2 Bedroom Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (91 Rentals) Page 2 of 2

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property at 320 Hammond Pond Pkwy

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

2 Bedroom, 2 Bath Condo for Rent

Available Now

320 Hammond Pond Pkwy, Unit 104

320 Hammond Pond Pkwy
NewtonMA02467
property at 11 Hammond Pond Pky

$3,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,450

Total Monthly Price
$3,450

2 Bedroom, 2 Bath Condo for Rent

Available Now

11 Hammond Pond Pky, Unit 203

11 Hammond Pond Pky
Chestnut HillMA02467
property at 6 South St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 1 Bath Condo for Rent

Available Now

6 South St, Unit uni3 2-bed 1-bath

6 South St
BostonMA02135
property at 2 Chestnut Pl

$3,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

2 Bedroom, 2 Bath Condo for Rent

Available Now

2 Chestnut Pl, Unit 1

2 Chestnut Pl
BostonMA02135
property at 99 Chestnut Hill Ave

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

2 Bedroom, 2 Bath Condo for Rent

Available Now

99 Chestnut Hill Ave, Unit 316

99 Chestnut Hill Ave
BostonMA02135
property at 56 Winship St

$3,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,850

Total Monthly Price
$3,850

2 Bedroom, 2 Bath Condo for Rent

Available Now

56 Winship St, Unit 102

56 Winship St
BostonMA02135
property at 25 Crosby Rd

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

2 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

25 Crosby Rd

Chestnut HillMA02467
property at 409 Washington St

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

409 Washington St, Unit 401

409 Washington St
BostonMA02135
property at 250 Hammond Pond Pky

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

250 Hammond Pond Pky, Unit 1203N

250 Hammond Pond Pky
Chestnut HillMA02467
property at 1945 Commonwealth Ave

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

1945 Commonwealth Ave, Unit 13C

1945 Commonwealth Ave
BostonMA02135
property at 26 Holly Ln

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

26 Holly Ln, Unit 2

26 Holly Ln
BrooklineMA02467
property at 321 Hammond Pond Pky

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

321 Hammond Pond Pky, Unit 301

321 Hammond Pond Pky
Chestnut HillMA02467
property at 1870 Commonwealth Ave

$4,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

2 Bedroom, 1 Bath Condo for Rent

Available Now

1870 Commonwealth Ave, Unit 12A

1870 Commonwealth Ave
BostonMA02135
property at 2017 Commonwealth Ave

$4,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,450

Total Monthly Price
$4,450

2 Bedroom, 1 Bath Condo for Rent

Available Now

2017 Commonwealth Ave, Unit #1

2017 Commonwealth Ave
BostonMA02135
property at 2016 Commonwealth Ave

$4,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,850

Total Monthly Price
$4,850

2 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1, 2026

2016 Commonwealth Ave, Unit 5

2016 Commonwealth Ave
BostonMA02135
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181 Washington St
$2,655
Total Monthly Price

Total Monthly Price

Base Rent
$2,220
Required Monthly Fees
$435

Total Monthly Price
$2,655
2 Bedroom Apartments Available Dec 23

181 Washington St

181 Washington StBoston, MA 02135
Furnished
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35 South St
$3,290
Total Monthly Price

Total Monthly Price

Base Rent
$2,850
Required Monthly Fees
$440

Total Monthly Price
$3,290
2 Bedroom Apartments Available May 1, 2026

35 South St

35 South StBoston, MA 02135
Furnished
property at 2031 Commonwealth Ave

$2,295

Total Monthly Price

Total Monthly Price

Base Rent
$2,295

Total Monthly Price
$2,295

2 Bedroom, 1 Bath Condo for Rent

Available Now

property at 461 Washington St

$2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

2 Bedroom, 1 Bath Condo for Rent

Available Now

461 Washington St

BostonMA02135
property at 2025 Commonwealth Ave

$2,850 - $3,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

2 Bedroom Rentals

Available Now

property at 31 Hammond Pond Pky

$2,900

Total Monthly Price

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Home for Rent

Available Jan 1, 2026

31 Hammond Pond Pky

NewtonMA02467
property at 2035 Commonwealth Ave

$2,900 - $3,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom Rentals

Available Now

property at 20 Hammond Pond Pkwy

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 1 Bath Condo for Rent

Available Now

property at 2 Hammond Pond Pkwy

$3,375

Total Monthly Price

Total Monthly Price

Base Rent
$3,375

Total Monthly Price
$3,375

2 Bedroom, 1 Bath Condo for Rent

Available Now

2 Hammond Pond Pkwy

NewtonMA02467
property at 25 Ripley Terrace

$3,650

Total Monthly Price

Total Monthly Price

Base Rent
$3,650

Total Monthly Price
$3,650

2 Bedroom, 2 Bath Townhome for Rent

Available Now

25 Ripley Terrace

NewtonMA02459
property at 124 Langley Rd

$3,495

Plus Fees12 Month Lease Term

2 Bedroom, 2 Bath Condo for Rent

Available Now

124 Langley Rd

NewtonMA02459

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 452 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 415 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $760 to $17,500.

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 $760 to $17,500 with an average monthly rent of $7,073.

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 $6,285, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $7,000. Four Bedroom Single-Family rentals are also available starting from $860 and Four Bedroom Apartments start at $3,200.

Expert Rental Resources

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.

Articles, How-To's, and Tips

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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.