Pet Friendly Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (139 Rentals) Page 2 of 3

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Homes for rent in the Chestnut Hill Middlesex area of Chestnut Hill that love your dogs or cats as much as you do!

property at 2001 Commonwealth Ave

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

2001 Commonwealth Ave, Unit 16

2001 Commonwealth Ave
BostonMA02135
property at 39 South St

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

39 South St, Unit 2

39 South St
BostonMA02135
property at 550 Washington St

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom, 1 Bath Condo for Rent

Available Now

550 Washington St, Unit 1

550 Washington St
BostonMA02135
property at 505 Washington St

$3,150

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,150

Total Monthly Price
$3,150

3 Bedroom, 1 Bath Condo for Rent

Available Now

505 Washington St, Unit 3

505 Washington St
BostonMA02135
property at 1868 Commonwealth Ave

$3,190

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,190

Total Monthly Price
$3,190

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

1868 Commonwealth Ave, Unit 5

1868 Commonwealth Ave
BostonMA02135
property at 130 Englewood Ave

$3,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,250

Total Monthly Price
$3,250

2 Bedroom, 1 Bath Condo for Rent

Available Now

130 Englewood Ave, Unit 4

130 Englewood Ave
BostonMA02135
property at 8 Oakland St

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

3 Bedroom, 1 Bath Condo for Rent

Available Now

8 Oakland St, Unit 1

8 Oakland St
BostonMA02135
property at 520 Washington St

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

3 Bedroom, 1 Bath Condo for Rent

Available Now

520 Washington St, Unit 1

520 Washington St
BostonMA02135
property at 541 Washington St

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

3 Bedroom, 1 Bath Condo for Rent

Available Now

541 Washington St, Unit 3

541 Washington St
BostonMA02135
property at 145 Chiswick Rd

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

3 Bedroom, 1 Bath Condo for Rent

Available Now

145 Chiswick Rd, Unit 8

145 Chiswick Rd
BostonMA02135
property at 91 Wallingford Rd

$3,350

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,350

Total Monthly Price
$3,350

3 Bedroom, 1 Bath Condo for Rent

Available Now

91 Wallingford Rd, Unit 3

91 Wallingford Rd
BostonMA02135
property at 54 Tremont St

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

3 Bedroom, 1 Bath Condo for Rent

Available Now

54 Tremont St, Unit 3

54 Tremont St
BostonMA02135
property at 79 Foster St

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

3 Bedroom, 1 Bath Condo for Rent

Available Now

79 Foster St, Unit 79 Foster

79 Foster St
BostonMA02135
property at 7 Lothian Rd

$3,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,450

Total Monthly Price
$3,450

3 Bedroom, 1 Bath Condo for Rent

Available Now

7 Lothian Rd, Unit 11

7 Lothian Rd
BostonMA02135
property at 22 Eastburn St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1.5 Bath Townhome for Rent

Available Now

22 Eastburn St

BostonMA02135
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 505 Washington St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

505 Washington St, Unit 1

505 Washington St
BostonMA02135
property at 71 Foster St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

71 Foster St, Unit 1

71 Foster St
BostonMA02135
property at 16 Gerald Rd

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Home for Rent

Available Now

16 Gerald Rd

BostonMA02135
property at 20 Anselm Ter

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Now

20 Anselm Ter, Unit 1

20 Anselm Ter
BostonMA02135
property at 27 Willoughby St

$3,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650

Total Monthly Price
$3,650

3 Bedroom, 1 Bath Condo for Rent

Available Now

27 Willoughby St, Unit 1

27 Willoughby 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 5 Glenley Terrace

$3,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

1 Bedroom, 2 Bath Condo for Rent

Available Now

5 Glenley Terrace, Unit 1

5 Glenley Terrace
BostonMA02135
property at 3 Glenley Ter

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 3 Bath Condo for Rent

Available Jan 1, 2026

3 Glenley Ter, Unit 1

3 Glenley Ter
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 14 Breck Ave

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 2 Bath Condo for Rent

Available Now

14 Breck Ave, Unit 2

14 Breck Ave
BostonMA02135
property at 137 Chiswick Terrace

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 1 Bath Condo for Rent

Available Now

137 Chiswick Terrace, Unit 5

137 Chiswick Terrace
BostonMA02135
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 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 9 Oak Square Ave

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

4 Bedroom, 2 Bath Condo for Rent

Available Now

9 Oak Square Ave, Unit 2

9 Oak Square Ave
BostonMA02135
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 328 Washington St

$4,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

4 Bedroom, 2 Bath Condo for Rent

Available Now

328 Washington St, Unit 1

328 Washington St
BostonMA02135
property at 35 Henshaw St

$4,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

3 Bedroom, 4 Bath Condo for Rent

Available Now

35 Henshaw St, Unit 1ZB

35 Henshaw St
BostonMA02135
property at 25 Embassy Rd

$4,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

4 Bedroom, 2 Bath Home for Rent

Available Now

25 Embassy Rd

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 195 Lake St

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

4 Bedroom, 2 Bath Condo for Rent

Available Now

195 Lake St, Unit 2

195 Lake St
BostonMA02135
property at 3 Glenley Ter

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

4 Bedroom, 2 Bath Home for Rent

Available Now

3 Glenley Ter

BostonMA02135
property at 29 Gerald Rd

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

29 Gerald Rd, Unit 1

29 Gerald Rd
BostonMA02135
property at 35 South St

$4,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,600

Total Monthly Price
$4,600

3 Bedroom, 1 Bath Condo for Rent

Available Now

35 South St, Unit 10

35 South St
BostonMA02135
property at 1999 Commonwealth Ave

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

1999 Commonwealth Ave, Unit 12

1999 Commonwealth Ave
BostonMA02135
property at 25 Greycliff Rd

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650

3 Bedroom, 1 Bath Condo for Rent

Available Now

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
property at 25 Greycliff Rd

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
property at 209 Chestnut Hill Ave

$4,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,700

Total Monthly Price
$4,700

4 Bedroom, 2 Bath Condo for Rent

Available Now

209 Chestnut Hill Ave, Unit 1

209 Chestnut Hill Ave
BostonMA02135
property at 132 Chiswick Rd

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

5 Bedroom, 2 Bath Condo for Rent

Available Now

132 Chiswick Rd, Unit 2

132 Chiswick Rd
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
property at 27 Eulita Ter

$4,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,950

Total Monthly Price
$4,950

4 Bedroom, 2 Bath Condo for Rent

Available Now

27 Eulita Ter, Unit 2

27 Eulita Ter
BostonMA02135
property at 209 Chestnut Hill Ave

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

4 Bedroom, 2 Bath Condo for Rent

Available Now

209 Chestnut Hill Ave, Unit 2

209 Chestnut Hill Ave
BostonMA02135
property at 36 Kenrick St

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 2 Bath Condo for Rent

Available Now

36 Kenrick St, Unit 1

36 Kenrick St
BostonMA02135

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 456 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 $730 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 $730 to $17,500 with an average monthly rent of $7,046.

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.