Winter Hill, MA homes for sale & real estate

14 homes

Sort:

Recommended

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Welcome to this charming 2+ bedroom, 1-bath condo in Somerville’s vibrant Union Square. Bursting with character, this home features beautiful hardwood floors, high ceilings, and loads of natural light. The well-designed layout offers spacious bedrooms, a comfortable living area, and a thoughtfully maintained kitchen, perfect for both daily living and entertaining. Enjoy access to a shared yard space, ideal for quaint garden. Just steps to the Ball Square, Green Line station, Tufts University, Davis Square, and Somerville’s best shops and restaurants, this condo combines classic New England charm with unbeatable convenience. An ideal opportunity for anyone seeking a warm, invitin

$649,000

2 beds1 bath1,140 sq ft

31 Thurston St #6, Somerville, MA 02145

Garden • Natural light • High ceilings

3D WALKTHROUGH

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
SPECIAL SELLER FINANCING. .. SELLER FUNDED BUY DOWN. .. 30 YR FIXED w/ 1st Yr @ 4.25%, 2nd Yr @ 5.25% , Yrs 3-30 @ 6.25%. w/ NO POINTS and 20% down. (Rate as of 10/2/25). FANTASTIC NEW CONSTRUCTION. Less than half mile to two Green Line stops. Designed with a Mansard Victorian influence inside & out. Fantastic luxurious 2 BDRM unit w/ 9 ft clngs, custom panneled walls, wide plank dirty blond flrs. Great natural ligt w/ large double paned wndws. Kitchen has all stainless appliances w/ quartz counters. Fantastic Bay Window Primary Bdrm w/ double sliders to a faux balcony. Gorgeous luxury bathroom, with huge large format faux marble tiles to give a sleek contemporary vibe. Great closet s

$664,900

2 beds1 bath798 sq ft

115-B Thurston St Unit B, Somerville, MA 02143

Quartz counters • New construction • Stainless appliances

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
This rare two-family property is full of potential and ready for its next owner to add the finishing touches. Near Green Line Extension (GLX) Medford/Tufts Station, with the bus stop conveniently located right at your doorstep, the property is located in a high-demand area with excellent potential for condo conversion and long-term value. Whether you're looking to live in one unit and rent the other unit. or reimagine the space with a modern update, this is a true hidden gem with endless possibilities. OPEN HOUSE SUNDAY 12 NOON TO 3:00PM.

$1,190,000

7 beds3 baths2,864 sq ft

400 Medford Steet, Somerville, MA 02145

Green line extension • Condo conversion • High-demand area

3D WALKTHROUGH

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
SPECIAL SELLER FINANCING. .. SELLER FUNDED BUY DOWN. .. 30 YR FIXED w/ 1st Yr @ 4.25%, 2nd Yr @ 5.25% , Yrs 3-30 @ 6.25% (w/ NO POINTS and 20% down owner occupied. .. Rate as of 10/2/25). FANTASTIC NEW CONSTRUCTION WITH HUGE EXCLUSIVE USE ROOF DECK AND STUNNING PANORAMIC VIEWS OF BOSTON. .. THE BEST VALUE NEW CONSTRUCTION PENTHOUSE ONE BEDROOM IN BOSTON. .. INCLUDES RARE GARAGE PARKING. Stunning Sun Splashed Luxurious top flr unit w/ 9 ft clngs, skylight & custom panneled walls. Wide plank dirty blond flrs. Kitchen has new stainless appliances with quartz brkfst islnd. Fantastic Primary Bedrooms with double sliders to a faux balcony, gorgeous double basin luxury bathroom and great clo

$759,900

1 bed1 bath798 sq ft

115-I Thurston St Unit I, Somerville, MA 02145

Big brick rear patio • Rare garage parking • In unit laundry

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Introducing a fully renovated and stabilized massive 6-unit building in the extremely desirable Winter Hill neighborhood of Somerville! This 8,060 sq foot building is nestled on a tree-lined one-way street and is directly across from the new Gilman Square green line stop and has a gross rent roll of $21,725 per month! The building has undergone extensive renovations including kitchen/bath/laundry work and plumbing/electric improvements in each unit (’21-’23), a new roof (’23), fully re-built rear decks (’24), and more (see full capex and rent roll list). Each unit is a 3 bed/1 bath unit with huge rooms and high ceilings that feel very spacious and leases are in place

