Winter Hill Real Estate

Winter Hill Real Estate

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

One of the standout features of Winter Hill is its diverse array of housing options. From classic Victorian homes to modern condos, there's something to suit every taste and budget. The tree-lined streets are not only picturesque but also foster a sense of community, with friendly neighbors and local gatherings that bring residents together.

Winter Hill is well-connected to the greater Boston area, with easy access to public transportation, including the nearby Alewife and Davis Square T stations. This makes commuting a breeze, whether you're heading to downtown Boston for work or exploring the city's vibrant cultural scene. For those who prefer to drive, major highways are just a stone's throw away.

Food lovers will delight in the culinary offerings of Winter Hill, which boasts an impressive selection of restaurants, cafes, and local eateries. From cozy brunch spots to international cuisine, there’s always something new to try. The neighborhood also features beautiful parks and green spaces, perfect for leisurely strolls, picnics, or enjoying a sunny afternoon with friends and family.

With its rich history, strong sense of community, and convenient location, Winter Hill is more than just a place to live—it's a place to thrive. Come explore all that this delightful neighborhood has to offer and discover your new home in Winter Hill!

Newest Listings in Winter Hill

$525,000
2 Beds ⋅ 2 Baths ⋅ 73575539 MLS ⋅ ['Summit Condominium'] BLDG.
Sweeping city views set the scene for this inviting 2-bedroom, 2-bath condo located in the heart of Winter Hill in a pet-friendly professionally maintained building. Where a connected urban lifestyle meets the comfort of a welcoming retreat. The spacious living/dining combo room features hardwood flooring, a fireplace, multi-closet storage, & sliding glass doors to a private balcony—an inviting setting for entertaining friends or settling in for a quiet evening. The kitchen pairs rich mahogany cabinetry with natural stone counters and stainless steel appliances. Both bedrooms offer generous space and excellent storage, with an oversized primary suite featuring its own bathroom, walk-in closet, and second private balcony. There’s plenty of room for a work-from-home setup, while two full bathrooms make sharing the home with a roommate comfortable and convenient. Central air, in-unit laundry, an elevator, one garage parking space, and additional basement storage offers all the features you need for easy living! Explore the shops and restaurants of nearby Magoun and Ball Squares, enjoy neighborhood parks and the community path, or head to Assembly Row for shopping and dining. With access to the Green Line, Boston, Cambridge, and I-93, this home puts the area’s many possibilities within reach.

390 Broadway Unit 51, Somerville

Listing courtesy of Listing Agent: Rebecca Riopelle from Listing Office: Blink Realty Group, LLC.
$445,000
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.
$1,188,888
3 Beds ⋅ 2 Baths ⋅ 73573052 MLS
Sun-Drenched Sophistication in the Heart of Winter Hill. 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 a 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. Work from home, dedicated office placed into a quiet corner of the unit means meetings and deep-focus days are no problem at all. Bike to Work from the nearby Green Line Bike Path. 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. Rounding out this exceptional offering: in-unit laundry, assigned off-street parking, and a basement bike room. Set within a boutique, fully remodeled 2021 building of just 6 owner-occupied units, 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.
$1,890,000
8 Beds ⋅ 4 Baths ⋅ 73553200 MLS
Outstanding investment opportunity in the highly desirable Winter Hill neighborhood of Somerville. This well-located 4-family property offers approximately 3,950 SF of living area with strong in-place income and excellent long-term upside in one of Greater Boston’s most competitive rental markets. The building consists of 8 bedrooms and 4 bathrooms across four units, each featuring functional layouts with strong rental appeal. Units include separate utilities, minimizing landlord expenses, and a walk-out basement with private laundry in each unit, adding convenience and value for tenants. Parking is street-based. Leases are structured on yearly terms, providing stable and predictable cash flow.

80 Heath Street, Somerville

Listing courtesy of Listing Agent: Wai Kit Or from Listing Office: V & E Realty.
$395,000
1 Beds ⋅ 1 Baths ⋅ 73546263 MLS
Attention investors and owner occupants!! Bright and spacious Winter Hill one bedroom!! Wonderful ambiance created by gleaming hardwood floors, and natural light. Unbeatable, vibrant location convenient to all things Somerville including Assembly Square, Orange/Green Lines, Rt. 93, Tufts University and unlimited shops and restaurants. Unit includes large bedroom, expansive living room, separate dining area and modern/updated galley kitchen. Condo fee includes heat, hot water and professional management. Parking, extra storage, laundry facility on premises and nicely landscaped building on tree lined street complete the whole package for this property. Disclosure: One owner has 10 units requiring special considerations for financing. See listing agent.

84 Grant St Unit 12, Somerville

Listing courtesy of Listing Agent: Joseph Drake from Listing Office: Coldwell Banker Realty - Newton.
$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.
$575,999
2 Beds ⋅ 2 Baths ⋅ 73541278 MLS
Welcome to this fully renovated 2 bedroom, 2 full bathroom condo located in the Winter Hill neighborhood of Somerville. This unit features an open floor plan with abundant natural light throughout. The updated kitchen offers ceiling height cabinetry, and modern finishes and flows directly into the open concept living area, creating a functional layout suitable for everyday living and entertaining. The spacious bedrooms provide comfortable retreats with ample room for furnishings and storage, both bathrooms have been renovated with contemporary fixtures and finishes. Ideally situated this condo offers exceptional access to public transportation multiple bus routes and the Green Line Extension, convenient access to route 93, and minutes from Assembly Row, local parks, neighborhood restaurants, cafés, shopping, and downtown Boston providing both urban convenience and a strong neighborhood setting. Ideal opportunity for owner seeking nicely renovated unit in a highly accessible location!!

60 Derby St Unit 1, Somerville

Listing courtesy of Listing Agent: Dot Collection from Listing Office: Access.
$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.
$1,650,000
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.
$1,850,000
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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