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 May 28, 2024
13
Listed
62
Avg. DOM
$717.50
Avg. $ / Sq.Ft.
$950,000
Med. List Price
13 Properties
Page 1 of 2
4
Beds
2F11/2
Baths
2,826
Sq.Ft.
1890
Year Built
43
Days on Site
73224486
MLS
$1,279,900
Condo: Fenwick
3
Beds
2F11/2
Baths
1,340
Sq.Ft.
1900
Year Built
26
Days on Site
73232956
MLS
$1,279,900
Condo: Fenwick
3
Beds
2F11/2
Baths
1,340
Sq.Ft.
1900
Year Built
26
Days on Site
73232964
MLS
3
Beds
3
Baths
1,759
Sq.Ft.
1920
Year Built
28
Days on Site
73231883
MLS
3
Beds
2
Baths
1,826
Sq.Ft.
2023
Year Built
183
Days on Site
73183129
MLS
$998,000
Condo: 241 School Street Condominium
3
Beds
3
Baths
1,939
Sq.Ft.
1900
Year Built
27
Days on Site
73232304
MLS
$950,000
Condo: 388 Medford Street Condominium
3
Beds
2
Baths
1,391
Sq.Ft.
1920
Year Built
329
Days on Site
73132510
MLS
Open 6/1
115 Thurston St #D Somerville,  MA 02145
3
Beds
2
Baths
1,047
Sq.Ft.
2023
Year Built
12
Days on Site
73240026
MLS
3
Beds
3
Baths
1,375
Sq.Ft.
1890
Year Built
35
Days on Site
73228514
MLS
3
Beds
2
Baths
1,960
Sq.Ft.
1885
Year Built
16
Days on Site
73237053
MLS
Open 6/1
115 Thurston St #I Somerville,  MA 02145
1
Beds
1
Baths
772
Sq.Ft.
2023
Year Built
12
Days on Site
73240027
MLS
$659,000
Condo: Sewall Court
2
Beds
1
Baths
1,029
Sq.Ft.
1920
Year Built
35
Days on Site
73228161
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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