$3,510,000

18 beds6 baths8,060 sq ft

109 Walnut St, Somerville, MA 02145

Fully renovated • Tree lined street • New roof

Property at 115 Highland Ave Ph 21, Somerville, MA 02143, 2 beds, 1 bath

$599,000

2 beds1 bath900 sq ft

115 Highland Ave Ph 21, Somerville, MA 02143

Property at 456 Medford St #3, Somerville, MA 02145, 1 bed, 1 bath

$549,000

1 bed1 bath675 sq ft

456 Medford St #3, Somerville, MA 02145

Property at 59 Dartmouth St Unit A, Somerville, MA 02145, 4 beds, 3 baths

$1,035,000

4 beds3 baths2,081 sq ft

59 Dartmouth St Unit A, Somerville, MA 02145

Property at 232 Pearl St, Somerville, MA 02145, 4 beds, 2.5 baths

$1,399,000

4 beds2.5 baths1,952 sq ft

232 Pearl St, Somerville, MA 02145

Property at 32 Radcliffe Rd, Somerville, MA 02145, 6 beds, 2 baths

$1,288,000

6 beds2 baths2,571 sq ft

32 Radcliffe Rd, Somerville, MA 02145

Property at 7 Stickney Ave, Somerville, MA 02145, 7 beds, 2.5 baths

$1,299,000

7 beds2.5 baths2,600 sq ft

7 Stickney Ave, Somerville, MA 02145

Property at 73 Bonair St, Somerville, MA 02145, 4 beds, 2 baths

$1,188,000

4 beds2 baths2,200 sq ft

73 Bonair St, Somerville, MA 02145

Property at 54 Bonair St, Somerville, MA 02145, 10 beds, 4 baths

$2,000,000

10 beds4 baths3,566 sq ft

54 Bonair St, Somerville, MA 02145

Property at 52 Bonair St, Somerville, MA 02145, 13 beds, 6 baths

$3,000,000

13 beds6 baths5,372 sq ft

52 Bonair St, Somerville, MA 02145

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

OPEN THU, 4:30PM TO 6PM

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Welcome to 13 Berkeley, a charming and well-maintained 2 bed, 1.5 bath home on one of Somerville’s most sought-after streets. Nestled in the heart of Spring Hill, this residence blends classic charm with thoughtful finishes. The inviting layout offers bright living spaces and a renovated kitchen. Lovingly cared for by its current owners, the home features hardwood floors, original details, and a warm, welcoming atmosphere that feels like home the moment you walk in. Enjoy back patio and side yard perfect for gardening, entertaining, or relaxing. Just a short walk to Union, Porter, and Davis Squares, with easy access to the Green Line, shops, restaurants, and parks. If you’re loo

$899,000

2 beds1.5 baths1,178 sq ft

13 Berkeley St, Somerville, MA 02143

3,050 sq ft lot • Walker's paradise

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Embrace the convenience of urban living at 59 Berkeley Street. Sited only blocks from Union Square, East Coast’s next innovation hub, and a skip, hop, and a jump to Harvard, Kendall, and beyond. Inside this bright and open home, the charm of city living seamlessly integrates with comfort through modern features like dimmable LED recessed lighting, Nest thermostat, and video intercom. The living space is graced with white oak floors and many skylights, while the kitchen showcases sleek quartz countertops and premium Jenn-Air appliances. Outside, life is complemented by an inviting private deck off the kitchen, and a common patio, elevating your lifestyle beyond the walls of your home.

$738,000

2 beds1 bath912 sq ft

59 Berkeley St #3, Somerville, MA 02143

$303 HOA • Community pool • Walker's paradise

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Don't miss this tremendous opportunity to own a gigantic Victorian rich with period details. Experience a “Wow” moment upon entering the grand foyer, complete with gorgeous oval windows and curved panel wainscoting. The first floor boasts oversized rooms, soaring ceilings, crown molding, and beautiful hardwood parquet flooring. Abundant natural light pours in through updated windows. The home offers incredible space with seven full-size bedrooms and a full tiled bath across the upper two floors. A bonus enclosed front porch is perfect for a future home office or sunroom. The unfinished basement, with full-size windows and two walk-out exits, is a tremendous opportunity to create

$1,499,000

7 beds2 baths3,212 sq ft

30 Walnut St, Somerville, MA 02143

5,492 sq ft lot • Walker's paradise

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Nestled perfectly between vibrant Assembly Row and trendy Winter Hill, this stylish 2-bedroom condo blends comfort, convenience, and character. The open-concept layout flows effortlessly from the chef-inspired kitchen with granite countertops to a bright and inviting living and dining area—ideal for entertaining or relaxing. The spacious primary bedroom features double closets, and you’ll love the ease of in-unit laundry. Stay cool year-round with energy-efficient mini-split A/Cs—the only unit in the building with this upgrade! Includes deeded basement storage, 1 parking spot, and pet-friendly living (2 allowed). Just moments from the Mystic River parks, top-rated restaura

$715,000

2 beds1 bath955 sq ft

77 Wheatland St #2, Somerville, MA 02145

$200 HOA • Walker's paradise

3D WALKTHROUGH

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Introducing Somerville’s first to market new construction cottage! A rare gem hits the market, this stunning 2 bedroom, 2.5 bath residence redefines condo living with the feel of a single family home. Boasting over 1,000 sq ft of expertly crafted space, this brand new cottage dazzles with its open layout, designer finishes, and sun splashed interiors. Highlights include; sleek, modern kitchen and baths. Expansive windows for natural light, private basement storage and one off-street parking space. Nestled in the heart of Magoun Square, you’re just steps from vibrant dining, shopping, and effortless transit options. This home is the perfect fusion of comfort, style, and city con

