Winter Hill Homes for Sale

Welcome to Winter Hill, a vibrant and inviting neighborhood nestled in the heart of Somerville, Massachusetts. Known for its rich history and eclectic charm, Winter Hill combines the best of urban living with a close-knit community feel. Residents enjoy a diverse array of cultural experiences, delicious dining options, and easy access to public transportation, making it an ideal location for both families and young professionals.

The neighborhood is characterized by its picturesque streets lined with beautifully maintained Victorian homes, modern condos, and cozy apartments. With homes for sale in various styles and price ranges, Winter Hill offers something for everyone. Whether you're seeking a spacious family home with a backyard or a chic urban loft, you'll find that Winter Hill caters to a variety of lifestyles and budgets.

One of the highlights of living in Winter Hill is the abundance of green spaces and parks, perfect for leisurely strolls, picnics, or simply unwinding after a long day. The community is also known for its lively atmosphere, with local events and farmers' markets bringing residents together throughout the year.

With its prime location just minutes from downtown Boston, Winter Hill provides easy access to the city’s bustling job market, cultural landmarks, and entertainment options. This neighborhood is not just a place to live; it’s a place to thrive.

Explore the homes for sale in Winter Hill today and discover the perfect blend of convenience, charm, and community spirit that makes this neighborhood truly special. Your dream home awaits!

Newest Winter Hill Homes for Sale

$1,275,000

5 Beds ⋅ 3 Baths ⋅ 73584422 MLS

Bold, bright and full of character, this iconic Winter Hill Victorian is move-in ready, while still allowing opportunity to tailor to your lifestyle. High ceilings, original wood floors, stained glass and beautiful period details pair with Pella windows, a modern kitchen and fresh updates throughout. The main level flows seamlessly from a gracious entry to living and dining rooms with bay windows, open kitchen and adjacent family room, perfect for movie nights, play space and everyday life. Upstairs find spacious bedrooms, including a primary with adjoining laundry room offering interesting potential for future primary bath. Ideal home office in bonus room that opens directly to lovely outdoor balcony. The third floor is perfect for guests, WFH, or growing needs, with two more bedrooms and a generous full bath. The unfinished walkout basement offers nice potential for additional finished space, if ever needed. Fenced backyard has plenty of room for kids and dogs and opportunity to reimagine the space as a fantastic urban retreat for gardening, play and outdoor entertaining. Driveway provides coveted off-street parking, and you are just MINUTES to Gilman Sq. T, Magoun Sq T, Sarma, Highland Kitchen, Winter Hill Brewing, and bike path.

77 Sycamore Street, Somerville

Listing courtesy of Listing Agent: Jessica Cohen Barmach from Listing Office: Gibson Sotheby's International Realty.

$739,000

3 Beds ⋅ 1 Baths ⋅ 73583920 MLS

Welcome to 91 Heath Street, a beautifully updated single-family home in Somerville’s desirable Winter Hill neighborhood. Offering three bedrooms, one full bath, approx 1,050 square feet of living space, and two off-street parking spaces, this inviting home combines thoughtful updates with the space and convenience of a true single-family residence. A bright three-season porch welcomes you into the home, while a second three-season porch off the kitchen by a charming Dutch door extends the living space and leads to a private deck and backyard—an ideal setting for morning coffee, summer dinners, or entertaining. At the heart of the home is a stunning eat-in chef’s kitchen, beautifully renovated with Bosch appliances, a Forno range, apron-front sink, Moen faucet, statement hood, and new hardwood flooring. The front-facing living room offers a comfortable space to relax, while upstairs, custom built-ins add character and organization. The unfinished walkout basement provides excellent storage. The location is equally compelling, with the Green Line T approximately a 10-minute walk away and convenient bus access to both the Orange and Red Lines. Fantastic walkability for everyday conveniences. Assembly Row and Bow Market are just minutes away by car, with downtown Boston approximately 15 minutes. 91 Heath Street offers an exceptional opportunity to enjoy the best of Somerville living in a welcoming single-family home. Skip the HOAs and settle on in to this private urban oasis!

91 Heath St, Somerville

Listing courtesy of Listing Agent: The Bohlin Group from Listing Office: Compass.

$700,000

3 Beds ⋅ 1 Baths ⋅ 73580658 MLS

The opportunity you have been waiting for! A pretty Colonial, nestled-in on a quiet dead-end street with a nice fenced-in back yard. This home offers peaceful privacy while providing convenient access to schools, parks, public transportation, and I-93, as well as Assembly Row & Wellington Circle shopping areas. Lovingly held by the same family for over 70 years, the home offers good size rooms, a large deck, some hardwoods and a maintenance-free exterior. An opportunity to own a single-family home in the highly desired city of Somerville.This is an estate sale and the property will be sold in as-is condition. Buyers are encouraged to make every effort to attend the open houses, as showing times are limited.

104 Fremont St, Somerville

Listing courtesy of Listing Agent: Christina Butler from Listing Office: Parkway Real Estate, LLC.

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