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 January 20, 2022
8
Listed
22
Avg. DOM
$621.53
Avg. $ / Sq.Ft.
$924,500
Med. List Price
8 Properties
3
Beds
2F11/2
Baths
2,315
Sq.Ft.
2021
Year Built
87
Days on Site
72912762
MLS
Stunning architecturally designed contemporary Townhome with all the bells and whistles! This new construction begins with an open plan and hardwood floors throughout. The chef s kitchen includes a...
4
Beds
4
Baths
2,077
Sq.Ft.
1900
Year Built
28
Days on Site
72929487
MLS
Currently zoned as a two family but was originally built as single family. Maybe convert back ? Rare opportunity to purchase this well maintained 2 family that has potential to convert i. Offers off...
Open 1/20
20 Richdale Ave #1 Somerville, MA 02145
$1,100,000
Condo: 20 Richdale Avenue Condominium
4
Beds
3
Baths
1,900
Sq.Ft.
1900
Year Built
2
Days on Site
72935008
MLS
Another gorgeous project delivered by well known builder in the area. This 2-level condo offers so much space: main level has open concept floor plan with living room, dining room and custom designed...
Open 1/20
20 Richdale Ave #2 Somerville, MA 02145
$1,100,000
Condo: 20 Richdale Avenue Condominium
4
Beds
3F11/2
Baths
1,600
Sq.Ft.
1900
Year Built
2
Days on Site
72935090
MLS
One more captivating project was delivered by a well-known builder in the area. This 2-level condo offers so much space: the main level has an open concept floor plan with living room, dining room,...
2
Beds
1F11/2
Baths
1,199
Sq.Ft.
1920
Year Built
17
Days on Site
72930851
MLS
This charming duplex home was completely renovated in 2018 and boasts quality craftsmanship, high-end finishes, and thoughtful design. The primary level features an open floor plan, with living room,...
Open 1/22
10 Wigglesworth Street #1 Somerville, MA 02145
2
Beds
2
Baths
1,145
Sq.Ft.
1900
Year Built
15
Days on Site
72912284
MLS
Stunning, gut rehab condo in stellar location East Somerville offers the perfect blend of location and amenities. This stylish 2 bed/2 bath condo has desirable open concept living space with tall...
Open 1/22
10 Wigglesworth Street #2 Somerville, MA 02145
2
Beds
2
Baths
1,086
Sq.Ft.
1900
Year Built
15
Days on Site
72912739
MLS
Stunning second floor, gut rehab condo in stellar location East Somerville offers the perfect blend of location and amenities. This stylish 2 bed/2 bath condo has desirable open concept living space...
$725,000
Condo: Highland Condominiums
3
Beds
1
Baths
1,170
Sq.Ft.
1978
Year Built
15
Days on Site
72931943
MLS
This Highland Avenue unit is settled amid the charming and magnetic neighborhoods of Winter Hill, Prospect Hill, and Spring Hill. With local dining favorites such as Sarma and Highland Kitchen...

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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