
Cheap Homes for Rent in Hillside Street Neighborhood of Milton, MA from $1,500 (17 Rentals)
Search the lowest-cost Homes available for rent right now in the Hillside Street area of Milton.


1144 River St

25 Alpine St

1140 River St

100 Readville St
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.

837 River St

230 Willard St, Unit 512

40 Hilda St, Unit 2

176 Safford St

289 Highland Ave, Unit 1L
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.

231 Fayette St, Unit 2

20 Larry St, Unit 2

6 Monponset St

29 Laurel Rd, Unit #0

230 Willard St
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.

837 River St

68 Readville St
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 | $2,870 | $2,200 | $4,800 |
| Hillside Street 3 Bedroom Homes for Rent | $3,796 | $2,950 | $4,600 |
| Hillside Street 4 Bedroom Homes for Rent | $5,433 | $4,500 | $6,800 |
Browse Homes for Rent in this Neighborhood
There are currently 17 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 |
| Residences at Great Pond | A1A | 1BR,1BA | $2,214 |
Best Value Apartments for Rent in Hillside Street, MA
As of February 11, 2026 the best value apartment in the Hillside Street area is the $0.34 price per square foot 55 Gordon Ave Model at 55 Gordon Ave, Unit #2 in the in the Brush Hill neighborhood starting from $3,400. The second greatest value Hillside Street apartment is the 176 Brush Hill Rd Model at 176 Brush Hill Rd, Unit 2 starting at $3,500 with a $2.06 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. |
|---|---|---|---|
| 55 Gordon Ave, Unit #2 | 55 Gordon Ave | 2BR,1BA | $0.34 |
| 176 Brush Hill Rd, Unit 2 | 176 Brush Hill Rd | 4BR,2BA | $2.06 |
| 36 Lexington Ave, Unit 1 | 36 Lexington Ave | 1BR,1BA | $1.87 |
| Ridge at Blue Hills | Plan E (B2G) | 2BR,2BA | $2.38 |
| 1 Larry Pl, Unit 204 | 1 Larry Pl | 2BR,2BA | $2.46 |
| 196 Reservation Rd, Unit 2 | 196 Reservation Rd | 2BR,1BA | $2.04 |
| 26 Dana Ave, Unit 3 | 26 Dana Ave | 3BR,1BA | $2.36 |
| Quarry Edge 445 | 1 Bedroom + Den | 1BR,1BA | $2.47 |
| 213 Dana Ave, Unit 1 | 213 Dana Ave | 1BR,1BA | $2.11 |
| Reed Street Apartments | Renovated 1 Bedroom | 1BR,1BA | $2.57 |
Don'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 #3
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 57 Single Family Homes for rent, Condos, and Townhome rentals currently available in Hillside Street ranging from $1,590 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 $1,590 to $6,800 with an average monthly rent of $3,565.
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 $5,520, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,950 to $4,600. Four Bedroom Single-Family rentals are also available starting from $4,500 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
Written by: Amelia Ramstead
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.