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    42 Properties
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    42 Properties Available In Winchester

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    CT >Winchester >
    Market Insights
    171 Reaching Hill Road, Winchester, CT 06098
    Open Sun 1PM-3PM

    $495,000

    171 Reaching Hill Road, Winchester, CT 06098

    3 Beds2 Baths2,700 SqFt

    Listed by Kelly Sullivan of Sullivan Real Estate Inc

    355 West Lake Street, Winchester, CT 06098
    Open Mon 1PM-3PM

    $979,000

    355 West Lake Street, Winchester, CT 06098

    5 Beds4 Baths3,216 SqFt

    Listed by David Sartirana of Northwest CT Realty

    19 Center Street #1R, Winchester, CT 06098
    New

    $1,595

    19 Center Street #1R, Winchester, CT 06098

    3 Beds1 Bath900 SqFt

    Listed by Amanda Balaski of Northwest CT Realty

    98 Spencer Street #4N, Winchester, CT 06098
    New

    $1,595

    98 Spencer Street #4N, Winchester, CT 06098

    4 Beds1 Bath1,000 SqFt

    Listed by Amanda Balaski of Northwest CT Realty

    51 Hinsdale Avenue, Winchester, CT 06098
    New

    $2,150

    51 Hinsdale Avenue, Winchester, CT 06098

    3 Beds2 Baths1,600 SqFt

    Listed by Suzie Larson of Turning Point Realty, LLC

    174 Main Street #C, Winchester, CT 06098
    Active

    $1,150

    174 Main Street #C, Winchester, CT 06098

    1 Bed1 Bath700 SqFt

    Listed by Amanda Balaski of Northwest CT Realty

    150 Mathew Road, Winchester, CT 06098
    Active

    $349,000

    150 Mathew Road, Winchester, CT 06098

    3 Beds2 Baths1,480 SqFt

    Listed by Josh Dionne of Commercial Services Realty

    469 Platt Hill Road, Winchester, CT 06098
    Active

    $995,000

    469 Platt Hill Road, Winchester, CT 06098

    4 Beds2 Baths3,088 SqFt

    Listed by Marshall Cohen of Cohen Agency

    9 John Street, Winchester, CT 06098
    Active

    $158,000

    9 John Street, Winchester, CT 06098

    1 Bed2 Baths1,172 SqFt

    Listed by Michelle Grant of Coldwell Banker Premier Real Estate

    144 Marshall Street, Winchester, CT 06098
    Active

    $579,999

    144 Marshall Street, Winchester, CT 06098

    3 Beds2 Baths1,744 SqFt

    Listed by Monica Palmerie of RE/MAX RISE

    39 South Main Street, Winchester, CT 06098
    Active

    $749,900

    39 South Main Street, Winchester, CT 06098

    7 Beds3 Baths3,486 SqFt

    Listed by Ryan Horvay of Smith & DeGroat Real Estate

    25 Center Street, Winchester, CT 06098
    Active

    $269,900

    25 Center Street, Winchester, CT 06098

    3 Beds1 Bath2,754 SqFt

    Listed by Jessica Lopez of Our Home Realty Advisors

    39 Orchard Street, Winchester, CT 06098
    Active

    $230,000

    39 Orchard Street, Winchester, CT 06098

    3 Beds2 Baths1,200 SqFt

    Listed by Michael Flaherty Jr of Sullivan Real Estate Inc

    119 West Wakefield Boulevard, Winchester, CT 06098
    Active

    $849,900

    119 West Wakefield Boulevard, Winchester, CT 06098

    4 Beds2 Baths1,781 SqFt

    Listed by Mela Veltri Case of KW Legacy Partners

    51 Pratt Street, Winchester, CT 06098
    Price Dropped by $30K

    $450,000

    51 Pratt Street, Winchester, CT 06098

    4 Beds2 Baths2,239 SqFt

    Listed by Lourdes Galvan-Dominguez of Coldwell Banker Realty

    175 Main Street, Winchester, CT 06098
    Active

    $950,000

    175 Main Street, Winchester, CT 06098

    5 Baths10,432 SqFt

    Listed by Ryan Rea of Berkshire Hathaway NE Prop.

    55 Walnut Street, Winchester, CT 06098
    Price Dropped by $25K

    $525,000

    55 Walnut Street, Winchester, CT 06098

    5 Beds4 Baths5,016 SqFt

    Listed by David Sartirana of Northwest CT Realty

    115 Willow Street, Winchester, CT 06098
    Active

    $165,000

    115 Willow Street, Winchester, CT 06098

    1 Bath780 SqFt

    Listed by Samantha Behm of William Pitt Sotheby's Int'l

    188 East Lake Street, Winchester, CT 06098
    Active

    $2,200

    188 East Lake Street, Winchester, CT 06098

    2 Beds1 Bath1,100 SqFt

    Listed by Annie Simard of KW Legacy Partners

    538 Wheelers Point, Winchester, CT 06098
    Active

    $1,699,500

    538 Wheelers Point, Winchester, CT 06098

    4 Beds3 Baths2,496 SqFt

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

    435/434 West Wakefield Boulevard, Winchester, CT 06098
    Active

    $1,500,000

    435/434 West Wakefield Boulevard, Winchester, CT 06098

    8 Beds5 Baths5,231 SqFt

    Listed by Heidi Picard-Ramsay of Berkshire Hathaway NE Prop.

    431 West Wakefield Boulevard, Winchester, CT 06098
    Price Dropped by $200K

    $2,600,000

    431 West Wakefield Boulevard, Winchester, CT 06098

    9 Beds6 Baths7,000 SqFt

    Listed by Lisa Ogren of Berkshire Hathaway NE Prop.

    711 West Wakefield Boulevard, Winchester, CT 06098
    Active

    $1,500,000

    711 West Wakefield Boulevard, Winchester, CT 06098

    3 Beds3 Baths2,664 SqFt

    Listed by Peter Kores of The Washington Agency

    354 Main Street, Winchester, CT 06098
    Active

    $950,000

    354 Main Street, Winchester, CT 06098

    4 Baths11,972 SqFt

    Listed by Jordan Ostrofsky of KW Legacy Partners

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    Taylor Shurtleff

    +1(860) 966-1834 taylorshurtleffhomes@gmail.com

    100 Pearl St, 14th fl., Hartford, 06103, USA

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      • Home
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      • Buy
        1. All Listings
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    Taylor Shurtleff
    Taylor Shurtleff

    +1(860) 966-1834 taylorshurtleffhomes@gmail.com

    100 Pearl St, 14th fl., Hartford, 06103, USA

    Get My App

    Powered by Lofty Inc. Copyright 2025. 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.