Winter Hill Real Estate

Welcome to Winter Hill, a vibrant neighborhood nestled in the heart of Somerville, Massachusetts. Known for its rich history and eclectic charm, Winter Hill offers a unique blend of urban convenience and suburban tranquility, making it a sought-after destination for families, young professionals, and everyone in between.

One of the most appealing aspects of Winter Hill is its diverse community. The area boasts a mix of long-standing residents and newcomers, creating a welcoming atmosphere that celebrates cultural diversity. The neighborhood is characterized by its tree-lined streets, classic New England architecture, and a variety of local businesses that reflect the area’s eclectic spirit.

Outdoor enthusiasts will appreciate Winter Hill’s proximity to several parks and green spaces, including the expansive Mystic River Reservation. This scenic area offers walking and biking trails, perfect for those looking to enjoy nature without leaving the city. Additionally, the neighborhood is conveniently located near public transportation, making commuting to Boston and beyond a breeze.

Food lovers will find a culinary paradise in Winter Hill, with an array of restaurants and cafes serving everything from traditional New England fare to international cuisines. The vibrant local dining scene is complemented by charming coffee shops and artisan bakeries, perfect for a leisurely weekend brunch or a quick caffeine fix.

With its unique character, strong sense of community, and convenient location, Winter Hill is more than just a neighborhood; it’s a place where you can truly feel at home. Whether you’re looking to buy, sell, or simply explore, Winter Hill invites you to discover all that this delightful area has to offer.

Newest Listings in Winter Hill

$1,749,000

7 Beds ⋅ 3 Baths ⋅ 73596280 MLS

Imagine owning a massive three-family residence in Winter Hill, a rare Somerville trifecta: approximately 4,261 square feet of living space, a two-car garage, and a long driveway for ample off-street parking. This property is an absolute powerhouse, perfectly positioned just minutes from the energy of Davis Square, Tufts University, and the Gilman Square Green Line station — with Magoun Square’s shops, cafes, and restaurants only a seven-minute walk from the front door. With effortless access to Route 93, the location is unbeatable for commuters and urban enthusiasts alike. Whether you seek addition to your investment portfolio or an owner-occupant looking for a property that generates significant rental income, this property delivers incredible scale and versatility in one of the region’s most sought-after neighborhoods. Schedule a showing or come to the open house this Saturday and Sunday, 11–1.

246 School St, Somerville

Listing courtesy of Listing Agent: Jack Lister from Listing Office: Berkshire Hathaway HomeServices Verani Realty.

$439,900

1 Beds ⋅ 1 Baths ⋅ 73596249 MLS

This beautiful and bright move-in-ready 1 BR updated Condo, features an efficient well-planned living area and provides a nice atmosphere for those looking for convenience. The property's location ensures effortless accessibility, just minutes to RT 93, multiple Bus Routes, Green, Red and Orange Lines, Assembly Row, Restaurants, Shops, Foss Park, Tufts University and everything else that Winter Hill has to offer. Freshly painted, new floors in Living Room, eat-in-Kitchen and Hallway, spacious Bedroom with a walk-in closet, is ideal for investors or owner-occupant. Includes on designated Parking Space. Pet Friendly. Laundry in Building and a low Association fee. This property is set upon a generous 17,660 square-foot lot, offering a sense of opened within the established community. We invite you to come to the Open Houses on Saturday and Sunday, 10/31-11/01, from 1-3 PM to experience this Somerville condominium firsthand. Offers due on November 4, at 5 PM.

326 Broadway Street Unit 11, Somerville

Listing courtesy of Listing Agent: Richard Gawel from Listing Office: First Estate Realty.

