58 Cherry Street, Winsted, CT 06098
OFF MARKET

$296,300

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,287 sqft

58 Cherry Street, Winsted, CT 06098

Refinance Your Home
Currently Off Market - Sold Apr 17, 2025 for $275,000

Home Value

Trulia Estimate
$296K
Since last month
Increased$200 (+0.1%)
Since last year
Increased$17K (+6%)
Since last sale
Increased$21K (+7.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +123% in the last 10 years
MonthEstimated value
2026
August 2026$296K
August 2026$296K
July 2026$296K
June 2026$291K
May 2026$289K
April 2026$288K
March 2026$291K
February 2026$289K
January 2026$286K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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 home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
71 Ridge Street, Winsted, CT 06098
0.05
$296,500
3
1
1,044
Off Market
39 Finn Street, Winsted, CT 06098
0.07
$289,100
3
1
1,175
Off Market
11 Cherry Street, Winsted, CT 06098
0.10
$352,100
3
1.5
1,324
Off Market
43 East Lake Street, Winsted, CT 06098
0.07
$920,000
4
3
2,131
Recently Sold
12 Cherry Street, Winsted, CT 06098
0.12
$333,100
4
1
1,492
Off Market
47 Orchard Street, Winsted, CT 06098
0.14
$425,900
4
2
1,818
Off Market
107 Birdsall Street, Winsted, CT 06098
0.16
$210,000
4
2
1,874
Recently Sold
81 Birdsall Street, Winsted, CT 06098
0.16
$356,800
5
3
2,764
Off Market
39 Orchard Street, Winsted, CT 06098
0.15
$290,000
3
1.5
1,200
Recently Sold
10 Hurlbut Street, Winsted, CT 06098
0.20
$251,200
3
1
900
Off Market
31 Hurlbut Street, Winsted, CT 06098
0.21
$230,300
2
2
1,242
Off Market

Local Information

  • Map ViewExplore the area around 58 Cherry Street.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1948
1,287 sqft
$230/sqft
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). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $296,300, with a rent estimate of $2,207/month.
Last check for updates: about 10 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

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

Price and Tax history

DateEventPrice
Apr 17, 2025
Source: Smart MLS #24079809
Sold
$275,000
Apr 2, 2025
Source: Smart MLS #24079809
Pending
$269,900
Mar 11, 2025
Source: Smart MLS #24079809
Listed For Sale
$269,900
Aug 3, 2009
Source: N/A
Sold
$160,000

Market trends in Winsted

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
12
2MoM

Around this home

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

LGBTQ Local Legal Protections

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.

Frequently asked questions about 58 Cherry Street

  • What is 58 Cherry Street estimated to be worth?
    Trulia's estimated value for 58 Cherry Street in Winsted, CT is $296,300.
  • What is the price history for 58 Cherry Street?
    58 Cherry Street in Winsted, CT last sold for $275,000 in April 2025.
  • Is Winsted a buyer's or seller's market?
    Winsted is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Winsted?
    Residents describe Winsted, CT as dog-friendly, walkable to restaurants, and well-kept. See recently sold homes in Winsted, CT.
  • Does 58 Cherry Street have laundry facilities?
    Yes, 58 Cherry Street in Winsted, CT has in-unit laundry.
  • How big is the lot at 58 Cherry Street?
    The lot at 58 Cherry Street in Winsted, CT is about 0.12 acres (5,227 sq ft).

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