Cheap Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $1,200 (124 Rentals)

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Cheap Homes in the Chestnut Hill Middlesex area of Chestnut Hill.

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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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 60 Undine Rd

60 Undine Rd

BostonMA02135
property at 32 Sidlaw Rd

32 Sidlaw Rd

BostonMA02135
Showing Results 1-50, Page 1 of 3

Chestnut Hill Middlesex, Boston College, MA Local Guide

Best Value Apartments for Rent in Chestnut Hill Middlesex, MA

As of May 02, 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
5 Pama Gdns, Unit 45 Pama Gdns1BR,1BA$0.22
36 Dighton St, Unit 336 Dighton St1BR,1BA$0.20
30 Academy Hill Rd, Unit 230 Academy Hill Rd1BR,1BA$0.24
12 Gerald Rd, Unit 2412 Gerald Rd1BR,1BA$0.24
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
2021 Commonwealth Ave, Unit #12021 Commonwealth Ave1BR,1BA$0.22

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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 1021 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $800 to $25,723. There are also 784 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,250 to $21,000.

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 $21,000 with an average monthly rent of $4,676.

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 $1,350 to $8,655, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $7,500. Four Bedroom Single-Family rentals are also available starting from $2,900 and Four Bedroom Apartments start at $900.

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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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.

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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Written by: Christine Leonard, Esq.

Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.

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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.