151

Recently Sold Winchester, CT Homes

Section Image
  • 147 Smith Hill Rd, Winsted, CT 06098

    $362,000 Sold Nov 18, 2025

    147 Smith Hill Rd, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 1,910 Sq Ft
    • Built 1949

    Last Sold Summary

    • 6% Below List Price
    • $190/SF
    • 84 Days On Market

    Current Estimated Value $367,196

    Last Listing Agent SHARON GILSON Northwest CT Realty

    147 Smith Hill Rd, Winsted, CT 06098
  • 43 E Lake St, Winsted, CT 06098

    $920,000 Sold Nov 17, 2025

    43 E Lake St, Winsted, CT 06098

    • 4 Beds
    • 3 Baths
    • 2,131 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Below List Price
    • $432/SF
    • 56 Days On Market

    Current Estimated Value $927,583

    Last Listing Agent Keith Meyer Northwest CT Realty

    43 E Lake St, Winsted, CT 06098
  • 288 Torringford St, Winsted, CT 06098

    $460,000 Sold Jun 20, 2025

    288 Torringford St, Winsted, CT 06098

    • 4 Beds
    • 3 Baths
    • 3,021 Sq Ft
    • Built 1875

    Last Sold Summary

    • 14% Below List Price
    • $152/SF
    • 128 Days On Market

    Current Estimated Value $473,102

    Last Listing Agent Mark Porriello RE/MAX Right Choice

    288 Torringford St, Winsted, CT 06098
  • 49 Walnut St, Winsted, CT 06098

    $305,000 Sold Dec 22, 2025

    49 Walnut St, Winsted, CT 06098

    • 5 Beds
    • 2 Baths
    • 2,344 Sq Ft
    • Built 1824

    Last Sold Summary

    • 2% Above List Price
    • $130/SF
    • 6 Days On Market

    Current Estimated Value $311,269

    Last Listing Agent David Sartirana Northwest CT Realty

    49 Walnut St, Winsted, CT 06098
  • 171 Wallens St, Winchester, CT 06098

    $370,000 Sold Mar 25, 2026

    171 Wallens St, Winchester, CT 06098

    • 2 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 1957

    Last Sold Summary

    • 3% Above List Price
    • $290/SF
    • 23 Days On Market

    Current Estimated Value $343,810

    Last Listing Agent Meagan Albert Tier 1 Real Estate

    171 Wallens St, Winchester, CT 06098
  • 39 Orchard St, Winsted, CT 06098

    $208,900 Sold Jul 18, 2025

    39 Orchard St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 1875

    Last Sold Summary

    • 9% Below List Price
    • $174/SF
    • 131 Days On Market

    Current Estimated Value $283,131

    Last Listing Agent Michael J Flaherty Jr Sullivan Real Estate Inc

    39 Orchard St, Winsted, CT 06098
  • 32 Charles St, Winsted, CT 06098

    $225,000 Sold Dec 10, 2025

    32 Charles St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,044 Sq Ft
    • Built 1953

    Last Sold Summary

    • 2% Below List Price
    • $216/SF
    • 41 Days On Market

    Current Estimated Value $230,049

    Last Listing Agent David Sartirana Northwest CT Realty

    32 Charles St, Winsted, CT 06098
  • 174 Boyd St, Winsted, CT 06098

    $280,000 Sold Jun 16, 2025

    174 Boyd St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,424 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Below List Price
    • $197/SF
    • 110 Days On Market

