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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, CT, 06098
1
12,000 Sq ft
ACTIVE
MLS# 24154804
WINCHESTER
$1,850,000
WINCHESTER
$1,850,000
431 West Wakefield Boulevard, Winchester, CT, 06098
9
6
7,000 Sq ft
ACTIVE
MLS# 24159989
WINCHESTER
$1,595,000
WINCHESTER
$1,595,000
424 East Wakefield Boulevard, Winchester, CT, 06098
5
2
3,693 Sq ft
CONTRACT
MLS# 24171266
WINCHESTER
$1,495,000
WINCHESTER
$1,495,000
129 East Lake Street, Winchester, CT, 06098
3
4
2,699 Sq ft
CONTRACT
MLS# 24166368
WINCHESTER
$1,249,900
WINCHESTER
$1,249,900
748 Lake Drive, Winchester, CT, 06098
5
4
3,584 Sq ft
Under Contract - Continue
MLS# 24171778
WINCHESTER
$998,000
WINCHESTER
$998,000
878 West Wakefield Boulevard, Winchester, CT, 06098
4
3
3,330 Sq ft
CONTRACT
MLS# 24176238
WINCHESTER
3D Tour
$990,000
WINCHESTER
Virtual Tour
$990,000
674 East Wakefield Boulevard, Winchester, CT, 06098
3
3
2,097 Sq ft
CONTRACT
MLS# 24170488
WINCHESTER
$899,000
WINCHESTER
$899,000
354 Main Street, Winchester, CT, 06098
3
11,972 Sq ft
CONTRACT
MLS# 24137086
WINCHESTER
$799,000
WINCHESTER
$799,000
257-259 Torringford Street, Winchester, CT, 06098
ACTIVE
MLS# 24157681
WINCHESTER
$795,000
WINCHESTER
$795,000
535,538 West Wakefield Boulevard, Winchester, CT, 06098
ACTIVE
MLS# 24037015
WINCHESTER
3D Tour
$795,000
WINCHESTER
Virtual Tour
$795,000
258 Perch Rock Trail, Winchester, CT, 06098
4
2
1,373 Sq ft
CONTRACT
MLS# 24171657
WINCHESTER
$749,999
WINCHESTER
$749,999
660 East Wakefield Boulevard, Winchester, CT, 06098
2
2
1,320 Sq ft
CONTRACT
MLS# 24174215
WINCHESTER
WINCHESTER
$1,900,000
144 Rowley Street, Winchester, CT, 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, CT, 06098
9
6
7,000 Sq ft
ACTIVE
MLS# 24159989

Listing Agent: Lisa Ogren

Listing Office: Berkshire Hathaway NE Prop.

WINCHESTER
WINCHESTER
$1,595,000
424 East Wakefield Boulevard, Winchester, CT, 06098
5
2
3,693 Sq ft
CONTRACT
MLS# 24171266

Listing Agent: Karen Newton

Listing Office: William Pitt Sotheby's Int'l

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

Listing Agent: Karen Newton

Listing Office: William Pitt Sotheby's Int'l

WINCHESTER
Newly Listed
WINCHESTER
$1,249,900
748 Lake Drive, Winchester, CT, 06098
5
4
3,584 Sq ft
Under Contract - Continue
MLS# 24171778

Listing Agent: Ryan Horvay

Listing Office: Smith & DeGroat Real Estate

WINCHESTER
Newly Listed
WINCHESTER
$998,000
878 West Wakefield Boulevard, Winchester, CT, 06098
4
3
3,330 Sq ft
CONTRACT
MLS# 24176238

Listing Agent: Annie Simard

Listing Office: LPT Realty

WINCHESTER
Virtual Tour
WINCHESTER
$990,000
674 East Wakefield Boulevard, Winchester, CT, 06098
3
3
2,097 Sq ft
CONTRACT
MLS# 24170488

Listing Agent: Matthew Smith

Listing Office: Smith & DeGroat Real Estate

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

Listing Agent: Arlene Gonzalez

Listing Office: The Gonzalez Property Group

WINCHESTER
WINCHESTER
$895,000
469 Platt Hill Road, Winchester, CT, 06098
4
2
3,088 Sq ft
ACTIVE
MLS# 24172121

Listing Agent: Marshall Cohen

Listing Office: Cohen Agency

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
$799,000
257-259 Torringford Street, Winchester, CT, 06098
ACTIVE
MLS# 24157681

Listing Agent: Lisa Toczko

Listing Office: Home Valley Realty, LLC

WINCHESTER
Newly Listed
WINCHESTER
$795,000
535,538 West Wakefield Boulevard, Winchester, CT, 06098
ACTIVE
MLS# 24037015

Listing Agent: Christian Marino

Listing Office: Cohen Agency

WINCHESTER

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