Winter Hill, MA homes for sale & real estate

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ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Inviting, corner unit one-bedroom, one-bathroom condominium offering 644 square feet of well-designed living space in the peak of Winter Hill. Built in 1978, the residence combines classic charm with efficient layout, making it an ideal choice for first-time buyers, urban professionals, or savvy investors. The thoughtful floor plan maximizes space, and includes an excellent private deck, creating a bright and versatile environment perfect for both relaxed daily living and effortless entertaining. The spacious living room, with fireplace, flows seamlessly into the kitchen, while the generously proportioned bedroom provides a peaceful private retreat. Freshly painted and cleaned, it is ready

$448,000

1 bed1 bath644 sq ft

390 Broadway #24, Somerville, MA 02145

Private deck • New water tank • New hvac

OPEN TODAY, 10:30AM TO 12:30PM3D WALKTHROUGH

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Spacious 2BR/2BA condo in a well-maintained building in Somerville’s ultra-convenient Winter Hill. This sunny first-floor home features an open living/dining area with hardwood floors, central air, and in-unit laundry. The kitchen offers a generous island ideal for cooking and entertaining, and both bedrooms provide comfortable, private retreats. Enjoy a deeded parking space and quick access to Assembly Row, the new Green Line extension, and I-93. Move-in ready with room to add your own updates and build future value through thoughtful improvements.

$574,000

2 beds2 baths885 sq ft

74 Gilman St #1, Somerville, MA 02145

Deeded parking space • Quick access to i-93 • Hardwood floors

OPEN TODAY, 11AM TO 12PMVIDEO TOUR

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
NEW YEAR, NEW HOME! This beautifully updated 2 bed/1 bath first-floor Somerville condo sits directly across from Foss Park and offers garage parking, central air, and in-unit, laundry. Fully renovated in 2015, and immaculately maintained with many updates since (below), this home boasts 9 ft ceilings, an open-concept living room, and a fully applianced stainless-steel kitchen. Bedrooms are generously sized, and the unit includes a great front porch plus ample, shared backyard space. Plenty of storage throughout . Prime location with easy access to I-93, the Orange and Green MBTA Lines and bus stop. Minutes to Boston, Harvard Sq, Davis Sq, and the areas top restaurants and entertainment. Imp

$649,000

2 beds1 bath784 sq ft

9 Montgomery Ave #1, Somerville, MA 02145

Fully renovated • Great front porch • In-unit laundry

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Welcome to 232 Pearl street Somerville MA. Don’t miss the opportunity to own a fantastic Two-Family Home located close to Magoun Square and just steps from the new Green Line, dinning, bars and bike path. First floor (Unit 1) has 3 rooms, 1 bedroom, 1 bathroom, living room and Kitchen. Second floor (Unit 2) has 6 rooms 3 bedrooms, 1 bathroom, kitchen, dining and living room. Off-street parking for 3 cars.

$1,099,000

4 beds2.5 baths1,952 sq ft

232 Pearl St, Somerville, MA 02145

Two-family home • Off-street parking • 2,380 sq ft lot

OPEN TODAY, 11:30AM TO 1PM3D WALKTHROUGH

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
SPECIAL 3.5% FINANCING FROM SELLER (as of 12/11/25). .. with 20% down and no points for owner occupants. . 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 closet space. In Unit Laundry. Full EXCLUSIVE FULL WALK UP to a huge 19 ft awesome r

$758,900

1 bed1 bath798 sq ft

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

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

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

$999,999

4 beds3 baths2,081 sq ft

59 Dartmouth St Unit A, 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

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ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Rare Development Opportunity with Endless Possibilities, This mixed-use building presents strong potential for high returns, whether you're considering residential, commercial, or combined development. Ideal for builders, developers, and investors. This mixed-use offering consists of two lots with 10 dedicated parking spaces, providing exceptional flexibility for future expansion or redevelopment. A Prime Locationj ust steps from multiple Orange Line stations and minutes to Route 93, Assembly Row, and Downtown Boston (approx. 10 minutes). Its unbeatable accessibility makes this property highly desirable for a wide range of uses. PROPERTY BEING SOLD WITH 45 Cross Street. MLS # 73461470.

$3,300,000

5 beds3 baths3,221 sq ft

43 Cross St, Somerville, MA 02145

Two lots • Minutes to route 93 • 4,853 sq ft lot

OPEN TODAY, 1PM TO 3PM

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Single family home not a condominium , experience privacy modern luxury at 51 Edgar Ave, Somerville — a stunning 4-bedroom, 4-bath residence showcasing high-end finishes and timeless sophistication. Designed for comfort and style, this home features gorgeous Brazilian hardwood floors, sun-drenched open spaces, and designer details throughout. The spa-inspired bathrooms offer a serene retreat with elegant tilework, soaking tubs, and sleek fixtures. The bright white lower level provides flexible living space—perfect for a media room, gym, or guest suite. Step outside to a gorgeous private backyard, ideal for entertaining, relaxing, or summer gatherings. Every element of this home

$1,789,000

4 beds3.5 baths3,264 sq ft

51 Edgar Ave #51, Somerville, MA 02145

Private backyard • High end finishes • 2 parking spots

OPEN TODAY, 12PM TO 1:30PM

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
This stunning 2020 condo features 2 bedrooms 1.5 baths with private yard! Large windows, crown molding, shiplap feature wall, beautiful built ins, and soaring ceiling heights are just a few of the highlights. The sprawling wide-open concept kitchen, living and dining areas are perfect for entertaining. Enjoy cozy winter nights by the gas fireplace. The immaculate chef's kitchen features custom cabinetry, stainless steel appliances and stainless steel hood, Calacatta quartz countertops and a 10 ft Island with plentiful seating. Steps to Union Sq, cafe's, shops & restaurants. Central air, in unit laundry, oak hardwood floors, Navien on demand water tank and hardie siding. A short dista