    Current Estimated Value $285,713

    Last Listing Agent Margaret Alexson Elyse Harney Real Estate

    174 Boyd St, Winsted, CT 06098
  • 331 Colebrook Rd, Winsted, CT 06098

    $300,000 Sold Nov 07, 2025

    331 Colebrook Rd, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1940

    Last Sold Summary

    • 7% Above List Price
    • $227/SF
    • 25 Days On Market

    Current Estimated Value $296,089

    Last Listing Agent Alison Malkin Essentia Realty

    331 Colebrook Rd, Winsted, CT 06098
  • 37 Riveredge Dr Unit 37, Winsted, CT 06098

    $160,000 Sold May 07, 2025

    37 Riveredge Dr Unit 37, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 992 Sq Ft
    • Built 1986

    Last Sold Summary

    • $161/SF
    • 37 Days On Market

    Current Estimated Value $164,532

    Last Listing Agent Erin Ruwet Century 21 AllPoints Realty

    37 Riveredge Dr Unit 37, Winsted, CT 06098
  • 704 W Wakefield Blvd, Winsted, CT 06098

    $495,000 Sold Jun 09, 2025

    704 W Wakefield Blvd, Winsted, CT 06098

    • 2 Beds
    • 2 Baths
    • 754 Sq Ft
    • Built 1911

    Last Sold Summary

    • 6% Above List Price
    • $656/SF
    • 4 Days On Market

    Current Estimated Value $483,943

    Last Listing Agent KAREN NEWTON William Pitt Sotheby's Int'l

    704 W Wakefield Blvd, Winsted, CT 06098
  • 266 Perch Rock Trail, Winsted, CT 06098

    $800,000 Sold Aug 04, 2025

    266 Perch Rock Trail, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1928

    Last Sold Summary

    • 7% Above List Price
    • $538/SF
    • 0 Days On Market

    Current Estimated Value $834,150

    Last Listing Agent Laurie Murray KW Legacy Partners

    266 Perch Rock Trail, Winsted, CT 06098
  • 39 Finn St, Winsted, CT 06098

    $269,000 Sold May 05, 2025

    39 Finn St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,175 Sq Ft
    • Built 1880

    Last Sold Summary

    • $229/SF
    • 35 Days On Market

    Current Estimated Value $263,328

    Last Listing Agent Christine Hunter Hunter Real Estate, LLC

    39 Finn St, Winsted, CT 06098
  • 830 Main St, Winsted, CT 06098

    $220,000 Sold Apr 24, 2025

    830 Main St, Winsted, CT 06098

    • 5 Beds
    • 4 Baths
    • 3,115 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $71/SF
    • 14 Days On Market

    Current Estimated Value $225,256

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    830 Main St, Winsted, CT 06098
  • 174 Wallens St Unit H1, Winsted, CT 06098

    $227,500 Sold Nov 20, 2025

    174 Wallens St Unit H1, Winsted, CT 06098

    • 1 Bed
    • 2 Baths
    • 1,334 Sq Ft
    • Built 2007

    Last Sold Summary

    • 3% Below List Price
    • $171/SF
    • 91 Days On Market

    Last Listing Agent Kim D'Andrea William Pitt Sotheby's Int'l

    174 Wallens St Unit H1, Winsted, CT 06098
  • 154 Wallens St, Winsted, CT 06098

    $190,000 Sold May 15, 2025

    154 Wallens St, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1905

    Last Sold Summary

    • 13% Below List Price
    • $103/SF
    • 20 Days On Market

    Current Estimated Value $195,236

    Last Listing Agent Adam Devine Dorrance Realty

    154 Wallens St, Winsted, CT 06098
  • 151 Losaw Rd, Winsted, CT 06098

    $690,000 Sold Feb 06, 2026

    151 Losaw Rd, Winsted, CT 06098

    • 5 Beds
    • 2.5 Baths
    • 2,950 Sq Ft
    • Built 2007

    Last Sold Summary

    • 14% Below List Price
    • $234/SF
    • 164 Days On Market

    Current Estimated Value $689,046

    Last Listing Agent Breanna Goebel Compass Connecticut, LLC

    151 Losaw Rd, Winsted, CT 06098
  • 12 Cherry St, Winsted, CT 06098

    $277,000 Sold Oct 09, 2025

    12 Cherry St, Winsted, CT 06098

    • 4 Beds
    • 1 Bath
    • 1,492 Sq Ft
    • Built 1800

    Last Sold Summary

    • 4% Below List Price
    • $186/SF
    • 54 Days On Market

    Current Estimated Value $283,076

    Last Listing Agent Susan MCGHEE The Washington Agency

    12 Cherry St, Winsted, CT 06098
  • 14 Riveredge Dr Unit 14, Winsted, CT 06098

    $160,000 Sold Apr 29, 2025

    14 Riveredge Dr Unit 14, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 992 Sq Ft
    • Built 1986

    Last Sold Summary

    • $161/SF
    • 0 Days On Market

    Current Estimated Value $163,130

    Last Listing Agent Maria Smith KW Legacy Partners

    14 Riveredge Dr Unit 14, Winsted, CT 06098
  • 106 Rockwell St, Winsted, CT 06098

    $230,000 Sold Mar 18, 2026

    106 Rockwell St, Winsted, CT 06098

    • 6 Beds
    • 3 Baths
    • 1,874 Sq Ft
    • Built 1850

    Last Sold Summary

    • 23% Below List Price
    • $123/SF
    • 23 Days On Market

    Current Estimated Value $281,437

    Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

    106 Rockwell St, Winsted, CT 06098
  • 39 Baker St, Winsted, CT 06098

    $225,000 Sold Jul 03, 2025

    39 Baker St, Winsted, CT 06098

    • 5 Beds
    • 2 Baths
    • 1,612 Sq Ft
    • Built 1900

    Last Sold Summary

    • $140/SF
    • 166 Days On Market

    Current Estimated Value $230,051

    Last Listing Agent Christine Hunter Hunter Real Estate, LLC

    39 Baker St, Winsted, CT 06098
  • 269 Walnut St, Winsted, CT 06098

    $45,000 Sold May 09, 2025

    269 Walnut St, Winsted, CT 06098

    • Land
    • 0.5 Acre
    • $90,000 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 72 Days On Market

