Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA(399 Rentals)Page 2 of 8

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37 Radnor Rd
$9,0006 Bedroom, 3 Bath Condo for RentAvailable Aug 24, 2025

37 Radnor Rd, Unit 1

37 Radnor Rd
Boston, MA 02135
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116 Lake St
$9,0006 Bedroom, 4 Bath Condo for RentAvailable Sep 1, 2025

116 Lake St

Boston, MA 02135
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116 Lake St
$9,0006 Bedroom, 4 Bath Condo for RentAvailable Sep 1, 2025

116 Lake St, Unit 1

116 Lake St
Boston, MA 02135
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116 Lake St
$9,0006 Bedroom, 4 Bath Home for RentAvailable Sep 1, 2025

116 Lake St

Boston, MA 02135
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44 Kirkwood Rd
$8,7004 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

44 Kirkwood Rd

Boston, MA 02135
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26 Kirkwood Rd
$8,7004 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

26 Kirkwood Rd

Boston, MA 02135
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44 Kirkwood Rd
$8,7004 Bedroom, 2 Bath Townhome for RentAvailable Sep 1, 2025

44 Kirkwood Rd

Boston, MA 02135
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30 Kirkwood Rd
$8,7004 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

30 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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116 Lake St
$8,5006 Bedroom, 4 Bath Condo for RentAvailable Now

116 Lake St

Boston, MA 02135
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80 Lake St
$8,0006 Bedroom, 4 Bath Condo for RentAvailable Aug 24, 2025

80 Lake St, Unit 1

80 Lake St
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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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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2021 Commonwealth Ave
$7,5005 Bedroom, 2 Bath Condo for RentAvailable Dec 26

2021 Commonwealth Ave

Boston, MA 02135
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22 Foster St
$7,2005 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

22 Foster St

Boston, MA 02135
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288 Foster St
$7,2005 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

288 Foster St

Boston, MA 02135
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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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38 Cabot St
$6,5003 Bedroom, 2 Bath Home for RentAvailable Now

38 Cabot St

Newton, MA 02458
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25 Wade St
$6,5005 Bedroom, 3 Bath Home for RentAvailable Sep 1, 2025

25 Wade St, Unit 280

25 Wade St
Boston, MA 02135
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68 Manet Rd
$6,5004 Bedroom, 2 Bath Condo for RentAvailable Jun 1, 2025

68 Manet Rd, Unit 1

68 Manet Rd
Chestnut Hill, MA 02467
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120 Lake St
$6,5006 Bedroom, 3 Bath Townhome for RentAvailable Sep 1, 2025

120 Lake St, Unit 1332

120 Lake St
Boston, MA 02135
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1 Glenley Terrace
$6,2006 Bedroom, 3 Bath Home for RentAvailable Now

1 Glenley Terrace, Unit 15

1 Glenley Terrace
Boston, MA 02135
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288 Foster St
$6,2004 Bedroom, 1 Bath Condo for RentAvailable Sep 1, 2025

288 Foster St, Unit 1

288 Foster St
Boston, MA 02135
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288 Foster St
$6,2004 Bedroom, 1 Bath Condo for RentAvailable Sep 1, 2025

288 Foster St, Unit 1

288 Foster St
Boston, MA 02135
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21 Radnor Rd
$6,2004 Bedroom, 1 Bath Townhome for RentAvailable Now

21 Radnor Rd

Boston, MA 02135
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64 Langley Rd
$6,0006 Bedroom, 4 Bath Home for RentAvailable Sep 1, 2025

64 Langley Rd

Boston, MA 02135
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25 Crosby Rd
$6,0004 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

25 Crosby Rd, Unit 2

25 Crosby Rd
Chestnut Hill, MA 02467
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64 Langley Rd
$6,0004 Bedroom, 2 Bath Condo for RentAvailable Sep 1, 2025

64 Langley Rd, Unit 64

64 Langley Rd
Boston, MA 02135
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1 Glenley Terrace
$5,9006 Bedroom, 3 Bath Condo for RentAvailable Now

1 Glenley Terrace, Unit 1

1 Glenley Terrace
Boston, MA 02135
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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 902 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $2,095 to $13,000. There are also 460 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $2,950 to $16,500.

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 $2,950 to $16,500 with an average monthly rent of $4,724.

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 $3,500 to $3,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,500 to $3,600. Four Bedroom Single-Family rentals are also available starting from $4,100 and Four Bedroom Apartments start at $4,100.

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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