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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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$899,000
WINCHESTER
$899,000
354 Main Street, Winchester, CT, 06098
3
11,972 Sq ft
ACTIVE
MLS# 24137086
WINCHESTER
$859,000
WINCHESTER
$859,000
257 Torringford Street, Winchester, CT, 06098
ACTIVE
MLS# 24157681
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
$749,900
WINCHESTER
$749,900
39 South Main Street, Winchester, CT, 06098
7
3
3,486 Sq ft
ACTIVE
MLS# 24083565
WINCHESTER
$649,900
WINCHESTER
$649,900
115 Old Robertsville Road, Winchester, CT, 06098
CONTRACT
MLS# 24104099
WINCHESTER
$540,000
WINCHESTER
$540,000
45 Elm Street, Winchester, CT, 06098
8
7,405 Sq ft
ACTIVE
MLS# 24131609
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
$399,000
WINCHESTER
$399,000
35 Glendale Avenue, Winchester, CT, 06098
3
2
2,196 Sq ft
ACTIVE
MLS# 24157783
WINCHESTER
$395,000
WINCHESTER
$395,000
720 Main Street, Winchester, CT, 06098
3
2
1,909 Sq ft
ACTIVE
MLS# 24138050
WINCHESTER
$395,000
WINCHESTER
$395,000
720 Main Street, Winchester, CT, 06098
2
1,909 Sq ft
ACTIVE
MLS# 24138743
WINCHESTER
WINCHESTER
$300,000
00 Chapel Road, Winchester, CT, 06098
ACTIVE
MLS# 24097613

Listing Agent: Linda Ganem

Listing Office: Borla & Associates Real Estate

WINCHESTER
WINCHESTER
$299,900
77 Hubbard Street, Winchester, CT, 06098
6
2
2,699 Sq ft
CONTRACT
MLS# 24059312

Listing Agent: Amy Rio

Listing Office: Executive Real Estate Inc.

WINCHESTER
WINCHESTER
$299,900
32 Norfolk Road, Winchester, CT, 06098
ACTIVE
MLS# 24130958

Listing Agent: David D'Amore

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$299,900
106 Rockwell Street, Winchester, CT, 06098
6
3
1,874 Sq ft
CONTRACT
MLS# 24139930

Listing Agent: Dawn Rousseau

Listing Office: Showcase Realty, Inc.

WINCHESTER
WINCHESTER
$299,000
38 Upland Road, Winchester, CT, 06098
3
2
1,736 Sq ft
CONTRACT
MLS# 24103381

Listing Agent: Holly Blinkoff

Listing Office: Cohen Agency

WINCHESTER
WINCHESTER
$295,000
393 Winchester Road, Winchester, CT, 06098
Under Contract - Continue
MLS# 170078080

Listing Agent: Thomas McGowan

Listing Office: Elyse Harney Real Estate

WINCHESTER
WINCHESTER
$289,000
174 Wallens Street UNIT A5, Winchester, CT, 06098
2
3
1,946 Sq ft
Under Contract - Continue
MLS# 24153820

Listing Agent: Lauren Iraeta

Listing Office: KW Legacy Partners

WINCHESTER
Newly Listed
WINCHESTER
$285,000
95 Colony Drive, Winchester, CT, 06098
3
2
1,008 Sq ft
CONTRACT
MLS# 24150993

Listing Agent: Raelyn Lawrence

Listing Office: Coldwell Banker Realty

WINCHESTER
Newly Listed
WINCHESTER
$279,900
44 Lewis Street, Winchester, CT, 06098
3
2
1,604 Sq ft
Under Contract - Continue
MLS# 24155057

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER
Newly Listed
WINCHESTER
$274,900
9 Central Avenue, Winchester, CT, 06098
3
2
1,267 Sq ft
Under Contract - Continue
MLS# 24153231

Listing Agent: Suzie Larson

Listing Office: Turning Point Realty, LLC

WINCHESTER
WINCHESTER
$269,999
118 Meadow Street, Winchester, CT, 06098
3
2
1,652 Sq ft
CONTRACT
MLS# 24140514

Listing Agent: Ashley Henry

Listing Office: The Washington Agency

WINCHESTER
WINCHESTER
$269,000
38 Upland Road, Winchester, CT, 06098
3
2
1,736 Sq ft
Under Contract - Continue
MLS# 24131432

Listing Agent: Marshall Cohen

Listing Office: Cohen Agency

WINCHESTER

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