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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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$1,900,000
WINCHESTER
$1,900,000
144 Rowley Street, Winchester, CONNECTICUT, 06098
1
12,000 Sq ft
ACTIVE
MLS# 24154804
WINCHESTER
$1,850,000
WINCHESTER
$1,850,000
431 West Wakefield Boulevard, Winchester, CONNECTICUT, 06098
9
6
7,000 Sq ft
ACTIVE
MLS# 24159989
WINCHESTER
$1,495,000
WINCHESTER
$1,495,000
129 East Lake Street, Winchester, CONNECTICUT, 06098
3
4
2,699 Sq ft
ACTIVE
MLS# 24166368
WINCHESTER
$899,000
WINCHESTER
$899,000
354 Main Street, Winchester, CONNECTICUT, 06098
3
11,972 Sq ft
CONTRACT
MLS# 24137086
WINCHESTER
$859,000
WINCHESTER
$859,000
257-259 Torringford Street, Winchester, CONNECTICUT, 06098
ACTIVE
MLS# 24157681
WINCHESTER
$779,900
WINCHESTER
$779,900
156 Shore Drive, Winchester, CONNECTICUT, 06098
5
2
1,258 Sq ft
ACTIVE
MLS# 24160676
WINCHESTER
$769,000
WINCHESTER
$769,000
121 West Wakefield Boulevard, Winchester, CONNECTICUT, 06098
4
4
2,265 Sq ft
ACTIVE
MLS# 24159801
WINCHESTER
$750,000
WINCHESTER
$750,000
436 Main Street, Winchester, CONNECTICUT, 06098
5,389 Sq ft
ACTIVE
MLS# 24135027
WINCHESTER
$750,000
WINCHESTER
$750,000
436 Main Street, Winchester, CONNECTICUT, 06098
4
2
5,389 Sq ft
ACTIVE
MLS# 24135030
WINCHESTER
$625,000
WINCHESTER
$625,000
162 Spencer Hill Road, Winchester, CONNECTICUT, 06098
3
3
2,144 Sq ft
ACTIVE
MLS# 24167312
WINCHESTER
$595,000
WINCHESTER
$595,000
45 Willow Street, Winchester, CONNECTICUT, 06098
9,438 Sq ft
ACTIVE
MLS# 24165997
WINCHESTER
$540,000
WINCHESTER
$540,000
45 Elm Street, Winchester, CONNECTICUT, 06098
8
7,405 Sq ft
ACTIVE
MLS# 24131609
WINCHESTER
WINCHESTER
$23,900
48 Bridge Street, Winchester, CONNECTICUT, 06098
CONTRACT
MLS# 24073721

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER
Newly Listed
WINCHESTER
$12,500
605 East Wakefield Boulevard, Winchester, CONNECTICUT, 06098
CONTRACT
MLS# 24139172

Listing Agent: Diane Gombieski

Listing Office: Carl Guild & Associates

WINCHESTER
WINCHESTER
$4,000
880 West Wakefield Boulevard, Winchester, CONNECTICUT, 06098
3
2
1,356 Sq ft
ACTIVE
MLS# 24136631

Listing Agent: Matthew Crossen

Listing Office: Coldwell Banker Realty

WINCHESTER
Newly Listed
WINCHESTER
$2,500
188 East Lake Street, Winchester, CONNECTICUT, 06098
2
1
1,100 Sq ft
ACTIVE
MLS# 24159128

Listing Agent: Annie Simard

Listing Office: LPT Realty

WINCHESTER
WINCHESTER
$2,450
91 Williams Avenue, Winchester, CONNECTICUT, 06098
3
2
1,600 Sq ft
ACTIVE
MLS# 24160451

Listing Agent: Suzie Larson

Listing Office: Turning Point Realty, LLC

WINCHESTER
WINCHESTER
$2,375
101 Norfolk Road, Winchester, CONNECTICUT, 06098
3
1
1,860 Sq ft
CONTRACT
MLS# 24158090

Listing Agent: Amanda Balaski

Listing Office: Northwest CT Realty

WINCHESTER
Newly Listed
WINCHESTER
$2,200
34 Rock Street, Winchester, CONNECTICUT, 06098
3
1
1,042 Sq ft
ACTIVE
MLS# 24166316

Listing Agent: Terry Cubeddu

Listing Office: Ameristar Royal Realty LLC

WINCHESTER
WINCHESTER
$1,700
180 Holabird Avenue, Winchester, CONNECTICUT, 06089
2,200 Sq ft
ACTIVE
MLS# 24148456

Listing Agent: Andrea Laviero Krawiecki

Listing Office: East Coast Real Est Assoc. LLC

WINCHESTER
WINCHESTER
$1,695
131-133 Willow Street, Winchester, CONNECTICUT, 06098
3
1
1,080 Sq ft
CONTRACT
MLS# 24151297

Listing Agent: Amanda Balaski

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$1,550
102 Elm Street, Winchester, CONNECTICUT, 06098
3
2
1,178 Sq ft
CONTRACT
MLS# 24164141

Listing Agent: Jeffrey Liskin

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$1,500
277 North Main Street, Winchester, CONNECTICUT, 06098
2,050 Sq ft
ACTIVE
MLS# 24155599

Listing Agent: Ryan Marconi

Listing Office: The Washington Agency

WINCHESTER
WINCHESTER
$1,500
22 Upson Avenue, Winchester, CONNECTICUT, 06098
2
1
1,199 Sq ft
ACTIVE
MLS# 24139617

Listing Agent: Kelly Sullivan

Listing Office: Sullivan Real Estate Inc

WINCHESTER

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