Cheap Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $700 (39 Rentals)

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Search the lowest-cost Homes available for rent right now in the Chestnut Hill Middlesex area of Chestnut Hill.

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.

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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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property at 2031 Commonwealth Ave

2031 Commonwealth Ave, Unit 12

2031 Commonwealth Ave
BostonMA02135
property at 4 Chiswick Rd

4 Chiswick Rd, Unit 5

4 Chiswick Rd
BostonMA02135

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.

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property at 1999 Commonwealth Ave

1999 Commonwealth Ave, Unit 01-2

1999 Commonwealth Ave
BostonMA02135
property at 4 Chiswick Rd

4 Chiswick Rd, Unit 24

4 Chiswick Rd
BostonMA02135
property at 19 Chestnut Hill Ave

19 Chestnut Hill Ave, Unit 3

19 Chestnut Hill Ave
BostonMA02135
property at 1872 Commonwealth Ave

1872 Commonwealth Ave, Unit 6

1872 Commonwealth Ave
BostonMA02135
property at 65 Strathmore Rd

65 Strathmore Rd

BostonMA02135
property at 1872 Commonwealth Ave

1872 Commonwealth Ave

BostonMA02135
property at 173 Chiswick Rd

173 Chiswick Rd, Unit 29

173 Chiswick Rd
BostonMA02135
property at 145 Englewood Ave

145 Englewood Ave, Unit 2##

145 Englewood Ave
BostonMA02135
property at 124 Academy Hill Rd

124 Academy Hill Rd, Unit B

124 Academy Hill Rd
BostonMA02135

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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property at 15 Beechcroft St

15 Beechcroft St

BostonMA02135
property at 10 Lothian Rd

10 Lothian Rd

BostonMA02135
property at 10 Lothian Rd

10 Lothian Rd, Unit 7

10 Lothian Rd
BostonMA02135
Showing Results 1-39, Page 1 of 1

Chestnut Hill Middlesex, Boston College, MA Local Guide

Best Value Apartments for Rent in Chestnut Hill Middlesex, MA

As of December 09, 2025 the best value apartment in the Chestnut Hill Middlesex area is the $0.20 price per square foot 2018 Commonwealth Avenue Model at 2018 Commonwealth Avenue, Unit 33 in the in the Chestnut Hill neighborhood starting from $1,950. The second greatest value Chestnut Hill Middlesex apartment is the 2016 Commonwealth Ave Model at 2016 Commonwealth Ave, Unit 2 starting at $1,950 with a $0.20 price per square foot in the Chestnut Hill neighborhood. Here is today’s list of the best values for Chestnut Hill Middlesex apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
2018 Commonwealth Avenue, Unit 332018 Commonwealth AvenueStudio ,1BA$0.20
2016 Commonwealth Ave, Unit 22016 Commonwealth AveStudio ,1BA$0.20
193 Strathmore Rd193 Strathmore Rd1BR,1BA$0.20
258 Chestnut Hill Ave, Unit 1258 Chestnut Hill AveStudio ,1BA$0.20
28 Sidlaw Rd, Unit 628 Sidlaw Rd1BR,1BA$0.20
20 Brock St, Unit 220 Brock St1BR,1BA$0.22
10 Trapelo St, Unit 210 Trapelo St1BR,1BA$0.22
7 Lothian Rd, Unit 37 Lothian Rd1BR,1BA$0.22
198 Strathmore Rd, Unit 3198 Strathmore Rd1BR,1BA$0.22
7 Trapelo St7 Trapelo St1BR,1BA$0.22

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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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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Pet Friendly Lifestyle
Chestnut Hill Middlesex, Chestnut Hill, MA

Ranked #1

Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Frequently Asked Questions about Chestnut Hill Middlesex

What type of rentals are currently available in Chestnut Hill Middlesex?

There are currently 464 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $945 to $14,300. There are also 409 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $730 to $17,500.

What is the current price range for Rental Homes in Chestnut Hill Middlesex?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestnut Hill Middlesex ranges from $730 to $17,500 with an average monthly rent of $7,010.

How much are larger Three and Four Bedroom Rentals in Chestnut Hill Middlesex?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestnut Hill Middlesex range from $2,550 to $6,220, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $7,000. Four Bedroom Single-Family rentals are also available starting from $830 and Four Bedroom Apartments start at $3,200.

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.

Articles, How-To's, and Tips

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

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.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

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.