Cheap Homes for Rent in Chestnut Hill Neighborhood of Boston, MA from $1,000 (115 Rentals)

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

property at 7 Timon Ave

7 Timon Ave, Unit 3

7 Timon Ave
Chestnut HillMA02467
property at 28 Sidlaw Rd

28 Sidlaw 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

Read Article
property at 6 Orkney Rd

6 Orkney Rd

BostonMA02135
property at 70 Strathmore Rd

70 Strathmore Rd

BostonMA02135
property at 12 Orkney Rd

12 Orkney Rd

BostonMA02135
property at 10 Orkney Rd

10 Orkney Rd

BostonMA02135
property at 32 Sidlaw Rd

32 Sidlaw Rd

BostonMA02135
property at 90 Kilsyth Rd

90 Kilsyth Rd

BostonMA02135
Showing Results 1-50, Page 1 of 3

Chestnut Hill, Boston, MA Local Guide

Best Value Apartments for Rent in Chestnut Hill, MA

As of March 28, 2025 the best value apartment in the Chestnut Hill area is the $0.23 price per square foot 90 Kilsyth Rd Model at 90 Kilsyth Rd, Unit 24 in the in the Chestnut Hill neighborhood starting from $2,300. The second greatest value Chestnut Hill apartment is the 48 Strathmore Rd Model at 48 Strathmore Rd, Unit #23 starting at $1,775 with a $0.18 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.
90 Kilsyth Rd, Unit 2490 Kilsyth Rd1BR,1BA$0.23
48 Strathmore Rd, Unit #2348 Strathmore RdStudio ,1BA$0.18
52 Lanark Rd, Unit #252 Lanark Rd1BR,1BA$0.22
24 Orkney Rd, Unit C24 Orkney Rd1BR,1BA$0.23
90 Kilsyth Rd, Unit 2490 Kilsyth Rd1BR,1BA$0.23
1933 Commonwealth Ave, Unit 171933 Commonwealth AveStudio ,1BA$0.20
90 Kilsyth Rd, Unit 2490 Kilsyth Rd1BR,1BA$0.23
70 Strathmore Rd, Unit 11A70 Strathmore RdStudio ,1BA$0.20
163 Strathmore Rd, Unit 4163 Strathmore Rd1BR,1BA$0.21
2016 Commonwealth Ave, Unit #1R2016 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 881 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $250 to $23,896. There are also 649 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $1,025 to $16,500.

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 $1,025 to $16,500 with an average monthly rent of $4,606.

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 $2,500 to $10,000, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $5,900. Four Bedroom Single-Family rentals are also available starting from $1,025 and Four Bedroom Apartments start at $250.

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.

decorative image for Understanding Amenity Fees: Know Where You Might Be Able to Save Money article

Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

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Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

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Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.