Winchester, CT homes for sale & real estate

6 days on Rocket

$4,144 Closing Credit¹

$349,000

3 beds • 2 baths • 1,480 sqft

150 Mathew Rd, Winchester, CT 06098

#24090132, Josh Dionne, Listing Office: Commercial Services Realty

7 days on Rocket

$10,000 Closing Credit¹

$979,000

5 beds • 3.5 baths • 3,216 sqft

355 W Lake St, Winchester, CT 06098

#24091474, David Sartirana, Listing Office: Northwest CT Realty

Save big

You could save thousands when you partner with Rocket Homes℠ and Rocket Mortgage®

$1,876 Closing Credit¹

$158,000

1 bed • 1.5 baths • 1,172 sqft

9 John St, Winchester, CT 06098

#24090596, Michelle Grant, Listing Office: Coldwell Banker Premier Real Estate

$10,000 Closing Credit¹

$995,000

4 beds • 2 baths • 3,088 sqft

469 Platt Hill Rd, Winchester, CT 06098

#24089885, Marshall Cohen, Listing Office: Cohen Agency

$2,374 Closing Credit¹

$199,900

3 beds • 2 baths • 1,768 sqft

9 Loomis St, Winchester, CT 06098

#24088887, Kristen Duchene, Listing Office: Litchfield County Real Estate

$1,350,000

Land • 124.92 Acres

Winsted Norfolk Rd, Colebrook, CT 06021

#24089254, Marshall Cohen, Listing Office: Cohen Agency

$6,887 Closing Credit¹

$579,999

3 beds • 2 baths • 1,744 sqft

144 Marshall St, Winchester, CT 06098

#24040600, Monica Palmerie, Listing Office: RE/MAX RISE

Room to negotiate?

Median Sold Price

$290K

Based on our April 2025 Market Report.

Backup offers

$3,561 Closing Credit¹

$299,900

2 beds • 1.5 baths • 1,536 sqft

155 Mathew Rd, Winchester, CT 06098

#24085896, Austin Brochu, Listing Office: Sullivan Real Estate Inc

Backup offers

$3,205 Closing Credit¹

$269,900

3 beds • 1 bath • 1,175 sqft

39 Finn St, Winchester, CT 06098

#24084562, Christine Hunter, Listing Office: Hunter Real Estate, LLC

$3,088 Closing Credit¹

$260,000

5 beds • 2 baths • 1,962 sqft

120 Torrington Rd, Winchester, CT 06098

#24084424, David Bolduc, Listing Office: Bolduc Realty Group

$8,905 Closing Credit¹

$749,900

7 beds • 3 baths • 3,486 sqft

39 S Main St, Winchester, CT 06098

#24083565, Ryan Horvay, Listing Office: Smith & DeGroat Real Estate

Backup offers

$4,750 Closing Credit¹

$400,000

3 beds • 2.5 baths • 2,209 sqft

110 Rugg Brook Rd, Winchester, CT 06098

#24083204, Michelle Grant, Listing Office: Coldwell Banker Premier Real Estate

$3,205 Closing Credit¹

$269,900

3 beds • 1 bath • 2,754 sqft

25 Center St, Winchester, CT 06098

#24082567, Jessica Lopez, Listing Office: Our Home Realty Advisors

$225,000

Land • 0.23 Acres

129 Shore Dr, Winchester, CT 06098

#24080977, Annie Simard, Listing Office: LPT Realty

$739,900

Land • 93.38 Acres

Old Robertsville Rd, Winchester, CT 06098

#24080217, David Sartirana, Listing Office: Northwest CT Realty

Backup offers

$2,968 Closing Credit¹

$249,900

4 beds • 2 baths • 2,094 sqft

150 Meadow St, Winchester, CT 06098

#24079880, David Sartirana, Listing Office: Northwest CT Realty

Backup offers

$2,731 Closing Credit¹

$230,000

3 beds • 1.5 baths • 1,200 sqft

39 Orchard St, Winchester, CT 06098

#24079182, Michael Flaherty Jr, Listing Office: Sullivan Real Estate Inc

$17,999

Land • 0.12 Acres

320 White Oak Trl, Winchester, CT 06098

#24078686, Dillon Cass, Listing Office: eRealty Advisors, Inc.

