Pet Friendly Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (142 Rentals) Page 3 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 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
property at 49 Breck Ave

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

5 Bedroom, 2 Bath Home for Rent

Available Now

49 Breck Ave

BostonMA02135
property at 16 South St

$5,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,400

Total Monthly Price
$5,400

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

16 South St, Unit 2

16 South St
BostonMA02135
property at 120 Kenrick St

$5,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

4 Bedroom, 2 Bath Condo for Rent

Available Now

120 Kenrick St, Unit 1

120 Kenrick St
BostonMA02135
property at 148 Strathmore Rd

$5,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

5 Bedroom, 3 Bath Condo for Rent

Available Sep 1, 2026

148 Strathmore Rd, Unit 2

148 Strathmore Rd
BostonMA02135
property at 6 Lothian Rd

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800

5 Bedroom, 2 Bath Condo for Rent

Available Now

6 Lothian Rd, Unit 2

6 Lothian Rd
BostonMA02135
property at 153 Foster St

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

4 Bedroom, 2 Bath Townhome for Rent

Available Sep 1, 2026

153 Foster St, Unit 1

153 Foster St
BostonMA02135
property at 288 Foster St

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

4 Bedroom, 1 Bath Condo for Rent

Available Now

288 Foster St, Unit 1

288 Foster St
BostonMA02135
property at 1 Glenley Terrace

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

6 Bedroom, 3 Bath Condo for Rent

Available Now

1 Glenley Terrace, Unit 1

1 Glenley Terrace
BostonMA02135
property at 64 Langley Rd

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

4 Bedroom, 2.5 Bath Home for Rent

Available Now

64 Langley Rd

BostonMA02135
property at 2021 Commonwealth Ave

$7,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,600

Total Monthly Price
$7,600

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

2021 Commonwealth Ave, Unit 2

2021 Commonwealth Ave
BostonMA02135
property at 116 Lake St

$9,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,000

Total Monthly Price
$9,000

6 Bedroom, 4 Bath Condo for Rent

Available Now

116 Lake St, Unit 1

116 Lake St
BostonMA02135
property at 44 Kirkwood Rd

$9,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,600

Total Monthly Price
$9,600

4 Bedroom, 2 Bath Condo for Rent

Available Aug 31, 2026

44 Kirkwood Rd, Unit 1

44 Kirkwood Rd
BostonMA02135
property at 1860 Commonwealth Ave

$11,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

6 Bedroom, 4.5 Bath Home for Rent

Available Sep 1, 2026

property at 52 Greycliff Rd

$11,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,100

Total Monthly Price
$11,100

6 Bedroom, 3 Bath Home for Rent

Available Sep 1, 2027

52 Greycliff Rd

BostonMA02135
property at 16 Gerald Rd

$13,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$13,500

Total Monthly Price
$13,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Sep 1, 2027

16 Gerald Rd, Unit 2

16 Gerald Rd
BostonMA02135
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181 Washington St
$3,025
Total Monthly Price

Total Monthly Price

Base Rent
$2,660
Required Monthly Fees
$365

Total Monthly Price
$3,025
Studio Apartments Available Jan 18, 2026

181 Washington St

181 Washington StBoston, MA 02135
Furnished
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181 Washington St
$2,915
Total Monthly Price

Total Monthly Price

Base Rent
$2,570
Required Monthly Fees
$345

Total Monthly Price
$2,915
Studio Apartments Available May 2, 2026

181 Washington St

181 Washington StBoston, MA 02135
Furnished
property at 405 Langley Rd

$3,300

Total Monthly Price

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 2 Bath Condo for Rent

Available Now

405 Langley Rd

NewtonMA02459
property at 14 Hammondswood Rd

$7,300

Total Monthly Price

Total Monthly Price

Base Rent
$7,300

Total Monthly Price
$7,300

6 Bedroom, 2 Bath Home for Rent

Available Now

14 Hammondswood Rd

NewtonMA02467
property at 82 Louise Rd

$11,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

4 Bedroom, 4 Bath Townhome for Rent

Available Now

82 Louise Rd

NewtonMA02467
property at 476 Heath St

$15,000

Total Monthly Price

Total Monthly Price

Base Rent
$15,000

Total Monthly Price
$15,000

9 Bedroom, 5.5 Bath Home for Rent

Available Now

476 Heath St

BrooklineMA02467
property at 458 Heath St

$16,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$16,500

Total Monthly Price
$16,500

5 Bedroom, 7 Bath Home for Rent

Available Now

458 Heath St

BrooklineMA02467
property at 29 Merrill Rd

$17,500

Total Monthly Price

Total Monthly Price

Base Rent
$17,500

Total Monthly Price
$17,500

5 Bedroom Rentals

Available Now

29 Merrill Rd

NewtonMA02459

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 467 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $17,000. There are also 421 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 $6,422.

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 How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips article

How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips

Written by: Justin Habersaat

Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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!