5 Bedroom Homes for Rent in Chestnut Hill, MA(244 Rentals)Page 5 of 5

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81 Gibbs St
$8,5005 Bedroom, 3 Bath Townhome for RentAvailable Aug 31, 2025

81 Gibbs St, Unit 1

81 Gibbs St
Brookline, MA 02446
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31-33 Greycliff Rd
$8,6005 Bedroom, 2 Bath Condo for RentAvailable Now

31-33 Greycliff Rd

Boston, MA 02135
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12 Gerald Rd
$9,0005 Bedroom, 3 Bath Condo for RentAvailable Now

12 Gerald Rd, Unit 1

12 Gerald Rd
Boston, MA 02135
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12 Gerald Rd
$9,5005 Bedroom, 3 Bath Condo for RentAvailable Sep 1, 2025

12 Gerald Rd

Boston, MA 02135
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12 Gerald Rd
$9,5005 Bedroom, 3 Bath Home for RentAvailable Sep 1, 2025

12 Gerald Rd

Boston, MA 02135
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12 Gerald Rd
$9,5005 Bedroom, 3 Bath Home for RentAvailable Sep 1, 2025

12 Gerald Rd

Boston, MA 02135
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23 Winchester Rd
$10,5005 Bedroom, 4 Bath Townhome for RentAvailable Now

23 Winchester Rd

Newton, MA 02458
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75 Somerset Rd
$11,5005 Bedroom, 2 Bath Townhome for RentAvailable Now

75 Somerset Rd

Brookline, MA 02445
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47 Orkney Rd
$5,2505 Bedroom, 2 Bath Condo for RentAvailable Now

47 Orkney Rd

Boston, MA 02135
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1914 Beacon St
$5,9005 Bedroom, 2 Bath Condo for RentAvailable Now

1914 Beacon St

Boston, MA 02135
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Frequently Asked Questions about Chestnut Hill

What type of rentals are currently available in Chestnut Hill?

There are currently 6499 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $825 to $45,000. There are also 2739 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $1,045 to $21,000.

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 $1,045 to $21,000 with an average monthly rent of $5,924.

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 $950 to $15,711, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,950 to $11,000. Four Bedroom Single-Family rentals are also available starting from $1,200 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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Signing Your Apartment Lease: The Basics

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When you're about to sign a lease for the first time, it can feel a bit overwhelming. You don’t want to miss any important details hidden in the fine print. While most leases...

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What to Know About Fees and Fines When Renting

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When it comes to renting a new apartment or home there can be a number of fees that you will want to keep in mind going into the process. While fees will range depending on...

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Real Estate Term Glossary: Your Guide to The A to Zs of Renting

Written by: Kevin Ready

Navigating the world of real estate can reveal an abundance of terminology and phrasing around the topics of renting and buying that for some may seem like a brand-new...

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Navigating the World of Low-Income Housing: A Comprehensive Guide

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Are you having difficulty keeping up with bills or paying the rent? If so, you are not alone. Many families struggle to keep up with rents that have increased up to 40% in...