$635,000
6558 Helmsley Circle
Windermere, FL 34786
Listing updated: June 11, 2026 at 9:11 PM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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!
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history0 days on market
- Status: ActiveJun 11, 2026
- Listed$635,000Jun 11, 2026
- Price increased$635,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 0
- Subdivision
- Preston Square
- County
- Orange
- Year built
- 2009
- Living area
- 2,575 sq ft
- Price/sq ft
- $247
- Building area
- 3,293 sq ft (Public Records)
- Lot size
- 5,500 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X
- Garage
- 2 spaces
- Annual taxes
- $4,553 (2025)
- Parcel #
- 25-23-27-6226-00-750
- Zoning
- P-D
- MLS #
- S5151342
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Flooring
- Carpet, Tile
- Appliances
- Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Solar Hot Water, Washer, Water Filtration System
- Interior features
- Ceiling Fans(s), Crown Molding, Eat-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
- Laundry Room
- Stories / Levels
- Two
- Direction faces
- North
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 2
- Attached garage
- Yes
HOA & Financial
- HOA fee
- $129 / Monthly
- Monthly HOA
- $129/mo
- Total monthly fees
- $129/mo
- Total annual fees
- $1,542
- HOA name
- Vanguard Mgt Group - Nadia Reveron
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- SEE HOA DOCS
Exterior & Construction
- Exterior features
- Sidewalk, Sliding Doors, Sprinkler Metered
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Slab
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available, Electricity Connected, Sprinkler Recycled
Community
- Pets allowed
- Yes
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 16x15 |
| Kitchen | First | 9x22 |
| Family Room | First | 14x22 |
| Primary Bedroom | First | 16x12 |
| Primary Bathroom | First | 12x10 |
| Bedroom 2 | First | 10x22 |
| Bedroom 3 | First | 12x10 |
| Bedroom 4 | Second | 10x16 |
| Bonus Room | Second | 12x21 |
Listing Details
- Listing date
- 2026-06-11
- On market date
- 2026-06-11
- Original list price
- $635,000
- Occupant type
- Owner
- MLS area
- 34786 - Windermere
- Listing AOR
- Osceola
- Status changed
- 2026-06-11
- Tax legal description
- PRESTON SQUARE 71/19 LOT 75
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From Winter Garden Vineland Road 535 turn onto Overstreet Road, left on Preston Square, left on Helmsley Circle. House on right
Property sale history
Public records6558 HELMSLEY CIR, Windermere 34786
- Apr 2025$620,000
2,575 sq ft · Built 2009 · 0.1263 acres
Sale data from Florida public records (Department of Revenue / county property appraiser). Deemed reliable but not guaranteed; may not reflect current market or MLS status. Not Stellar MLS data.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 11, 2026 at 9:11 PM ET. All data is obtained from various sources and may not have been verified by 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.
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