Winter Hill Homes under $2 million

Welcome to Winter Hill, a vibrant neighborhood nestled in the heart of Somerville, Massachusetts, within the picturesque Middlesex County. This charming community is renowned for its rich history, diverse culture, and a unique blend of urban convenience and suburban tranquility. Winter Hill offers residents a welcoming atmosphere with tree-lined streets, local parks, and an array of dining and shopping options that reflect the area’s eclectic spirit.

One of the standout features of Winter Hill is its accessibility. With easy access to public transportation, including the nearby Alewife and Alewife subway stations, commuting to Boston and surrounding areas is a breeze. This makes Winter Hill an ideal choice for professionals and families alike, seeking a balance between city life and suburban comfort.

For those looking to invest in their dream home, Winter Hill presents an enticing opportunity with homes available under $2 million. Whether you are searching for a charming Victorian, a modern condo, or a cozy single-family home, the real estate market in Winter Hill offers a diverse selection to suit various tastes and lifestyles. Many homes feature contemporary amenities while retaining the character and charm that define this historic neighborhood.

Living in Winter Hill means being part of a close-knit community that celebrates local events, art, and culture. Enjoy weekend strolls to nearby parks, indulge in delicious cuisine at local eateries, or take part in community gatherings that foster connection and camaraderie.

Discover the allure of Winter Hill, where your dream home awaits amidst a backdrop of history and charm!

Newest Winter Hill Homes under $2 million

$1,298,500

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.

$849,000

2 Beds ⋅ 2 Baths ⋅ 73586866 MLS

Beautifully renovated 2-bedroom duplex offering two levels of thoughtfully designed living space in a fantastic Somerville location. Renovated in 2018, this inviting home features an open-concept main level with a spacious living and dining area and a modern kitchen with quartz countertops, stainless steel appliances, floor-to-ceiling custom cabinetry, and a stylish backsplash. Upstairs are two generously sized bedrooms, a full bath, and convenient in-unit laundry. Central A/C, a NEST thermostat, excellent closet space, and abundant additional storage make the home as practical as it is comfortable. Enjoy rear outdoor space along with the convenience of one off-street parking space located directly beside the home’s private rear entrance—an especially valuable feature for everyday living. Ideally situated just outside Magoun Square, approximately 0.4 miles from the Green Line and close to the Somerville Community Path, providing easy access to Davis Square, Cambridge, and Boston. Walk to neighborhood favorites including Sarma, along with local cafés, restaurants, parks, playgrounds, and shops. A move-in-ready home offering the ideal combination of space, storage, parking, private entry, and access to everything Somerville has to offer.

466-468 Medford St Unit 2, Somerville

Listing courtesy of Listing Agent: Batya & Alex Team from Listing Office: William Raveis R.E. & Home Services.

$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

OPEN HOUSE CANCELED DUE TO ACCEPTED OFFER 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.

$695,000

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.

$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.

$849,000

3 Beds ⋅ 4 Baths ⋅ 73574093 MLS

A complete 2026 gut renovation, THREE private en-suite bedrooms plus powder room, private deck, yard, and walkable Green Line access make this turnkey Winter Hill residence a rare find under $850,000! Set on the second floor of a newly converted three-unit condominium, Unit 2 combines modern design and exceptional craftsmanship with the character of a classic Somerville home. The light-filled, open-concept living and dining area flows seamlessly into a beautifully designed chef’s kitchen featuring custom cabinetry, quartz countertops, a generous center island, recessed lighting and new appliances, including gas range. Three well-proportioned bedrooms offer excellent closet space, each complemented by its own luxurious en-suite bath with tiled shower, glass enclosure, designer vanity and quartz finishes. A separate powder room serves guests. Major improvements include all-new electrical, plumbing, roof, siding, Harvey windows, central air and natural-gas heating—delivering a true like-new living experience. Step outside to a private rear deck or enjoy the shared yard below--great for pets. Additional private basement storage and in-unit laundry complete the home. On-street parking with off-street potential. Just off Broadway on tree-lined one-way street, approximately a half mile from the Gilman Square Green Line station, with convenient access to the Community Path, Magoun Square, Assembly Row, Sullivan Square and I-93. Penthouse unit also available!

13 Langmaid Ave Unit 2, Somerville

Listing courtesy of Listing Agent: Easter Entwistle Advisors from Listing Office: Douglas Elliman Real Estate - Easter Entwistle Advisors.

$1,088,888

3 Beds ⋅ 2 Baths ⋅ 73573052 MLS

Huge Price Improvement! Welcome home to this stunning, fully updated 3-bedroom, 2-bath condominium offering over 1,700 square feet of beautifully designed living space. Just moments from the Gilman Square Green Line station and Orange Line, this is city convenience meeting elevated living.Step inside to soaring high ceilings, gleaming hardwood floors, and a light-filled open layout that flows effortlessly from room to room. The thoughtfully designed floor plan tucks bedrooms away from the main living areas, giving everyone room to breathe.At the heart of the home, a chef-worthy kitchen dazzles with custom birch cabinetry, sleek quartz countertops, newer stainless steel appliances, and an expansive peninsula made for gathering. Pouring a glass of your favorite vintage is even easier with the built-in wine refrigerator — all opening seamlessly into the living and dining areas for effortless entertaining.Working from home is a breeze with a dedicated office tucked into a quiet corner of the unit, perfect for meetings and deep-focus days alike. Prefer to pedal in? Hop on the nearby Green Line Bike Path for an easy commute.Storage will never be a worry here — closets throughout plus additional storage in the basement keep everything organized and out of sight.And then there's the outdoor living, a rare find in condo life. Enjoy not one, but two private decks, front and back, ideal for morning coffee, evening wine, or weekend entertaining. When you want more room to roam, the common area yard and garden offer additional green space to enjoy.Retreat to the spacious primary suite, and unwind in either of the two full baths, both finished with spa-inspired, updated details — including luxurious heated floors.Rounding out this exceptional offering: in-unit laundry, assigned off-street parking, and a basement bike room. Set within a boutique building of just 6 owner-occupied units, fully remodeled in 2021, this home offers a rare blend of privacy, community, and pride of ownership.

34 Heath St Unit 3, Somerville

Listing courtesy of Listing Agent: David Morganti from Listing Office: Jason Mitchell Group.

$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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