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 September 29, 2023
12
Listed
39
Avg. DOM
$687.89
Avg. $ / Sq.Ft.
$974,500
Med. List Price
12 Properties
Open 10/1
123 Central Street Somerville,  MA 02145
6
Beds
3
Baths
3,100
Sq.Ft.
1969
Year Built
15
Days on Site
73159908
MLS
This versatile, generous size home offers, 5 to 6 bedrooms and 3 full baths. You will be welcomed by a first-floor open foyer. Living room has fireplace and opens to formal dining room. The large...
Open 9/30
8 Lee St #2 Somerville,  MA 02145
4
Beds
3
Baths
2,258
Sq.Ft.
1905
Year Built
47
Days on Site
73145878
MLS
Luxury living 5 bed, 3 bath with a walk score of 92 plus garage awaits. This 2023 gut renovation features all new wood floors, central air & central heat system, appliances, windows, roof, vinyl...
Open 9/30
229 Pearl Street Somerville,  MA 02145
4
Beds
2F11/2
Baths
1,878
Sq.Ft.
1900
Year Built
51
Days on Site
73147227
MLS
Welcome to this exquisite single family home nestled at 229 Pearl Street. This gut-renovated property embodies luxury and sophistication, boasting a seamless blend of modern design and classic charm....
3
Beds
1
Baths
922
Sq.Ft.
1952
Year Built
99
Days on Site
73129129
MLS
DEVELOPMENT POTENTIAL OF UP TO THREE UNITS...ONLY A BLOCK AWAY FROM THE GILMAN SQ GREEN LINE STOP... Seller will wait for buyer to obtain necessary building approvals prior to closing. Up to 3 units...
3
Beds
2F11/2
Baths
1,959
Sq.Ft.
1887
Year Built
53
Days on Site
73145830
MLS
STUNNING RENOVATED HOME. A rare gem with lovingly restored period details throughout, this ~1,950+ sqft 3 bedroom/2.5 bath + home office TRIPLEX welcomes you! Porch entry leads to the front door to...
Open 9/30
33 Glenwood Rd #1 Somerville,  MA 02145
2
Beds
2F11/2
Baths
1,859
Sq.Ft.
1900
Year Built
3
Days on Site
73164295
MLS
33 Glenwood Street unit 1 is a perfect home for commuters not wanting to be far from downtown. Only a few blocks from Magoun Square, which loaded with restaurants and shops, plus a 3-minute walk to...
Open 9/30
388 Medford St #1 Somerville,  MA 02145
$950,000
Condo: 388 Medford Street Condominium
3
Beds
2
Baths
1,391
Sq.Ft.
1920
Year Built
87
Days on Site
73132510
MLS
This oversized 3 bed, sun filled condo has it all. Perfectly nestled into a residential nook of Somerville, this unit is just blocks from several parks & schools, restaurants & cafes, the community...
Open 9/30
100 Bartlett St #2 Somerville,  MA 02145
2
Beds
2
Baths
915
Sq.Ft.
1910
Year Built
11
Days on Site
73161106
MLS
Welcome to your dream home in the heart of Somerville! Gut renovation in 2018/2019, you're located just moments away from vibrant dining, shopping, and entertainment, this second-floor unit is a...
3
Beds
2
Baths
1,422
Sq.Ft.
1910
Year Built
22
Days on Site
73157513
MLS
OPEN HOUSE Saturday 9/23 between 11am-12:30pm-Tastefully renovated open floor concept with 3br/2 baths Condo on 1st fl in Winter Hill area of Somerville - Features include new kitchen with new...
Open 9/29
396 Broadway #1B Somerville,  MA 02145
$760,000
Condo: 396 & 398 Broadway Condominium
3
Beds
1F11/2
Baths
1,350
Sq.Ft.
1880
Year Built
11
Days on Site
73160873
MLS
This splendid three-bedroom condo, renovated in 2000, seamlessly blends modern comfort with timeless elegance. It boasts central air conditioning, updated kitchen and baths, and in-unit laundry,...
2
Beds
1
Baths
1,076
Sq.Ft.
1900
Year Built
16
Days on Site
73159619
MLS
Welcome home! Newly renovated top floor two-bedroom residence in the vibrant Winter Hill neighborhood, offering easy access to Union Square, Tufts University and the new Green Line stations at Gilman...
2
Beds
1
Baths
1,021
Sq.Ft.
1900
Year Built
64
Days on Site
73141797
MLS
Welcome home! Newly renovated light-filled two-bedroom residence in the vibrant Winter Hill neighborhood, offering easy access to Union Square, Tufts University and the new Green Line stations at...

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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