    Last Listing Agent David Sartirana Northwest CT Realty

    269 Walnut St, Winsted, CT 06098
  • 508 W Wakefield Blvd, Winsted, CT 06098

    $1,575,000 Sold Jun 30, 2025

    508 W Wakefield Blvd, Winsted, CT 06098

    • 7 Beds
    • 4 Baths
    • 2,687 Sq Ft
    • Built 1890

    Last Sold Summary

    • 5% Below List Price
    • $586/SF
    • 316 Days On Market

    Current Estimated Value $1,622,303

    Last Listing Agent Pierre Moran William Pitt Sotheby's Int'l

    508 W Wakefield Blvd, Winsted, CT 06098
  • 187 Torringford St, Winsted, CT 06098

    $360,000 Sold Feb 25, 2026

    187 Torringford St, Winsted, CT 06098

    • 4 Beds
    • 1.5 Baths
    • 2,365 Sq Ft
    • Built 1800

    Last Sold Summary

    • 16% Below List Price
    • $152/SF
    • 109 Days On Market

    Current Estimated Value $396,977

    Last Listing Agent Jessica Washington William Raveis Real Estate

    187 Torringford St, Winsted, CT 06098
  • 155 Rockwell St, Winsted, CT 06098

    $151,000 Sold Feb 20, 2026

    155 Rockwell St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,317 Sq Ft
    • Built 1953

    Last Sold Summary

    • 5% Below List Price
    • $115/SF
    • 11 Days On Market

    Current Estimated Value $251,338

    Last Listing Agent Joseph Caslin Sailpoint Property Group

    155 Rockwell St, Winsted, CT 06098
  • 39 Colony Dr, Winsted, CT 06098

    $279,900 Sold Sep 12, 2025

    39 Colony Dr, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,183 Sq Ft
    • Built 1969

    Last Sold Summary

    • $237/SF
    • 65 Days On Market

    Current Estimated Value $287,615

    Last Listing Agent Alison Behlman Tier 1 Real Estate

    39 Colony Dr, Winsted, CT 06098
  • 107 Old Rd N, Winchester, CT 06098

    $320,000 Sold Sep 03, 2025

    107 Old Rd N, Winchester, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Above List Price
    • $198/SF
    • 24 Days On Market

    Last Listing Agent Jill Rubino Century 21 AllPoints Realty

    107 Old Rd N, Winchester, CT 06098
  • 56 Lakeview Rd, Winsted, CT 06098

    $279,000 Sold May 19, 2025

    56 Lakeview Rd, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,101 Sq Ft
    • Built 1956

    Last Sold Summary

    • 16% Above List Price
    • $253/SF
    • 6 Days On Market

    Current Estimated Value $242,938

    Last Listing Agent Tony Goia The Washington Agency

    56 Lakeview Rd, Winsted, CT 06098
  • 110 South Rd, Winsted, CT 06098

    $679,000 Sold Apr 30, 2025

    110 South Rd, Winsted, CT 06098

    • 4 Beds
    • 3 Baths
    • 3,870 Sq Ft
    • Built 1984

    Last Sold Summary

    • $175/SF
    • 5 Days On Market

    Current Estimated Value $719,621

    Last Listing Agent Matthew Egan Regency Real Estate, LLC

    110 South Rd, Winsted, CT 06098
  • 62 Fruit St Unit 64, Winsted, CT 06098

    $326,000 Sold Oct 31, 2025

    62 Fruit St Unit 64, Winsted, CT 06098

    • 6 Beds
    • 2 Baths
    • 3,078 Sq Ft
    • Built 1902

    Last Sold Summary

    • $106/SF
    • 13 Days On Market

    Current Estimated Value $304,666

    Last Listing Agent Antonio De La Cruz Eagle Eye Realty PLLC

    62 Fruit St Unit 64, Winsted, CT 06098
  • 226 E Wakefield Blvd, Winsted, CT 06098

    $380,000 Sold Sep 17, 2025

    226 E Wakefield Blvd, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,196 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Above List Price
    • $318/SF
    • 38 Days On Market

