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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.

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$2,199,000
WINCHESTER
$2,199,000
431 West Wakefield Boulevard, Winchester, CT, 06098
9
6
7,000 Sq ft
ACTIVE
MLS# 24042374
WINCHESTER
3D Tour
$1,270,000
WINCHESTER
Virtual Tour
$1,270,000
722 Lake Drive, Winchester, CT, 06098
3
3
2,420 Sq ft
ACTIVE
MLS# 24105754
WINCHESTER
$1,200,000
WINCHESTER
$1,200,000
257 Torringford Street, Winchester, CT, 06098
ACTIVE
MLS# 24097522
WINCHESTER
3D Tour
$1,149,000
WINCHESTER
Virtual Tour
$1,149,000
674 East Wakefield Boulevard, Winchester, CT, 06098
3
3
2,097 Sq ft
ACTIVE
MLS# 24118799
WINCHESTER
$949,000
WINCHESTER
$949,000
43 East Lake Street, Winchester, CT, 06098
4
3
2,131 Sq ft
Under Contract - Continue to Show
MLS# 24128011
WINCHESTER
$899,000
WINCHESTER
$899,000
354 Main Street, Winchester, CT, 06098
3
11,972 Sq ft
ACTIVE
MLS# 24137086
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# 24058804
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# 24075940
WINCHESTER
$750,000
WINCHESTER
$750,000
436 Main Street, Winchester, CT, 06098
5,389 Sq ft
ACTIVE
MLS# 24135027
WINCHESTER
$750,000
WINCHESTER
$750,000
436 Main Street, Winchester, CT, 06098
4
2
5,389 Sq ft
ACTIVE
MLS# 24135030
WINCHESTER
$749,999
WINCHESTER
$749,999
151 Losaw Road, Winchester, CT, 06098
5
3
2,950 Sq ft
ACTIVE
MLS# 24121140
WINCHESTER
$749,900
WINCHESTER
$749,900
39 South Main Street, Winchester, CT, 06098
7
3
3,486 Sq ft
ACTIVE
MLS# 24083565
WINCHESTER
Newly Listed
WINCHESTER
$429,000
187 Torringford Street, Winchester, CT, 06098
4
2
2,365 Sq ft
ACTIVE
MLS# 24138466

Listing Agent: Jessica Washington

Listing Office: William Raveis Real Estate

WINCHESTER
WINCHESTER
$419,000
117 South Road, Winchester, CT, 06098
3
3
2,747 Sq ft
Under Contract - Continue to Show
MLS# 24096267

Listing Agent: Christina Niziolek

Listing Office: William Raveis Real Estate

WINCHESTER
WINCHESTER
$399,000
51 Pratt Street, Winchester, CT, 06098
4
2
2,239 Sq ft
ACTIVE
MLS# 24116007

Listing Agent: Arlene Gonzalez

Listing Office: The Gonzalez Property Group

WINCHESTER
WINCHESTER
$395,000
720 Main Street, Winchester, CT, 06098
2
1,909 Sq ft
ACTIVE
MLS# 24138743

Listing Agent: Ryan Marconi

Listing Office: The Washington Agency

WINCHESTER
WINCHESTER
$395,000
720 Main Street, Winchester, CT, 06098
3
2
1,909 Sq ft
ACTIVE
MLS# 24138050

Listing Agent: Ryan Marconi

Listing Office: The Washington Agency

WINCHESTER
WINCHESTER
$394,900
212 Spencer Hill Road, Winchester, CT, 06098
2
2
1,440 Sq ft
ACTIVE
MLS# 24121793

Listing Agent: Tammy Powling

Listing Office: Coldwell Banker Realty

WINCHESTER
WINCHESTER
$389,000
7 Stadler Heights, Winchester, CT, 06098
ACTIVE
MLS# 24122124

Listing Agent: Hector Ortiz

Listing Office: KW Legacy Partners

WINCHESTER
WINCHESTER
$380,000
166 Torringford Street, Winchester, CT, 06098
3
2
2,024 Sq ft
CONTRACT
MLS# 24120271

Listing Agent: Lana Van Valkenburgh

Listing Office: Vision Real Estate

WINCHESTER
WINCHESTER
$375,000
57 Main Street, Winchester, CT, 06098
3
3,660 Sq ft
ACTIVE
MLS# 24112807

Listing Agent: Stacy LaQuerre

Listing Office: Regall Realty, LLC

WINCHESTER
WINCHESTER
$375,000
57 Main Street, Winchester, CT, 06098
1
3,660 Sq ft
ACTIVE
MLS# 24112471

Listing Agent: Stacy LaQuerre

Listing Office: Regall Realty, LLC

WINCHESTER
WINCHESTER
$350,000
147 Smith Hill Road, Winchester, CT, 06098
4
2
1,910 Sq ft
CONTRACT
MLS# 24111148

Listing Agent: Sharon Gilson

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$349,900
135 Elm Street, Winchester, CT, 06098
4
2
3,303 Sq ft
Under Contract - Continue to Show
MLS# 24134631

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER

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