2 Hillside Pl, Winsted, CT 06098
Property image
Property image
OFF MARKET

2 Hillside Pl
Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 2,812 sqft (on 0.76 acres)

$399,100

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $2,666/mo*
Refinance Your Home

$399,100

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $2,666/mo*
Refinance Your Home
4 Beds
1.5 Baths
2,812 sqft
(on 0.76 acres)

Local Information

  • Map ViewExplore the area around 2 Hillside Pl.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Beautiful Victorian tucked away on a private lane of Hillside Ave. This lovely historic home has many architectural period details such as crown and floor moldings, wood trim, built in bookcases and ornate fireplaces. The first floor has a nice open floor plan with a large kitchen and separate eat in area, dining room with fireplace, large living room and front foyer with built in and fireplace. The upper floors consist of a large master bedroom with its own living area with built ins and fireplace and an additional 3-4 bedrooms, laundry and full bath. This is a special home.
2 Hillside Pl, Winsted, CT 06098 is a 4 bedroom, 2 bathroom, 2,812 sqft single-family home built in 1886. It last sold for $190,000 on Jun 23, 2016. It is currently off market. The Trulia Estimate is $399,100, with a rent estimate of $2,925/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 2 Hillside Pl

Interior Features

Interior Details
BasementAtticNumber of Rooms: 10Types of Rooms: Laundry Room
Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
Cable ReadyRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodGardenPatioPorch
Parking & Garage
GarageParking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 1886
Property Type / Style
Property Type: Single Family HomeArchitecture: Queen Anne / Victorian

Community

Units in Building: 1

Lot Information

Lot Area: 0.76 acres

Price History for 2 Hillside Pl

DatePriceEventSource
09/18/2019$199,000ListingRemovedAgent Provided
04/26/2019$199,000PriceChange
Agent Provided
11/26/2018$205,000Listed For SaleAgent Provided
06/23/2016$190,000Sold
Smart MLS #L10057088
01/09/2016$195,000ListingRemovedAgent Provided
06/22/2015$195,000Listed For SaleAgent Provided

Market trends in Winsted

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
11
1MoM
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Property Tax and Assessment

Year2025
Tax$5,703
Assessment$195,510
Home facts updated by county records

Comparable Sales for 2 Hillside Pl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
28 Spring St, Winsted, CT
0.21
Single-Family Home
$260,000
12/18/25
5
2
2,676
27 Fairview Ave, Winsted, CT
0.21
Single-Family Home
$250,000
05/11/26
5
2
3,063
61 Rock St, Winsted, CT
0.17
Single-Family Home
$240,000
01/14/26
4
2
1,559
155 Rockwell Street, Winsted, CT
0.27
Single-Family Home
$151,000
02/20/26
3
1
1,317
38 Upland Road, Winsted, CT
0.34
Single-Family Home
$240,000
03/11/26
3
1.5
1,736
17 Woodland Avenue, Winsted, CT
0.34
Single-Family Home
$410,000
07/31/25
3
2
2,105
30 Mountain Avenue, Winsted, CT
0.67
Single-Family Home
$178,500
08/29/25
5
1.5
2,310
101 Ridge St, Winsted, CT
0.41
Single-Family Home
$280,000
07/28/25
3
1
1,422
107 Birdsall Street, Winsted, CT
0.57
Single-Family Home
$210,000
07/02/26
4
2
1,874
155 Spencer St, Winsted, CT
0.52
Single-Family Home
$455,000
09/10/25
3
2
1,786

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Hillside Pl.
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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Apartments for Rent

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Explore by feature - Pet Friendly

12 pet-friendly rentals in Winsted, CT

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6 rentals with a washer/dryer in Winsted, CT

Homes for sale near 2 Hillside Pl

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Off Market Homes Near 2 Hillside Pl

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