    Current Estimated Value $382,100

    Last Listing Agent Pascale Nejaime William Pitt Sotheby's Int'l

    226 E Wakefield Blvd, Winsted, CT 06098
  • 148 Danbury Quarter Rd, Winchester, CT 06098

    $320,000 Sold Feb 17, 2026

    148 Danbury Quarter Rd, Winchester, CT 06098

    • 4 Beds
    • 2 Baths
    • 1,999 Sq Ft
    • Built 1800

    Last Sold Summary

    • 6% Below List Price
    • $160/SF
    • 86 Days On Market

    Current Estimated Value $315,698

    Last Listing Agent Susan MCGHEE The Washington Agency

    148 Danbury Quarter Rd, Winchester, CT 06098
  • 343 W Wakefield Blvd, Winsted, CT 06098

    $236,434 Sold Aug 25, 2025

    343 W Wakefield Blvd, Winsted, CT 06098

    • 2 Beds
    • 1 Bath
    • 674 Sq Ft
    • Built 1923

    Last Sold Summary

    • 15% Below List Price
    • $351/SF
    • 40 Days On Market

    Current Estimated Value $261,927

    Last Listing Agent Patrick Precourt Meridian Realty Group LLC

    343 W Wakefield Blvd, Winsted, CT 06098
  • 9 Loomis St, Winsted, CT 06098

    $144,000 Sold May 29, 2025

    9 Loomis St, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,768 Sq Ft
    • Built 1910

    Last Sold Summary

    • 28% Below List Price
    • $81/SF
    • 18 Days On Market

    Current Estimated Value $151,214

    Last Listing Agent Kristen Duchene Litchfield County Real Estate

    9 Loomis St, Winsted, CT 06098
  • 131 Willow St, Winsted, CT 06098

    $293,000 Sold Oct 30, 2025

    131 Willow St, Winsted, CT 06098

    • 6 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $136/SF
    • 83 Days On Market

    Last Listing Agent Amanda Balaski Northwest CT Realty

    131 Willow St, Winsted, CT 06098
  • 17 Adams St, Winsted, CT 06098

    $315,000 Sold Sep 29, 2025

    17 Adams St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,747 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Above List Price
    • $180/SF
    • 85 Days On Market

    Current Estimated Value $314,065

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    17 Adams St, Winsted, CT 06098
  • 325 E Wakefield Blvd, Winsted, CT 06098

    $270,000 Sold Mar 31, 2025

    325 E Wakefield Blvd, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 1,192 Sq Ft
    • Built 1930

    Last Sold Summary

    • 4% Above List Price
    • $227/SF
    • 39 Days On Market

    Current Estimated Value $286,927

    Last Listing Agent Brigitte Richter William Pitt Sotheby's Int'l

    325 E Wakefield Blvd, Winsted, CT 06098
  • 22 Curtice St, Winsted, CT 06098

    $243,000 Sold Nov 17, 2025

    22 Curtice St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,334 Sq Ft
    • Built 1900

    Last Sold Summary

    • $182/SF
    • 33 Days On Market

    Current Estimated Value $244,150

    Last Listing Agent Terence Dominick Exceptional Real Estate LLC

    22 Curtice St, Winsted, CT 06098
  • 115 Laurel Way, Winsted, CT 06098

    $261,000 Sold Oct 17, 2025

    115 Laurel Way, Winsted, CT 06098

    • 1 Bed
    • 1 Bath
    • 604 Sq Ft
    • Built 1940

    Last Sold Summary

    • 4% Above List Price
    • $432/SF
    • 9 Days On Market

    Current Estimated Value $250,380

    Last Listing Agent Jill Menard Realty One Group Cutting Edge

    115 Laurel Way, Winsted, CT 06098
  • 174 Wallens St Unit D3, Winsted, CT 06098

    $260,000 Sold Sep 05, 2025

    174 Wallens St Unit D3, Winsted, CT 06098

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Above List Price
    • $192/SF
    • 1 Day On Market

    Last Listing Agent Mary New Berkshire Hathaway NE Prop.

    174 Wallens St Unit D3, Winsted, CT 06098

Showing Results 1 - 40, Page 1 of 4

Connecticut Litchfield County Winchester

Recently Sold Real Estate & Homes in Winchester, CT

Frequently Asked Questions

What is the average home price in Winchester, CT?
Homes for sale in Winchester, CT have an average home price of $347,425.
What is the average time to sell a house in Winchester, CT?
The houses for sale in Winchester, CT spend an average of 50 days on the market.
What is the number of active homes for sale in Winchester, CT?
There are 0 active homes for sale in Winchester, CT.
How many homes have sold over the last 12 months in Winchester, CT?
4 homes have sold in Winchester, CT over the last 12 months.

Home Trends in Winchester, CT

On average, homes in Winchester, CT sell after 50 days on the market compared to the national average of 55 days. The median sale price for homes in Winchester, CT over the last 12 months is $345,000, down 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$345,000
Median Single Family Sale Price
$345,000
Average Price Per Sq Ft
$248
Number of Homes for Sale
0
Last 12 months Home Sales
4
Months of Supply
0.00
Median List Price
$349,900
Median Change From 1st List Price
-2%
Median Home Sale Price YoY Change
-10%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group