Century 21 Cityside
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128 Properties

128 Properties Available

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  • 3 Chesterford Terrace, Winchester, MA 01890
    1/35 35
    Pending

    $ 1,300,000

    3 Beds1.5 Baths2,006 SqFt

    3 Chesterford Terrace, Winchester, MA 01890

    Single Family Home

    Listed by The Fenway Group of Compass

  • 1 Town Way, Winchester, MA 01890
    3D
    Open Sun 11:30AM-1PM

    $ 1,799,000

    3 Beds3.5 Baths3,010 SqFt

    1 Town Way, Winchester, MA 01890

    Single Family Home

    Listed by Vita Realty Group of Compass

  • 8 Oak Street, Winchester, MA 01890
    1/38 38
    Open Sat 12PM-1:30PM

    $ 1,125,000

    5 Beds2.5 Baths2,391 SqFt

    8 Oak Street, Winchester, MA 01890

    Single Family Home

    Listed by The Synergy Group of The Synergy Group

  • 42 Wildwood Street, Winchester, MA 01890
    1/42 42
    Open Thu 5PM-6PM

    $ 2,299,000

    7 Beds4.5 Baths4,930 SqFt

    42 Wildwood Street, Winchester, MA 01890

    Single Family Home

    Listed by Carolyn Walsh of Better Homes and Gardens Real Estate - The Shanahan Group

  • 8-10 Oak St, Winchester, MA 01890
    1/38 38
    Open Sat 12PM-1:30PM

    $ 1,125,000

    5 Beds2.5 Baths2,391 SqFt

    8-10 Oak St, Winchester, MA 01890

    Multi-Family

    Listed by The Synergy Group of The Synergy Group

  • 241 Ridge St, Winchester, MA 01890
    1/37 37
    Open Sat 11AM-1PM

    $ 1,599,000

    4 Beds3 Baths2,480 SqFt

    241 Ridge St, Winchester, MA 01890

    Single Family Home

    Listed by Team Lillian Montalto of Lillian Montalto Signature Properties

  • 247 Washington St #11, Winchester, MA 01890
    1/23 23
    Open Sat 11AM-12PM

    $ 729,000

    3 Beds2.5 Baths1,494 SqFt

    247 Washington St #11, Winchester, MA 01890

    Condo

    Listed by Heejeong Joo of Coldwell Banker Realty - Lexington

  • 46 Clark St, Winchester, MA 01890
    3D
    Open Sat 11AM-12PM

    $ 1,064,000

    4 Beds1.5 Baths1,777 SqFt

    46 Clark St, Winchester, MA 01890

    Single Family Home

    Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest

  • 79 Grove St, Winchester, MA 01890
    1/41 41
    Open Sat 12PM-1:30PM

    $ 1,899,000

    5 Beds3.5 Baths3,210 SqFt

    79 Grove St, Winchester, MA 01890

    Single Family Home

    Listed by Pirani & Wile Group of Gibson Sotheby's International Realty

  • 14 Hillside Ave, Winchester, MA 01890
    1/40 40
    Open Sun 2PM-3:30PM

    $ 2,300,000

    4 Beds4.5 Baths3,881 SqFt

    14 Hillside Ave, Winchester, MA 01890

    Single Family Home

    Listed by Rebecca Huang of William Raveis R.E. & Home Services

  • 26 N Gateway, Winchester, MA 01890
    1/36 36
    Open Sun 11AM-12PM

    $ 2,099,000

    4 Beds3.5 Baths3,210 SqFt

    26 N Gateway, Winchester, MA 01890

    Single Family Home

    Listed by Pirani & Wile Group of Gibson Sotheby's International Realty

  • 38 Robinhood Rd, Winchester, MA 01890
    1/32 32
    Open Sun 1PM-2PM

    $ 1,175,000

    3 Beds2 Baths1,736 SqFt

    38 Robinhood Rd, Winchester, MA 01890

    Single Family Home

    Listed by Catherine Albiani of Better Homes and Gardens Real Estate - The Shanahan Group

