58 Cherry Street, Winsted, CT 06098
OFF MARKET

58 Cherry Street
Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,287 sqft

$291,400

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $1,999/mo*
Refinance Your Home

$291,400

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $1,999/mo*
Refinance Your Home
3 Beds
2 Baths
1,287 sqft

Local Information

  • Map ViewExplore the area around 58 Cherry Street.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1948
Living Area
1,287 sqft
Price/Sqft
$226
Parking
3 Parking Spaces

About this House

Charming Cape Cod retreat just a short stroll from the beautiful beaches of Highland Lake! This well-maintained 3-bedroom, 2-bath home has been a cherished getaway for years, offering the perfect blend of comfort and convenience. The main level features a sun-filled living room, a dining room ideal for gatherings, and a kitchen with a center island for easy meal prep. A cozy bedroom and a full bath complete this level. Upstairs, you'll find two generously sized bedrooms and a full bath with laundry for added convenience. The home's mechanicals, windows, and roof are all in excellent condition. Outside, enjoy the spacious yard, perfect for outdoor activities, complete with a fire pit for relaxing evenings. A large shed provides ample storage. Just minutes away, the Highland Lake Marina offers boat rentals, while Main Street's shops and restaurants are easily accessible. Whether you're looking for a seasonal escape or a year-round home, this gem is ready for you!
58 Cherry Street, Winsted, CT 06098 is a 3 bedroom, 2 bathroom, 1,287 sqft single-family home built in 1948. It last sold for $275,000 on Apr 17, 2025 (2% above the $269,900 asking price). It is currently off market. The Trulia Estimate is $291,400, with a rent estimate of $2,505/month.

Home Details for 58 Cherry Street

Interior Features

Interior Details
Basement: FullNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1287 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Oven/Range, Refrigerator, Washer, Dryer, Water HeaterDryerLaundry: Upper LevelRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane WindowsDoor: Storm Door(s)
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: AsphaltFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageParking Spaces: 3Parking: None,Off Street
Frontage
Waterfront: Walk to WaterNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1287 Square Feet

Property Information

Year Built
Year Built: 1948
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 928686

Price & Status

Price
List Price: $269,900
Status Change & Dates
Off Market Date: Wed Mar 19 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: WinchesterCommunity: Winsted
School Information
Elementary School: Per Board of EdHigh School: Gilbert

Building

Building Area
Building Area: 1287 Square Feet

HOA

No HOA

Lot Information

Lot Area: 5227.2 sqft

Energy

Energy Efficiency Features: Thermostat, Doors, Windows

Miscellaneous

BasementMls Number: 24079809Attic: NoneWater ViewWater View: WaterAbove Grade Unfinished Area: 1287
Last check for updates: about 9 hours ago
Listed by David Sartirana, (860) 806-0225
Northwest CT Realty, (860) 379-7245
Bought with: Christine A. Hunter, (860) 480-5591, Hunter Real Estate, LLC, (860) 480-5591
Source: Smart MLS, MLS#24079809

Price History for 58 Cherry Street

DatePriceEventSource
04/17/2025$275,000Sold
Smart MLS #24079809
04/02/2025$269,900PendingSmart MLS #24079809
03/11/2025$269,900Listed For SaleSmart MLS #24079809
08/03/2009$160,000Sold
N/A

Market trends in Winsted

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
10
1MoM
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Property Tax and Assessment

Year2025
Tax$4,059
Assessment$139,160
Home facts updated by county records

Comparable Sales for 58 Cherry Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
39 Orchard Street, Winsted, CT
0.15
Single-Family Home
$290,000
11/26/25
3
1.5
1,200
152 East Lake Street, Winsted, CT
0.24
Single-Family Home
$310,000
11/03/25
2
2
900
14 Pratt Street, Winsted, CT
0.29
Single-Family Home
$167,900
11/14/25
3
1.5
1,340
230 East Wakefield Boulevard, Winsted, CT
0.53
Single-Family Home
$300,000
05/11/26
3
2
1,536
44 Lewis Street, Winsted, CT
0.31
Single-Family Home
$335,000
04/07/26
3
2
1,604
57 Bridge Street, Winsted, CT
0.38
Single-Family Home
$276,000
05/27/26
4
1.5
1,416
107 Birdsall Street, Winsted, CT
0.16
Single-Family Home
$210,000
07/02/26
4
2
1,874
12 Cherry Street, Winsted, CT
0.12
Single-Family Home
$277,000
10/09/25
4
1
1,492
156 Shore Drive, Winsted, CT
0.29
Single-Family Home
$691,000
05/21/26
5
1.5
1,258

