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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.

Map of the area

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$2,600,000
WINCHESTER
$2,600,000
431 West Wakefield, Winchester, CT, 06098
9
6
5,530 Sq ft
ACTIVE
MLS# 24042374
WINCHESTER
$1,699,500
WINCHESTER
$1,699,500
538 Wheelers, Winchester, CT, 06098
4
3
2,112 Sq ft
ACTIVE
MLS# 24052635
WINCHESTER
$1,650,000
WINCHESTER
$1,650,000
508 West Wakefield, Winchester, CT, 06098
7
4
2,687 Sq ft
CONTRACT
MLS# 24024787
WINCHESTER
$1,500,000
WINCHESTER
$1,500,000
711 West Wakefield, Winchester, CT, 06098
3
3
ACTIVE
MLS# 24022821
WINCHESTER
3D Tour
$1,400,000
WINCHESTER
Virtual Tour
$1,400,000
435/434 West Wakefield, Winchester, CT, 06098
8
5
5,231 Sq ft
ACTIVE
MLS# 24047556
WINCHESTER
$995,000
WINCHESTER
$995,000
469 Platt Hill, Winchester, CT, 06098
4
2
3,088 Sq ft
ACTIVE
MLS# 24089885
WINCHESTER
$979,000
WINCHESTER
Featured
$979,000
355 West Lake, Winchester, CT, 06098
5
4
2,768 Sq ft
ACTIVE
MLS# 24091474
WINCHESTER
3D Tour
$968,000
WINCHESTER
Virtual Tour
$968,000
112 Shore, Winchester, CT, 06098
3
3
1,284 Sq ft
COMING SOON
MLS# 24086841
WINCHESTER
$950,000
WINCHESTER
$950,000
354 Main, Winchester, CT, 06098
4
11,972 Sq ft
ACTIVE
MLS# 24016392
WINCHESTER
$950,000
WINCHESTER
$950,000
175 Main, Winchester, CT, 06098
14
7
4,860 Sq ft
ACTIVE
MLS# 24073478
WINCHESTER
$950,000
WINCHESTER
$950,000
175 Main, Winchester, CT, 06098
5
4,860 Sq ft
ACTIVE
MLS# 24073477
WINCHESTER
3D Tour
$849,900
WINCHESTER
Virtual Tour
$849,900
119 West Wakefield, Winchester, CT, 06098
4
2
1,781 Sq ft
ACTIVE
MLS# 24058804
WINCHESTER
3D Tour
$849,900
WINCHESTER
Virtual Tour
$849,900
119 West Wakefield, Winchester, CT, 06098
4
2
1,781 Sq ft
ACTIVE
MLS# 24075940
WINCHESTER
$699,000
WINCHESTER
$699,000
115 Main, Winchester, CT, 06098
2,400 Sq ft
ACTIVE
MLS# 24054820
WINCHESTER
$650,000
WINCHESTER
$650,000
18-4A Taylor Brook, Winchester, CT, 06098
3
3
ACTIVE
MLS# 170551066
WINCHESTER
$525,000
WINCHESTER
Featured
$525,000
55 Walnut, Winchester, CT, 06098
5,016 Sq ft
ACTIVE
MLS# 24071862
WINCHESTER
$525,000
WINCHESTER
Featured
$525,000
55 Walnut, Winchester, CT, 06098
5
4
5,016 Sq ft
ACTIVE
MLS# 24071827
WINCHESTER
$525,000
WINCHESTER
$525,000
117 South, Winchester, CT, 06098
3
3
2,747 Sq ft
ACTIVE
MLS# 24096267
WINCHESTER
$495,000
WINCHESTER
$495,000
171 Reaching Hill, Winchester, CT, 06098
3
2
1,740 Sq ft
ACTIVE
MLS# 24095351
WINCHESTER
$465,000
WINCHESTER
$465,000
704 West Wakefield, Winchester, CT, 06098
2
2
754 Sq ft
CONTRACT
MLS# 24096546
WINCHESTER
$460,000
WINCHESTER
$460,000
288 Torringford, Winchester, CT, 06098
4
3
3,021 Sq ft
Under Contract - Continue to Show
MLS# 24067951
WINCHESTER
$450,000
WINCHESTER
$450,000
51 Pratt, Winchester, CT, 06098
4
2
2,239 Sq ft
ACTIVE
MLS# 24073605
WINCHESTER
$400,000
WINCHESTER
$400,000
110 Rugg Brook, Winchester, CT, 06098
3
3
2,209 Sq ft
Under Contract - Continue to Show
MLS# 24083204
WINCHESTER
$375,000
WINCHESTER
$375,000
323 East Wakefield, Winchester, CT, 06098
3
3
1,253 Sq ft
CONTRACT
MLS# 24088496
WINCHESTER
$349,000
WINCHESTER
$349,000
150 Mathew, Winchester, CT, 06098
3
2
768 Sq ft
ACTIVE
MLS# 24090132
WINCHESTER
$325,000
WINCHESTER
Featured
$325,000
Undisclosed Address, Winchester, CT, 06098
