100 Flint St
SomervilleMA02145
Cheap Apartments for Rent in the Winter Hill Neighborhood of Somerville, MA from $1,000 (47 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winter Hill area of Somerville.
100 Flint St
SomervilleMA02145
100 Flint St
SomervilleMA02145
Private bedroom in 4 bed/1.5 bath Home
17 Kenneson Rd
SomervilleMA02145
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from $1,725Studio Apartment Available Now
11 Langmaid Ave, Unit #C3
11 Langmaid AveSomerville, MA 02145
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from $1,850Studio Apartment Available Aug 1
145 Highland Ave, Unit 3
145 Highland AveSomerville, MA 02143
Private bedroom in 4 bed/1 bath Home
59 Glenwood Rd
SomervilleMA02145
335 Broadway
SomervilleMA02145
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
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Rent Specials
from $2,050Studio to 3 Bedroom Apartments Available Now
Somerville Square
379-385 BroadwaySomerville, MA 02145
134 Pearl St
SomervilleMA02145
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from $2,1001 Bedroom Apartment Available Now
138 Pearl St, Unit 134-2
138 Pearl StSomerville, MA 02145
48 Highland Ave
SomervilleMA02143
155 Pearl St
SomervilleMA02145
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from $2,2001 Bedroom Apartment Available Sep 1
131 Summer St, Unit 1R
131 Summer StSomerville, MA 02143
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
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from $2,2002 Bedroom Apartment Available Jul 1
129 Summer St, Unit 1B
129 Summer StSomerville, MA 02143
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from $2,215Studio Apartment Available Now
130 Highland Ave, Unit 3
130 Highland AveSomerville, MA 02143
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from $2,250Studio Apartment Available Now
145 Highland Ave, Unit #30
145 Highland AveSomerville, MA 02143
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Rent Specials
from $2,250Studio to 1 Bedroom Apartments Available Now
136 & 138 Highland Avenue
136-138 Highland AveSomerville, MA 02143
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from $2,3001 Bedroom Apartment Available Now
481 Medford St, Unit #1
481 Medford StSomerville, MA 02145
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from $2,350Studio Apartment Available Now
129 Highland Ave, Unit 26
129 Highland AveSomerville, MA 02143
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from $2,4002 Bedroom Apartment Available Now
465 Medford St, Unit 3
465 Medford StSomerville, MA 02145
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
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from $2,4001 Bedroom Apartment Available Aug 31
30 Pembroke St, Unit A
30 Pembroke StSomerville, MA 02145
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from $2,4001 Bedroom Apartment Available Aug 31
162 Broadway, Unit 8u
162 BroadwaySomerville, MA 02145
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136 Highland Ave
SomervilleMA02143
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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from $2,4501 Bedroom Apartment Available Sep 1
455 Broadway, Unit 465 Broadway #6
455 BroadwaySomerville, MA 02145
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from $2,4501 Bedroom Apartment Available Jul 1
131 Summer St, Unit 10F
131 Summer StSomerville, MA 02143
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from $2,5001 Bedroom Apartment Available Now
108 Thurston St, Unit 6
108 Thurston StSomerville, MA 02145
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52 Laurel St
SomervilleMA02143
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Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead
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Private bedroom in 4 bed/1.5 bath Home
17 Kenneson
BostonMA02145
Showing Results 1-47, Page 1 of 1
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 an apartment in Winter Hill?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Hill Studio Apartments | $2,272 | $1,725 | $2,675 |
| Winter Hill 1 Bedroom Apartments | $2,635 | $2,100 | $4,400 |
| Winter Hill 2 Bedroom Apartments | $3,364 | $2,200 | $5,000 |
| Winter Hill 3 Bedroom Apartments | $3,733 | $2,695 | $5,500 |
| Winter Hill 4 Bedroom Apartments | $4,123 | $1,075 | $6,050 |
| Winter Hill 5 Bedroom Apartments | $5,306 | $4,150 | $6,500 |
Browse Apartments in this Neighborhood
There are currently 47 rentals with your search options within a 2 mile radius of the Winter Hill Neighborhood of Somerville, MA.
See all Apartments in SomervilleExplore Somerville
Winter Hill, Somerville, MA Local Guide
- Nearby Somerville neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Winter Hill Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 136 & 138 Highland Avenue | Studio | Studio,1BA | $2,250 |
Best Value Apartments for Rent in Winter Hill, MA
As of June 23, 2025 the best value apartment in the Winter Hill area is the $0.28 price per square foot 25 MacArthur St Model at 25 MacArthur St, Unit 1R in the in the Kendall Square neighborhood starting from $2,800. The second greatest value Winter Hill apartment is the 55 Marshall St Model at 55 Marshall St, Unit 1 starting at $3,500 with a $0.35 price per square foot in the Kendall Square neighborhood. Here is today’s list of the best values for Winter Hill apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 25 MacArthur St, Unit 1R | 25 MacArthur St | 1BR,1BA | $0.28 |
| 55 Marshall St, Unit 1 | 55 Marshall St | 2BR,1BA | $0.35 |
| 90 Gilman St, Unit 1 | 90 Gilman St | 3BR,1BA | $0.35 |
| 171 Walnut St, Unit 5 | 171 Walnut St | 3BR,2BA | $0.40 |
| 22 Grand View Ave, Unit 1 | 22 Grand View Ave | 3BR,1BA | $0.36 |
| 510 Medford St, Unit 1 | 510 Medford St | 3BR,2BA | $0.38 |
| 110 Central St, Unit 1 | 110 Central St | 3BR,1BA | $0.28 |
| 67 Avon St, Unit 1 | 67 Avon St | 3BR,1BA | $0.30 |
| 67 Wheatland St, Unit 1 | 67 Wheatland St | 2BR,1BA | $0.32 |
| 238 School St, Unit P3 | 238 School St | 2BR,1BA | $0.30 |
Quick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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If you’re an expert on all things Winter Hill, tell us what you love (and don't) by rating it and writing a review.
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Pet Friendly LifestyleWinter Hill, Somerville, MA
Ranked #11
Among neighborhoods in Somerville, MA for Apartment listings with Pet Friendly Amenities
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Getting Around the Winter Hill Neighborhood in Somerville, MA
Walk Score®
90 / 100
Walker’s Paradise
Daily errands do not require a car
Bike Score®
85 / 100
Very Bikeable
Biking is convenient for most trips
Transit Score®
55 / 100
Good Transit
Many nearby public transportation options
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Winter Hill Apartments
What is the Cheapest Studio apartment in Winter Hill?
Currently the most affordable Cheap Studio Apartment in Winter Hill is at 136 & 138 Highland Avenue listed at $2,250.
What is the lowest price for a Cheap Two Bedroom Winter Hill Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winter Hill is starting from $2,590 at Somerville Square.
What is the most affordable Winter Hill Three Bedroom Apartment?
The best deal on a cheap Winter Hill Three Bedroom Apartment rental is at Somerville Square and starts from $3,125.
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.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.