2 Bedroom Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (85 Rentals) Page 2 of 2

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property at 321 Hammond Pond Pky

321 Hammond Pond Pky, Unit 106

321 Hammond Pond Pky
Chestnut HillMA02467
property at 386 Market St

386 Market St, Unit 2

386 Market St
BostonMA02135
property at 2 Chestnut Pl

2 Chestnut Pl, Unit 1

2 Chestnut Pl
BostonMA02135
property at 99 Chestnut Hill Ave

99 Chestnut Hill Ave, Unit 316

99 Chestnut Hill Ave
BostonMA02135
property at 163 Chestnut Hill Ave
property at 56 Winship St

56 Winship St, Unit 102

56 Winship St
BostonMA02135
property at 25 Crosby Rd

25 Crosby Rd

Chestnut HillMA02467
property at 250 Hammond Pond Pky

250 Hammond Pond Pky, Unit 1203N

250 Hammond Pond Pky
Chestnut HillMA02467
property at 26 Holly Ln

26 Holly Ln, Unit 2

26 Holly Ln
BrooklineMA02467
property at 1945 Commonwealth Ave

1945 Commonwealth Ave, Unit 13C

1945 Commonwealth Ave
BostonMA02135
property at 321 Hammond Pond Pky

321 Hammond Pond Pky, Unit 301

321 Hammond Pond Pky
Chestnut HillMA02467
property at 1870 Commonwealth Ave

1870 Commonwealth Ave, Unit 12A

1870 Commonwealth Ave
BostonMA02135
property at 99 Chestnut Hill Ave

99 Chestnut Hill Ave, Unit 318

99 Chestnut Hill Ave
BostonMA02135
property at 2017 Commonwealth Ave

2017 Commonwealth Ave, Unit #1

2017 Commonwealth Ave
BostonMA02135
property at 1870 Commonwealth Ave

1870 Commonwealth Ave, Unit 12A

1870 Commonwealth Ave
BostonMA02135
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35 South St
$3,050
Total Monthly Price

Total Monthly Price

Base Rent
$2,610
Required Monthly Fees
$440

Total Monthly Price
$3,050
2 Bedroom Apartments Available Jan 18, 2026

35 South St

35 South StBoston, MA 02135
Furnished
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181 Washington St
$3,325
Total Monthly Price

Total Monthly Price

Base Rent
$2,890
Required Monthly Fees
$435

Total Monthly Price
$3,325
2 Bedroom Apartments Available Dec 21

181 Washington St

181 Washington StBoston, MA 02135
Furnished
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181 Washington St
$4,035
Total Monthly Price

Total Monthly Price

Base Rent
$3,600
Required Monthly Fees
$435

Total Monthly Price
$4,035
2 Bedroom Apartments Available Jan 1, 2026

181 Washington St

181 Washington StBoston, MA 02135
Furnished
property at 112 Lake Shore Rd

112 Lake Shore Rd

BostonMA02135
property at 5 Lothian Rd

5 Lothian Rd

BostonMA02135
property at 2031 Commonwealth Ave
property at 153 Strathmore Rd

153 Strathmore Rd

BostonMA02135
property at 144 Kenrick St

144 Kenrick St

BostonMA02135
property at 151 Strathmore Rd

151 Strathmore Rd

BostonMA02135
property at 32 Sidlaw Rd

32 Sidlaw Rd

BostonMA02135
property at 461 Washington St

461 Washington St

BostonMA02135
property at 163 Chestnut Hill Ave
property at 62 Crosby Rd

62 Crosby Rd

NewtonMA02467
property at 2025 Commonwealth Ave
property at 2 Hammond Pond Pkwy

2 Hammond Pond Pkwy

NewtonMA02467
property at 629 Hammond St

629 Hammond St

BrooklineMA02467
property at 99 Chestnut Hill Ave

Frequently Asked Questions about Chestnut Hill Middlesex

What type of rentals are currently available in Chestnut Hill Middlesex?

There are currently 431 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $13,500. There are also 470 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $980 to $36,000.

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 $980 to $36,000 with an average monthly rent of $6,807.

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 $5,955, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $6,500. Four Bedroom Single-Family rentals are also available starting from $1,080 and Four Bedroom Apartments start at $3,150.

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.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

decorative image for Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between article

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.