• About
    1. Home
    2. About Us
    3. Reviews
  • Buy
    1. All Listings
    2. Sold Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
  • Spinella Homes Team
  • Areas
    1. Braintree Overview
    2. Weymouth Overview
    3. Scituate Overview
    4. Norwell Overview
    5. Cohasset Overview
    6. Hanover Overview
    7. Marshfield Overview
    8. Hingham Overview
    9. Quincy Overview
    10. Milton Overview
    11. Hull Overview
    12. Dedham Overview
    13. Rockland Overview
    14. Pembroke Overview
    15. Kingston Overview
    16. Plympton Overview
  • Market Snapshot
    • Register
    • Sign In
    Filters Reset
    Save Search (2)
    Save your search to get Alerts
    78 Properties

    78 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)
    MA >Winchester >
    Market Insights
    14 Hillside Ave, Winchester, MA 01890
    1/42 42
    Price Dropped by $100K

    $ 1,499,000

    3 Beds2.5 Baths2,605 SqFt

    14 Hillside Ave, Winchester, MA 01890

    Single Family Home

    Listed by Seeme Moreira of Coldwell Banker Realty - Lexington

    31 Coolidge St #0, Winchester, MA 01890
    1/38 38
    Price Dropped by $1K

    $ 9,800

    4 Beds4 Baths4,650 SqFt

    31 Coolidge St #0, Winchester, MA 01890

    Single Family Home

    Listed by Carlos Xu of Lexwin Realty

    48 Spruce #48, Winchester, MA 01890
    1/18 18
    Active

    $ 5,500

    4 Beds3.5 Baths2,500 SqFt

    48 Spruce #48, Winchester, MA 01890

    Multi-Family, Townhouse

    Listed by Julia Marino of Archambault Real Estate

    14 Nassau Drive, Winchester, MA 01890
    1/42 42
    Active

    $ 2,950,000

    6 Beds6 Baths6,968 SqFt

    14 Nassau Drive, Winchester, MA 01890

    Single Family Home

    Listed by Weidong Li of WINN Real Estate & Consulting

    11 Taft Dr, Winchester, MA 01890
    1/5 5
    Active

    $ 2,899,000

    5 Beds5.5 Baths4,627 SqFt

    11 Taft Dr, Winchester, MA 01890

    Single Family Home

    Listed by The Marrocco Group of Coldwell Banker Realty - Lexington

    23 Jefferson Road, Winchester, MA 01890
    1/42 42
    Active

    $ 9,500

    6 Beds4.5 Baths3,118 SqFt

    23 Jefferson Road, Winchester, MA 01890

    Single Family Home

    Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest

    5 Squire Rd, Winchester, MA 01890
    1/40 40
    Price Dropped by $100K

    $ 2,099,000

    6 Beds3.5 Baths4,696 SqFt

    5 Squire Rd, Winchester, MA 01890

    Single Family Home

    Listed by Alina Wang Team of Coldwell Banker Realty - Lexington

    171 Swanton Street #63, Winchester, MA 01890
    1/23 23
    Active

    $ 4,500

    3 Beds2.5 Baths1,823 SqFt

    171 Swanton Street #63, Winchester, MA 01890

    Condo

    Listed by Gary Vrotsos Team of Coldwell Banker Realty - Cambridge

    27 Everett Ave, Winchester, MA 01890
    1/41 41
    Active

    $ 3,599,000

    6 Beds5.5 Baths7,431 SqFt

    27 Everett Ave, Winchester, MA 01890

    Single Family Home

    Listed by The Pallotta Group of Advisors Living - Winchester

    34 Glen Road, Winchester, MA 01890
    1/39 39
    Active

    $ 11,000

    7 Beds3.5 Baths3,300 SqFt

    34 Glen Road, Winchester, MA 01890

    Single Family Home

    Listed by Kim Covino & Co. Team of Compass

    5 Azalea Rd, Winchester, MA 01890
    1/13 13
    Active

    $ 2,449,000

    4 Beds3.5 Baths4,959 SqFt

    5 Azalea Rd, Winchester, MA 01890

    Single Family Home

    Listed by Giordana Fioravanti Smith of Berkshire Hathaway HomeServices Commonwealth Real Estate

    11 Viking Rd, Winchester, MA 01890
    1/4 4
    Active

    $ 3,799,900

    7 Beds7.5 Baths7,429 SqFt

    11 Viking Rd, Winchester, MA 01890

    Single Family Home

    Listed by The McLaren Team of Compass

    71 Woodside Rd, Winchester, MA 01890
    1/22 22
    Active

    $ 1,295,000

    4 Beds1.5 Baths2,202 SqFt

    71 Woodside Rd, Winchester, MA 01890

    Single Family Home

    Listed by Jorge Rodriguez of Carlton's Wharf & Co.