Nearby homes

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Assigned Schools

These are the assigned schools for 58 Cherry Street.
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 Winsted

At least 82 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 85 % Say there's wildlife

  • 82 % Say it's dog friendly

  • 67 % Say it's walkable to restaurants

  • 67 % Say there's holiday spirit

  • 67 % Say yards are well-kept

  • 67 % Say parking is easy

  • 62 % Say streets are well-lit

  • 59 % Say kids play outside

  • 58 % Say there are sidewalks

  • 57 % Say neighbors are friendly

  • 52 % Say people would walk alone at night

  • 44 % Say it's quiet

  • 39 % Say they plan to stay for at least 5 years

  • 30 % Say it's walkable to grocery stores

  • 18 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Amber Matarainen
    "Takes forever to get anywhere worthy of being. Traffic gets backed up midday, and people speed through lights all the time"
    0
    Flag
  • Linda Kaiser
    "Small town feel with all of the required amenities. People are friendly and there are several excellent eateries. "
    0
    Flag
  • Nick W.
    " great schools nice tonw friendly people and streets are fimmaly getting repaved though some aren't even tho they need it Really badly "
    2
    Flag
  • Tammy W.
    "I really like it here just really wish that we had a grocery store in walking distance. There is only one in this town and if you don’t have a car you can not get to it."
    0
    Flag
  • Tammy W.
    "It’s not a bad place to live. Most of the people are nice and it is a clean place. I am just looking for a place with a bigger yard and closer to grocery stores. That is the biggest problem with this town. If you don’t have a car it is very hard to live here. If they could fix that problem I would not be looking to move out of town."
    0
    Flag
  • Tammy W.
    "People are always walking their dogs around my neighborhood. Just have to remind a few of them that they need to clean up after their dogs and not leave it there. But it is nice to see that family’s still walk around and enjoy themselves."
    2
    Flag
  • Tammy W.
    "This is a nice place to raise your kids. And it is a very safe place as well. I have lived here my whole life."
    5
    Flag
  • Tammy W.
    "Great. The driver was very nice and helpful when needed. It is not expensive to ride the bus. I would recommend public transit to everybody that needs it. The drivers are very nice about stopping close to your designation."
    1
    Flag
  • Trulia User
    "My neighborhood is close to downtown, close to the Main Street and easily accessible for the public transportation "
    0
    Flag
  • Nick W.
    "I think most of the surrounding areas within Winsted are Gradually getting better, Great schools, Awsome neighbors(Most) small town feel is good for me."
    0
    Flag
  • Shanura G.
    "I've lived here for over 25 yrs and love...very great neighborhood and friendly people...school system is great"
    0
    Flag
  • Ericka A.
    "watch out for walkways they need work and the best parks for kids is the baseball/memorial park and peirson elementary park there enclosed "
    0
    Flag
  • Jennifer M.
    "Winsted is a small working class town. the schools are improving and you g families should definitely consider moving here. "
    0
    Flag
  • Bruinssox1
    "No dog parks to bring your dog too. The parks we do have are no dogs allowed.There is a lot of traffic to watch out for"
    0
    Flag
  • Kaeabalan
    "There are a million dogs on my street and the surrounding streets. I see people out walking dogs frequently, day and night. On the occasion my dog gets loose, the neighbors are a great help in bringing him home. "
    2
    Flag
  • Eric R.
    "Great access to parks and public activities. Close to local community college, private neighbors, easy access to local hospitals."
    1
    Flag
  • Choiniere j.
    "Been here almost a year, and its what you make of it. Could be better her and there, but its a nice town for your family. Not too much in the cost of living, which is a plus!"
    6
    Flag
  • liz
    "Nice and quiet area where neighbors look out for each other's property."
    1
    Flag

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Explore by feature - Pet Friendly

15 pet-friendly rentals in Winsted, CT

Homes for sale near 58 Cherry Street

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Off Market Homes Near 58 Cherry Street

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