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. Known for its eclectic charm and rich history, Winter Hill offers a unique blend of urban convenience and suburban tranquility, making it an ideal place for families, young professionals, and anyone looking to immerse themselves in a dynamic community.

Winter Hill boasts a diverse mix of architectural styles, from quaint Victorian homes to modern condominiums, reflecting the area’s evolution over the years. As you stroll through its tree-lined streets, you’ll discover a variety of local shops, cafes, and restaurants that cater to every palate. Whether you’re in the mood for a cozy brunch spot or a trendy eatery, Winter Hill has something to satisfy your cravings.

One of the neighborhood’s standout features is its proximity to public transportation, making commuting to Boston and surrounding areas a breeze. The nearby Assembly Row, a bustling shopping and entertainment district, offers an array of retail options, dining experiences, and recreational activities, ensuring that residents have everything they need right at their fingertips.

Winter Hill is also home to several parks and green spaces, perfect for outdoor enthusiasts and families seeking a place to relax and unwind. With a strong sense of community and a calendar full of local events, Winter Hill fosters connections among its residents, making it easy to feel right at home.

If you’re considering a move to Somerville, Winter Hill is a neighborhood that truly has it all—character, convenience, and a welcoming atmosphere. Discover your new home in Winter Hill 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
Rare fully vacant triple-decker opportunity in one of Somerville's most sought-after neighborhoods! Situated on a prime corner lot at the end of a quiet dead-end street, this beautifully maintained property offers three spacious units, each featuring 3 bedrooms and 1 bath. All three units will be delivered vacant as of 9/1, creating a rare opportunity for buyers to immediately occupy, lease, or reposition the property to maximize its full potential. Perfect for owner-occupants, investors, multi-generational living, or condo conversion potential.Enjoy a private yard for relaxing or entertaining, plus the rare advantage of off-street parking for four cars and a garage—a true game changer in the city. Ideally located just moments from award-winning Sarma and convenient to the Green Line for easy commuting. Pride of ownership shines throughout, offering a turnkey opportunity with endless possibilities in a premier Somerville location. Don't miss your chance to own this exceptional property in the heart of Somerville.

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.
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