Winter Hill Homes for Sale

Welcome to Winter Hill, a vibrant and charming neighborhood nestled in Somerville, Massachusetts, within the heart of Middlesex County. Known for its rich history and eclectic character, Winter Hill is a delightful blend of urban convenience and suburban charm. This area is renowned for its friendly community atmosphere, making it a perfect place for families, young professionals, and anyone seeking a welcoming environment.

Winter Hill boasts an array of homes for sale, ranging from classic Victorian-style houses to modern condominiums, catering to diverse tastes and lifestyles. Whether you’re a first-time homebuyer or looking to upgrade, you’ll find a variety of options that fit your needs. Many properties feature spacious layouts, updated amenities, and outdoor spaces ideal for entertaining or relaxing. The neighborhood's tree-lined streets and well-maintained parks provide a picturesque backdrop for your new home.

In addition to its residential charm, Winter Hill is conveniently located near an array of local shops, restaurants, and cafes that give the area its unique flair. Enjoy a leisurely stroll to the nearby Assembly Row or explore the vibrant dining scene that Somerville is famous for. With easy access to public transportation, commuting to Boston or other parts of the Greater Boston area is a breeze.

Discover the warmth and community spirit of Winter Hill, where your dream home awaits among the charming streets and welcoming neighbors. Explore the homes for sale today and take the first step towards making this wonderful neighborhood your own!

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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