David Sartirana logo
David Sartirana logo
David Sartirana logo
inception-app-prod/MmIwNmU4YmUtNzFkOC00MjBhLWFjOTMtZWJjM2Q0MDM3OTdl/content/2024/07/4ba3b5c70c3e19d91845bdd2ad4150577a5023e6.JPG

WINCHESTER

Winchester, Connecticut, is a charming small town nestled in the scenic Litchfield Hills. Known for its picturesque landscapes and historic character, Winchester boasts a mix of quaint residential areas and lush, rolling countryside. The town is home to the serene Highland Lake, a popular spot for boating and fishing, as well as a vibrant community that embraces local events and traditions. With its well-preserved 19th-century architecture and a warm, welcoming atmosphere, Winchester offers both residents and visitors a glimpse into classic New England charm while providing ample opportunities for outdoor recreation and a close-knit community feel.

Map of the area

Creating your map with the top listings, almost there...

$1,900,000
WINCHESTER
$1,900,000
144 Rowley Street, Winchester, CT, 06098
1
12,000 Sq ft
ACTIVE
MLS# 24154804
WINCHESTER
$1,850,000
WINCHESTER
$1,850,000
431 West Wakefield Boulevard, Winchester, CT, 06098
9
6
7,000 Sq ft
CONTRACT
MLS# 24159989
WINCHESTER
$1,600,000
WINCHESTER
$1,600,000
752 Lake Drive, Winchester, CT, 06098
4
3
2,129 Sq ft
Under Contract - Continue
MLS# 24187886
WINCHESTER
$1,600,000
WINCHESTER
$1,600,000
752 Lake Drive, Winchester, CT, 06098
4
3
2,129 Sq ft
Under Contract - Continue
MLS# 24190733
WINCHESTER
$999,000
WINCHESTER
$999,000
380 Main Street, Winchester, CT, 06098
5
6,200 Sq ft
ACTIVE
MLS# 24134408
WINCHESTER
$959,900
WINCHESTER
$959,900
204 East Wakefield Boulevard, Winchester, CT, 06098
2
2
1,472 Sq ft
CONTRACT
MLS# 24194765
WINCHESTER
3D Tour
$849,900
WINCHESTER
Virtual Tour
$849,900
119 West Wakefield Boulevard, Winchester, CT, 06098
4
2
1,781 Sq ft
ACTIVE
MLS# 24191186
WINCHESTER
3D Tour
$849,900
WINCHESTER
Virtual Tour
$849,900
119 West Wakefield Boulevard, Winchester, CT, 06098
4
2
1,781 Sq ft
ACTIVE
MLS# 24191163
WINCHESTER
3D Tour
$799,900
WINCHESTER
Virtual Tour
$799,900
804 West Wakefield Boulevard, Winchester, CT, 06098
2
1
1,044 Sq ft
ACTIVE
MLS# 24195283
WINCHESTER
$799,000
WINCHESTER
$799,000
257-259 Torringford Street, Winchester, CT, 06098
ACTIVE
MLS# 24157681
WINCHESTER
$795,000
WINCHESTER
$795,000
535,538 West Wakefield Boulevard, Winchester, CT, 06098
ACTIVE
MLS# 24037015
WINCHESTER
$749,900
WINCHESTER
$749,900
812 West Wakefield Boulevard, Winchester, CT, 06098
2
1
760 Sq ft
CONTRACT
MLS# 24192463
WINCHESTER
WINCHESTER
$1,900,000
144 Rowley Street, Winchester, CT, 06098
1
12,000 Sq ft
ACTIVE
MLS# 24154804

Listing Agent: Ryan Horvay

Listing Office: Smith & DeGroat Real Estate

WINCHESTER
WINCHESTER
$1,850,000
431 West Wakefield Boulevard, Winchester, CT, 06098
9
6
7,000 Sq ft
CONTRACT
MLS# 24159989

Listing Agent: Lisa Ogren

Listing Office: Berkshire Hathaway NE Prop.

WINCHESTER
WINCHESTER
$1,600,000
752 Lake Drive, Winchester, CT, 06098
4
3
2,129 Sq ft
Under Contract - Continue
MLS# 24190733

Listing Agent: Pam Famiglietti

Listing Office: William Raveis Real Estate

WINCHESTER
WINCHESTER
$1,600,000
752 Lake Drive, Winchester, CT, 06098
4
3
2,129 Sq ft
Under Contract - Continue
MLS# 24187886

Listing Agent: Pam Famiglietti

Listing Office: William Raveis Real Estate

WINCHESTER
Newly Listed
WINCHESTER
$999,000
380 Main Street, Winchester, CT, 06098
5
6,200 Sq ft
ACTIVE
MLS# 24134408

Listing Agent: Anthony Gioia

Listing Office: The Washington Agency

WINCHESTER
Newly Listed
WINCHESTER
$959,900
204 East Wakefield Boulevard, Winchester, CT, 06098
2
2
1,472 Sq ft
CONTRACT
MLS# 24194765

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$895,000
469 Platt Hill Road, Winchester, CT, 06098
4
2
3,088 Sq ft
ACTIVE
MLS# 24172121

Listing Agent: Marshall Cohen

Listing Office: Cohen Agency

WINCHESTER
WINCHESTER
$879,990
000000 Norfolk Road, Winchester, CT, 06098
ACTIVE
MLS# 24131284

Listing Agent: John Harney

Listing Office: William Pitt Sotheby's Int'l

WINCHESTER
Virtual Tour
WINCHESTER
$849,900
119 West Wakefield Boulevard, Winchester, CT, 06098
4
2
1,781 Sq ft
ACTIVE
MLS# 24191163

Listing Agent: Mela Veltri Case

Listing Office: KW Legacy Partners

WINCHESTER
Virtual Tour
WINCHESTER
$849,900
119 West Wakefield Boulevard, Winchester, CT, 06098
4
2
1,781 Sq ft
ACTIVE
MLS# 24191186

Listing Agent: Mela Veltri Case

Listing Office: KW Legacy Partners

WINCHESTER
Newly Listed
Virtual Tour
WINCHESTER
$799,900
804 West Wakefield Boulevard, Winchester, CT, 06098
2
1
1,044 Sq ft
ACTIVE
MLS# 24195283

Listing Agent: Pamela Dostilio

Listing Office: Coldwell Banker Realty

WINCHESTER
WINCHESTER
$799,000
257-259 Torringford Street, Winchester, CT, 06098
ACTIVE
MLS# 24157681

Listing Agent: Lisa Toczko

Listing Office: Home Valley Realty, LLC

WINCHESTER

No results found

Please remove some of the selected filters.
1 2 3 … 7
The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright SmartMLS, Inc. Updated: 21st August, 2026 11:57 PM (UTC)