  • 53 Winford Way, Winchester, MA 01890
    1/24 24
    Open Sat 12:30PM-1:30PM

    $ 2,399,000

    5 Beds4 Baths5,083 SqFt

    53 Winford Way, Winchester, MA 01890

    Single Family Home

    Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest

  • 129 Washington St #129, Winchester, MA 01890
    1/30 30
    Open Sun 11AM-12:30PM

    $ 1,099,000

    3 Beds3.5 Baths2,420 SqFt

    129 Washington St #129, Winchester, MA 01890

    Condo

    Listed by The Mary Scimemi Team of Leading Edge Real Estate

  • 1 Plymouth Rd, Winchester, MA 01890
    1/37 37
    Open Sun 1PM-2:30PM

    $ 3,299,000

    7 Beds7.5 Baths7,226 SqFt

    1 Plymouth Rd, Winchester, MA 01890

    Single Family Home

    Listed by The Sarkis Team of Douglas Elliman Real Estate - The Sarkis Team

  • 83 Church Street #15, Winchester, MA 01890
    1/37 37
    Open Sun 11:30AM-12:30PM

    $ 999,000

    2 Beds1.5 Baths1,365 SqFt

    83 Church Street #15, Winchester, MA 01890

    Condo

    Listed by Paula R. Sughrue of Better Homes and Gardens Real Estate - The Shanahan Group

  • 50 Holland Street, Winchester, MA 01890
    1/42 42
    New

    $ 1,549,000

    3 Beds2.5 Baths2,640 SqFt

    50 Holland Street, Winchester, MA 01890

    Single Family Home

    Listed by Kim Covino & Co. Team of Compass

  • 11 Viking Road, Winchester, MA 01890
    1/36 36
    New

    $ 3,600,000

    7 Beds7.5 Baths7,429 SqFt

    11 Viking Road, Winchester, MA 01890

    Single Family Home

    Listed by Post Advisory Group of Engel & Volkers Boston

  • 7 Wainwright Road #113, Winchester, MA 01890
    1/42 42
    New

    $ 2,100,000

    4 Beds3.5 Baths3,640 SqFt

    7 Wainwright Road #113, Winchester, MA 01890

    Condo

    Listed by Kim Covino & Co. Team of Compass

  • 200 Swanton St #228, Winchester, MA 01890
    1/9 9
    New

    $ 2,200

    1 Bed1 Bath606 SqFt

    200 Swanton St #228, Winchester, MA 01890

    Condo

    Listed by Jing Chen of Boston Hub Real Estate

  • 15 Clark St, Winchester, MA 01890
    1/22 22
    New

    $ 849,000

    3 Beds1.5 Baths1,340 SqFt

    15 Clark St, Winchester, MA 01890

    Single Family Home

    Listed by Jeffrey Hsu of Coldwell Banker Realty - Milton

  • 8 Mason Street #8, Winchester, MA 01890
    1/31 31
    New

    $ 2,100

    1 Bed1 Bath600 SqFt

    8 Mason Street #8, Winchester, MA 01890

    Multi-Family, Townhouse

    Listed by Melanie Lentini of Leading Edge Real Estate

  • 161 Highland Ave #n/a, Winchester, MA 01890
    1/28 28
    New

    $ 8,500

    6 Beds2 Baths3,000 SqFt

    161 Highland Ave #n/a, Winchester, MA 01890

    Single Family Home

    Listed by Lisa Godwin of Gibson Sotheby's International Realty

  • 6 Davey Ln, Winchester, MA 01890
    1/34 34
    Active Under Contract

    $ 2,225,000

    4 Beds3 Baths4,210 SqFt

    6 Davey Ln, Winchester, MA 01890

    Single Family Home

    Listed by Gretchen Papineau of Coldwell Banker Realty - Andovers/Readings Regional

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craig
Century 21 Cityside

Craig Carpenter License ID: 9​5​7​4​3​2​4

+1(413) 454-2785 [email protected]

232 Clarendon St, Boston, Massachusetts, 02116, United States

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craig
Century 21 Cityside

Craig Carpenter License ID: 9​5​7​4​3​2​4

+1(413) 454-2785 [email protected]

232 Clarendon St, Boston, Massachusetts, 02116, United States

    • Buyers
    • Sellers
    • Search

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.