Winter Hill Real Estate

Winter Hill Real Estate

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 a perfect blend of urban convenience and suburban tranquility.

Winter Hill boasts a unique character, with tree-lined streets and a mix of residential homes, local businesses, and green spaces. The neighborhood is steeped in history, with roots dating back to the 19th century, and it has evolved into a dynamic community that celebrates its heritage while embracing modern living.

One of the standout features of Winter Hill is its accessibility. With excellent public transportation options, including the nearby Alewife and Davis Square T stations, residents can easily commute to Boston and beyond. This makes Winter Hill an ideal location for professionals and families alike, providing the perfect balance of city life and neighborhood charm.

Outdoor enthusiasts will appreciate the proximity to parks and recreational areas. The nearby Somerville Community Path offers a scenic route for walking, jogging, or biking, while the lush parks provide ample space for picnics and outdoor activities.

Winter Hill is also home to an array of dining options, from cozy cafes to trendy restaurants, showcasing the diverse culinary scene that Somerville is known for. Local shops and markets add to the community's charm, making it a delightful place to explore.

Whether you’re seeking a cozy home or a vibrant community, Winter Hill offers a welcoming atmosphere that invites you to experience the best of Somerville living. Discover your new home in this enchanting neighborhood today!

Newest Listings in Winter Hill

$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. Unit currently rents for $2,400. Rented unit 8/31/26. 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.
$1,195,000
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. 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.
$1,699,000
9 Beds ⋅ 3 Baths ⋅ 73524198 MLS
Discover an incredible opportunity for OWNER OCCUPIED HOME WITH INCOME on a prime corner lot at the end of a quiet dead-end street in one of Somerville’s most sought-after neighborhoods! This beautifully maintained triple-decker offers three spacious units, two will be delivered VACANT, each with 3 bedrooms and 1 bath—perfect for investors or savvy owner-occupants. Units 1 and 2 are vacant, offering flexibility for immediate occupancy or strong rental potential, while the 3rd floor features a long-term at-will tenant who can provide steady rental income from day one. Enjoy a private yard for relaxing or entertaining, plus the rare advantage of off-street parking for 4 cars and a garage—a true game changer in the city! Just moments from award-winning Sarma and close to the Green Line for easy commuting. Pride of ownership shines throughout—this is a rare opportunity you won’t want to miss!

45 Jackson Rd, Somerville

Listing courtesy of Listing Agent: Melissa Meyer from Listing Office: Lawton Real Estate, Inc.
$678,000
3 Beds ⋅ 2 Baths ⋅ 73523791 MLS
Sunny top-floor 3-bedroom condo on a quiet cul-de-sac in Winter Hill. Hardwood floors, recessed lighting, and oversized windows create a warm and inviting living space filled with natural light. The front bedroom features bay windows and a ceiling fan. The living room includes a decorative mantel, ceiling fan, and mini-split. Thoughtfully designed floor plan with all three bedrooms separated from one another. Spacious eat-in kitchen with ample cabinetry, stainless steel appliances, and room for dining. Full bath with tub/shower, plus a half bath with side-by-side laundry. Enjoy summer evenings on the private covered rear deck. Additional highlights include private basement storage and rare two-car tandem parking for Unit 3 in the shared driveway. Conveniently located five minutes from Sarma Restaurant and just a half mile from the Green Line Station at Gilman Square, and enjoying easy access to Union Square and Assembly Row. Walk Score® of 89— very close to many convenient amenities.

12 Walter Terrace Unit 3, Somerville

Listing courtesy of Listing Agent: Maggie Dee + Charles Cherney Team from Listing Office: Compass.
$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. OPEN HOUSE SATURDAY MAY 30 FROM 11:30AM - 1:00PM.

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.
$1,029,999
4 Beds ⋅ 2 Baths ⋅ 73491171 MLS
Great two-family opportunity in Somerville! Well-located multi-family property offering strong potential for investors or owner-occupants. Each unit features bright living spaces with functional layouts. The property offers convenient off/on-site coin-operated laundry and private storage in the basement. Enjoy a beautiful backyard patio, perfect for relaxing or entertaining. Conveniently located near public transportation, restaurants, shopping, parks, and major commuting routes. Excellent opportunity to own in a desirable Somerville location.

7 Jaques St, Somerville

Listing courtesy of Listing Agent: Pratt Properties Team from Listing Office: Century 21 North East.
Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.