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 December 9, 2022
16
Listed
52
Avg. DOM
$657.62
Avg. $ / Sq.Ft.
$798,900
Med. List Price
16 Properties
Page 1 of 2
4
Beds
3
Baths
1,741
Sq.Ft.
1900
Year Built
36
Days on Site
73055467
MLS
ONE YEAR BUILDER'S WARRANTY. You won't find a better deal. Newly renovated luxury Gilman Sq 4-bed condo. Situated on a quiet tree-lined street, just minutes to the new Gilman green line station This...
Open 12/10
14 Pembroke Street #2 Somerville, MA 02145
$1,099,900
Condo: 14 Pembroke Condominiums
3
Beds
2
Baths
1,779
Sq.Ft.
1900
Year Built
92
Days on Site
73034609
MLS
Extensively renovated multi-family condo conversion in the Winter Hill neighborhood. Both units 1 & 2 available. All electric & plumbing, and re-insulated from top to bottom. Original home built @...
3
Beds
2F11/2
Baths
2,313
Sq.Ft.
2014
Year Built
171
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 12/10
14 Pembroke Street #1 Somerville, MA 02145
$999,900
Condo: 14 Pembroke Street Condominiums
3
Beds
3
Baths
1,816
Sq.Ft.
1900
Year Built
70
Days on Site
73043318
MLS
Extensive renovation down to the studs w/ support beams for unique open layout, a redesigned interior layout for today's homeowner. Common outdoor area w/ patio. Conveniently located in Winter Hill...
3
Beds
2
Baths
1,424
Sq.Ft.
2019
Year Built
23
Days on Site
73059284
MLS
Located in RED HOT Winter Hill, Somerville. This top-floor unit has 3 BED, 2 FULL BATH and a living space of 1,424 Sq. Ft. ft. High ceiling and open floor plan creates an inviting atmosphere and...
Open 12/11
53 Adams St #1 Somerville, MA 02145
2
Beds
1F11/2
Baths
1,188
Sq.Ft.
1920
Year Built
95
Days on Site
73032703
MLS
NEW VICTORIAN RESTORATION THAT'S 'OFF THE HOOK' and over 200 SQ FT OF OUTSIDE STUDIO SPACEIf you've been wating for something truly special? Incredible craftsmansip, with every attention to detail......
Open 12/10
242 Broadway #1 Somerville, MA 02145
3
Beds
3
Baths
2,465
Sq.Ft.
9
Days on Site
73062326
MLS
Stunning condominium with GARAGE parking in the Winter Hill Neighborhood of Somerville! This gut-renovated 3 bed + office, 3 bath condo is flooded with natural sunlight. The open and spacious living...
2
Beds
2
Baths
1,000
Sq.Ft.
1900
Year Built
86
Days on Site
73037038
MLS
Beautiful design and contemporary luxury are seamlessly incorporated in this gut renovated Somerville unit, with open living and dining spaces, white washed colored oak floors, and plenty of recessed...
$798,800
Condo: 108 Gilman Condominium
2
Beds
2
Baths
1,000
Sq.Ft.
1900
Year Built
45
Days on Site
73052234
MLS
Beautiful design and contemporary luxury are seamlessly incorporated in this gut renovated Somerville unit, with open living and dining spaces, white washed colored oak floors, and plenty of recessed...
4
Beds
1F11/2
Baths
1,938
Sq.Ft.
1920
Year Built
10
Days on Site
73061609
MLS
Contractors and developers - GUT REHAB - PRICED ACCORDINGLY - Colonial Style property in Winter Hill neighborhood w/3 floors of living space, 9 rooms, 4+ bedrooms and 1.5 bathrooms w/full basement....
3
Beds
1
Baths
1,170
Sq.Ft.
1978
Year Built
45
Days on Site
73052169
MLS
This Highland Avenue property is located in the vibrant Spring Hill neighborhood. Bright airy 3 bedroom w/ 2 parking spaces. Nearby are local foodie favorites Sarma, Highland Kitchen, 7Ate9 Bakery...
2
Beds
1F11/2
Baths
850
Sq.Ft.
2022
Year Built
86
Days on Site
73037037
MLS
Beautiful design and contemporary luxury are seamlessly incorporated in this new construction Somerville unit, with open living and dining spaces, white washed colored oak floors, and plenty of...

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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