18 Highland Ave, Unit 1
18 Highland Ave
SomervilleMA02143
Luxury Homes for Rent in Winter Hill Neighborhood of Somerville, MA (111 Rentals) Page 2 of 3
The most luxurious Homes in the Winter Hill area of Somerville with high-end amenities, features, and finishes.
79 Bailey Rd, Unit 1##
79 Bailey Rd
SomervilleMA02145
171 Walnut St, Unit 2
171 Walnut St
SomervilleMA02145
10 Evergreen Ave, Unit 3
10 Evergreen Ave
SomervilleMA02145
10 Evergreen Ave, Unit 3
10 Evergreen Ave
SomervilleMA02145
101 Heath St, Unit 1
101 Heath St
SomervilleMA02145
7 Landers St, Unit 2
7 Landers St
SomervilleMA02143
101 School St, Unit 2
101 School St
SomervilleMA02143
43 Thurston St, Unit 2
43 Thurston St
SomervilleMA02145
45 Thurston St, Unit 2
45 Thurston St
SomervilleMA02145
27R Albion St, Unit 1
27R Albion St
SomervilleMA02143
41 Sycamore St, Unit 41
41 Sycamore St
SomervilleMA02143
27R Albion St, Unit 1
27R Albion St
SomervilleMA02143
27R Albion St, Unit 1
27R Albion St
SomervilleMA02143
109 Summer St, Unit 3
109 Summer St
SomervilleMA02143
103 Summer St, Unit 3
103 Summer St
SomervilleMA02143
105 Summer St, Unit 3
105 Summer St
SomervilleMA02143
103 Summer St, Unit 3
103 Summer St
SomervilleMA02143
103 Summer St, Unit M-3
103 Summer St
SomervilleMA02143
103 Summer St, Unit 3
103 Summer St
SomervilleMA02143
110 Central St, Unit 3R
110 Central St
SomervilleMA02143
88 Gilman St, Unit 2
88 Gilman St
SomervilleMA02145
22 Hamlet St, Unit 4
22 Hamlet St
SomervilleMA02143
50 Derby St, Unit 2
50 Derby St
SomervilleMA02145
50 Derby St, Unit 2
50 Derby St
SomervilleMA02145
31 Wheatland St, Unit 1
31 Wheatland St
SomervilleMA02145
106 Summer St, Unit 3
106 Summer St
SomervilleMA02143
133 Cross St, Unit 2
133 Cross St
SomervilleMA02145
22 Grand View Ave, Unit 2
22 Grand View Ave
SomervilleMA02143
122 Cross St, Unit 6
122 Cross St
SomervilleMA02145
126 Cross St, Unit #4
126 Cross St
SomervilleMA02145
25 MacArthur St, Unit 2
25 MacArthur St
SomervilleMA02145
25 MacArthur St, Unit 2
25 MacArthur St
SomervilleMA02145
62 Governor Winthrop Rd, Unit 2##
62 Governor Winthrop Rd
SomervilleMA02145
27R Albion St, Unit 5-bed 2bathU2
27R Albion St
SomervilleMA02143
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$2,500
Plus Fees
Studio Apartments Available Nov 15, 2026138 Highland Ave
138 Highland AveSomerville, MA 02143
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$3,000
Plus Fees
2 Bedroom Apartments Available Now123 Highland Ave
123 Highland AveSomerville, MA 02143
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$3,600
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Now39 Bradley St.
39 Bradley St.Somerville, MA 02145
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$3,500
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Now58 Vinal Ave
58 Vinal AveSomerville, MA 02143
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$3,000
Plus Fees
2 Bedroom Apartments Available Now123 Highland Ave
123 Highland AveSomerville, MA 02143
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$4,035
Total Monthly Price
2 Bedroom Apartments Available May 12, 2026Total Monthly Price
Base Rent
$3,620
Required Monthly Fees
$415
Total Monthly Price
$4,035
400 Mystic Ave
400 Mystic AveSomerville, MA 02145
90 Glenwood Rd
SomervilleMA02145
25 Putnam St
SomervilleMA02143
102 Grant St
SomervilleMA02145
2 Auburn Ave
SomervilleMA02145
3 Edgar Terrace
SomervilleMA02145
372 Medford St
SomervilleMA02145
Winter Hill, Somerville, MA Local Guide
Sunset on the Mystic by Flickr User: ekilby is licensed under CC BY 2.0
How much does it cost to rent a home in Winter Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winter Hill 2 Bedroom Homes for Rent | $3,044 | $2,200 | $3,700 |
| Winter Hill 3 Bedroom Homes for Rent | $3,719 | $2,500 | $5,800 |
| Winter Hill 4 Bedroom Homes for Rent | $3,883 | $1,100 | $5,400 |
| Winter Hill 5 Bedroom Homes for Rent | $5,280 | $3,400 | $6,500 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 111 rentals with your search options within a 2 mile radius of the Winter Hill Neighborhood of Somerville, MA.
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Frequently Asked Questions about Winter Hill
What type of rentals are currently available in Winter Hill?
There are currently 268 Apartments for Rent in Winter Hill, MA with pricing that ranges from $950 to $7,700. There are also 129 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Hill ranging from $1,100 to $6,500.
What is the current price range for Rental Homes in Winter Hill?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winter Hill ranges from $1,100 to $6,500 with an average monthly rent of $3,523.
How much are larger Three and Four Bedroom Rentals in Winter Hill?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winter Hill range from $2,700 to $7,700, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $5,800. Four Bedroom Single-Family rentals are also available starting from $1,100 and Four Bedroom Apartments start at $3,400.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
The 10 Best Affordable Neighborhoods in Boston, MA
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.