6552 Helmsley Cir, Windermere, FL 34786
PENDING
3D VIEW

6552 Helmsley Cir
Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 1,980 sqft

$469,000

Est. Mortgage $3,549/mo*
Get Pre-Qualified

$469,000

Est. Mortgage $3,549/mo*
Get Pre-Qualified
4 Beds
3 Baths
1,980 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Under contract-accepting backup offers. Welcome home to Preston Square in beautiful Windermere! This stunning corner-unit townhome with 4 bedroom, 3 bathrooms offers the perfect blend of comfort, style, and convenience, with a new roof and fresh exterior paint. Step onto the cozy front porch and into a bright, inviting two-story home filled with natural light. The main living areas feature tile flooring throughout; great room showcases a mirror accent wall along with board and batten in the dining area. Kitchen features granite countertops, breakfast bar, stainless steel appliances, and stone backsplash. Sliding glass door leads to a private paver patio, perfect for relaxing or entertaining. Downstairs bedroom with full bath, inside laundry room plus a utility sink leads to the attached two-car garage with long driveway for additional parking. Upstairs you will find 3 additional bedrooms, stunning primary suite with balcony views. Primary bath features dual sinks, large garden tub, and separate shower. Preston Square offers amenities including a stunning community pool, playground, mature landscaping, basketball court, green space for events, and fitness stations. Ideally located near local dining, shopping, top-rated schools, golf courses, hospitals, and major roadways and attractions.

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Patio
View
No Info
HOA
$315/Monthly
Price/Sqft
$237
Listed
75 days ago

Home Details for 6552 Helmsley Cir

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 1980 Square Feet
Appliances & Utilities
Utilities: PublicAppliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Range, Refrigerator, WasherDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Door: Sliding DoorsFlooring: Carpet, TileCommon Walls: Corner Unit
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Tile
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Front Porch, PatioVegetation: Trees/LandscapedExterior: Balcony, Irrigation System, Lighting, SidewalkFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Curb Parking,Driveway,Garage Door Opener,Garage Faces Rear,Guest,On Street
Frontage
Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 68Days on Market: 75

Property Information

Year Built
Year Built: 2008
Property Type / Style
Property Type: ResidentialProperty Subtype: Townhouse
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 272325622601400

Price & Status

Price
List Price: $469,000Price Per Sqft: $237
Status Change & Dates
Off Market Date: Sun May 31 2026

Active Status

MLS Status: Pending

Media

Location

Direction & Address
City: WINDERMERECommunity: PRESTON SQUARE
School Information
Elementary School: Sunset Park ElemJr High / Middle School: Horizon West Middle SchoolHigh School: Windermere High School

Agent Information

Listing Agent
Listing ID: O6392752

Building

Building Area
Building Area: 2587 Square Feet

Community

Community Features: Community Mailbox, Deed Restrictions, Playground, Pool, SidewalksNot Senior Community
Other
Playground

HOA

HOA Fee Includes: Community Pool, Maintenance Structure, Maintenance Grounds, Pest Control, Pool MaintenanceHOA Name: Jedi ManagementHOA Phone: 689-204-2057Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $315/Monthly

Lot Information

Lot Area: 4377 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6392752Universal Property Id: US-12095-N-272325622601400-R-N

Additional Information

HOA Amenities: Basketball Court,Maintenance,Park,Playground,Pool
Last check for updates: about 16 hours ago
Listing Provided by: Morgan Horsley, (256) 283-8747
THE REAL ESTATE COLLECTION LLC, (407) 656-7814
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6392752
Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Market trends in Windermere

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$698K
$15KMoM
Sale-to-List Price
97.2%
0.0%MoM
Price per sq ft
$268
$8MoM
Available listings
293
3MoM

Price History for 6552 Helmsley Cir

DatePriceEventSource
05/31/2026$469,000PendingStellar MLS #O6392752
04/23/2026$469,000PriceChange
Stellar MLS #O6392752
03/24/2026$479,000Listed For SaleStellar MLS #O6392752
12/29/2008$265,000Sold
N/A

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Property Tax and Assessment

Year2024
Tax$3,181
Assessment$383,055
Home facts updated by county records

Comparable Sales for 6552 Helmsley Cir

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
7028 Ventnor Dr, Windermere, FL
0.06
Townhouse
$470,000
03/26/26
4
3
1,980
11692 Water Run Aly, Windermere, FL
0.45
Townhouse
$459,000
01/14/26
3
2.5
1,712
12840 Calderdale Ave, Windermere, FL
0.52
Townhouse
$423,000
03/24/26
4
3.5
1,905
7348 Yoder St, Windermere, FL
0.54
Townhouse
$370,000
09/03/25
3
2.5
1,479
12884 Calderdale Ave, Windermere, FL
0.53
Townhouse
$390,000
08/25/25
3
2.5
1,565
11746 Water Run Aly, Windermere, FL
0.47
Townhouse
$418,000
06/18/25
3
2.5
1,588
12879 Emersondale Ave, Windermere, FL
0.55
Townhouse
$390,000
04/30/26
3
2.5
1,565
11818 Water Run Aly, Windermere, FL
0.48
Townhouse
$410,000
02/23/26
3
2.5
1,588
11854 Water Run Alley, Windermere, FL
0.50
Townhouse
$400,000
04/30/26
3
2.5
1,588
7482 Bentonshire Ave, Windermere, FL
0.59
Townhouse
$390,000
01/29/26
3
2.5
1,428