$890,000

3 Beds ⋅ 2 Baths ⋅ 73596245 MLS ⋅ ['371 Broadway Somerville Condominium'] BLDG.

This first-floor Philly-style condo seamlessly blends classic architectural charm with thoughtful modern updates. A welcoming foyer highlighted by stained-glass windows leads to the sun-filled living and dining areas, where high ceilings, bay windows, and an original built-in China cabinet showcase the home's timeless character. Wood and tile flooring run throughout, and abundant natural light fills the space. The first floor includes a spacious bedroom and full bath with classic tile finishes, while two additional bedrooms upstairs provide flexible space for family, guests, or a home office. The updated 2019 kitchen features granite countertops, stainless steel appliances, and modern wood cabinetry. A half bath with laundry, convenient storage closets, and private basement storage add everyday functionality. Enjoy use of the deeded enclosed rear porch, half of the backyard, and front porch, creating a rare urban retreat with indoor and outdoor living space. Ideally located near some of Somerville’s most vibrant destinations, this home offers easy access to Assembly Row (1.1 mi), Magoun Square (0.7 mi), Union Square (1.2 mi), Ball Square (0.8 mi), Davis Square (2 mi), and Porter Square (2 mi), with an array of dining, shopping, and entertainment options nearby. Commuters will appreciate convenient access to the Orange, Green, and Red Lines, commuter rail service, multiple bus routes, and the Magoun Square Green Line Extension station just 0.8 miles away or Gilman Square Green Line Extension (1 mi). Enjoy nearby parks and quick connections to Routes 2, 16, 28, 38, 93, and 95, McGrath Highway, downtown Boston, and Logan Airport.

371 Broadway Unit 1, Somerville

Listing courtesy of Listing Agent: Team Jen & Lynn from Listing Office: Thalia Tringo & Associates Real Estate, Inc..

$1,275,000

4 Beds ⋅ 4 Baths ⋅ 73588098 MLS ⋅ ['23 Jaques'] BLDG.

Stunning luxury 4 bedroom, 3.5 bath upper duplex with roofdeck, side yard and 2 parking spaces! Full building renovation in 2022. Freshly painted, ready to move into, quick closing possible. Experience grand-scale living and entertaining within this breathtaking, meticulously renovated four bedroom, three and a half bathroom penthouse duplex. Transformed in 2022 with the privacy and presence of a single family home, this sun-filled residence features striking Calcutta quartz, a custom fireplace, and wide-plank oak flooring throughout. The main level offers an open chef's kitchen built for entertaining, expansive living and dining rooms, a private balcony, a powder room, and two gracious bedrooms anchored by a full bath. Front and rear stairways lead to the upper level, featuring a primary suite with two walk-in closets and a stunning spa-inspired en-suite bathroom. A flexible fourth bedroom with a private bath sits adjacent to the dedicated family lounge, featuring a custom refreshment bar that opens to a fantastic private roof deck. Gas heating and cooking, central air, tandem parking for two cars (three possible) and a low maintenance two-unit association. Close to shopping, highway and Downtown Boston.

23 Jaques St Unit B, Somerville

Listing courtesy of Listing Agent: Martyn Scott from Listing Office: Gibson Sotheby's International Realty.

$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.

390 Broadway Unit 35, Somerville

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

$428,000

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.

$2,988,000

11 Beds ⋅ 8 Baths ⋅ 73542693 MLS

Three gut-renovated residences! 11 bedrooms, 8 full baths, and about 5,921 gross square feet offered together in Winter Hill. The first-floor/lower-level duplex has 6 bedrooms, 4 full baths, a large family/recreation room, and a deck off the kitchen opening to the fenced side yard. The second floor is a 3 bed, 2 bath with a waterfall island and primary suite. The top floor is a 2 bed, 2 bath with skylights and a primary suite. Each unit has central air, in-unit laundry, and one off-street parking space, and the building is sprinklered. One-year builder's warranty. Condominium plans have been prepared, so a buyer can hold all three, live in one, or pursue unit sales. About a 15 minute walk to Assembly Row, past Foss Park and Stop & Shop, and a 9 minute walk to the Gilman Square Green Line station.

