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42 Properties Available In Winchester
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$ 349,000
150 Mathew Road, Winchester, CT 06098
Single Family Home
Listed by Josh Dionne of Commercial Services Realty

$ 260,000
120 Torrington Road, Winchester, CT 06098
Single Family Home
Listed by David Bolduc of Bolduc Realty Group

$ 1,195
174 Main Street #C, Winchester, CT 06098
Multi-Family
Listed by Amanda Balaski of Northwest CT Realty

$ 979,000
355 West Lake Street, Winchester, CT 06098
Single Family Home
Listed by David Sartirana of Northwest CT Realty

$ 1,295
88 Spencer Street #2, Winchester, CT 06098
Multi-Family
Listed by Amanda Balaski of Northwest CT Realty

$ 995,000
469 Platt Hill Road, Winchester, CT 06098
Single Family Home
Listed by Marshall Cohen of Cohen Agency

$ 158,000
9 John Street, Winchester, CT 06098
Single Family Home
Listed by Michelle Grant of Coldwell Banker Premier Real Estate

$ 199,900
9 Loomis Street, Winchester, CT 06098
Single Family Home
Listed by Kristen Duchene of Litchfield County Real Estate

$ 579,999
144 Marshall Street, Winchester, CT 06098
Single Family Home
Listed by Monica Palmerie of RE/MAX RISE

$ 749,900
39 South Main Street, Winchester, CT 06098
Multi-Family
Listed by Ryan Horvay of Smith & DeGroat Real Estate

$ 269,900
25 Center Street, Winchester, CT 06098
Multi-Family
Listed by Jessica Lopez of Our Home Realty Advisors

$ 849,900
119 West Wakefield Boulevard, Winchester, CT 06098
Multi-Family
Listed by Mela Veltri Case of KW Legacy Partners

$ 460,000
288 Torringford Street, Winchester, CT 06098
Single Family Home
Listed by Mark Porriello of RE/MAX Right Choice

$ 480,000
51 Pratt Street, Winchester, CT 06098
Single Family Home
Listed by Lourdes Galvan-Dominguez of Coldwell Banker Realty

$ 950,000
175 Main Street, Winchester, CT 06098
Commercial
Listed by Ryan Rea of Berkshire Hathaway NE Prop.

$ 165,000
115 Willow Street, Winchester, CT 06098
Commercial
Listed by Samantha Behm of William Pitt Sotheby's Int'l

$ 2,200
188 East Lake Street, Winchester, CT 06098
Multi-Family
Listed by Annie Simard of KW Legacy Partners

$ 1,699,500
538 Wheelers Point, Winchester, CT 06098
Single Family Home
Listed by Karen Newton of William Pitt Sotheby's Int'l

$ 1,500,000
435/434 West Wakefield Boulevard, Winchester, CT 06098
Single Family Home
Listed by Heidi Picard-Ramsay of Berkshire Hathaway NE Prop.

$ 349,900
116 Ashley Road, Winchester, CT 06058
Single Family Home
Listed by Michael Morris of Vylla Home (CT) LLC

$ 2,600,000
431 West Wakefield Boulevard, Winchester, CT 06098
Single Family Home
Listed by Lisa Ogren of Berkshire Hathaway NE Prop.

$ 1,500,000
711 West Wakefield Boulevard, Winchester, CT 06098
Single Family Home
Listed by Peter Kores of The Washington Agency

$ 950,000
354 Main Street, Winchester, CT 06098
Commercial
Listed by Jordan Ostrofsky of KW Legacy Partners

$ 650,000
18-4A Taylor Brook Road, Winchester, CT 06098
Single Family Home
Listed by Peter Kores of The Washington Agency