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 6552 Helmsley Cir.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windermere

At least 270 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say car is needed

  • 87 % Say parking is easy

  • 81 % Say people would walk alone at night

  • 80 % Say it's quiet

  • 79 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 75 % Say streets are well-lit

  • 64 % Say yards are well-kept

  • 60 % Say they plan to stay for at least 5 years

  • 59 % Say it's walkable to grocery stores

  • 56 % Say there's wildlife

  • 55 % Say it's walkable to restaurants

  • 54 % Say neighbors are friendly

  • 40 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Anjalique Creative Concepts
    "We’ve lived in this area for 5 years and absolutely love it! The people in the community are always friendly, welcoming and supportive of one another. All the surrounding neighborhoods are well maintained and there are always organized activities in the community that makes it fun to meet new residents moving in."
    0
    Flag
  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
    Flag
  • Valentina
    "Trick or treating is big but it’s more about small groups of neighbors doing things together rather than large activities in the entire neighborhood."
    0
    Flag
  • Juliana Daurio
    "I moved to Windermere in 2004. When my kids were 3 and 4. This feels like home since then. Now that my kids are gone I see no need to move. I have many nice neighbors and enjoy everything that this area has to offer. "
    0
    Flag
  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
    Flag
  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
    Flag
  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
    Flag
  • Datylberman
    "I work at home so I’m not versed in the commute anywhere.many people in Windermere work at hone also.friends who work downtown are happy with their commute."
    0
    Flag
  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
    Flag
  • Garrett Hendrickson
    "Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
    0
    Flag
  • Ngandhi62
    "Great areas to walk dogs and great puppy parks. Very close convenient veterinarians and pet supply stores. There are also many pet owners in area, therefore a nice social community is created."
    5
    Flag
  • Sean H.
    "It is a very pet friendly neighborhood. And has many fenced in dog areas and 90% of people are respectful enough to clean up after their dogs."
    3
    Flag
  • Limegreenlilo
    "Quiet & neighbors look out for one another. We have a FB page for residents to help each other out. I have been a resident ten years and love living here. HOA is good and they keep everything nice."
    0
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  • Carylpalmerini17
    "Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
    3
    Flag
  • Carylpalmerini17
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
    3
    Flag
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
    1
    Flag
  • Msldancer
    "See lots of dogs in the area, most are very social. But I do not like that some owners do not put their dogs on leashes, they also then get mad when you come by even though you’re dog is leashes as it should be."
    2
    Flag
  • Mckenziejl
    "They would like the many trails and dog parks. Most of the neighborhoods are not gated or man guarded, so you can easily move in and out of them. Each neighborhood is unique and wherher you're going for walk with or without you pet, the time would be enjoyable."
    0
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  • Jessica
    "30min or less to get to any of the central Florida locations. Some locations can even see fireworks. Traffic can be a little heavy during the am/pm rush but nothing super crazy."
    2
    Flag
  • Stephanie F.
    "Easy to get to Disney. I work on Disney property. High traffic during rush hour times. Very quick during non peak rush hour times. "
    1
    Flag
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
    0
    Flag
  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
    Flag
  • David M.
    "I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
    0
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  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
    2
    Flag
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
    1
    Flag
  • Dasom.jang
    "It’s a nice and safe area to live in. There isn’t much going on, but there are food truck nights once a month, and farmer’s market on every Saturday in Winter Garden. "
    0
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  • John F.
    "I have lived in Windermere for 20 years. Very safe and good clean people. The cops are very responsive and people are rich and have class "
    0
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  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
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  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
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  • Evelyn T.
    "It’s a small oasis away from the hustle and bustle of such a vacation heavy town. I love getting to feel like I’m actually away from work and in a calm space but still be a 20 minute commute."
    1
    Flag
  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
    0
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  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
    1
    Flag
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
    0
    Flag
  • Loypippin
    "It’s a safe area but growing too quickly. Too many new houses and schools getting crowded. The schools are great, but need to be built faster to keep up. "
    1
    Flag
  • Beverly B.
    "It is very safe well lighted small community with many families with and without children. Everyone is friendly and keep their properties in great shape"
    0
    Flag
  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
    1
    Flag
  • Princess J.
    "Great place to live, and I feel safe in this area. I moved to this area when I moved to Florida and it was the best decision. "
    1
    Flag
  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
    0
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LGBTQ Local Legal Protections

Morgan Horsley, THE REAL ESTATE COLLECTION LLC, (407) 656-7814
Agent Phone: (256) 283-8747
6552 Helmsley Cir, Windermere, FL 34786 is a 4 bedroom, 3 bathroom, 1,980 sqft townhouse built in 2008. This property is currently available for sale and was listed by Stellar MLS on Mar 24, 2026. The MLS # for this home is MLS# O6392752.