Cheap Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $900 (64 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 1880 Commonwealth Ave

1880 Commonwealth Ave

BostonMA02135
property at 24 John St

24 John St, Unit 4

24 John St
NewtonMA02459
property at 2016 Commonwealth Ave

2016 Commonwealth Ave, Unit 1B

2016 Commonwealth Ave
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 1880 Commonwealth Ave

1880 Commonwealth Ave, Unit 15

1880 Commonwealth Ave
BostonMA02135
property at 189 Chestnut Hill Ave

189 Chestnut Hill Ave, Unit 1

189 Chestnut Hill Ave
BostonMA02135
property at 4 Chiswick Rd

4 Chiswick Rd

BostonMA02135
property at 4 Chiswick Rd

4 Chiswick Rd, Unit 5

4 Chiswick Rd
BostonMA02135
property at 2001 Commonwealth Ave

2001 Commonwealth Ave

BostonMA02135
property at 1999 Commonwealth Ave

1999 Commonwealth Ave, Unit 01-2

1999 Commonwealth Ave
BostonMA02135
property at 141 Englewood Ave

141 Englewood Ave, Unit 2

141 Englewood 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

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 145 Englewood Ave

145 Englewood Ave

BostonMA02135
property at 145 Englewood Ave

145 Englewood Ave, Unit 2

145 Englewood Ave
BostonMA02135
property at 247 Chestnut Hill Ave

247 Chestnut Hill 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

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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Showing Results 1-50, Page 1 of 2

Chestnut Hill Middlesex, Boston College, MA Local Guide

Cheapest Available Chestnut Hill Middlesex Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
Chiswick BuildingChiswick StudioStudio,1BA$2,200

Best Value Apartments for Rent in Chestnut Hill Middlesex, MA

As of October 24, 2025 the best value apartment in the Chestnut Hill Middlesex area is the $0.22 price per square foot 20 Brock St Model at 20 Brock St, Unit 2 in the in the St. Elizabeth's neighborhood starting from $2,200. The second greatest value Chestnut Hill Middlesex apartment is the 193 Strathmore Rd Model at 193 Strathmore Rd, Unit 10 starting at $2,000 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.
20 Brock St, Unit 220 Brock St1BR,1BA$0.22
193 Strathmore Rd, Unit 10193 Strathmore Rd1BR,1BA$0.20
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
20 Brock St, Unit 220 Brock St1BR,1BA$0.22
258 Chestnut Hill Ave, Unit 1258 Chestnut Hill AveStudio ,1BA$0.20
28 Sidlaw Rd, Unit 628 Sidlaw Rd1BR,1BA$0.20
7 Trapelo St7 Trapelo St1BR,1BA$0.22
7 Trapelo St, Unit A7 Trapelo St1BR,1BA$0.22

Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

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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

3.5
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 434 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $13,500. There are also 498 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $950 to $36,000.

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 $950 to $36,000 with an average monthly rent of $6,832.

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 $6,005, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $6,500. Four Bedroom Single-Family rentals are also available starting from $950 and Four Bedroom Apartments start at $3,150.

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.

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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.

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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.

decorative image for Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between article

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.