Winter Hill Real Estate

Winter Hill Real Estate

Welcome to Winter Hill, a charming neighborhood nestled in the heart of Somerville, Massachusetts. Located in Middlesex County, Winter Hill offers a perfect blend of urban convenience and suburban tranquility.

With tree-lined streets and a strong sense of community, Winter Hill is a highly sought-after area for both young professionals and families. The neighborhood boasts a mix of historic homes and modern developments, providing a diverse range of housing options for residents.

One of the highlights of Winter Hill is its proximity to Boston, just a short drive or public transportation ride away. Residents can easily access all the amenities and cultural attractions of the city while enjoying the quieter pace of suburban life.

In Winter Hill, you'll find a variety of local shops, restaurants, and parks to explore. From cozy cafes to trendy boutiques, there's something for everyone in this vibrant neighborhood. Outdoor enthusiasts will appreciate the nearby parks and green spaces, perfect for a leisurely stroll or a weekend picnic.

Whether you're a first-time homebuyer or looking to upgrade to a larger space, Winter Hill has something for everyone. Come discover the charm and convenience of this wonderful neighborhood in Somerville, Massachusetts.

Newest Listings in Winter Hill

23 Jaques St Unit B, Somerville
$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.
466-468 Medford St Unit 2, Somerville
$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.
400 Broadway Unit 7, Somerville
$565,000
1 Beds ⋅ 1 Baths ⋅ 73581642 MLS ⋅ ['Mansard Place Condominium'] BLDG.
Set high on Winter Hill, this oversized one-bedroom occupies the upper level of a striking Mansard Victorian and blends historic character with the updates buyers want today. Oversized windows, high ceilings, deep crown moldings, and hardwood floors give the home plenty of charm, while the natural light and city views make the space feel bright and open. The kitchen features granite countertops, generous cabinet storage, and a peninsula with seating, opening directly into a spacious living area with bay windows and plenty of room for both a full dining setup and everyday living. The oversized bedroom also includes a flexible bonus room that works well as a home office, workout space, dressing room, or additional storage. Central A/C, in-unit laundry, and deeded basement storage make day-to-day living easy. The location is another major plus, with convenient access to the Green Line, multiple bus routes, and nearby Red Line connections. Magoun Square, Assembly Row, Porter Square, Sullivan Square, restaurants, shops, and neighborhood favorites are all close by.

400 Broadway Unit 7, Somerville

Listing courtesy of Listing Agent: Carlisle Group from Listing Office: Compass.
390 Broadway Unit 35, Somerville
$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.
390 Broadway Unit 54, Somerville
$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.
34 Heath St Unit 3, Somerville
$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.
174 Walnut Street, Somerville
$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.
8 Melvin St Unit 2, Somerville
$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.
12 Douglas Ave, Somerville
$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.
15 Kenneson Rd, Somerville
$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.
33-35 Sewall Street, Somerville
$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.
3 Lee Street, Somerville
$1,775,000
6 Beds ⋅ 6 Baths ⋅ 73496734 MLS
This distinctive building offers strong curb appeal and undeniable character. Located on a tree-lined street, the property features six 1-bedroom, 1-bath units, making it an ideal addition to any investor’s portfolio. Front and back porches enhance tenant appeal. The building is equipped with central heat and hot water, providing efficiency and convenience. Paved driveway. Situated in a prime locale, this property offers easy access to the Gilman Square MBTA Green Line Station, connecting to Cambridge, Boston, and beyond. Close proximity to shops, dining, and entertainment. Current lease agreements in place through May 31, 2027.

3 Lee Street, Somerville

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