Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (415 Rentals) Page 8 of 9

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property at 11 Clovelly Rd

$14,000

Total Monthly Price

Total Monthly Price

Base Rent
$14,000

Total Monthly Price
$14,000

5 Bedroom, 6 Bath Home for Rent

Available Now

11 Clovelly Rd

NewtonMA02467
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 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
property at 250 Hammond Pond Pkwy

$2,600

Total Monthly Price

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 Bedroom, 1.5 Bath Condo for Rent

Available Now

property at 27 Commonwealth Ave

$3,350

Total Monthly Price

Total Monthly Price

Base Rent
$3,350

Total Monthly Price
$3,350

1 Bedroom, 1 Bath Condo for Rent

Available Now

27 Commonwealth Ave

NewtonMA02467
property at 629 Hammond St

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 2 Bath Condo for Rent

Available Now

629 Hammond St

BrooklineMA02467
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 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 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 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 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 12 Gerald Rd

$9,500

Total Monthly Price

Total Monthly Price

Base Rent
$9,500

Total Monthly Price
$9,500

5 Bedroom, 3 Bath Home for Rent

Available Now

12 Gerald Rd

BostonMA02135
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 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 36 Lorna Rd

$7,750

Total Monthly Price

Total Monthly Price

Base Rent
$7,750

Total Monthly Price
$7,750

4 Bedroom, 4 Bath Home for Rent

Available Now

36 Lorna Rd

NewtonMA02459
property at 28 Exmoor Rd

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

3 Bedroom, 2.5 Bath Home for Rent

Available Now

28 Exmoor Rd

NewtonMA02459
property at 2001 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 Now

property at 44 Greycliff Rd

$12,000

Total Monthly Price

Total Monthly Price

Base Rent
$12,000

Total Monthly Price
$12,000

7 Bedroom, 3 Bath Townhome for Rent

Available Now

44 Greycliff Rd

BostonMA02135
property at 65 Strathmore Rd

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

1 Bedroom, 1 Bath Condo for Rent

Available Now

65 Strathmore Rd

BostonMA02135
property at 1945 Commonwealth Ave

$2,250

Total Monthly Price

Total Monthly Price

Base Rent
$2,250

Total Monthly Price
$2,250

1 Bedroom, 1 Bath Condo for Rent

Available Now

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.