4 Bedroom Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA(205 Rentals)Page 3 of 5

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288 Foster St
$7,2005 Bedroom, 2 Bath Condo for RentUnavailable

288 Foster St

Boston, MA 02135
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22 Foster St
$7,2005 Bedroom, 2 Bath Condo for RentUnavailable

22 Foster St

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

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 RentUnavailable

2021 Commonwealth Ave

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

40 Kirkwood Rd

Boston, MA 02135
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80 Lake St
$8,0006 Bedroom, 4 Bath Condo for RentUnavailable

80 Lake St, Unit 1

80 Lake St
Boston, MA 02135
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116 Lake St
$8,5006 Bedroom, 4 Bath Condo for RentUnavailable

116 Lake St

Boston, MA 02135
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31-33 Greycliff Rd
$8,6005 Bedroom, 2 Bath Condo for RentUnavailable

31-33 Greycliff 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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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 Condo for RentAvailable Sep 1, 2025

44 Kirkwood Rd

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

12 Gerald Rd, Unit 1

12 Gerald Rd
Boston, MA 02135
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42 Radnor Rd
$9,0006 Bedroom, 3 Bath Condo for RentUnavailable

42 Radnor Rd, Unit 1

42 Radnor Rd
Boston, MA 02135
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37 Radnor Rd
$9,0006 Bedroom, 3 Bath Condo for RentUnavailable

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 RentUnavailable

116 Lake St, Unit 8 BED

116 Lake St
Boston, MA 02135
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116 Lake St
$9,0006 Bedroom, 4 Bath Condo for RentUnavailable

116 Lake St

Boston, MA 02135
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116 Lake St
$9,0006 Bedroom, 4 Bath Home for RentUnavailable

116 Lake St

Boston, MA 02135
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116 Lake St
$9,0006 Bedroom, 4 Bath Condo for RentUnavailable

116 Lake St, Unit 1

116 Lake St
Boston, MA 02135
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116 Lake St
$9,0006 Bedroom, 4 Bath Condo for RentUnavailable

116 Lake St, Unit 1

116 Lake St
Boston, MA 02135
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118 Lake St
$9,0006 Bedroom, 4 Bath Home for RentUnavailable

118 Lake St

Boston, MA 02135
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116 Lake St
$9,0006 Bedroom, 4 Bath Condo for RentUnavailable

116 Lake St

Boston, MA 02135
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12 Gerald Rd
$9,5005 Bedroom, 3 Bath Home for RentUnavailable

12 Gerald Rd

Boston, MA 02135
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12 Gerald Rd
$9,5005 Bedroom, 3 Bath Home for RentUnavailable

12 Gerald Rd

Boston, MA 02135
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12 Gerald Rd
$9,5005 Bedroom, 3 Bath Condo for RentUnavailable

12 Gerald Rd

Boston, MA 02135
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44 Kirkwood Rd
$9,6004 Bedroom, 2 Bath Condo for RentAvailable Aug 31, 2026

44 Kirkwood Rd, Unit 1

44 Kirkwood Rd
Boston, MA 02135
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38 Kirkwood Rd
$9,6004 Bedroom, 2 Bath Condo for RentAvailable Aug 31, 2026

38 Kirkwood Rd

Boston, MA 02135
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44 Kirkwood Rd
$9,6004 Bedroom, 2 Bath Condo for RentAvailable Aug 30, 2026

44 Kirkwood Rd, Unit 2

44 Kirkwood Rd
Boston, MA 02135
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44 Greycliff Rd
$9,6256 Bedroom, 3 Bath Condo for RentUnavailable

44 Greycliff Rd, Unit 2

44 Greycliff Rd
Brighton, MA 02135
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44 Greycliff Rd
$9,6256 Bedroom, 3 Bath Condo for RentUnavailable

44 Greycliff Rd

Brighton, MA 02135
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16 Gerald Rd
$9,9006 Bedroom, 2 Bath Condo for RentUnavailable

16 Gerald Rd, Unit 2

16 Gerald Rd
Boston, MA 02135
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16 Gerald Rd
$9,9006 Bedroom, 2 Bath Condo for RentUnavailable

16 Gerald Rd

Boston, MA 02135
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52 Greycliff Rd
$10,5006 Bedroom, 3 Bath Home for RentUnavailable

52 Greycliff Rd

Boston, MA 02135
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44 Greycliff Rd
$10,5006 Bedroom, 2 Bath Condo for RentUnavailable

44 Greycliff Rd

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 891 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $925 to $21,000. There are also 446 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,900 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 $1,900 to $21,000 with an average monthly rent of $5,826.

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 $2,700 to $10,000, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $8,900. Four Bedroom Single-Family rentals are also available starting from $2,900 and Four Bedroom Apartments start at $925.

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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