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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
Newly Listed
WINCHESTER
$1,900,000
144 Rowley Street, Winchester, CONNECTICUT, 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, CONNECTICUT, 06098
9
6
7,000 Sq ft
ACTIVE
MLS# 24159989

Listing Agent: Lisa Ogren

Listing Office: Berkshire Hathaway NE Prop.

WINCHESTER
Newly Listed
WINCHESTER
$1,495,000
129 East Lake Street, Winchester, CONNECTICUT, 06098
3
4
2,699 Sq ft
ACTIVE
MLS# 24166368

Listing Agent: Karen Newton

Listing Office: William Pitt Sotheby's Int'l

WINCHESTER
WINCHESTER
$899,000
354 Main Street, Winchester, CONNECTICUT, 06098
3
11,972 Sq ft
CONTRACT
MLS# 24137086

Listing Agent: Arlene Gonzalez

Listing Office: The Gonzalez Property Group

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

Listing Agent: John Harney

Listing Office: William Pitt Sotheby's Int'l

WINCHESTER
WINCHESTER
$859,000
257-259 Torringford Street, Winchester, CONNECTICUT, 06098
ACTIVE
MLS# 24157681

Listing Agent: Lisa Toczko

Listing Office: Home Valley Realty, LLC

WINCHESTER
WINCHESTER
$779,900
156 Shore Drive, Winchester, CONNECTICUT, 06098
5
2
1,258 Sq ft
ACTIVE
MLS# 24160676

Listing Agent: Bryan Palladino

Listing Office: Showcase Realty, Inc.

WINCHESTER
Newly Listed
WINCHESTER
$769,000
121 West Wakefield Boulevard, Winchester, CONNECTICUT, 06098
4
4
2,265 Sq ft
ACTIVE
MLS# 24159801

Listing Agent: Elizabeth Stockwell

Listing Office: Coldwell Banker Realty

WINCHESTER
WINCHESTER
$750,000
436 Main Street, Winchester, CONNECTICUT, 06098
5,389 Sq ft
ACTIVE
MLS# 24135027

Listing Agent: Anthony Gioia

Listing Office: The Washington Agency

WINCHESTER
WINCHESTER
$750,000
436 Main Street, Winchester, CONNECTICUT, 06098
4
2
5,389 Sq ft
ACTIVE
MLS# 24135030

Listing Agent: Anthony Gioia

Listing Office: The Washington Agency

WINCHESTER
WINCHESTER
$739,900
Old Robertsville Road, Winchester, CONNECTICUT, 06098
CONTRACT
MLS# 24080217

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$649,900
115 Old Robertsville Road, Winchester, CONNECTICUT, 06098
CONTRACT
MLS# 24104099

Listing Agent: Jared Tedesco

Listing Office: Litchfield County Real Estate

WINCHESTER

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