4,852 Sq ft
ACTIVE
MLS# 24052116
WINCHESTER
$320,000
WINCHESTER
$320,000
711 West Wakefield, Winchester, CT, 06098
1,015 Sq ft
ACTIVE
MLS# 24020414
WINCHESTER
$299,900
WINCHESTER
$299,900
155 Mathew, Winchester, CT, 06098
2
2
768 Sq ft
Under Contract - Continue to Show
MLS# 24085896
WINCHESTER
$299,900
WINCHESTER
$299,900
77 Hubbard, Winchester, CT, 06098
6
2
2,699 Sq ft
CONTRACT
MLS# 24059312
WINCHESTER
$295,000
WINCHESTER
$295,000
393 Winchester, Winchester, CT, 06098
ACTIVE
MLS# 170078080
WINCHESTER
$289,000
WINCHESTER
$289,000
174 Boyd, Winchester, CT, 06098
3
1
1,424 Sq ft
CONTRACT
MLS# 24066803
WINCHESTER
$286,000
WINCHESTER
$286,000
421 UNIT  y, Winchester, CT, 06098
3
2
1,440 Sq ft
CONTRACT
MLS# 24085643
WINCHESTER
$275,000
WINCHESTER
Featured
$275,000
896-898 Main, Winchester, CT, 06098
648 Sq ft
ACTIVE
MLS# 24048775
WINCHESTER
$269,900
WINCHESTER
$269,900
25 Center, Winchester, CT, 06098
3
1
2,754 Sq ft
ACTIVE
MLS# 24082567
WINCHESTER
$249,900
WINCHESTER
$249,900
150 Meadow, Winchester, CT, 06098
4
2
2,094 Sq ft
Under Contract - Continue to Show
MLS# 24079880
WINCHESTER
3D Tour
$230,000
WINCHESTER
Virtual Tour
$230,000
39 Orchard, Winchester, CT, 06098
3
2
1,200 Sq ft
ACTIVE
MLS# 24079182
WINCHESTER
$225,000
WINCHESTER
$225,000
129 Shore, Winchester, CT, 06098
ACTIVE
MLS# 24080977
WINCHESTER
$165,000
WINCHESTER
$165,000
115 Willow, Winchester, CT, 06098
1
264 Sq ft
ACTIVE
MLS# 24070789
WINCHESTER
$165,000
WINCHESTER
$165,000
9 Loomis, Winchester, CT, 06098
3
2
1,768 Sq ft
CONTRACT
MLS# 24088887
WINCHESTER
$158,000
WINCHESTER
Featured
$158,000
843-845 (lots - 10A,10 &1 East wakefield, Winchester, CT, 06098
ACTIVE
MLS# 24003236
WINCHESTER
$158,000
WINCHESTER
$158,000
9 John, Winchester, CT, 06098
1
2
1,172 Sq ft
Under Contract - Continue to Show
MLS# 24090596
WINCHESTER
$59,900
WINCHESTER
Featured
$59,900
105,107 Mountain, Winchester, CT, 06098
ACTIVE
MLS# 170616672
WINCHESTER
$55,000
WINCHESTER
$55,000
130 Alpha, Winchester, CT, 06098
ACTIVE
MLS# 24096577
WINCHESTER
$49,000
WINCHESTER
Featured
$49,000
99 Hubbard, Winchester, CT, 06098
832 Sq ft
ACTIVE
MLS# 24073744
WINCHESTER
$29,000
WINCHESTER
Featured
$29,000
124 Rockwell, Winchester, CT, 06098
1,882 Sq ft
ACTIVE
MLS# 24073710
WINCHESTER
$23,900
WINCHESTER
$23,900
48 Bridge, Winchester, CT, 06098
1,428 Sq ft
ACTIVE
MLS# 24073721
WINCHESTER
$23,900
WINCHESTER
$23,900
19 Hill, Winchester, CT, 06098
ACTIVE
MLS# 24073702
WINCHESTER
$17,999
WINCHESTER
$17,999
320 White Oak, Winchester, CT, 06098
ACTIVE
MLS# 24078686
WINCHESTER
$3,700
WINCHESTER
$3,700
115 Main, Winchester, CT, 06098
2,400 Sq ft
ACTIVE
MLS# 24037328
WINCHESTER
$2,200
WINCHESTER
$2,200
188 East Lake, Winchester, CT, 06098
2
1
2,080 Sq ft
ACTIVE
MLS# 24055876
WINCHESTER
$2,150
WINCHESTER
$2,150
51 Hinsdale, Winchester, CT, 06098
3
2
3,538 Sq ft
ACTIVE
MLS# 24094193
WINCHESTER
$1,595
WINCHESTER
$1,595
98 Spencer UNIT 4N, Winchester, CT, 06098
4
1
5,645 Sq ft
ACTIVE
MLS# 24094750
WINCHESTER
$1,595
WINCHESTER
$1,595
19 Center UNIT 1R, Winchester, CT, 06098
3
1
ACTIVE
MLS# 24094775
WINCHESTER
$1,150
WINCHESTER
$1,150
174 Main C UNIT c, Winchester, CT, 06098
1
1
ACTIVE
MLS# 24092171
WINCHESTER
WINCHESTER
$2,600,000
431 West Wakefield, Winchester, CT, 06098
9
6
5,530 Sq ft
ACTIVE
MLS# 24042374