174 Walnut Street, Somerville

Listing courtesy of Listing Agent: Kirsten McEleney from Listing Office: KM Real Estate Group.

$919,000

3 Beds ⋅ 2 Baths ⋅ 73541863 MLS

PRICE IMPROVEMENT-Tastefully renovated open floor concept with 3br/2 baths Condo on 2nd fl in Winter Hill area of Somerville - Features include new kitchen with new cabinets, quartz countertop, new stainless steel appliances including gas stove & microwave, master suite with attached full bath, good sized bedrooms, hardwood flooring throughout, Tile flooring in baths, ample storage space including direct & private access to the basement, one floor living, laundry hookup, enclosed deck, upgraded electric wiring & panels, new WH, new HVAC, 2 deeded tandem off-street parking spaces etc. Easy access to the new Green line extension, Assembly Row, Restaurants, Shopping, Tufts, Logan airport, downtown Boston- A commuter's dream! Association fee, taxes & assessed value are approximate & will be revised. Association fee includes master insurance, common lights, landscaping & snow removal.

8 Melvin St Unit 2, Somerville

Listing courtesy of Listing Agent: Maha Krishnakumar from Listing Office: LXTN Realty.

$1,149,000

6 Beds ⋅ 2 Baths ⋅ 73541807 MLS

Welcome to 12 Douglas Avenue, a rare opportunity to acquire a well-maintained two-family property in Somerville's highly sought-after Winter Hill neighborhood. Ideal for both owner-occupants and investors, the property features two spacious residential units, off-street parking for two vehicles, and strong in-place rental income with additional upside potential. Leases signed through 3/31/27. Perched atop Winter Hill on a dead-end street, the property enjoys elevated skyline views in a peaceful residential setting. The property also includes an unfinished attic and basement, presenting potential value-add opportunities for future expansion. Just minutes from Assembly Row, Union Square, public transportation, and major employment hubs. Offering a unique combination of income, location, and long-term appreciation potential, 12 Douglas Avenue is an exceptional opportunity in one of Greater Boston's most desirable multifamily markets.

12 Douglas Ave, Somerville

Listing courtesy of Listing Agent: from Listing Office: Block Realty.

$1,200,000

6 Beds ⋅ 4 Baths ⋅ 73516128 MLS

Rare opportunity to own a well-located 4-unit property in the highly desirable Winter Hill neighborhood. Ideal for investors or developers looking to capitalize on strong rental demand and future long-term upside with rents currently below market. The property features a total of 6 bedrooms and 4 bathrooms across the four units, providing flexible living arrangements and consistent rental appeal. Additional highlights include 2 parking spaces (1 off street and 1 "private way" parking space directly in front of the building). Conveniently situated near public transportation, Assembly Row, Union Square, East Somerville, local restaurants, shopping, parks, and major commuter routes, the location provides easy access to downtown Boston and surrounding communities.

15 Kenneson Rd, Somerville

Listing courtesy of Listing Agent: Shane Marrion from Listing Office: Benoit Real Estate Group ,LLC.

$1,625,000

6 Beds ⋅ 3 Baths ⋅ 73496741 MLS

Winter Hill triple-decker offering strong investment opportunity. Each unit features hardwood floors, abundant natural light, and a comfortable, functional layout. Enjoy covered front and rear porches, perfect for relaxing or entertaining. Generous parking includes a three-car garage plus additional off-street spaces — rare for the area. Easy access to Boston and Cambridge. Close proximity to Foss Park and Assembly Square adds to the appeal with nearby recreation, dining, and retail options. A solid addition to any portfolio in a highly desirable Somerville location. Current lease agreements in place through May 31, 2027.

33-35 Sewall Street, Somerville

Listing courtesy of Listing Agent: Maggie Dee + Charles Cherney Team from Listing Office: Compass.

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Winter Hill Real Estate

Newest Listings in Winter Hill

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