Winter Hill Homes under $750,000

Welcome to Winter Hill, a vibrant neighborhood nestled in the heart of Somerville, Massachusetts, within Middlesex County. This charming area is known for its rich history, diverse community, and an array of amenities that make it an ideal place to call home. With its close proximity to Boston, Winter Hill offers residents the perfect blend of suburban tranquility and urban excitement.

One of the standout features of Winter Hill is its eclectic mix of homes, many of which are available for under $750,000. Whether you’re a first-time homebuyer, looking to downsize, or seeking a cozy place to settle down, Winter Hill has something to suit every lifestyle. From classic Victorian-style houses to modern condominiums, the real estate options here are as diverse as the community itself.

Residents enjoy easy access to a variety of parks, local shops, and dining options that showcase the area’s culinary diversity. The nearby Assembly Row, with its trendy restaurants and shopping opportunities, is just a stone's throw away, making it easy to enjoy a night out or a leisurely weekend stroll. Additionally, Winter Hill boasts excellent public transportation options, ensuring that commuting to Boston is a breeze.

Living in Winter Hill means embracing a community that values connection and inclusivity. With its friendly neighbors, community events, and an active local scene, you’ll find that this neighborhood truly feels like home. Explore the charming homes available under $750,000 and discover the vibrant lifestyle that awaits you in Winter Hill!

Newest Winter Hill Homes under $750,000

$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.

$429,900

1 Beds ⋅ 1 Baths ⋅ 73581034 MLS ⋅ ['Summit Condominium'] BLDG.

Commuter’s dream in Somerville! Enjoy Green Line T access to Boston plus garage parking in a well-managed condo association. This move-in ready freshly painted third floor unit boasts an oversized bedroom, private outdoor balcony, in-unit laundry, storage space, new water heater and HVAC installed in 2025. Great for owner occupants and investors alike, this is an ideal choice for those seeking convenience in a vibrant and popular location. Excellent rental history and no known upcoming special assessments. 2026 Meeting Minutes and Budget attached in MLS. Showings begin at first open house, Thursday 9/24 5-6:30PM.

390 Broadway Unit 35, Somerville

Listing courtesy of Listing Agent: Evelyn Ullman from Listing Office: Coldwell Banker Realty - Lynnfield.

$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.

$439,000

1 Beds ⋅ 1 Baths ⋅ 73574205 MLS ⋅ ['390 Broadway'] BLDG.

This sunny fifth-floor corner condo sits in a fantastic Winter Hill spot, putting you just minutes from Assembly Row, Davis Square, and easy transit into Boston or Cambridge. It’s been completely updated from top to bottom, so all you have to do is unpack. You’ll love the brand-new kitchen with fresh cabinets, modern counters, and new appliances, plus new flooring, fresh paint, and updated mechanicals—a new HVAC setup and hot water heater that take all the stress out of maintenance. The layout feels open and airy, with windows on two sides that bring in tons of natural light and great views of the city skyline right from your bedroom. Step outside onto your private back balcony to grab a morning coffee or unwind after work. You also get the convenience of in-unit laundry, a dedicated garage parking spot, extra storage space, and an elevator in the building. It’s a great fit if you're looking to stop renting and buy your first place in a super convenient, walkable Somerville neighborhood.

390 Broadway Unit 54, Somerville

Listing courtesy of Listing Agent: Gary S. Vrotsos from Listing Office: Coldwell Banker Realty - Cambridge.

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