Tour

$10,000 Closing Credit¹

$849,900

4 beds • 2 baths • 1,781 sqft

119 W Wakefield Blvd, Winchester, CT 06098

#24075940, Mela Veltri Case, Listing Office: KW Legacy Partners

$5,463 Closing Credit¹

$460,000

4 beds • 3 baths • 3,021 sqft

288 Torringford St, Winchester, CT 06098

#24067951, Mark Porriello, Listing Office: RE/MAX Right Choice

$5,344 Closing Credit¹

$450,000

4 beds • 1.5 baths • 2,239 sqft

51 Pratt St, Winchester, CT 06098

#24073605, Lourdes Galvan-Dominguez, Listing Office: Coldwell Banker Realty

$49,000

Land • 0.37 Acres

99 Hubbard St, Winchester, CT 06098

#24073744, David Sartirana, Listing Office: Northwest CT Realty

48 Bridge St, Winchester CT, 06098 land for sale

$23,900

Land • 0.15 Acres

48 Bridge St, Winchester, CT 06098

#24073721, David Sartirana, Listing Office: Northwest CT Realty

$29,000

Land • 0.44 Acres

124 Rockwell St, Winchester, CT 06098

#24073710, David Sartirana, Listing Office: Northwest CT Realty

19 Hill St, Winchester CT, 06098 land for sale

$23,900

Land • 0.22 Acres

19 Hill St, Winchester, CT 06098

#24073702, David Sartirana, Listing Office: Northwest CT Realty

32 Norfolk Rd, Winchester CT, 06098 land for sale

$299,900

Land • 63 Acres

32 Norfolk Rd, Winchester, CT 06098

#24071804, David D'Amore, Listing Office: Northwest CT Realty

$10,000 Closing Credit¹

$1,699,500

4 beds • 3 baths • 2,496 sqft

538 Wheelers Pt, Winchester, CT 06098

#24052635, Karen Newton, Listing Office: William Pitt Sotheby's Int'l

$10,000 Closing Credit¹

$1,500,000

8 beds • 4.5 baths • 5,231 sqft

435/434 W Wakefield Blvd, Winchester, CT 06098

#24047556, Heidi Picard-Ramsay, Listing Office: Berkshire Hathaway NE Prop.

$2,600,000

9 beds • 5.5 baths • 7,000 sqft

431 W Wakefield Blvd, Winchester, CT 06098

#24042374, Lisa Ogren, Listing Office: Berkshire Hathaway NE Prop.

$10,000 Closing Credit¹

$1,500,000

3 beds • 2.5 baths • 2,664 sqft

711 W Wakefield Blvd, Winchester, CT 06098

#24022821, Peter Kores, Listing Office: The Washington Agency

$320,000

Land • 0.61 Acres

711 W Wakefield Blvd, Winchester, CT 06098

#24020414, Peter Kores, Listing Office: The Washington Agency

$158,000

Land • 1.18 Acres

843-845(lots-10A,10 E Wakefield Boulevard, Winchester, CT 06098

#24003236, David D'Amore, Listing Office: Northwest CT Realty

$39,900

Land • 0.92 Acres

256 Colebrook Rd, Winchester, CT 06098

#170567861, Austin Brochu, Listing Office: Sullivan Real Estate Inc

$7,719 Closing Credit¹

$650,000

3 beds • 2.5 baths • 2,135 sqft

18-4A Taylor Brook Rd, Winchester, CT 06098

#170551066, Peter Kores, Listing Office: The Washington Agency

$295,000

Land • 51 Acres

393 Winchester Rd, Winchester, CT 06098

#170078080, Thomas McGowan, Listing Office: Elyse Harney Real Estate

Winchester, CT Real Estate Market Overview

Browse 35 homes for sale in Winchester, CT. View properties, photos, nearby real estate with school and housing market information. The inventory of homes for sale in Winchester, CT between March 2025 and April 2025 decreased by 4.2%. In April 2025, listings were on the market for 0 days. During the same period, the median list price in this real estate market was $290,000. In April 2025, from all listings sold in Winchester, CT there were more than 7 sold above asking price, over 4 sold below and more than 2 were sold right at the asked price.

From Rocket Homes Real Estate and based on county public records data

What is it like to live in Winchester, CT

Overview

Winchester is located in Litchfield County, Connecticut. There are roughly 11,089 residents, living in 4,737 households. The average temperature for Winchester this time of the year is low of 43F and high of 67F. On average, Winchester gets about 4.77 inches of precipitation in May. Most residents are home owners (63%), have a high school diploma (47%) and are single, no kids (45%).

Data provided by Home Junction

Schools near Winchester, CT

Elementary Schools

Pearson School
2 Wetmore Ave
Public District 3-6

Middle Schools

Northwestern Regional Middle School
100 Battistoni Rd
Public District 7-8

High Schools

The Gilbert School
200 Williams Ave
Public District 7-12
Explorations
71 Spencer St
Public Charter 9-12
Northwestern Regional High School
100 Battistoni Rd
Public District 9-12

Data provided by Great Schools

Homes for sale in Winchester, CT

Winchester, CT Real Estate Market Overview

What is it like to live in Winchester, CT

Overview

Schools near Winchester, CT

Housing market reports in Litchfield County

Homes for sale near Winchester, CT

Top real estate cities in Connecticut