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 August 18, 2022
18
Listed
35
Avg. DOM
$584.23
Avg. $ / Sq.Ft.
$924,900
Med. List Price
18 Properties
Page 1 of 2
6
Beds
2F11/2
Baths
2,180
Sq.Ft.
1890
Year Built
26
Days on Site
73016642
MLS
For the first time in over 30 years, this stunning multi-level single family home consisting of 6 bedrooms and 2.5 baths, is on the market. This well-maintained property features 12 rooms, an...
$1,214,000
Condo: 33 Glenwood Road Condominium Trust
2
Beds
2F11/2
Baths
1,860
Sq.Ft.
1900
Year Built
36
Days on Site
73012294
MLS
10k BACK TO BUYER FOR CLOSING COSTS OR BUY A POINT ON YOU MORTAGE AND LOWER YOUR PAYMENT! Luxury living, prime location! Gorgeous 2 bedroom, 2.5 bath, garage and patio. Huge open concept with...
4
Beds
2F11/2
Baths
1,660
Sq.Ft.
1900
Year Built
44
Days on Site
73008317
MLS
A charming single family Colonial home on a quite tree lined street is awaiting its new owner. This commuter friendly home offers a 40+ foot driveway and is steps to anticipated Gilman Square Station....
Open 8/21
32 Jackson Road #A Somerville, MA 02145
3
Beds
2F11/2
Baths
2,308
Sq.Ft.
1890
Year Built
38
Days on Site
73011000
MLS
Presenting 32 Jackson Road Unit A - a 3 Bed, 2.5 Bath home in the heart of Somerville's "Winter Hill". Having been renovated in 2019, this unit is as good as new featuring hardwood flooring, recessed...
3
Beds
2F11/2
Baths
2,313
Sq.Ft.
2014
Year Built
58
Days on Site
73001625
MLS
A total of 3beds, 2.5baths and 2 car garage, built new in 2014! Here's a tremendous opportunity to own a sunny & bright townhouse corner unit in the central Somerville. This wide open spacious...
Open 8/21
12 Sunnyside Avenue Somerville, MA 02145
3
Beds
2F11/2
Baths
2,561
Sq.Ft.
1924
Year Built
15
Days on Site
73021652
MLS
Home sweet home! An inviting single family with a big back yard located on a pleasant side street in Winter Hill, not far from Union Square. Enjoy central AC + high ceilings on both the first and...
6
Beds
3
Baths
2,245
Sq.Ft.
1890
Year Built
30
Days on Site
73014883
MLS
Unbeatable location near public transit, parks, shopping, and dining! With Four levels of living space, this move-in ready home features an open concept kitchen/living area plus separate dining with...
Open 8/19
242R Broadway #2 Somerville, MA 02145
3
Beds
2F11/2
Baths
1,587
Sq.Ft.
36
Days on Site
73012437
MLS
Stunning top-floor condominium with GARAGE parking in the Winter Hill Neighborhood of Somerville! Tucked away from the street, this gut-renovated 3 bed 2.5 bath condo is flooded with natural sunlight....
Open 8/19
242 Broadway #3 Somerville, MA 02145
3
Beds
2
Baths
1,390
Sq.Ft.
92
Days on Site
72985040
MLS
Penthouse condominium with GARAGE parking in the Winter Hill Neighborhood of Somerville! This gut-renovated 3 bed 2 bath condo is flooded with natural sunlight. The open and spacious living room and...
Open 8/19
242R Broadway #1 Somerville, MA 02145
2
Beds
2F11/2
Baths
1,385
Sq.Ft.
36
Days on Site
73012433
MLS
Stunning condominium with off-street parking in the Winter Hill Neighborhood of Somerville! Tucked away from the street, this gut-renovated 2 beds 2.5 bath condo is finished with today's modern...
5
Beds
3
Baths
2,500
Sq.Ft.
1920
Year Built
77
Days on Site
72992195
MLS
Fantastic Find! Single Family 5 Bedroom/ 3 Full bathroom property in prime Somerville location! The property consists of 3 levels of living space with hardwoods throughout the main living space and...
Open 8/20
18 Main St #3 Somerville, MA 02145
2
Beds
2F11/2
Baths
1,424
Sq.Ft.
2009
Year Built
3
Days on Site
73025736
MLS
Rare opportunity for this modern and updated townhouse style condo in desirable Somerville neighborhood! Exceptional ceiling heights with an open concept first floor living space. Living...

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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