74 Oak St
RandolphMA02368
Cheap Homes for Rent in Hillside Street Neighborhood of Milton, MA from $1,100 (15 Rentals)
Search the lowest-cost Homes available for rent right now in the Hillside Street area of Milton.
25 Alpine St
BostonMA02126
36 Fitzgerald St
RandolphMA02368
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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.
1144 River St
BostonMA02136
141 Willard St
QuincyMA02169
310 Copeland St
QuincyMA02169
40 Hilda St, Unit 2
40 Hilda St
QuincyMA02169
289 Highland Ave, Unit 1L
289 Highland Ave
QuincyMA02170
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
231 Fayette St
QuincyMA02170
20 Larry St, Unit 2
20 Larry St
QuincyMA02169
29 Laurel Rd, Unit #0
29 Laurel Rd
MiltonMA02186
16 Central Ave
BostonMA02136
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Cash 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.
Showing Results 1-15, Page 1 of 1
Hillside Street, Milton, MA Local Guide
Puget Sound by Will is licensed under CC BY 2.0
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 | $2,840 | $2,000 | $4,800 |
| Hillside Street 3 Bedroom Homes for Rent | $3,206 | $2,395 | $4,100 |
| Hillside Street 4 Bedroom Homes for Rent | $3,816 | $3,200 | $4,500 |
| Hillside Street 5 Bedroom Homes for Rent | $6,000 | $6,000 | $6,000 |
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 15 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
- Nearby Cities
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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. Logan Square Residences - 55+ Community has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,530. 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 |
| Logan Square Residences - 55+ Community | One Bedroom 50% | 1BR,1BA | $1,530 |
| Reed Street Apartments | Renovated Studio | Studio,1BA | $1,675 |
| J.E. Furnished Apartments of Quincy | Furnished Studio | Studio,1BA | $1,800 |
| 10 Thorn | 1BR | 1BR,1BA | $1,900 |
Best Value Apartments for Rent in Hillside Street, MA
As of December 16, 2025 the best value apartment in the Hillside Street area is the $0.38 price per square foot 12 Radcliffe Rd Model at 12 Radcliffe Rd, Unit 1 in the in the Brush Hill neighborhood starting from $3,795. 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. |
|---|---|---|---|
| 12 Radcliffe Rd, Unit 1 | 12 Radcliffe Rd | 3BR,1BA | $0.38 |
| 176 Brush Hill Rd, Unit 2 | 176 Brush Hill Rd | 4BR,1.5BA | $2.06 |
| 2205 Washington St, Unit 2 | 2205 Washington St | 3BR,1.5BA | $2.13 |
| 36 Lexington Ave, Unit 1 | 36 Lexington Ave | 1BR,1BA | $1.87 |
| Ridge at Blue Hills | Plan E (B2G) | 2BR,2BA | $2.45 |
| 1 Larry Pl, Unit 204 | 1 Larry Pl | 2BR,2BA | $2.46 |
| 26 Dana Ave, Unit 3 | 26 Dana Ave | 3BR,1BA | $2.55 |
| Quarry Edge 445 | 1 Bedroom + Den | 1BR,1BA | $2.47 |
| 10 Thorn | 1BR | 1BR,1BA | $2.53 |
| The Pryde – 62+ SENIOR | Studio | Studio ,1BA | $2.62 |
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.
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The 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.
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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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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 205 Apartments for Rent in Hillside Street, MA with pricing that ranges from $1,400 to $5,000. There are also 60 Single Family Homes for rent, Condos, and Townhome rentals currently available in Hillside Street ranging from $1,150 to $6,000.
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 $1,150 to $6,000 with an average monthly rent of $3,621.
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 $4,391, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,395 to $4,100. Four Bedroom Single-Family rentals are also available starting from $3,200 and Four Bedroom Apartments start at $3,400.
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
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.
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.