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 23, 2023
4
Listed
40
Avg. DOM
$606.06
Avg. $ / Sq.Ft.
$704,500
Med. List Price
4 Properties
2
Beds
2F11/2
Baths
1,860
Sq.Ft.
1900
Year Built
23
Days on Site
73083286
MLS
Don't miss out on this beautiful unit offering an open living space perfect for hosting. Chef's Kitchen with Viking appliances, oversized pantry, waterfall quartz countertop, and your dream island....
Open 3/25
9 Virginia St Somerville,  MA 02145
$759,000
Neighborhood: East Somerville
4
Beds
1
Baths
1,650
Sq.Ft.
1900
Year Built
2
Days on Site
73090264
MLS
Welcome home to 9 Virginia St, an elusive Somerville single family with a driveway and a YARD! This lovingly maintained single family home in the heart of Somerville offers plenty of space for...
$650,000
Condo: Sewall Court
2
Beds
1
Baths
1,176
Sq.Ft.
1920
Year Built
16
Days on Site
73085483
MLS
This one is a must see! Top floor, bright, sunny, and exclusive deck that feels like another room! This condo features a large kitchen with ample cabinet storage, granite countertops and gas cooking....
2
Beds
1
Baths
731
Sq.Ft.
1900
Year Built
121
Days on Site
73060419
MLS
Location, Location, Location! Only a few hundred feet away from the newly opened Gilman Sqr Green line T stop! Freshly painted and ready to move in. So many shops and eateries nearby. This unit has...

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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