5 Bedroom Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (68 Rentals)

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16 Priscilla Rd
$4,2005 Bedroom, 2 Bath Condo for RentAvailable Sep 1

16 Priscilla Rd, Unit 2

16 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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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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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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28 Priscilla Rd
$4,8005 Bedroom, 2 Bath Condo for RentAvailable Sep 1

28 Priscilla Rd, Unit 4

28 Priscilla Rd
Boston, MA 02135
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132 Chiswick Rd
$4,8005 Bedroom, 2 Bath Condo for RentAvailable Sep 1

132 Chiswick Rd, Unit 2

132 Chiswick Rd
Boston, MA 02135
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18 Malbert Rd
$4,8005 Bedroom, 3 Bath Condo for RentAvailable Sep 1

18 Malbert Rd, Unit 1

18 Malbert Rd
Boston, MA 02135
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91 Wallingford Rd
$5,0005 Bedroom, 2 Bath Condo for RentAvailable Sep 1

91 Wallingford Rd, Unit 4

91 Wallingford Rd
Boston, MA 02135
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29 Leicester St
$5,0005 Bedroom, 3 Bath Home for RentAvailable Sep 1

29 Leicester St

Boston, MA 02135
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49 Breck Ave
$5,2005 Bedroom, 2 Bath Home for RentAvailable Sep 1

49 Breck Ave

Boston, MA 02135
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77 Wallingford Rd
$5,3005 Bedroom, 2 Bath Condo for RentAvailable Sep 1

77 Wallingford Rd, Unit 2

77 Wallingford Rd
Boston, MA 02135
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39 Trapelo St
$5,5005 Bedroom, 2 Bath Condo for RentAvailable Now

39 Trapelo St, Unit 2

39 Trapelo St
Boston, MA 02135
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34 Manet Rd
$5,8005 Bedroom, 1 Bath Condo for RentAvailable Sep 1

34 Manet Rd, Unit 1

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

28 Manet Rd, Unit #1

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

20 Manet Rd, Unit 1

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

28 Manet Rd

Chestnut Hill, MA 02467
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6 Lothian Rd
$5,8005 Bedroom, 2 Bath Condo for RentAvailable Sep 1

6 Lothian Rd, Unit 2

6 Lothian Rd
Boston, MA 02135
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28 Manet Rd
$5,8005 Bedroom, 1 Bath Condo for RentAvailable Sep 1

28 Manet Rd

Chestnut Hill, MA 02467
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25 Wade St
$6,5005 Bedroom, 3 Bath Home for RentAvailable Sep 1

25 Wade St, Unit 280

25 Wade St
Boston, MA 02135
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15 Glenmont Rd
$6,7005 Bedroom, 2 Bath Condo for RentAvailable Now

15 Glenmont Rd, Unit 2

15 Glenmont Rd
Boston, MA 02135
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21 Glenmont Rd
$6,9005 Bedroom, 2 Bath Condo for RentAvailable Aug 15

21 Glenmont Rd, Unit 1

21 Glenmont Rd
Boston, MA 02135
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14 Glenmont Rd
$6,9005 Bedroom, 2 Bath Condo for RentAvailable Aug 15

14 Glenmont Rd, Unit 2

14 Glenmont Rd
Boston, MA 02135
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14 Glenmont Rd
$6,9005 Bedroom, 2 Bath Condo for RentAvailable Sep 1

14 Glenmont Rd, Unit 2

14 Glenmont Rd
Boston, MA 02135
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10 Glenmont Rd
$6,9005 Bedroom, 2 Bath Condo for RentAvailable Aug 15

10 Glenmont Rd, Unit 2

10 Glenmont Rd
Boston, MA 02135
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31 Glenmont Rd
$6,9005 Bedroom, 2 Bath Condo for RentAvailable Aug 15

31 Glenmont Rd, Unit 2

31 Glenmont Rd
Boston, MA 02135
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31 Bostonia Ave
$6,9005 Bedroom, 2 Bath Condo for RentAvailable Aug 15

31 Bostonia Ave, Unit 2

31 Bostonia Ave
Brighton, MA 02135
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28 Glenmont Rd
$6,9005 Bedroom, 2 Bath Condo for RentAvailable Aug 15

28 Glenmont Rd

Boston, MA 02135
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14 Glenmont Rd
$6,9005 Bedroom, 2 Bath Condo for RentAvailable Aug 15

14 Glenmont Rd, Unit 2

14 Glenmont Rd
Boston, MA 02135
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18 Glenmont Rd
$6,9005 Bedroom, 2 Bath Condo for RentAvailable Aug 15

18 Glenmont Rd

Boston, MA 02135
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26 Glenmont Rd
$6,9005 Bedroom, 2 Bath Condo for RentAvailable Aug 15

26 Glenmont Rd

Boston, MA 02135
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25 Crosby Rd
$7,0005 Bedroom, 2 Bath Condo for RentAvailable Sep 1

25 Crosby Rd, Unit 1

25 Crosby Rd
Chestnut Hill, MA 02467
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40 Kirkwood Rd
$7,5005 Bedroom, 2 Bath Condo for RentAvailable Now

40 Kirkwood Rd, Unit #1

40 Kirkwood Rd
Boston, MA 02135
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40 Kirkwood Rd
$7,5005 Bedroom, 2 Bath Condo for RentAvailable Now

40 Kirkwood Rd, Unit 1

40 Kirkwood Rd
Boston, MA 02135
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40 Kirkwood Rd
$7,5005 Bedroom, 2 Bath Condo for RentAvailable Now

40 Kirkwood Rd

Boston, MA 02135
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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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260 Foster St
$8,6505 Bedroom, 2 Bath Townhome for RentAvailable Aug 24, 2026

260 Foster St

Boston, MA 02135
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2021 Commonwealth Ave
$8,7505 Bedroom, 2 Bath Condo for RentAvailable Aug 30

2021 Commonwealth Ave, Unit D

2021 Commonwealth Ave
Boston, MA 02135
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Chestnut Hill Middlesex, Boston College, MA Local Guide

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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 1165 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $825 to $21,000. There are also 716 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,100 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 $1,100 to $21,000 with an average monthly rent of $6,597.

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 $2,550 to $10,000, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,550 to $8,900. Four Bedroom Single-Family rentals are also available starting from $1,100 and Four Bedroom Apartments start at $995.

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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