Flooring: Carpet, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Clubhouse, Park, Playground, Pool

Exterior

  • Exterior Features: Irrigation System, Sidewalk, Sliding Doors, Sprinkler Metered

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34786 - Windermere
  • County: Orange
  • Development Name: 34786 - Windermere
  • Subdivision: PRESTON SQUARE
  • Driving Directions: From Winter Garden Vineland Road 535 turn onto Overstreet Road, left on Preston Square, left on Helmsley Circle. House on right
  • Direction Faces: North

Community

  • Community Name: 34786 - Windermere
  • Community Features: Clubhouse, Deed Restrictions, Park, Playground, Pool
  • Optional Amenities: Clubhouse, Park, Playground, Pool
  • Association: Yes
  • Assoc. Name: Vanguard Mgt Group - Nadia Reveron
  • Assoc. Fees Include: Community Pool, Recreational Facilities
  • Pet Restrictions: SEE HOA DOCUMENTS

Heating & Cooling

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

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Connected, Sprinkler Recycled, Street Lights

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 2,575
  • Sq. Ft. Source: Public Records
  • Year Built: 2009

Lot Features

  • Lot Size (Acres): 0.13
  • Lot Size (Sq. Ft.): 5,500
  • Lot Size: 5500
  • Street/Road Desc.: Asphalt
  • Fencing (Description): Vinyl

Financial Considerations

  • Association Fee: $129
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $4,553
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: PRESTON SQUARE 71/19 LOT 75
  • Flood Zone Info: X
  • APN: 252327622600750
  • Property ID: 252327622600750
  • Block/Lot/Section: 00/750

Listed by Watson Realty Corp.

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Listing agent

— 6558 Helmsley Cir —

  • Watson Realty Corp.

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 6558 Helmsley Cir

School District:Orange County School District
NameGradesDistance
Sunset Park Elementary School, Windermere, FL
12050 Overstreet Road, Windermere, FL 34786
K-50.3 mi
Horizon West Middle School
8200 Tattant Boulevard, Windermere, FL 34786
6-80.6 mi
Windermere High School
5523 Winter Garden Vineland Road, Windermere, FL 34786
9-121.9 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 6558 Helmsley Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/11/2026
Listed
$635,000
2.42%
MLS
4/24/2025
Sold
$620,000
—
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 6558 Helmsley Cir

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,553
—
$541,150
-1%
2025
$4,553
5%
$547,620
100%
2024
$4,320
7%
$273,549
3%
2023
$4,021
6%
$265,582
6%
2021
$3,802
-2%
$250,337
-3%
2022
$3,863
2%
$257,847
4%
2021
$3,802
2%
$246,881
2%
2019
$3,726
1%
$241,330
2%
2018
$3,694
2%
$236,830
2%
2017
$3,634
1%
$231,959
2%
2016
$3,603
-2%
$227,188
1%
2015
$3,660
-2%
$225,609
1%
2014
$3,717
2%
$223,818
2%
2013
$3,642
—
$220,510
—
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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Listed by Watson Realty Corp.

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6558 Helmsley Circle, Windermere, FL 34786 (MLS# S5151342) is a Single Family property with 4 bedrooms and 3 full bathrooms. 6558 Helmsley Circle is currently listed for $635,000 and was received on June 11, 2026. Want to learn more about 6558 Helmsley Circle? 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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