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

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28 Manet Rd
$5,6005 Bedroom, 1 Bath Condo for RentAvailable Now

28 Manet Rd

Chestnut Hill, MA 02467
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28 Manet Rd
$5,8005 Bedroom, 1 Bath Condo for RentAvailable Sep 1, 2025

28 Manet Rd

Chestnut Hill, MA 02467
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28 Manet Rd
$5,8005 Bedroom, 1 Bath Condo for RentAvailable Sep 1, 2025

28 Manet Rd

Chestnut Hill, MA 02467
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794 Boylston St
$5,9505 Bedroom, 2 Bath Condo for RentAvailable Now

794 Boylston St

Chestnut Hill, MA 02467
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25 Crosby Rd
$7,0005 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

25 Crosby Rd, Unit 1

25 Crosby Rd
Chestnut Hill, MA 02467
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25 Crosby Rd
$7,0005 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

25 Crosby Rd

Chestnut Hill, MA 02467
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1789 Commonwealth Ave
$4,0005 Bedroom, 2 Bath Condo for RentAvailable Now

1789 Commonwealth Ave

Boston, MA 02135
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32 Bayard St
$4,2505 Bedroom, 2 Bath Condo for RentAvailable Now

32 Bayard St, Unit 3

32 Bayard St
Boston, MA 02134
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35 Long Ave
$4,2505 Bedroom, 2 Bath Condo for RentAvailable Now

35 Long Ave, Unit 2

35 Long Ave
Boston, MA 02134
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16 Alcott St
$4,4005 Bedroom, 2 Bath Condo for RentAvailable Now

16 Alcott St, Unit 2

16 Alcott St
Boston, MA 02134
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23 Aldie St
$4,4005 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

23 Aldie St, Unit 1

23 Aldie St
Boston, MA 02134
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35 Long Ave
$4,4405 Bedroom, 2 Bath Condo for RentAvailable Now

35 Long Ave, Unit 2

35 Long Ave
Boston, MA 02134
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91 Wallingford Rd
$4,5005 Bedroom, 2 Bath Condo for RentAvailable Now

91 Wallingford Rd, Unit 4

91 Wallingford Rd
Boston, MA 02135
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20 Priscilla Rd
$4,5005 Bedroom, 2 Bath Condo for RentAvailable Now

20 Priscilla Rd, Unit 4

20 Priscilla Rd
Boston, MA 02135
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24 Priscilla Rd
$4,5005 Bedroom, 2 Bath Condo for RentAvailable Now

24 Priscilla Rd, Unit 4

24 Priscilla Rd
Boston, MA 02135
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32 Blenford Rd
$4,5005 Bedroom, 2 Bath Condo for RentAvailable Now

32 Blenford Rd, Unit 3

32 Blenford Rd
Boston, MA 02135
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18 Malbert Rd
$4,5005 Bedroom, 3 Bath Condo for RentAvailable Now

18 Malbert Rd, Unit 1

18 Malbert Rd
Boston, MA 02135
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28 Priscilla Rd
$4,5005 Bedroom, 2 Bath Condo for RentAvailable Now

28 Priscilla Rd, Unit 4

28 Priscilla Rd
Boston, MA 02135
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42 Gerrish St
$4,5005 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

42 Gerrish St

Boston, MA 02135
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16 Priscilla Rd
$4,5005 Bedroom, 2 Bath Condo for RentAvailable Now

16 Priscilla Rd, Unit 2

16 Priscilla Rd
Boston, MA 02135
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23 Priscilla Rd
$4,5005 Bedroom, 2 Bath Condo for RentAvailable Now

23 Priscilla Rd, Unit 1

23 Priscilla Rd
Boston, MA 02135
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40 Orchard Rd
$4,5505 Bedroom, 2 Bath Condo for RentAvailable Now

40 Orchard Rd, Unit 2

40 Orchard Rd
Brookline, MA 02445
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64-66 Litchfield St
$4,6005 Bedroom, 2 Bath Condo for RentAvailable Now

64-66 Litchfield St, Unit 1

64-66 Litchfield St
Boston, MA 02135
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39 Falkland St
$4,6005 Bedroom, 2 Bath Condo for RentAvailable Now

39 Falkland St, Unit 2

39 Falkland St
Boston, MA 02135
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194 Kelton St
$4,6005 Bedroom, 2 Bath Condo for RentAvailable Now

194 Kelton St

Boston, MA 02134
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119 Glenville Ave
$4,7005 Bedroom, 2 Bath Condo for RentAvailable Now

119 Glenville Ave, Unit 1

119 Glenville Ave
Boston, MA 02134
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100C Allandale St
$4,7005 Bedroom, 3 Bath Home for RentAvailable Now

100C Allandale St

Boston, MA 02130
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68 Etna St
$4,7505 Bedroom, 2 Bath Condo for RentAvailable Now

68 Etna St, Unit 2

68 Etna St
Boston, MA 02135
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64 Litchfield St
$4,8005 Bedroom, 2 Bath Condo for RentAvailable Now

64 Litchfield St, Unit #1

64 Litchfield St
Boston, MA 02135
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46 Ashford St
$4,8005 Bedroom, 2 Bath Condo for RentAvailable Now

46 Ashford St, Unit 2

46 Ashford St
Boston, MA 02134
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132 Chiswick Rd
$4,8005 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

132 Chiswick Rd, Unit 2

132 Chiswick Rd
Boston, MA 02135
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127 Glenville Ave
$4,9005 Bedroom, 3 Bath Condo for RentAvailable Now

127 Glenville Ave, Unit 1

127 Glenville Ave
Boston, MA 02134
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8 Glenville Ave
$4,9005 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

8 Glenville Ave, Unit 5

8 Glenville Ave
Boston, MA 02134
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26 Ashford St
$4,9505 Bedroom, 1 Bath Condo for RentAvailable Sep 1, 2025

26 Ashford St, Unit 2

26 Ashford St
Boston, MA 02134
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133 Glenville Ave
$4,9505 Bedroom, 3 Bath Condo for RentAvailable Now

133 Glenville Ave, Unit 1

133 Glenville Ave
Boston, MA 02134
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42 Gerrish St
$5,0005 Bedroom, 1 Bath Condo for RentAvailable Now

42 Gerrish St, Unit 1

42 Gerrish St
Boston, MA 02135
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Chestnut Hill, MA Local Guide

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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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What to Know About Fees and Fines When Renting

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

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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...