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    Winchester, CT
    Map
    71 Properties Available

    71 Properties Available

    The average price in the selected areas has remained stable. Learn more
    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    51 Hinsdale Avenue, Winchester, CT 06098
    Open 5/3 11AM-3PM

    $475,000

    7 Beds5 Baths3,538 SqFt

    51 Hinsdale Avenue, Winchester, CT 06098

    Listed by Suzie Larson of Turning Point Realty, LLC

    150 Oak Street, Winchester, CT 06098
    1/8
    Coming Soon

    $579,000

    11 Beds6 Baths5,233 SqFt

    150 Oak Street, Winchester, CT 06098

    Listed by Pamela Silvestri of Turning Point Realty, LLC

    102 Wallens Street, Winchester, CT 06098
    1/25
    New

    $349,900

    3 Beds2 Baths1,898 SqFt

    102 Wallens Street, Winchester, CT 06098

    Listed by Amanda Balaski of Northwest CT Realty

    9 Colony Drive, Winchester, CT 06098
    1/33
    New

    $329,900

    3 Beds2 Baths1,582 SqFt

    9 Colony Drive, Winchester, CT 06098

    Listed by David Sartirana of Northwest CT Realty

    277 N. Main Street ##3, Winchester, CT 06098
    1/14
    New

    $900

    1 Bed1 Bath650 SqFt

    277 N. Main Street ##3, Winchester, CT 06098

    Listed by Ryan Marconi of The Washington Agency

    722 Lake Drive, Winchester, CT 06098
    1/38
    Under Contract

    $1,200,000

    3 Beds3 Baths1,556 SqFt

    722 Lake Drive, Winchester, CT 06098

    Listed by Joanne Donne of The Washington Agency

    129 East Lake Street, Winchester, CT 06098
    1/35
    New

    $1,495,000

    3 Beds4 Baths2,699 SqFt

    129 East Lake Street, Winchester, CT 06098

    Listed by Karen Newton of William Pitt Sotheby's Int'l

    20-22 Allen Street #2nd flr rs, Winchester, CT 06098
    1/13
    New

    $1,365

    1 Bed1 Bath800 SqFt

    20-22 Allen Street #2nd flr rs, Winchester, CT 06098

    Listed by Suzie Larson of Turning Point Realty, LLC

    162 Spencer Hill Road, Winchester, CT 06098
    1/35
    New

    $625,000

    3 Beds3 Baths2,144 SqFt

    162 Spencer Hill Road, Winchester, CT 06098

    Listed by Kelly Sullivan of Sullivan Real Estate Inc

    57 Bridge Street, Winchester, CT 06098
    1/33
    New

    $275,000

    4 Beds2 Baths1,416 SqFt

    57 Bridge Street, Winchester, CT 06098

    Listed by David Sartirana of Northwest CT Realty

    118 South Road, Winchester, CT 06098
    1/36
    Under Contract

    $419,000

    4 Beds3 Baths2,240 SqFt

    118 South Road, Winchester, CT 06098

    Listed by Becky Grieco of Berkshire Hathaway NE Prop.

    34 Rock Street, Winchester, CT 06098
    1/21
    Active

    $2,200

    3 Beds1 Bath1,042 SqFt

    34 Rock Street, Winchester, CT 06098

    Listed by Terry Cubeddu of Ameristar Royal Realty LLC

    174 Main Street #1, Winchester, CT 06098
    Active

    $1,495

    3 Beds1 Bath1,000 SqFt

    174 Main Street #1, Winchester, CT 06098

    Listed by Amanda Balaski of Northwest CT Realty

    5 Brookside Avenue, Winchester, CT 06098
    1/7
    Active

    $1,350

    2 Beds1 Bath1,250 SqFt

    5 Brookside Avenue, Winchester, CT 06098

    Listed by Mark Digalbo of Mark DiGalbo Realty LLC

    26 Elm Street, Winchester, CT 06098
    1/14
    Active

    $398,000

    5 Beds3 Baths2,496 SqFt

    26 Elm Street, Winchester, CT 06098

    Listed by Annie Simard of LPT Realty

    440 Main Street #B, Winchester, CT 06098
    1/5
    Active

    $1,200

    2 Beds1 Bath4,668 SqFt

    440 Main Street #B, Winchester, CT 06098

    Listed by Linda Ganem of Borla & Associates Real Estate

    111 Riverton Road #28, Winchester, CT 06098
    1/22
    Under Contract

    $184,900

    2 Beds2 Baths1,204 SqFt

    111 Riverton Road #28, Winchester, CT 06098

    Listed by Ellen Sebastian of William Pitt Sotheby's Int'l

    43 Wallens Street #1, Winchester, CT 06098
    1/13
    Under Contract

    $1,300

    1 Bed1 Bath595 SqFt

    43 Wallens Street #1, Winchester, CT 06098

    Listed by Diane Carroll of The Washington Agency

    123 Old North Road, Winchester, CT 06098
    1/28
    Under Contract

    $425,000

    3 Beds2 Baths1,781 SqFt

    123 Old North Road, Winchester, CT 06098

    Listed by Rick Berkenstock of Century 21 AllPoints Realty

    40A High Street, Winchester, CT 06098
    1/11
    Active

    $850

    1 Bed1 Bath450 SqFt

    40A High Street, Winchester, CT 06098

    Listed by Alan Hill of eXp Realty

    1 Hamill Drive, Winchester, CT 06098
    1/29
    Active

    $359,900

    3 Beds2 Baths1,600 SqFt

    1 Hamill Drive, Winchester, CT 06098

    Listed by Paul Duh of Realty ONE Group Connect

    147 Winchester Drive, Southington, CT 06489
    1/40
    Under Contract

    $949,900

    5 Beds3 Baths2,741 SqFt

    147 Winchester Drive, Southington, CT 06489

    Listed by Renee Lovley of Century 21 AllPoints Realty

    121 West Wakefield Boulevard, Winchester, CT 06098
    1/38
    Active

    $769,000

    4 Beds4 Baths2,265 SqFt

    121 West Wakefield Boulevard, Winchester, CT 06098

    Listed by Elizabeth Stockwell of Coldwell Banker Realty

    90 Colony Drive, Winchester, CT 06098
    1/22
    Price Dropped by $14K

    $335,000

    3 Beds1 Bath1,282 SqFt

    90 Colony Drive, Winchester, CT 06098

    Listed by Michelle Grant of Coldwell Banker Premier Real Estate

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    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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    image0 (1)Fusion

    William Pitt Sotheby's International Realty

    Jay Contessa Lic# RES.0816734

    +1(203) 461-3880 jcontessa@wpsir.com

    470 Main Street, Ridgefield, CT, 06877

    Get My App

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    SITE MAP

        Home
        My Listings
        1. Featured Listings
        2. Sold Listings
        Communities
        1. Ridgefield
        2. Redding
        3. Fairfield
        Sell My Home
        Services
        Resources
        1. iBuyer Guide
        2. Affordability Calculator
        3. Mortgage Calculator
        4. Market Snapshot
        About
        1. My Story
        2. My Resume
        3. Client Survey
        4. Testimonials
        5. Contact Me
    image0 (1)Fusion

    William Pitt Sotheby's International Realty

    Jay Contessa Lic# RES.0816734

    +1(203) 461-3880 jcontessa@wpsir.com

    470 Main Street, Ridgefield, CT, 06877

    Get My App

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility