153 Mathew Road, Winchester, CT 06098
OFF MARKET

$311,500

Trulia Estimate
  • 2 Beds
  • 1.5 Baths
  • 1,544 sqft

153 Mathew Road, Winchester, CT 06098

Est. Refi. Payment $2,175/mo*
Refinance Your Home
Currently Off Market - Sold Nov 21, 2024 for $290,000

Home Value

Trulia Estimate
$312K
Since last month
Increased$2K (+0.7%)
Since last year
Increased$14K (+4.6%)
Since last sale
Increased$23K (+7.9%)
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 +117% in the last 10 years
MonthEstimated value
2026
September 2026$313K
August 2026$311K
July 2026$311K
June 2026$313K
May 2026$312K
March 2026$314K
February 2026$310K
January 2026$307K
2025
2024
2023
2022
2021
2020
2019

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
230 East Wakefield Boulevard, Winsted, CT
0.16
Single-Family Home
$300,000
05/11/26
3
2
1,536
204 East Wakefield Boulevard, Winsted, CT
0.10
Single-Family Home
$960,000
09/01/26
2
1.5
1,472
152 East Lake Street, Winsted, CT
0.45
Single-Family Home
$310,000
11/03/25
2
2
900
156 Shore Drive, Winsted, CT
0.18
Single-Family Home
$691,000
05/21/26
5
1.5
1,258
258 Perch Rock Trail, Winsted, CT
0.28
Single-Family Home
$925,000
06/04/26
4
2
1,373
39 Orchard Street, Winsted, CT
0.53
Single-Family Home
$290,000
11/26/25
3
1.5
1,200
12 Cherry Street, Winsted, CT
0.50
Single-Family Home
$277,000
10/09/25
4
1
1,492
107 Birdsall Street, Winsted, CT
0.52
Single-Family Home
$210,000
07/02/26
4
2
1,874
44 Lewis Street, Winsted, CT
0.68
Single-Family Home
$335,000
04/07/26
3
2
1,604
15 John Street, Winsted, CT
0.87
Single-Family Home
$288,557
10/29/25
3
2
1,538

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
155 Mathew Road, Winsted, CT 06098
0.01
$339,100
2
1.5
1,536
Off Market
151 East Wakefield Boulevard, Winsted, CT 06098
0.04
$289,500
3
1
946
Off Market
157 East Wakefield Boulevard, Winsted, CT 06098
0.03
$178,900
1
1
592
Off Market
150 Mathew Road, Winsted, CT 06098
0.03
$337,500
3
2
1,480
Off Market
130 Alpha Avenue, Winsted, CT 06098
0.10
-
-
-
-
Off Market
180 Shore Drive, Winsted, CT 06098
0.10
$749,900
3
2
1,131
For Sale
152 Lincoln Avenue, Winsted, CT 06098
0.12
$268,600
3
1
1,135
Off Market
142 Belvedere Avenue, Winsted, CT 06098
0.07
$224,100
1
1
910
Off Market
204 East Wakefield Boulevard, Winsted, CT 06098
0.10
$960,000
2
1.5
1,472
Recently Sold
133 East Wakefield Boulevard, Winsted, CT 06098
0.16
$369,200
3
2
1,594
Off Market
337 Norwood Road, Winsted, CT 06098
0.18
$183,400
2
1
600
Off Market

Local Information

  • Map ViewExplore the area around 153 Mathew Road.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1800
1,544 sqft
$202/sqft

About this House

Price Reduced! This charming two-bedroom, one and one half -bathroom house is situate in Highland Lake community. The property boasts a generous 1,278 square feet of living space, with an open floor plan that creates a spacious and airy feel. New split system air conditioning. Custom moldings, new doors, high quality hardware/ lighting fixtures have been installed, beautiful attention to style detail. The kitchen has been recently updated with stainless steel appliances, refinished cabinetry, butcher block counter tops a breakfast bar island and new flooring providing a updated touch to the home. There is a slider to the large deck off of the kitchen. The laundry room is located on the main level, making it easy to navigate the home. The foyer is large enough to be used as a home office, with a view of the lake. Living room has an electric fireplace that also gives off heat for your winter comfort. There is a bonus room in the basement that is walk out level to the back yard. The unfinished part of the basement has been improved with French drains and a sump pump. The furnace was replaced in 2020. Highland Lake has a public boat launch, making it perfect for water activities such as boating, waterskiing, jet skiing, or a quiet kayak or canoe paddle. The city water and sewer connection is a huge bonus, providing convenience and reliability. **This home is being sold furnished so move right in and start enjoying the lake this summer.**
153 Mathew Road, Winchester, CT 06098 is a 2 bedroom, 2 bathroom, 1,544 sqft single-family home built in 1800. It last sold for $290,000 on Nov 21, 2024 (4% above the $279,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $311,500, with a rent estimate of $2,270/month.
Last check for updates: about 20 hours ago
Listed by Liz Zakrzewski, (203) 213-5891
Coldwell Banker Realty, (203) 239-2553
Bought with: Ethan Watt, (860) 671-1936, William Pitt Sotheby's Int'l, (860) 435-2400
Source: Smart MLS, MLS#24029997

Home Details for 153 Mathew Road

Interior Features

Interior Details
Basement: Full,Partially FinishedNumber of Rooms: 4Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Other
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1544 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Water HeaterDishwasherLaundry: Main LevelMicrowaveRefrigerator
Heating & Cooling
Heating: Hot Water,OilHas CoolingAir Conditioning: Ductless,Wall Unit(s)Has HeatingHeating Fuel: Hot Water
Fireplace & Spa
No Fireplace
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckExterior: Rain GuttersFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageParking: None
Frontage
Waterfront: Walk to Water, AccessNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1278 Square FeetFinished Area (below surface): 266 Square Feet

Property Information

Year Built
Year Built: 1800
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 2549168

Price & Status

Price
List Price: $279,900
Status Change & Dates
Off Market Date: Sat Nov 30 2024Possession Timing: Neg.

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 1544 Square Feet

HOA

No HOA

Lot Information

Lot Area: 5662.8 sqft

Miscellaneous

BasementMls Number: 24029997Attic: Pull Down StairsWater ViewWater View: WaterAbove Grade Unfinished Area: 1278

Price and Tax history

DateEventPrice
Nov 21, 2024
Source: Smart MLS #24029997
Sold
$290,000
Aug 9, 2024
Source: Smart MLS #24029997
PriceChange
$279,900
Price decreased by 2%
Jul 22, 2024
Source: Smart MLS #24029997
PriceChange
$285,000
Price decreased by 5%
Jul 3, 2024
Source: Smart MLS #24029997
Listed For Sale
$299,000
Feb 21, 2024
Source: Smart MLS #170612118
Sold
$175,000

Market trends in Winsted

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
15
3MoM

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

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Frequently asked questions about 153 Mathew Road

  • What is 153 Mathew Road estimated to be worth?
    Trulia's estimated value for 153 Mathew Road in Winchester, CT is $311,500.
  • What is the price history for 153 Mathew Road?
    153 Mathew Road in Winchester, CT last sold for $290,000 in November 2024.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Winchester?
    Residents describe Winchester, CT as dog-friendly, walkable to restaurants, and well-kept. See recently sold homes in Winchester, CT.
  • Does 153 Mathew Road have air conditioning?
    Yes, 153 Mathew Road in Winchester, CT has air conditioning.
  • Does 153 Mathew Road have laundry facilities?
    Yes, 153 Mathew Road in Winchester, CT has laundry facilities.

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