6558 HELMSLEY CIRCLE, Windermere, FL 34786
OFF MARKET

6558 HELMSLEY CIRCLE
Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,575 sqft

$617,000

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $4,322/mo*
Refinance Your Home

$617,000

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $4,322/mo*
Refinance Your Home
4 Beds
3 Baths
2,575 sqft

Local Information

  • Map ViewExplore the area around 6558 HELMSLEY CIRCLE.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2009
Living Area
2,575 sqft
Price/Sqft
$240
Parking
2 Car Garage
HOA
$105/Monthly

About this House

This Stunning Windermere 4-bedroom, 3-bath home has it all. Tile floors in all the living areas and vinyl plank everywhere else, 10-foot-high ceilings and crown molding, and plantation shutters, give the home a luxury and elegant feel. The kitchen features a dining area, upgraded appliances, granite counter tops and 42-inch cabinets. The master bedroom is downstairs and features a beautiful a tray ceiling, and a large walk-in closet with built-ins. The spacious master bath has a separate shower, spa tub, and two vanities fit with high-end counter tops. The Downstairs also includes two extra bedrooms and a full bath. The large bedroom and bath upstairs as well as a spacious bonus room could double as a perfect in law suite or a kid's paradise. The backyard has been completely converted to turf to take away the pesky Maintenace and provide you with your own Sancturary. The property includes a water purification system, full roof solar panel system, brand new roof, and Privacy fenced back yard/spacious screened patio. Solar energy system has proven to offset exorbitant power bills. Zoned for some of the most sought-after public schools in the district. Reach out to make this dream home your new home!
6558 HELMSLEY CIRCLE, Windermere, FL 34786 is a 4 bedroom, 3 bathroom, 2,575 sqft single-family home built in 2009. It last sold for the $620,000 asking price on Apr 24, 2025. It is currently off market. The Trulia Estimate is $617,000, with a rent estimate of $3,398/month.

Home Details for 6558 HELMSLEY CIRCLE

Interior Features

Interior Details
Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Primary Bathroom, Bonus Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2575 Square Feet
Appliances & Utilities
Utilities: Cable Available, Sprinkler Meter, Sprinkler Recycled, Street LightsAppliances: Dishwasher, Disposal, Microwave, Range, Refrigerator, Solar Hot Water OwnedDishwasherDisposalLaundry: Inside,Laundry RoomMicrowaveRefrigerator
Heating & Cooling
Heating: Central,Electric,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Window: Blinds, Insulated Windows, Shutters, Window TreatmentsDoor: Sliding DoorsFlooring: Carpet, Ceramic Tile, Vinyl
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Ceramic Tile, Vinyl
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, ScreenedVegetation: Mature LandscapingExterior: Irrigation System, Sprinkler MeteredFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garage Dimensions: 20x20No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Frontage
Road Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 49

Property Information

Year Built
Year Built: 2009
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Bungalow
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 252327622600750

Price & Status

Price
List Price: $620,000
Status Change & Dates
Off Market Date: Mon Mar 24 2025

Active Status

MLS Status: Sold

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

Building

Building Area
Building Area: 3293 Square Feet

Community

Community Features: Deed RestrictionsNot Senior Community

HOA

HOA Name: Leland ManagementHOA Phone: 407-781-1188Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $105/Monthly

Lot Information

Lot Area: 5500 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, Lease Option, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6277279Showing Requirements: Call Listing Agent, Combination Lock BoxUniversal Property Id: US-12095-N-252327622600750-R-N

Additional Information

HOA Amenities: Playground,Pool
Last check for updates: about 6 hours ago
Listed by Corey Cannon, (407) 615-0215
BHHS FLORIDA REALTY, (407) 876-2090
Bought with: Mark Rankin, (407) 989-8881, DOWNTOWN REALTY, (407) 989-8881
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6277279
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

Price History for 6558 HELMSLEY CIRCLE

DatePriceEventSource
07/20/2026$630,000ListingRemovedStellar MLS #S5151342
06/29/2026$630,000PriceChange
Stellar MLS #S5151342
06/11/2026$635,000Listed For SaleStellar MLS #S5151342
04/24/2025$620,000Sold
Stellar MLS #O6277279
03/31/2025$620,000PendingStellar MLS #O6277279
03/26/2025$620,000PriceChange
Stellar MLS #O6277279
03/12/2025$660,000PriceChange
Stellar MLS #O6277279
02/04/2025$670,000Listed For SaleStellar MLS #O6277279
11/10/2018$339,000ListingRemovedAgent Provided
10/17/2018$339,000PriceChange
Agent Provided
08/30/2018$349,000PriceChange
Agent Provided
07/28/2018$359,000Listed For SaleAgent Provided
03/18/2009$308,800Sold
N/A

Market trends in Windermere

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$722K
$50KMoM
Sale-to-List Price
97.3%
0.2%MoM
Price per sq ft
$273
$11MoM
Available listings
285
6MoM
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Property Tax and Assessment

Year2024
Tax$4,320
Assessment$527,848
Home facts updated by county records

Comparable Sales for 6558 HELMSLEY CIRCLE

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
6573 HELMSLEY CIRCLE, Windermere, FL
0.04
Single-Family Home
$631,900
04/30/26
4
3.5
2,664
6841 HELMSLEY CIRCLE, Windermere, FL
0.17
Single-Family Home
$625,000
03/20/26
4
3
2,371
6799 HELMSLEY CIRCLE, Windermere, FL
0.18
Single-Family Home
$645,000
06/16/26
4
3.5
2,615
6897 NORTHWICH DRIVE, Windermere, FL
0.23
Single-Family Home
$565,000
06/30/26
4
3
2,229
6891 NORTHWICH DRIVE, Windermere, FL
0.24
Single-Family Home
$620,000
02/17/26
5
2.5
2,759
6840 HELMSLEY CIRCLE, Windermere, FL
0.14
Single-Family Home
$620,000
06/16/26
4
4
2,847
6615 HELMSLEY CIRCLE, Windermere, FL
0.09
Single-Family Home
$705,000
06/12/26
5
3.5
3,390
6846 HELMSLEY CIRCLE, Windermere, FL
0.14
Single-Family Home
$620,000
04/24/26
5
3
2,555
6871 HELMSLEY CIRCLE, Windermere, FL
0.14
Single-Family Home
$545,000
04/03/26
3
2
1,772

Nearby homes

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Assigned Schools

These are the assigned schools for 6558 HELMSLEY CIRCLE.
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
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  • 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
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  • 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
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  • 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
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  • 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
    Flag
  • 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
    Flag
  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
    Flag
  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

44 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

49 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

57 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

82 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

50 rentals with a washer/dryer in Windermere, FL

Explore by feature - Outdoor Space

21 rentals with an outdoor space in Windermere, FL

Homes for sale near 6558 HELMSLEY CIRCLE

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Off Market Homes Near 6558 HELMSLEY CIRCLE

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