Listing Agent: Lisa Ogren

Listing Office: Berkshire Hathaway NE Prop.

WINCHESTER
WINCHESTER
$1,699,500
538 Wheelers, Winchester, CT, 06098
4
3
2,112 Sq ft
ACTIVE
MLS# 24052635

Listing Agent: Karen Newton

Listing Office: William Pitt Sotheby's Int'l

WINCHESTER
WINCHESTER
$1,650,000
508 West Wakefield, Winchester, CT, 06098
7
4
2,687 Sq ft
CONTRACT
MLS# 24024787

Listing Agent: Pierre Moran

Listing Office: William Pitt Sotheby's Int'l

WINCHESTER
WINCHESTER
$1,500,000
711 West Wakefield, Winchester, CT, 06098
3
3
ACTIVE
MLS# 24022821

Listing Agent: Peter Kores

Listing Office: The Washington Agency

WINCHESTER
Virtual Tour
WINCHESTER
$1,400,000
435/434 West Wakefield, Winchester, CT, 06098
8
5
5,231 Sq ft
ACTIVE
MLS# 24047556

Listing Agent: Heidi Picard-Ramsay

Listing Office: Berkshire Hathaway NE Prop.

WINCHESTER
WINCHESTER
$995,000
469 Platt Hill, Winchester, CT, 06098
4
2
3,088 Sq ft
ACTIVE
MLS# 24089885

Listing Agent: Marshall Cohen

Listing Office: Cohen Agency

WINCHESTER
WINCHESTER
Featured
$979,000
355 West Lake, Winchester, CT, 06098
5
4
2,768 Sq ft
ACTIVE
MLS# 24091474

Listing Agent: David Sartirana

Listing Office: Northwest CT Realty

WINCHESTER
Virtual Tour
WINCHESTER
$968,000
112 Shore, Winchester, CT, 06098
3
3
1,284 Sq ft
COMING SOON
MLS# 24086841

Listing Agent: Nancy Reardon

Listing Office: Berkshire Hathaway NE Prop.

WINCHESTER
WINCHESTER
$950,000
354 Main, Winchester, CT, 06098
4
11,972 Sq ft
ACTIVE
MLS# 24016392

Listing Agent: Jordan Ostrofsky

Listing Office: KW Legacy Partners

WINCHESTER
WINCHESTER
$950,000
175 Main, Winchester, CT, 06098
14
7
4,860 Sq ft
ACTIVE
MLS# 24073478

Listing Agent: Ryan Rea

Listing Office: Berkshire Hathaway NE Prop.

WINCHESTER
WINCHESTER
$950,000
175 Main, Winchester, CT, 06098
5
4,860 Sq ft
ACTIVE
MLS# 24073477

Listing Agent: Ryan Rea

Listing Office: Berkshire Hathaway NE Prop.

WINCHESTER
Virtual Tour
WINCHESTER
$849,900
119 West Wakefield, Winchester, CT, 06098
4
2
1,781 Sq ft
ACTIVE
MLS# 24058804

Listing Agent: Mela Veltri Case

Listing Office: KW Legacy Partners

WINCHESTER

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