    846 Main Street #4, Winchester, MA 01890
    1/18 18
    Active

    $ 7,500

    3 Beds2.5 Baths2,900 SqFt

    846 Main Street #4, Winchester, MA 01890

    Condo

    Listed by Anthony Marino of The Marino Group Collection

    61 Westland Avenue, Winchester, MA 01890
    1/16 16
    Price Dropped by $49K

    $ 1,150,000

    4 Beds2 Baths2,621 SqFt

    61 Westland Avenue, Winchester, MA 01890

    Single Family Home

    Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

    40 Church #A, Winchester, MA 01890
    1/23 23
    Active

    $ 6,500

    4 Beds3.5 Baths4,000 SqFt

    40 Church #A, Winchester, MA 01890

    Multi-Family, Townhouse

    Listed by Sarkis James Kavlakian of Real Estate by Hughes & Assoc. Inc.

    8 Tanglewood Lane, Winchester, MA 01890
    1/42 42
    Price Dropped by $200K

    $ 2,650,000

    4 Beds3 Baths4,276 SqFt

    8 Tanglewood Lane, Winchester, MA 01890

    Single Family Home

    Listed by Kim Covino & Co. Team of Compass

    20 Amberwood Dr, Winchester, MA 01890
    1/34 34
    Price Dropped by $200K

    $ 3,698,000

    6 Beds7 Baths8,866 SqFt

    20 Amberwood Dr, Winchester, MA 01890

    Single Family Home

    Listed by Sino-US Realty Team of Keller Williams Realty

    26 Swan Road, Winchester, MA 01890
    1/42 42
    Active

    $ 3,989,000

    6 Beds6.5 Baths8,463 SqFt

    26 Swan Road, Winchester, MA 01890

    Single Family Home

    Listed by Kim Covino & Co. Team of Compass

    8 Chestnut St, Winchester, MA 01890
    1/42 42
    Price Dropped by $109K

    $ 2,890,000

    5 Beds5 Baths5,354 SqFt

    8 Chestnut St, Winchester, MA 01890

    Single Family Home

    Listed by The McLaren Team of Compass

    17 Russell Rd, Winchester, MA 01890
    1/13 13
    Active

    $ 4,500

    3 Beds1.5 Baths1,657 SqFt

    17 Russell Rd, Winchester, MA 01890

    Single Family Home

    Listed by Tsz Mui Kwan of Kwan Realty Inc.

    7 Conant Rd #20, Winchester, MA 01890
    1/37 37
    Active

    $ 699,900

    2 Beds2 Baths1,168 SqFt

    7 Conant Rd #20, Winchester, MA 01890

    Condo

    Listed by Brian Woods of Woods Properties Inc.

    54 Johnson Road, Winchester, MA 01890
    1/42 42
    Active

    $ 3,699,000

    7 Beds7.5 Baths7,982 SqFt

    54 Johnson Road, Winchester, MA 01890

    Single Family Home

    Listed by Kim Covino & Co. Team of Compass

    189 Mystic Valley Pkwy, Winchester, MA 01890
    3D
    Price Dropped by $49K

    $ 1,550,000

    6 Beds2.5 Baths3,543 SqFt

    189 Mystic Valley Pkwy, Winchester, MA 01890

    Single Family Home

    Listed by Anne Spry of Barrett Sotheby's International Realty

    • 1
    • 2
    • 3
    • 4

    explore listings in Winchester

    • Open House
    • Price Reduced
    • Virtual Tour
    • 3D Tour
    site logo
      • About
        1. Home
        2. About Us
        3. Reviews
        Areas
        1. Braintree Overview
        2. Weymouth Overview
        3. Scituate Overview
        4. Norwell Overview
        5. Cohasset Overview
        6. Hanover Overview
        7. Marshfield Overview
        8. Hingham Overview
        9. Quincy Overview
        10. Milton Overview
        11. Hull Overview
        12. Dedham Overview
        13. Rockland Overview
        14. Pembroke Overview
        15. Kingston Overview
        16. Plympton Overview
      • Buy
        1. All Listings
        2. Sold Listings
        Market Snapshot
      • Sell
        1. Sell My Home
        2. Home Valuation
    Spinella Homes Team
    Joe Spinella Jr

    +1(781) 635-2333 joespinella96@gmail.com

    1151 Washington St, Braintree, MA, 02184-5439, 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.
    site logo
      • About
        1. Home
        2. About Us
        3. Reviews
        Areas
        1. Braintree Overview
        2. Weymouth Overview
        3. Scituate Overview
        4. Norwell Overview
        5. Cohasset Overview
        6. Hanover Overview
        7. Marshfield Overview
        8. Hingham Overview
        9. Quincy Overview
        10. Milton Overview
        11. Hull Overview
        12. Dedham Overview
        13. Rockland Overview
        14. Pembroke Overview
        15. Kingston Overview
        16. Plympton Overview
      • Buy
        1. All Listings
        2. Sold Listings
        Market Snapshot
      • Sell
        1. Sell My Home
        2. Home Valuation
    Spinella Homes Team
    Joe Spinella Jr

    +1(781) 635-2333 joespinella96@gmail.com

    1151 Washington St, Braintree, MA, 02184-5439, 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.