$1,150,000

2 beds2.5 baths1,088 sq ft

35 Richardson St Unit Cottage, Somerville, MA 02145

1,000 sq ft lot • Very walkable

3D WALKTHROUGH

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Introducing Somerville’s first to market new construction cottage! A rare gem hits the market, this stunning 2 bedroom, 2.5 bath residence redefines condo living with the feel of a single family home. Boasting over 1,000 sq ft of expertly crafted space, this brand new cottage dazzles with its open layout, designer finishes, and sun splashed interiors. Highlights include; sleek, modern kitchen and baths. Expansive windows for natural light, private basement storage and one off-street parking space. Nestled in the heart of Magoun Square, you’re just steps from vibrant dining, shopping, and effortless transit options. This home is the perfect fusion of comfort, style, and city conv

$1,150,000

2 beds2.5 baths1,088 sq ft

35 Richardson St #4, Somerville, MA 02145

$310 HOA • Very walkable

Property at 441 Broadway, Somerville, MA 02145, 10 beds, 5 baths

$1,775,000

10 beds5 baths4,184 sq ft

441 Broadway, Somerville, MA 02145

Property at 142 Cross St, Somerville, MA 02145, 10 beds, 6.5 baths

$949,900

10 beds6.5 baths5,735 sq ft

142 Cross St, Somerville, MA 02145

Property at 105 Central St, Somerville, MA 02143, 8 beds, 2 baths

$1,299,000

8 beds2 baths3,957 sq ft

105 Central St, Somerville, MA 02143

Property at 16 Bonair St #16, Somerville, MA 02145, 3 beds, 3.5 baths

$1,350,000

3 beds3.5 baths2,124 sq ft

16 Bonair St #16, Somerville, MA 02145

Property at 14 Bonair St #14, Somerville, MA 02145, 4 beds, 4 baths

$1,399,000

4 beds4 baths2,115 sq ft

14 Bonair St #14, Somerville, MA 02145

Property at 7-9-11 Bond St, Somerville, MA 02145, 18 beds, 9 baths

$5,000,000

18 beds9 baths9,049 sq ft

7-9-11 Bond St, Somerville, MA 02145

Property at 19 Fenwick #4, Somerville, MA 02145, 3 beds, 2.5 baths

$899,000

3 beds2.5 baths1,366 sq ft

19 Fenwick #4, Somerville, MA 02145

Property at 35 Richardson #2, Somerville, MA 02145, 3 beds, 2 baths

$1,299,900

3 beds2 baths1,706 sq ft

35 Richardson #2, Somerville, MA 02145

Property at 303 Lowell St #1, Somerville, MA 02145, 2 beds, 1 bath

$430,000

2 beds1 bath842 sq ft

303 Lowell St #1, Somerville, MA 02145

Property at 94 Jaques St Unit B, Somerville, MA 02145, 4 beds, 2.5 baths

$1,295,000

4 beds2.5 baths2,778 sq ft

94 Jaques St Unit B, Somerville, MA 02145

Property at 29-31 Fenwick St, Somerville, MA 02145, 7 beds, 2 baths

$1,299,000

7 beds2 baths4,397 sq ft

29-31 Fenwick St, Somerville, MA 02145

Property at 147 - 149 Pearl, Somerville, MA 02145, 11 beds, 4 baths

$1,850,000

11 beds4 baths4,491 sq ft

147 - 149 Pearl, Somerville, MA 02145

Property at 496 Medford St, Somerville, MA 02145, 2 beds, 1.5 baths

$1,150,000

2 beds1.5 baths1,244 sq ft

496 Medford St, Somerville, MA 02145

Property at 32 Rush St, Somerville, MA 02145, 8 beds, 4 baths

$1,375,000

8 beds4 baths3,855 sq ft

32 Rush St, Somerville, MA 02145

Average home prices near Winter Hill, MA

Cities

Neighborhoods

Downtown Boston homes for sale
$1,847,500
West End homes for sale
$759,000
Fenway-Kenmore homes for sale
$1,672,500
North End homes for sale
$1,169,000
Back Bay homes for sale
$2,100,000
Charlestown homes for sale
$949,000
West Medford homes for sale
$995,000
Allston homes for sale
$634,000
East Cambridge homes for sale
$899,000
Beacon Hill homes for sale
$3,470,000

Winter Hill, MA real estate trends

All Home Types trends in Winter Hill, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,080,000

+12.5% YoY | Sep 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Sep 2025

Growth

% YoY

Winter Hill, MA

$1,080,000

+12.5%

See more Winter Hill, MA market insights

More to explore in Winter Hill, MA

How to buy a house in Winter Hill, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Massachusetts

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.