175 Main St, Winchester, CT 06098
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Property image
OFF MARKET

175 Main St
Winchester, CT 06098

  • 14 Beds
  • 7 Baths
  • 4,860 sqft

$752,200

Trulia Estimate
as of Jul 13, 2026
Est. Refi. Payment $4,963/mo*
Refinance Your Home

$752,200

Trulia Estimate
as of Jul 13, 2026
Est. Refi. Payment $4,963/mo*
Refinance Your Home
14 Beds
7 Baths
4,860 sqft

Local Information

  • Map ViewExplore the area around 175 Main St.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Addresses include 175 Main Street and 183 Main Street in Winsted, CT. Amazing opportunity to acquire a 9 Unit Asset (7 Apartments + 2 Retail in Winsted with anchor tenant Noli's Restaurant (Rent $2,266 w 3% increase/year w over 20 years in business Pride of Ownership is evident with Capital Improvements made by the current owners, including: new water heaters, heating zones, electrical upgrades, fire rated tenant main doors & new fire alarms/strobes in both buildings. The unit mix is: 1, 4 bedroom ($1,100; 4, 2 bedrooms ($1,000; $1,050; $900; the other can be rented for up to $1500 per month and 2, 1 bedroom units ($950 each. The 175 Main St had a roof replacement in 2021, a privacy fence enclosure installed & all 4 residential units have gone through renovations. 183 Main St has had a roof replacement in 2023, aft wall structural repair, new studs, insulation, beams & siding. 183 2A has been refurbished. One retail space is leased to Noli's Restaurant which has a patio. Noli's pays their heat and electric. The current owner leased the second retail space to Northwest Soup & Deli ($1500 then $1650 on 1/1/2025 and this establishment has all new equipment. They pay their own electric and a fixed gas, water/sewer reimbursement to the Owner. The residential tenants pay their electric. Owners are very meticulous and detail oriented. This is a seamless opportunity to own a well-run asset. Properties being sold together.
175 Main St, Winchester, CT 06098 is a 14 bedroom, 7 bathroom, 4,860 sqft multi-family built in 1900. It last sold for $600,000 on Feb 5, 2021 (37% below the $950,000 asking price). It is currently off market. The Trulia Estimate is $752,200, with a rent estimate of $1,677/month.
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Home Highlights

Parking
None
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 175 Main St

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: Central AirHeating Fuel: Baseboard

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Multi Family

Exterior Features

Parking & Garage
Parking: None

Price History for 175 Main St

DatePriceEventSource
08/05/2025$950,000ListingRemovedSmart MLS #24073478
02/08/2025$950,000Listed For SaleSmart MLS #24073478
01/27/2025$995,000ListingRemovedSmart MLS #24037338
11/05/2024$995,000PriceChange
Smart MLS #24037338
08/03/2024$1,100,000Listed For SaleSmart MLS #24037338
02/05/2021$600,000Sold
Smart MLS #170265583
12/14/2020$669,000ContingentSmart MLS #170265583
09/02/2020$669,000PendingAgent Provided
09/02/2020$669,000Listed For SaleAgent Provided
02/04/2020$669,000ListingRemovedAgent Provided
01/22/2020$669,000Listed For SaleAgent Provided
04/12/2018$150,000Sold
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$5,699
Assessment$195,370
Home facts updated by county records

Comparable Sales for 175 Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
27 Thibault Avenue, Winsted, CT
0.33
Multi-Family Home
$389,900
11/06/25
8
5
7,372
203 Holabird Avenue, Winsted, CT
0.33
Multi-Family Home
$370,000
07/21/25
5
3
3,690
51 Hinsdale Avenue, Winsted, CT
0.63
Multi-Family Home
$485,000
06/22/26
7
5
3,538
142 Main St, Winsted, CT
0.07
Multi-Family Home
$255,000
12/23/25
4.5
3,965
131 Willow Street, Winsted, CT
0.10
Multi-Family Home
$293,000
10/30/25
6
2
2,160
49 Walnut Street, Winsted, CT
0.19
Multi-Family Home
$305,000
12/22/25
5
2
2,344
62 Fruit Street, Winsted, CT
0.36
Multi-Family Home
$326,000
10/31/25
6
2
3,078
25 Center Street, Winsted, CT
0.28
Multi-Family Home
$315,000
04/09/26
3
2.5
2,754
68 Wetmore Avenue, Winsted, CT
0.35
Multi-Family Home
$190,000
12/23/25
6
2.5
2,555
135 Elm Street, Winsted, CT
0.38
Multi-Family Home
$324,900
11/21/25
4
2
3,303

Nearby homes

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Assigned Schools

These are the assigned schools for 175 Main St.
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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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Apartments for Rent

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Explore by feature - Pet Friendly

17 pet-friendly rentals in Winchester, CT

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Winchester, CT

Homes for sale near 175 Main St

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Off Market Homes Near 175 Main St

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