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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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$739,900
WINCHESTER
$739,900
Old Robertsville Road, Winchester, CT, 06098
CONTRACT
MLS# 24080217
WINCHESTER
$649,900
WINCHESTER
$649,900
115 Old Robertsville Road, Winchester, CT, 06098
5
2
2,304 Sq ft
ACTIVE
MLS# 24104078
WINCHESTER
$649,900
WINCHESTER
$649,900
115 Old Robertsville Road, Winchester, CT, 06098
CONTRACT
MLS# 24104099
WINCHESTER
$499,999
WINCHESTER
$499,999
55 Walnut Street, Winchester, CT, 06098
5,016 Sq ft
ACTIVE
MLS# 24071862
WINCHESTER
$499,999
WINCHESTER
$499,999
55 Walnut Street, Winchester, CT, 06098
5
4
5,016 Sq ft
ACTIVE
MLS# 24071827
WINCHESTER
$499,000
WINCHESTER
$499,000
197 Spencer Hill Road, Winchester, CT, 06098
3
2
2,167 Sq ft
Under Contract - Continue
MLS# 24134519
WINCHESTER
$399,000
WINCHESTER
$399,000
208 Spencer Hill Road, Winchester, CT, 06098
3
2
1,969 Sq ft
CONTRACT
MLS# 24142296
WINCHESTER
$385,000
WINCHESTER
$385,000
160 Williams Avenue, Winchester, CT, 06098
6
4
3,302 Sq ft
ACTIVE
MLS# 24150736
WINCHESTER
$359,900
WINCHESTER
$359,900
171 Wallens Street, Winchester, CT, 06098
2
2
1,274 Sq ft
ACTIVE
MLS# 24152814
WINCHESTER
$339,900
WINCHESTER
$339,900
123 Wetmore Avenue, Winchester, CT, 06098
4
2
2,345 Sq ft
Under Contract - Continue
MLS# 24150199
WINCHESTER
$339,000
WINCHESTER
$339,000
157 Elm Street, Winchester, CT, 06098
6
3
2,376 Sq ft
CONTRACT
MLS# 24142357
WINCHESTER
$319,900
WINCHESTER
$319,900
25 Center Street, Winchester, CT, 06098
3
3
2,754 Sq ft
Under Contract - Continue
MLS# 24131214
WINCHESTER
WINCHESTER
$500,000
440 Platt Hill Road, Winchester, CT, 06098
4
3
3,416 Sq ft
CONTRACT
MLS# 24132598

Listing Agent: David D'Amore

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$499,999
55 Walnut Street, Winchester, CT, 06098
5,016 Sq ft
ACTIVE
MLS# 24071862

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$499,999
55 Walnut Street, Winchester, CT, 06098
5
4
5,016 Sq ft
ACTIVE
MLS# 24071827

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$499,000
197 Spencer Hill Road, Winchester, CT, 06098
3
2
2,167 Sq ft
Under Contract - Continue
MLS# 24134519

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$419,000
117 South Road, Winchester, CT, 06098
3
3
2,747 Sq ft
CONTRACT
MLS# 24096267

Listing Agent: Christina Niziolek

Listing Office: William Raveis Real Estate

WINCHESTER
WINCHESTER
$399,000
208 Spencer Hill Road, Winchester, CT, 06098
3
2
1,969 Sq ft
CONTRACT
MLS# 24142296

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$399,000
187 Torringford Street, Winchester, CT, 06098
4
2
2,365 Sq ft
Under Contract - Continue
MLS# 24138466

Listing Agent: Jessica Washington

Listing Office: William Raveis Real Estate

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

Listing Agent: Hector Ortiz

Listing Office: KW Legacy Partners

WINCHESTER
Newly Listed
WINCHESTER
$385,000
160 Williams Avenue, Winchester, CT, 06098
6
4
3,302 Sq ft
ACTIVE
MLS# 24150736

Listing Agent: Tina Frigeri

Listing Office: KW Legacy Partners

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

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