- Home
- Search Listings
- Fairfield County
- Fairfield County Towns
- Greenwich Overview
- Darien Overview
- New Canaan Overview
- Stamford Overview
- Bethel Overview
- Bridgeport Overview
- Brookfield Overview
- Danbury Overview
- Easton Overview
- Fairfield Overview
- Monroe Overview
- New Fairfield Overview
- Newtown Overview
- Norwalk Overview
- Redding Overview
- Ridgefield Overview
- Shelton Overview
- Sherman Overview
- Stratford Overview
- Trumbull Overview
- Weston Overview
- Westport Overview
- Wilton Overview
- Westchester County
- About Us
- Contact Us
- Register
- /
- Sign In
61 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)

$ 375,000
57 Main Street, Winchester, CT 06098
Commercial
Listed by Stacy LaQuerre of Regall Realty, LLC

$ 975,000
469 Platt Hill Road, Winchester, CT 06098
Single Family Home
Listed by Marshall Cohen of Cohen Agency

$ 899,000
354 Main Street, Winchester, CT 06098
Commercial
Listed by Arlene Gonzalez of The Gonzalez Property Group

$ 299,900
49 Walnut Street, Winchester, CT 06098
Multi-Family
Listed by David Sartirana of Northwest CT Realty

$ 229,900
32 Charles Street, Winchester, CT 06098
Single Family Home
Listed by David Sartirana of Northwest CT Realty

$ 4,000
880 West Wakefield Boulevard, Winchester, CT 06098
Single Family Home
Listed by Matthew Crossen of Coldwell Banker Realty

$ 1,475
103 Elm Street, Winchester, CT 06098
Multi-Family
Listed by Amanda Balaski of Northwest CT Realty

$ 1,950
69 Upson Avenue, Winchester, CT 06098
Multi-Family
Listed by Gabby Addison of Keller Williams Realty

$ 309,900
156 Lincoln Avenue, Winchester, CT 06098
Single Family Home
Listed by Kristin Leblanc of Mary LeBlanc Realty

$ 2,500
26 Elm Street, Winchester, CT 06098
Multi-Family
Listed by Annie Simard of LPT Realty

$ 499,000
197 Spencer Hill Road, Winchester, CT 06098
Single Family Home
Listed by David Sartirana of Northwest CT Realty

$ 500,000
440 Platt Hill Road, Winchester, CT 06098
Single Family Home
Listed by David D'Amore of Northwest CT Realty

$ 620,000
45 Elm Street, Winchester, CT 06098
Commercial
Listed by Ashley Chaia of Oxford Realty

$ 279,999
73 Norfolk Road, Winchester, CT 06098
Single Family Home
Listed by Lisa Hilliard of Litchfield Hills Real Estate

$ 4,000
121 West Wakefield Boulevard, Winchester, CT 06098
Single Family Home
Listed by Elizabeth Stockwell of Coldwell Banker Realty

$ 194,900
111 Riverton Road #Apt 61, Winchester, CT 06098
Condo
Listed by Bethany Lydem of Stone Crest Realty LLC

$ 1,600
29 Benton Street, Winchester, CT 06098
Multi-Family
Listed by Victoria Stillings of Coldwell Banker Realty

$ 2,500
220 Walnut Street, Winchester, CT 06098
Single Family Home
Listed by Justin Mokerzecki of Glanville Real Estate

$ 1,250
217 North Main Street #2, Winchester, CT 06098
Multi-Family
Listed by Michaela Rousseau of Showcase Realty, Inc.

$ 339,999
157 Elm Street, Winchester, CT 06098
Single Family Home
Listed by Doreen Gagnon of Coldwell Banker Realty

$ 394,900
212 Spencer Hill Road, Winchester, CT 06098
Single Family Home
Listed by Tammy Powling of Coldwell Banker Realty

$ 749,999
151 Losaw Road, Winchester, CT 06098
Single Family Home
Listed by Breanna Goebel of Compass Connecticut, LLC

$ 189,900
14 Curtice Street, Winchester, CT 06098
Single Family Home
Listed by Michael Johnson of Lock and Key Realty, Inc

$ 1,275
111 Rockwell Street #2nd Floor, Winchester, CT 06098
Multi-Family
Listed by Colin Murray of Dorrance Realty