Cheap Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $900 (157 Rentals)

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Search the lowest-cost Apartments 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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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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Chestnut Hill Middlesex, Boston College, MA Local Guide

Best Value Apartments for Rent in Chestnut Hill Middlesex, MA

As of July 11, 2025 the best value apartment in the Chestnut Hill Middlesex area is the $0.19 price per square foot 30 Bentley St Model at 30 Bentley St, Unit 3 in the in the St. Elizabeth's neighborhood starting from $1,900. The second greatest value Chestnut Hill Middlesex apartment is the 5 Chestnut Hill Ave Model at 5 Chestnut Hill Ave, Unit 2-4 starting at $2,000 with a $0.20 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.
30 Bentley St, Unit 330 Bentley StStudio ,1BA$0.19
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
549 Washington St, Unit 1549 Washington St1BR,1BA$0.22
19 Chestnut Hill Ave, Unit 319 Chestnut Hill AveStudio ,1BA$0.22
1933 Commonwealth Ave, Unit 171933 Commonwealth Ave1BR,1BA$0.23
183 Strathmore Rd, Unit 2183 Strathmore Rd2BR,1BA$0.23
30 Academy Hill Rd, Unit 230 Academy Hill Rd1BR,1BA$0.24
2000 Commonwealth Ave, Unit 2018-012000 Commonwealth Ave1BR,1BA$0.24
2000 Commonwealth Ave, Unit 2018-12000 Commonwealth Ave1BR,1BA$0.24

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Pet Friendly Lifestyle
Chestnut Hill Middlesex, Chestnut Hill, MA

Ranked #2

Among neighborhoods in Chestnut Hill, MA for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Getting Around the Chestnut Hill Middlesex Neighborhood in Chestnut Hill, MA

Walk Score®

59 / 100

Somewhat Walkable

Some errands can be accomplished on foot

Bike Score®

47 / 100

Somewhat Bikeable

Minimal bike infrastructure

Transit Score®

53 / 100

Good Transit

Many nearby public transportation options

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Cheap Chestnut Hill Middlesex Apartments

How much is rent for a Cheap One Bedroom Chestnut Hill Middlesex Apartment?

The lowest price for a Cheap One Bedroom Chestnut Hill Middlesex Apartment is $2,195 at 31-35 South Street.

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.