Century 21 Cityside
  • Buyers
  • Sellers
  • Search
  • Register
  • Sign In
Filters Reset
Save Search (2)
Save your search to get Alerts
19 Properties

19 Properties Available

  • Default
  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
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 Fri 11AM-12PM

$ 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 Fri 11AM-12PM

$ 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

50 Middlesex Street #50, Winchester, MA 01890
1/21 21
Open Sat 11AM-1PM

$ 799,000

2 Beds2 Baths1,036 SqFt

50 Middlesex Street #50, Winchester, MA 01890

Condo

Listed by The North Star Group of Keller Williams Realty Evolution

84 Oak Street, Winchester, MA 01890
1/40 40
Open Fri 4PM-5PM

$ 888,000

4 Beds2 Baths2,083 SqFt

84 Oak Street, Winchester, MA 01890

Single Family Home

Listed by John E. Magazzu of Charlesgate Realty Group LLC

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

117 Highland Ave, Winchester, MA 01890
1/40 40
Open Sun 12:30PM-2PM

$ 1,675,000

5 Beds3.5 Baths3,722 SqFt

117 Highland Ave, Winchester, MA 01890

Single Family Home

Listed by Dara Singleton of Better Homes and Gardens Real Estate - The Shanahan Group

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

8 Priscilla Ln, Winchester, MA 01890
3D
Open Sat 12PM-1PM

$ 3,149,000

5 Beds5.5 Baths6,500 SqFt

8 Priscilla Ln, Winchester, MA 01890

Single Family Home

Listed by The Pezzano Group of Rise Signature Homes

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

  • 1

explore listings

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
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.
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.