Winter Hill Real Estate

Winter Hill is a densely settled neighborhood in Somerville known for its local character and tight-knit community. The area draws its name from the historic 120-foot hill dating from the 18th century that overlooks the neighborhood. With its large Irish and Italian populations, Winter Hill is a mecca for eateries and pizza establishments. A number of new restaurants, cafes, and shops have all entered the neighborhood in the last couple of years as the area has experienced gentrification and a resulting rise in property values. Many houses in the community feature distinctive flowering gardens designed for smaller spaces while newly renovated condos and single-families sit next to more traditional triple-deckers.  Read more about Winter Hill real estate.

Winter Hill Homes & Condos For Sale

81 Gilman Street, Somerville
  • Income/Multi Family
  • 6 Beds
  • 2 Baths
  • 2,582 SqFt

81 Gilman Street, Somerville

$1,390,000
459 Medford Street, Somerville
  • Income/Multi Family
  • 5 Beds
  • 4 Baths
  • 3,672 SqFt

459 Medford Street, Somerville

$1,350,000
7 Kenneson Road, Somerville
  • Income/Multi Family
  • 5 Beds
  • 4 Baths
  • 2,664 SqFt

7 Kenneson Road, Somerville

$1,100,000
New
32 Jackson Road #a, Somerville
  • Single Family
  • 3 Beds
  • 2.5 Baths
  • 2,300 SqFt

32 Jackson Road #a, Somerville

$1,099,000
41 Sargent Avenue #2, Somerville
  • Single Family
  • 3 Beds
  • 2.5 Baths
  • 1,724 SqFt

41 Sargent Avenue #2, Somerville

$889,900
35 Moreland Street #3, Somerville
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,500 SqFt

35 Moreland Street #3, Somerville

$879,000
35 Moreland Street #2, Somerville
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,500 SqFt

35 Moreland Street #2, Somerville

$859,000 ↓ $20,000
275 Medford Street #2, Somerville
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,600 SqFt

275 Medford Street #2, Somerville

$775,000
49 Thurston Street #1, Somerville
  • Single Family
  • 2 Beds
  • 1.5 Baths
  • 1,659 SqFt

49 Thurston Street #1, Somerville

$699,000
New
21 Edmands Street #3, Somerville
  • Single Family
  • 3 Beds
  • 1 Baths
  • 1,234 SqFt

21 Edmands Street #3, Somerville

$585,000

More About Winter Hill Real Estate

 Winter Hill Location

Winter Hill is located north of Medford Street; west of McGrath Highway; and east of Magoun Square. The neighborhood also borders Interstate 93 for easy commuting purposes. The closest MBTA Station is Assembly on the Red Line. Once the Green Line extension is completed, residents will be able to more easily walk to an MBTA Station that will help them get to Cambridge, Boston, Brookline, and Newton.

Winter Hill History

Winter Hill played a crucial role in the Revolutionary War. Paul Revere galloped across many of Winter Hill’s streets during his Midnight Ride while the slope itself served as a stronghold in the Colonists’ successful retreat after the Battle of Bunker Hill. In more modern times Winter Hill had the dubious reputation as the home base of Irish gangsters Whitey Bulger, Howie Winter, and the notorious Winter Hill Gang.

In the late 1980s former president Barack Obama made Winter Hill his home, occupying 365 Broadway while studying at Harvard Law School.

 

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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