Winter Hill
A residential hilltop neighborhood with long views, strong community, and prices that still offer value relative to Davis Square and the Green Line corridor.
About Winter Hill
Winter Hill sits on elevated terrain in central Somerville, and it has always been a bit removed from the action — which is exactly why some buyers love it. The streets are residential and quiet by Somerville standards. The views from the hilltop are surprisingly expansive — you can see the Boston skyline, the Bunker Hill Monument, and on clear days, the Blue Hills to the south. The housing stock is classic Somerville triple-deckers and two-families, and prices remain below Davis Square and Union Square, making Winter Hill one of the last relative values in a city that has gotten expensive fast. Broadway, the main commercial street, has a mix of local businesses, ethnic restaurants, and auto shops — it's not polished, but it's real. The Green Line Extension runs nearby, and the neighborhood's central location means you can be in Davis Square, Assembly Row, or on the Orange Line in minutes.
Property Character
Classic Somerville triple-deckers and two-families on hillside streets, some with views. Older housing stock — many homes haven't been renovated, creating value-add opportunities. More owner-occupied than the areas closer to Tufts.
Typical Home Styles
Best For
Local Highlights
- •Hilltop location with views of the Boston skyline and Bunker Hill Monument
- •Among the last relative values in increasingly expensive Somerville
- •Central location — easy access to Davis Square, Assembly Row, and multiple T lines
- •Quiet residential streets with a settled, community-oriented feel
Getting Around
Bus routes along Broadway connect to Sullivan Square (Orange Line) and Downtown. Green Line Extension stations at nearby Gilman Square and East Somerville. A 10-15 min walk to Davis Square's Red Line. Centrally located for multiple transit options.
Schools Serving Winter Hill
Somerville Public Schools. Healey School and Winter Hill Community Innovation School serve the area. Somerville High School for upper grades. The schools reflect the neighborhood's diversity.
Frequently Asked Questions About Winter Hill
What is Winter Hill in Somerville like?
A residential hilltop neighborhood with long views, strong community, and prices that still offer value relative to Davis Square and the Green Line corridor. Winter Hill sits on elevated terrain in central Somerville, and it has always been a bit removed from the action — which is exactly why some buyers love it. The streets are residential and quiet by Somerville standards. The views from the hilltop are surprisingly expansive — you can see the Boston skyline, the Bunker Hill Monument, and on clear days, the Blue Hills to the south. The housing stock is classic Somerville triple-deckers and two-families, and prices remain below Davis Square and Union Square, making Winter Hill one of the last relative values in a city that has gotten expensive fast. Broadway, the main commercial street, has a mix of local businesses, ethnic restaurants, and auto shops — it's not polished, but it's real. The Green Line Extension runs nearby, and the neighborhood's central location means you can be in Davis Square, Assembly Row, or on the Orange Line in minutes. Winter Hill is especially popular with value-oriented buyers who want a somerville address at a lower price point and multi-family investors seeking triple-deckers with renovation upside. Contact Steinmetz Real Estate for a personalized tour of Winter Hill.
What are home prices in Winter Hill, Somerville?
Homes in Winter Hill typically range from $425K (1BR condo) – $1.2M (triple-decker). The Somerville market has seen a +5.5% year-over-year price change. Sarina Steinmetz has 26+ years of experience in this neighborhood — call (617) 610-0207 for a precise valuation.
What types of homes are in Winter Hill?
Winter Hill features Triple-Decker, Two-Family, Condo Conversion, Multi-Family homes. Classic Somerville triple-deckers and two-families on hillside streets, some with views. Older housing stock — many homes haven't been renovated, creating value-add opportunities. More owner-occupied Browse active listings in Somerville on our listings page.
How is the commute from Winter Hill, Somerville?
Bus routes along Broadway connect to Sullivan Square (Orange Line) and Downtown. Green Line Extension stations at nearby Gilman Square and East Somerville. A 10-15 min walk to Davis Square's Red Line. Centrally located for multiple transit options. From Somerville, the drive to Downtown Boston (Park Street) is approximately 15-30 min and 20-30 min (Red Line from Davis) by transit.
What are the best schools near Winter Hill?
Somerville Public Schools. Healey School and Winter Hill Community Innovation School serve the area. Somerville High School for upper grades. The schools reflect the neighborhood's diversity. Top-rated schools include Somerville High School (6/10), West Somerville Neighborhood School (6/10), East Somerville Community School (5/10). The Steinmetz team can help you verify school zones for specific addresses in Winter Hill.
Explore more of Somerville
Winter Hill is just one part of what makes Somerville special.