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

Winter Hill Homes & Condos For Sale March 28, 2024
17
Listed
55
Avg. DOM
$607.88
Avg. $ / Sq.Ft.
$1,150,000
Med. List Price
17 Properties
Page 1 of 2
Open 3/30
42 Sargent Avenue Somerville,  MA 02145
4
Beds
2F11/2
Baths
2,826
Sq.Ft.
1890
Year Built
73
Days on Site
73193820
MLS
Open 3/30
421 Medford #421 Somerville,  MA 02145
4
Beds
3F11/2
Baths
3,056
Sq.Ft.
2023
Year Built
4
Days on Site
73216086
MLS
Open 3/30
421 Medford #421 Somerville,  MA 02145
4
Beds
3F11/2
Baths
3,056
Sq.Ft.
2023
Year Built
4
Days on Site
73216113
MLS
Open 3/30
25 Tennyson #25 Somerville,  MA 02145
3
Beds
2F11/2
Baths
2,215
Sq.Ft.
1900
Year Built
16
Days on Site
73212164
MLS
Open 3/30
25 Tennyson Somerville,  MA 02145
3
Beds
2F11/2
Baths
2,215
Sq.Ft.
1900
Year Built
16
Days on Site
73212181
MLS
5
Beds
2F11/2
Baths
3,169
Sq.Ft.
1900
Year Built
18
Days on Site
73210836
MLS
4
Beds
3F11/2
Baths
2,316
Sq.Ft.
1887
Year Built
63
Days on Site
73196882
MLS
Open 3/30
15 Jackson Rd Somerville,  MA 02145
$1,299,000
Neighborhood: Gilman Square
5
Beds
3F11/2
Baths
2,355
Sq.Ft.
1915
Year Built
10
Days on Site
73213776
MLS
3
Beds
2
Baths
1,771
Sq.Ft.
2023
Year Built
122
Days on Site
73183127
MLS
3
Beds
2
Baths
1,826
Sq.Ft.
2023
Year Built
122
Days on Site
73183129
MLS
$950,000
Condo: 388 Medford Street Condominium
3
Beds
2
Baths
1,391
Sq.Ft.
1920
Year Built
268
Days on Site
73132510
MLS
3
Beds
3
Baths
1,830
Sq.Ft.
1910
Year Built
9
Days on Site
73214433
MLS

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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