$795,000

2 beds1.5 baths1,160 sq ft

144 Highland Ave #1, Somerville, MA 02143

Custom cabinetry • Gas fireplace • Private yard

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Attention Developers & Investors! Exciting opportunity in one of Somerville’s most desirable neighborhoods — Magoun Square! Located at 9–11 Norwood Ave, this property sits on a large lot, offering exceptional potential for new construction or redevelopment (buyer to perform due diligence). The existing structure provides a foundation for your vision—perfect for creating a modern multi-unit residence, luxury single-family home, or income-producing investment. Surrounded by vibrant local amenities, popular dining, and excellent transit options, including a short 7-minute (0.3 mile) walk to the new Lowell St. Green Line station, this location delivers long-term va

$850,000

4 beds2 baths1,796 sq ft

9-11 Norwood Ave, Somerville, MA 02145

New construction • Large lot • 2,648 sq ft lot

OPEN SUN, 11AM TO 1PM

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Well-located 4-unit multifamily in East Somerville with a desirable mix of (2) 2-bed/1-bath and (2) 4-bed/1-bath units. Two of the four units are currently tenant-at-will, providing near-term flexibility. With straightforward cosmetic updates, pro forma rents indicate solid upside potential and improved cash flow. The property includes at least six off-street parking spaces, offering optional additional income. Each unit has separately metered water, and the landlord pays no utilities, keeping operating expenses predictable. Strong East Somerville location with consistent rental demand and long-term appreciation—a solid opportunity for investors or owner-occupants.

$2,099,000

12 beds6 baths4,556 sq ft

19-21 Everett Ave, Somerville, MA 02145

Cosmetic updates • Off-street parking • 6,000 sq ft lot

ABOUT THIS HOME
Winter Hill, MA Homes for Sale
Welcome to this beautifully renovated home in the heart of Somerville, offering the perfect blend of charm, comfort, and modern convenience. This bright three-bedroom home features a highly desirable layout designed for everyday living. The first floor includes a spacious open layout with a eat-in kitchen with a built-in island ideal for breakfast stools, a functional dining room, an inviting living room filled with natural light, and a convenient half bathroom. Upstairs, you’ll find three generous bedrooms along with a full bathroom that provides comfort and practicality for all. Every detail in this property reflects thoughtful updates and quality workmanship. A truly wonderful spac

$849,999

3 beds1.5 baths1,727 sq ft

9 Cross St, Somerville, MA 02145

2,060 sq ft lot • Built 1890 • Listed 14 days

Property at 28 Highland Ave #3, Somerville, MA 02143, 2 beds, 1 bath

$685,000

2 beds1 bath907 sq ft

28 Highland Ave #3, Somerville, MA 02143

Property at 36 Everett Ave, Somerville, MA 02145, 7 beds, 7 baths

$2,699,999

7 beds7 baths3,952 sq ft

36 Everett Ave, Somerville, MA 02145

Property at 72 Governor Winthrop Rd #2, Somerville, MA 02145, 4 beds, 4 baths

$1,195,000

4 beds4 baths2,171 sq ft

72 Governor Winthrop Rd #2, Somerville, MA 02145

Property at 3 Vinal St, Somerville, MA 02145, 3 beds, 2.5 baths

$914,999

3 beds2.5 baths1,469 sq ft

3 Vinal St, Somerville, MA 02145

Property at 4 Cross St, Somerville, MA 02145, 5 beds, 3 baths

$929,500

5 beds3 baths1,953 sq ft

4 Cross St, Somerville, MA 02145

Property at 15 Albion, Somerville, MA 02143, 8 beds, 5 baths

$2,100,000

8 beds5 baths4,628 sq ft

15 Albion, Somerville, MA 02143

Property at 35 Richardson St Unit Cottage, Somerville, MA 02145, 2 beds, 2.5 baths

$1,150,000

2 beds2.5 baths1,088 sq ft

35 Richardson St Unit Cottage, Somerville, MA 02145

Property at 35 Richardson St #4, Somerville, MA 02145, 2 beds, 2.5 baths

$1,150,000

2 beds2.5 baths1,088 sq ft

35 Richardson St #4, Somerville, MA 02145

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

$1,750,000

10 beds5 baths4,184 sq ft

441 Broadway, Somerville, MA 02145

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

$929,900

10 beds6.5 baths5,735 sq ft

142 Cross St, Somerville, MA 02145

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

Average home prices near Winter Hill, MA

Cities

Neighborhoods

Downtown Boston homes for sale
$1,800,000
West End homes for sale
$739,000
Fenway-Kenmore homes for sale
$1,895,000
Cambridgeport homes for sale
$1,199,900
North End homes for sale
$1,314,000
Back Bay homes for sale
$2,350,000
Charlestown homes for sale
$949,995
West Medford homes for sale
$887,450
Allston homes for sale
$609,000
Beacon Hill homes for sale
$4,942,500

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)

$1,022,500

+4.3% YoY | Oct 2025

1 year
3 year
5 year

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

Location

Data

Oct 2025

Growth

% YoY

Winter Hill, MA

$1,022,500

+4.3%

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