Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (542 Rentals)Page 4 of 11

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1961 Commonwealth Ave
$4,5003 Bedroom, 1 Bath Condo for RentAvailable Sep 1

1961 Commonwealth Ave, Unit 5

1961 Commonwealth Ave
Boston, MA 02135
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44 Greycliff Rd
$9,6256 Bedroom, 3 Bath Condo for RentAvailable Now

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 RentAvailable Now

44 Greycliff Rd

Brighton, MA 02135
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52 Greycliff Rd
$10,5006 Bedroom, 3 Bath Home for RentAvailable Aug 31, 2026

52 Greycliff Rd

Boston, MA 02135
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52 Greycliff Rd
$10,5006 Bedroom, 3 Bath Condo for RentAvailable Sep 1, 2026

52 Greycliff Rd

Boston, MA 02135
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52 Greycliff Rd
$10,5006 Bedroom, 3 Bath Home for RentAvailable Aug 31, 2026

52 Greycliff Rd

Boston, MA 02135
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289 Foster St
$7,5004 Bedroom, 1 Bath Condo for RentAvailable Sep 1

289 Foster St, Unit 1

289 Foster St
Boston, MA 02135
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64 Greycliff Rd
$10,0001 Bedroom, 1 Bath Townhome for RentAvailable Now

64 Greycliff Rd, Unit 1

64 Greycliff Rd
Boston, MA 02135
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37 Radnor Rd
$9,0006 Bedroom, 3 Bath Condo for RentAvailable Aug 24

37 Radnor Rd, Unit 1

37 Radnor Rd
Boston, MA 02135
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2003 Commonwealth Ave
$2,4701 Bedroom, 1 Bath Condo for RentAvailable Now

2003 Commonwealth Ave

Boston, MA 02135
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65 Strathmore Rd
$2,7001 Bedroom, 1 Bath Condo for RentAvailable Now

65 Strathmore Rd, Unit 25

65 Strathmore Rd
Boston, MA 02135
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25 South St
$3,5002 Bedroom, 1 Bath Condo for RentAvailable Now

25 South St, Unit south st

25 South St
Boston, MA 02135
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38 Radnor Rd
$4,5003 Bedroom, 1 Bath Condo for RentAvailable Sep 1

38 Radnor Rd, Unit 5

38 Radnor Rd
Boston, MA 02135
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53 Radnor Rd
$5,5004 Bedroom, 2 Bath Condo for RentAvailable Aug 24

53 Radnor Rd, Unit 2

53 Radnor Rd
Boston, MA 02135
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42 Radnor Rd
$10,7506 Bedroom, 2 Bath Condo for RentAvailable Aug 24, 2026

42 Radnor Rd, Unit #2

42 Radnor Rd
Boston, MA 02135
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44 Lane Park
$4,2004 Bedroom, 2 Bath Condo for RentAvailable Now

44 Lane Park, Unit 4

44 Lane Park
Boston, MA 02135
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116 Lake St
$8,2006 Bedroom, 4 Bath Home for RentAvailable Sep 1

116 Lake St

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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116 Lake St
$9,0006 Bedroom, 4 Bath Condo for RentAvailable Sep 1

116 Lake St

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

116 Lake St

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

116 Lake St

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

116 Lake St, Unit 1

116 Lake St
Boston, MA 02135
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6 South St
$3,6002 Bedroom, 2 Bath Condo for RentAvailable Sep 1

6 South St, Unit 3

6 South St
Boston, MA 02135
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229 Chestnut Hill Ave
$3,6003 Bedroom, 2 Bath Condo for RentAvailable Sep 1

229 Chestnut Hill Ave, Unit 3

229 Chestnut Hill Ave
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 1030 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $976 to $21,000. There are also 542 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,799 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 $1,799 to $21,000 with an average monthly rent of $6,595.

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 $2,600 to $8,900. Four Bedroom Single-Family rentals are also available starting from $2,900 and Four Bedroom Apartments start at $1,000.

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

Written by: Trey Huguley

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.

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What to Know About Fees and Fines When Renting

Written by: Trey Huguley

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.

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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 language.

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

Written by: Kevin Ready

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 the past decade.