Cheap Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $1,200 (156 Rentals)

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

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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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 60 Undine Rd

60 Undine 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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Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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property at 32 Sidlaw Rd

32 Sidlaw Rd

BostonMA02135
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Chestnut Hill Middlesex, Boston College, MA Local Guide

Best Value Apartments for Rent in Chestnut Hill Middlesex, MA

As of June 23, 2025 the best value apartment in the Chestnut Hill Middlesex area is the $0.25 price per square foot 2018 Commonwealth Avenue Model at 2018 Commonwealth Avenue, Unit 45 in the in the Chestnut Hill neighborhood starting from $2,500. The second greatest value Chestnut Hill Middlesex apartment is the 549 Washington St Model at 549 Washington St, Unit 1 starting at $2,200 with a $0.22 price per square foot in the St. Elizabeth's 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 452018 Commonwealth Avenue1BR,1BA$0.25
549 Washington St, Unit 1549 Washington St1BR,1BA$0.22
49 Winship St, Unit 12b49 Winship St2BR,1BA$0.25
30 Bentley St, Unit 330 Bentley StStudio ,1BA$0.19
30 Academy Hill Rd, Unit 230 Academy Hill Rd1BR,1BA$0.24
183 Strathmore Rd, Unit 2183 Strathmore Rd2BR,1BA$0.23
5 Chestnut Hill Ave, Unit 2-45 Chestnut Hill AveStudio ,1BA$0.20
5 Chestnut Hill Ave, Unit 2-45 Chestnut Hill AveStudio ,1BA$0.20
4 Chiswick Rd, Unit 354 Chiswick Rd1BR,1BA$0.24
1959 Commonwealth Ave, Unit 71959 Commonwealth AveStudio ,1BA$0.24

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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 1029 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $975 to $23,500. There are also 836 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,250 to $40,000.

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 $1,250 to $40,000 with an average monthly rent of $5,593.

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 $2,500 to $7,200, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,550 to $9,000. Four Bedroom Single-Family rentals are also available starting from $3,400 and Four Bedroom Apartments start at $1,025.

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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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.