6558 Helmsley Cir

Windermere, FL 34786

$635,000
Price
4
Beds
2,575 Sq. Ft.
$247 / Sq. Ft.
2,575
Sq. Ft.
$247
per Sq. Ft.
Get preapproved with Rocket Mortgage1

Description

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...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!
  1. Listed by Sue Webb • Brokerage DRE #2018807 • WATSON REALTY CORP.
    P: (407)-361-6425 C: (407)-361-6425 suewebb@watsonrealtycorp.com

Property Details for 6558 Helmsley Circle

Subdivision Name
PRESTON SQUARE
Township
23
Garage Spaces
2
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 06/14/2026 03:11 PM

Property Details for 6558 Helmsley Circle

StatusActive
MLS #S5151342
Days on Market4
Taxes$4,553 / year
HOA Fees$129 / month
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2009
Lot Size0.13 AC / 5,500 SF
CountyOrange County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of WATSON REALTY CORP., Sue Webb
Add your commute

Building Information for 6558 Helmsley Circle

Stories-Year Built2009Building Size-Lot Size0.13 AC / 5,500 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$3,673 per month

30 year fixed, 6.36% Interest

Principal and Interest

$3,164

Property Taxes

$379

HOA Dues

$129

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 6558 Helmsley Circle

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 3293.0
  • Building Area Units: Square Feet
  • Community Features: Clubhouse, Deed Restrictions, Park, Playground, Pool
  • Direction Faces: North
  • Directions: From Winter Garden Vineland Road 535 turn onto Overstreet Road, left on Preston Square, left on Helmsley Circle. House on right
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 6558
  • Street Name: HELMSLEY
  • Street Suffix: CIRCLE
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
Taxes and HOA Information
  • Association Approval Required: No
  • Association Fee Includes: Community Pool, Recreational Facilities
  • Association Fee Requirement: Required
  • Association Name: Vanguard Mgt Group - Nadia Reveron
  • Association Phone: 813 930 8036
  • Association: Yes
  • CDD: No
  • Pet Restrictions: SEE HOA DOCUMENTS
  • Tax Block: 00/750
  • Tax Book Number: 71-19
  • Tax Legal Description: PRESTON SQUARE 71/19 LOT 75
  • Tax Lot: 75
  • Tax Year: 2025
Virtual Tour
Property
Lot Information
  • Additional Parcels: No
  • Parcel Number: 252327622600750
  • Total Acreage: 0 to less than 1/4
  • Water Access: No
  • Water Extras: No
  • Zoning: P-D
  • Living Area: 2575
Property and Assessments
  • Year Built Numeric: 2009
  • Association Amenities: Clubhouse, Park, Playground, Pool
  • Flood Zone Code: X
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 27
  • Public Survey Section: 25
Utilities
  • Sewer: Public Sewer
  • Utilities: Cable Available, Electricity Connected, Sprinkler Recycled, Street Lights
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Stucco
  • Exterior Features: Irrigation System, Sidewalk, Sliding Doors, Sprinkler Metered
  • Fencing: Vinyl
  • Foundation Details: Slab
  • Levels: Two
  • Pool Private: No
  • Pool: Community
  • Pool Private: Yes
  • Roof: Shingle
  • Waterfront Feet Total: 0
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 3
  • Additional Rooms: Bonus Room
  • Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Solar Hot Water Owned, Washer, Water Filtration System
  • Cooling: Central Air, Zoned
  • Fireplace: No
  • Flooring: Carpet, Tile
  • Heating: Central, Electric
  • Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Tray Ceiling(s), Walk-In Closet(s), Window Treatments
  • Laundry Features: Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 9.0
  • Water View: No
  • Bathrooms Half: 0
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 6558 Helmsley Circle

DateEvent & SourcePriceAppreciation
Jun 11, 2026

Listed (Active)

MFRMLS #S5151342

$635,000—
Apr 24, 2025

Sold (Public Record)

Public Record #1556667492

$620,000—
Apr 24, 2025

Sold (Public Record)

Public Record #1556789564

$620,000

+4.4% / yr

DateEvent & SourcePrice
06/11/2026

Listed (Active)

MFRMLS #S5151342

$635,000
04/24/2025

Sold (Public Record)

Public Record #1556667492

$620,000
04/24/2025

Sold (Public Record)

Public Record #1556789564

$620,000

+4.4% / yr

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 6558 Helmsley Circle

Taxable ValueLand-Additions-Total-
Tax Record2024$4,320 ($360 / month)
Home Facts
Beds4Total Finished SqFt2,575 SqFtAbove Grade Finished SqFt2,575 SqFtStories2Lot Size5,500 SqFtStyleSingle Family ResidenceYear Built2009ZoningP-DCountyORANGEAPN25-23-27-6226-00-750

Schools near 6558 Helmsley Circle

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Sunset Park Elementary School
Public - K to 5
Cornerstone Academy Charter
Charter - K to 8
Horizon West Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Sunset Park Elementary School
PublicK to 5

Cornerstone Academy Charter
CharterK to 8

Horizon West Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Explore Nearby Homes

More information about 6558 Helmsley Circle, Windermere, FL 34786

6558 Helmsley Circle is a single family home for sale in Windermere, FL 34786. This property was listed for sale on June 11, 2026 by WATSON REALTY CORP., it's currently listed at $635,000. It has been on the market for a total of 4 days and was last sold on April 24, 2025. This listing's school district is Orange County Public Schools. Nearby schools include Sunset Park Elementary School, Cornerstone Academy Charter and Horizon West Middle School. 6558 Helmsley Circle is a 4-bed, 3-bath, 2,575 sqft single family home built in 2009.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of WATSON REALTY CORP., Sue Webb

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 06/14/2026 03:11 PM