Cheap Homes for Rent in Chestnut Hill, MA from $1,000 (591 Rentals)

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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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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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Boston's Best Affordable Neighborhoods

Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

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Chestnut Hill, MA Local Guide

Cheapest Available Chestnut Hill Apartments for Rent

 

The cheapest available apartment rental in Chestnut Hill, MA is a Studio unit found at CHR Brookline - Coolidge Corner Communities in the Kendall Square neighborhood priced from $1,750. Stony Brook Village in the Brush Hill neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,752. Here is today’s list of the most affordable Chestnut Hill apartments for rent:

Apartment ListingModel NameBed/BathPriced From
CHR Brookline - Coolidge Corner CommunitiesHampton Court - Studio/1 BathStudio,1BA$1,750
Stony Brook VillageOne Bedroom1BR,1BA$1,752
176 Naples RdStudioStudio,1BA$1,775

Best Value Apartments for Rent in Chestnut Hill, MA

As of June 24, 2025 the best value apartment in the Chestnut Hill area is the $0.18 price per square foot 22 Shepard St Model at 22 Shepard St, Unit B in the in the St. Elizabeth's neighborhood starting from $1,800. The second greatest value Chestnut Hill apartment is the 15 Walbridge St Model at 15 Walbridge St, Unit 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 apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
22 Shepard St, Unit B22 Shepard St1BR,1BA$0.18
15 Walbridge St, Unit 415 Walbridge St1BR,1BA$0.20
84 Gordon St, Unit 10184 Gordon StStudio ,1BA$0.19
1669 Commonwealth Ave, Unit 221669 Commonwealth AveStudio ,1BA$0.20
30 Bentley St, Unit 330 Bentley StStudio ,1BA$0.19
1440 Commonwealth Ave, Unit 121440 Commonwealth AveStudio ,1BA$0.19
317 Allston St, Unit 15317 Allston StStudio ,1BA$0.20
1460 Commonwealth Ave, Unit 1450-111460 Commonwealth AveStudio ,1BA$0.21
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

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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Frequently Asked Questions about Chestnut Hill

What type of rentals are currently available in Chestnut Hill?

There are currently 8200 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $900 to $50,000. There are also 6507 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $1,075 to $40,000.

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

Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestnut Hill ranges from $1,075 to $40,000 with an average monthly rent of $5,644.

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

For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestnut Hill range from $1,100 to $18,471, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,950 to $12,000. Four Bedroom Single-Family rentals are also available starting from $1,075 and Four Bedroom Apartments start at $920.

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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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.

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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.