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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
$920,000
WINCHESTER
$920,000
469 Platt Hill Road, Winchester, CT, 06098
4
2
3,088 Sq ft
ACTIVE
MLS# 24089885
WINCHESTER
$899,000
WINCHESTER
$899,000
354 Main Street, Winchester, CT, 06098
3
11,972 Sq ft
ACTIVE
MLS# 24137086
WINCHESTER
$750,000
WINCHESTER
$750,000
436 Main Street, Winchester, CT, 06098
4
2
5,389 Sq ft
ACTIVE
MLS# 24135030
WINCHESTER
$750,000
WINCHESTER
$750,000
436 Main Street, Winchester, CT, 06098
5,389 Sq ft
ACTIVE
MLS# 24135027
WINCHESTER
$540,000
WINCHESTER
$540,000
45 Elm Street, Winchester, CT, 06098
8
7,405 Sq ft
ACTIVE
MLS# 24131609
WINCHESTER
$500,000
WINCHESTER
$500,000
440 Platt Hill Road, Winchester, CT, 06098
4
3
3,416 Sq ft
CONTRACT
MLS# 24132598
WINCHESTER
$499,999
WINCHESTER
Featured
$499,999
55 Walnut Street, Winchester, CT, 06098
5,016 Sq ft
ACTIVE
MLS# 24071862
WINCHESTER
$499,999
WINCHESTER
Featured
$499,999
55 Walnut Street, Winchester, CT, 06098
5
4
5,016 Sq ft
ACTIVE
MLS# 24071827
WINCHESTER
$419,000
WINCHESTER
$419,000
117 South Road, Winchester, CT, 06098
3
3
2,747 Sq ft
CONTRACT
MLS# 24096267
WINCHESTER
$399,000
WINCHESTER
$399,000
187 Torringford Street, Winchester, CT, 06098
4
2
2,365 Sq ft
Under Contract - Continue
MLS# 24138466
WINCHESTER
$395,000
WINCHESTER
$395,000
720 Main Street, Winchester, CT, 06098
2
1,909 Sq ft
ACTIVE
MLS# 24138743
WINCHESTER
WINCHESTER
$2,199,000
431 West Wakefield Boulevard, Winchester, CT, 06098
9
6
7,000 Sq ft
ACTIVE
MLS# 24042374

Listing Agent: Lisa Ogren

Listing Office: Berkshire Hathaway NE Prop.

WINCHESTER
WINCHESTER
$920,000
469 Platt Hill Road, Winchester, CT, 06098
4
2
3,088 Sq ft
ACTIVE
MLS# 24089885

Listing Agent: Marshall Cohen

Listing Office: Cohen Agency

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

Listing Agent: Arlene Gonzalez

Listing Office: The Gonzalez Property Group

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

Listing Agent: John Harney

Listing Office: William Pitt Sotheby's Int'l

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

Listing Agent: Anthony Gioia

Listing Office: The Washington Agency

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

Listing Agent: Anthony Gioia

Listing Office: The Washington Agency

WINCHESTER
WINCHESTER
$749,999
151 Losaw Road, Winchester, CT, 06098
5
3
2,950 Sq ft
CONTRACT
MLS# 24121140

Listing Agent: Breanna Goebel

Listing Office: Compass Connecticut, LLC

WINCHESTER
WINCHESTER
$749,900
39 South Main Street, Winchester, CT, 06098
7
3
3,486 Sq ft
ACTIVE
MLS# 24083565

Listing Agent: Ryan Horvay

Listing Office: Smith & DeGroat Real Estate

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

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER
WINCHESTER
$649,900
115 Old Robertsville Road, Winchester, CT, 06098
5
2
2,304 Sq ft
ACTIVE
MLS# 24104078

Listing Agent: Jared Tedesco

Listing Office: Litchfield County Real Estate

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

Listing Agent: Jared Tedesco

Listing Office: Litchfield County Real Estate

WINCHESTER
WINCHESTER
$540,000
45 Elm Street, Winchester, CT, 06098
8
7,405 Sq ft
ACTIVE
MLS# 24131609

Listing Agent: Ashley Chaia

Listing Office: Oxford Realty

WINCHESTER

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