Cheap Homes for Rent in Chestnut Hill Neighborhood of Boston, MA from $1,800 (160 Rentals)

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Cheap Homes in the Chestnut Hill area of Boston.

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 70 Strathmore Rd

70 Strathmore Rd

BostonMA02135

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

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property at 32 Sidlaw Rd

32 Sidlaw Rd

BostonMA02135
property at 90 Kilsyth Rd

90 Kilsyth Rd

BostonMA02135

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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property at 21 Kinross Rd

21 Kinross Rd

BostonMA02135
Showing Results 1-50, Page 1 of 4

Chestnut Hill, Boston, MA Local Guide

Cheapest Available Chestnut Hill Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
Flats on CommDartmouth One Bed1BR,1BA$2,050
35 Orkney Rd1 beds, 1 bath1BR,1BA$2,075

Best Value Apartments for Rent in Chestnut Hill, MA

As of May 09, 2025 the best value apartment in the Chestnut Hill 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 apartment is the 43 Selkirk Rd Model at 43 Selkirk Rd, Unit #61 - 4 starting at $2,350 with a $0.24 price per square foot in the Chestnut Hill 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.
2018 Commonwealth Avenue, Unit 452018 Commonwealth Avenue1BR,1BA$0.25
43 Selkirk Rd, Unit #61 - 443 Selkirk Rd1BR,1BA$0.24
48 Strathmore Rd, Unit #2348 Strathmore RdStudio ,1BA$0.18
24 Orkney Rd, Unit C24 Orkney Rd1BR,1BA$0.23
132 Sutherland Rd, Unit A132 Sutherland Rd1BR,1BA$0.24
90 Kilsyth Rd, Unit 2490 Kilsyth Rd1BR,1BA$0.23
21 Orkney Rd, Unit 521 Orkney Rd1BR,1BA$0.23
2 Sutherland Rd, Unit 22 Sutherland Rd2BR,1BA$0.24
12 Gerald Rd, Unit 2412 Gerald Rd1BR,1BA$0.24
2021 Commonwealth Ave, Unit #12021 Commonwealth Ave1BR,1BA$0.22

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Frequently Asked Questions about Chestnut Hill

What type of rentals are currently available in Chestnut Hill?

There are currently 733 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,025 to $29,749. There are also 657 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $1,825 to $45,000.

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 $1,825 to $45,000 with an average monthly rent of $4,975.

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 $1,250 to $8,655, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,895 to $7,500. Four Bedroom Single-Family rentals are also available starting from $3,525 and Four Bedroom Apartments start at $1,075.

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.

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

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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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.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.

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Rise of Digital Nomads: Remote Work Tips for Apartment Renters

Written by: Brandie Parton

As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.