153 Mathew Road, Winchester, CT 06098
OFF MARKET

153 Mathew Road
Winchester, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 1,544 sqft

$313,700

Trulia Estimate
as of Jul 14, 2026
Est. Refi. Payment $2,126/mo*
Refinance Your Home

$313,700

Trulia Estimate
as of Jul 14, 2026
Est. Refi. Payment $2,126/mo*
Refinance Your Home
2 Beds
1.5 Baths
1,544 sqft

Local Information

  • Map ViewExplore the area around 153 Mathew Road.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

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). It is currently off market. The Trulia Estimate is $313,700, with a rent estimate of $2,293/month.

Home Highlights

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

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
Last check for updates: about 12 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

Price History for 153 Mathew Road

DatePriceEventSource
11/21/2024$290,000Sold
Smart MLS #24029997
08/09/2024$279,900PriceChange
Smart MLS #24029997
07/22/2024$285,000PriceChange
Smart MLS #24029997
07/03/2024$299,000Listed For SaleSmart MLS #24029997
02/21/2024$175,000Sold
Smart MLS #170612118
01/09/2024$174,900PriceChange
Smart MLS #170612118
12/26/2023$184,900PendingToActiveSmart MLS #170612118
12/10/2023$184,900ContingentSmart MLS #170612118
12/04/2023$184,900Listed For SaleSmart MLS #170612118
10/02/2021ListingRemovedSmart MLS #170431393
09/13/2021$176,900PriceChange
Smart MLS #170431393
08/22/2021$184,900Listed For SaleSmart MLS #170431393
02/03/2020$152,000ListingRemovedAgent Provided
11/25/2019$152,000Listed For SaleAgent Provided
05/13/2009$136,000Sold
Smart MLS #L130095
10/26/2008$139,900PriceChange
Agent Provided
10/16/2008$144,900PriceChange
Agent Provided
09/14/2008$149,900PriceChange
Agent Provided
08/26/2008$154,900PriceChange
Agent Provided
08/23/2008$159,900Listed For SaleAgent Provided
07/01/2008$169,900ListingRemovedAgent Provided
05/24/2008$169,900Listed For SaleAgent Provided
02/03/2006$82,400Sold
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$4,396
Assessment$150,710
Home facts updated by county records

Comparable Sales for 153 Mathew Road

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
226 East Wakefield Boulevard, Winsted, CT
0.15
Single-Family Home
$380,000
09/17/25
3
1.5
1,196
152 East Lake Street, Winsted, CT
0.45
Single-Family Home
$310,000
11/03/25
2
2
900
266 Perch Rock Trail, Winsted, CT
0.30
Single-Family Home
$800,000
08/04/25
3
2
1,488
156 Shore Drive, Winsted, CT
0.18
Single-Family Home
$691,000
05/21/26
5
1.5
1,258
112 Shore Drive, Winsted, CT
0.20
Single-Family Home
$862,500
07/23/25
3
2
2,113
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

Nearby homes

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Assigned Schools

These are the assigned schools for 153 Mathew Road.
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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
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  • 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

17 pet-friendly rentals in Winchester, CT

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6 rentals with a washer/dryer in Winchester, CT

Homes for sale near 153 Mathew Road

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Off Market Homes Near 153 Mathew Road

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