
Cheap Homes for Rent in Hillside Street Neighborhood of Milton, MA from $2,000 (18 Rentals)
Search the lowest-cost Homes available for rent right now in the Hillside Street area of Milton.


4 Eva Cir

40 Hilda St, Unit 2

289 Highland Ave, Unit 1L

6 Monponset St

231 Fayette St, Unit 2
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

20 Larry St, Unit 2

1416 Hyde Park Ave

29 Laurel Rd, Unit #0

790 Willard St

790 Willard St

36 Hillside Ave, Unit 2
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.

27 Roosevelt Rd, Unit 1

790 Willard St

Furnished Studio-Boston - Braintree

6 Monponset St

17 Albany St, Unit 1

60 Exeter St, Unit 2
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.
Hillside Street, Milton, MA Local Guide

How much does it cost to rent a home in Hillside Street?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Hillside Street 2 Bedroom Homes for Rent | $2,920 | $2,450 | $4,800 |
| Hillside Street 3 Bedroom Homes for Rent | $3,536 | $2,600 | $6,000 |
| Hillside Street 4 Bedroom Homes for Rent | $4,780 | $3,000 | $6,800 |
Browse Homes for Rent in this Neighborhood
There are currently 18 rentals with your search options within a 3 mile radius of the Hillside Street Neighborhood of Milton, MA.
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Hillside Street, Milton, MA Local Guide
- Nearby Milton neighborhoods
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Cheapest Available Hillside Street Apartments for Rent
 The cheapest available apartment rental in the Hillside Street area of Boston, MA is a Studio unit found at The Pryde – 62+ SENIOR priced from $1,483. J.E. Furnished Apartments of Quincy has the second lowest priced unit, which is a Studio apartment currently listed from $1,800. Here are the most affordable Hillside Street apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Pryde – 62+ SENIOR | Studio | Studio,1BA | $1,483 |
| J.E. Furnished Apartments of Quincy | Furnished Studio | Studio,1BA | $1,800 |
| Reed Street Apartments | Renovated 1 Bedroom | 1BR,1BA | $1,925 |
| Elmwood Park | One Bed One Bath | 1BR,1BA | $1,995 |
| Francis Crossing Apartment Homes | 1 Bedroom 1 Bathroom | 1BR,1BA | $2,125 |
Best Value Apartments for Rent in Hillside Street, MA
As of March 28, 2026 the best value apartment in the Hillside Street area is the $0.26 price per square foot 186 Summit Ave Model at 186 Summit Ave in the in the Quincy Center neighborhood starting from $2,600. The second greatest value Hillside Street apartment is the 39 Austin St Model at 39 Austin St, Unit 104 starting at $3,200 with a $0.32 price per square foot in the Brush Hill neighborhood. Here is today’s list of the best values for Hillside Street apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 186 Summit Ave | 186 Summit Ave | 2BR,1BA | $0.26 |
| 39 Austin St, Unit 104 | 39 Austin St | 1BR,1BA | $0.32 |
| 170 Summit Ave, Unit 2 | 170 Summit Ave | 2BR,1BA | $0.25 |
| 55 Gordon Ave, Unit #2 | 55 Gordon Ave | 2BR,1BA | $0.34 |
| 25 Austin St, Unit 301 | 25 Austin St | 2BR,1BA | $0.34 |
| 36 Lexington Ave, Unit 1 | 36 Lexington Ave | 1BR,1BA | $1.87 |
| Ridge at Blue Hills | Plan E (B2G) | 2BR,2BA | $2.41 |
| 196 Reservation Rd, Unit 2 | 196 Reservation Rd | 2BR,1BA | $2.04 |
| 26 Dana Ave, Unit 3 | 26 Dana Ave | 3BR,1BA | $2.36 |
| 213 Dana Ave, Unit 1 | 213 Dana Ave | 1BR,1BA | $2.11 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read ArticleDon't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleQuick 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.
Pet Friendly LifestyleHillside Street, Milton, MA
Ranked #2
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Best Local Schools in Hillside Street, Milton, MA
School data provided by Great Schools
Frequently Asked Questions about Hillside Street
What type of rentals are currently available in Hillside Street?
There are currently 216 Apartments for Rent in Hillside Street, MA with pricing that ranges from $1,483 to $8,200. There are also 52 Single Family Homes for rent, Condos, and Townhome rentals currently available in Hillside Street ranging from $2,000 to $6,800.
What is the current price range for Rental Homes in Hillside Street?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Hillside Street ranges from $2,000 to $6,800 with an average monthly rent of $3,461.
How much are larger Three and Four Bedroom Rentals in Hillside Street?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Hillside Street range from $2,600 to $5,585, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $6,000. Four Bedroom Single-Family rentals are also available starting from $3,000 and Four Bedroom Apartments start at $3,150.
Expert Rental Resources
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.
Helpful Local Expert Guides

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.

A Local Experts Guide to the Top Boston Neighborhoods for College Renters
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Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!

Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.