Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (409 Rentals) Page 4 of 9

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property at 36 Colwell Ave

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 1 Bath Condo for Rent

Available Now

36 Colwell Ave, Unit 1

36 Colwell Ave
BostonMA02135
property at 1868 Commonwealth Ave

$3,354

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,354

Total Monthly Price
$3,354

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

1868 Commonwealth Ave, Unit 5Q

1868 Commonwealth Ave
BostonMA02135
property at 1868 Commonwealth Ave

$3,354

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,354

Total Monthly Price
$3,354

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

1868 Commonwealth Ave, Unit 5

1868 Commonwealth Ave
BostonMA02135
property at 370 Chestnut Hill Ave

$4,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

3 Bedroom, 1 Bath Condo for Rent

Available Now

370 Chestnut Hill Ave, Unit 21

370 Chestnut Hill Ave
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 1868 Commonwealth Ave

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

3 Bedroom, 2 Bath Condo for Rent

Available Aug 28, 2026

1868 Commonwealth Ave, Unit A

1868 Commonwealth 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 141 Englewood Ave

$1,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,850

Total Monthly Price
$1,850

Studio, 1 Bath Condo for Rent

Available Now

141 Englewood Ave, Unit 1

141 Englewood Ave
BostonMA02135
property at 145 Englewood Ave

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

1 Bedroom, 1 Bath Condo for Rent

Available Now

145 Englewood Ave, Unit 43

145 Englewood Ave
BostonMA02135
property at 7 Lothian Rd

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

7 Lothian Rd, Unit 3

7 Lothian Rd
BostonMA02135
property at 50 Larch St

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

50 Larch St, Unit 2

50 Larch St
BostonMA02135
property at 145 Englewood Ave

$3,195

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,195

Total Monthly Price
$3,195

2 Bedroom, 1 Bath Condo for Rent

Available Now

145 Englewood Ave, Unit 2

145 Englewood Ave
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 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 2 Braemore Rd

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

1 Bedroom, 1 Bath Condo for Rent

Available Now

2 Braemore Rd, Unit 1

2 Braemore Rd
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 145 Chiswick Rd

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

145 Chiswick Rd, Unit B

145 Chiswick Rd
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 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 4 Chiswick Rd

$1,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,950

Total Monthly Price
$1,950

1 Bedroom, 1 Bath Condo for Rent

Available Now

4 Chiswick Rd, Unit 5

4 Chiswick Rd
BostonMA02135
property at 4 Chiswick Rd

$2,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

Studio, 1 Bath Condo for Rent

Available Now

4 Chiswick Rd, Unit 24

4 Chiswick Rd
BostonMA02135
property at 28 Sidlaw Rd

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Now

28 Sidlaw Rd, Unit 6

28 Sidlaw Rd
BostonMA02135
property at 133 Chiswick Rd

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

133 Chiswick Rd, Unit B

133 Chiswick Rd
BostonMA02135
property at 135 Chiswick Rd

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

1 Bedroom, 1 Bath Condo for Rent

Available Now

135 Chiswick Rd, Unit 512

135 Chiswick Rd
BostonMA02135
property at 133 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

133 Chiswick Rd

BostonMA02135
property at 133 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

133 Chiswick Rd, Unit B

133 Chiswick Rd
BostonMA02135
property at 133 Chiswick Rd

$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

133 Chiswick Rd, Unit B

133 Chiswick Rd
BostonMA02135
property at 133 Chiswick Rd

$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

133 Chiswick Rd

BostonMA02135
property at 114 Strathmore Rd

$2,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

1 Bedroom, 1 Bath Condo for Rent

Available Now

114 Strathmore Rd, Unit 406

114 Strathmore Rd
BostonMA02135
property at 27 South Crescent Circuit

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 2 Bath Townhome for Rent

Available Now

property at 27 South Crescent Circuit

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 2.5 Bath Condo for Rent

Available Now

27 South Crescent Circuit, Unit A

27 South Crescent Circuit
BostonMA02135
property at 27 S Crescent Circuit

$3,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,550

Total Monthly Price
$3,550

3 Bedroom, 2 Bath Condo for Rent

Available Now

27 S Crescent Circuit, Unit B

27 S Crescent Circuit
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 110 Strathmore Rd

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

110 Strathmore Rd, Unit 204

110 Strathmore Rd
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 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 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 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 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 Home for Rent

Available Now

1 Glenley Terrace

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 159 Foster St

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

159 Foster St, Unit 1

159 Foster St
BostonMA02135
property at 27 Bostonia Ave

$9,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,500

Total Monthly Price
$9,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Now

27 Bostonia Ave

BrightonMA02135
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 52 Bostonia Ave

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500

Total Monthly Price
$10,500

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31, 2026

52 Bostonia Ave, Unit 1

52 Bostonia Ave
BrightonMA02135
property at 46 Bostonia Ave

$11,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,200

Total Monthly Price
$11,200

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31, 2026

46 Bostonia Ave, Unit 1

46 Bostonia Ave
BrightonMA02135
property at 29 Wiltshire Rd

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

3 Bedroom, 1 Bath Condo for Rent

Available Now

29 Wiltshire Rd, Unit 1

29 Wiltshire Rd
BostonMA02135
property at 96 Brayton Rd

$3,600

Total Monthly Price9 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2.5 Bath Condo for Rent

Available Now

96 Brayton Rd, Unit 1

96 Brayton Rd
BostonMA02135
property at 44 Bostonia Ave

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500

Total Monthly Price
$10,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 31, 2026

44 Bostonia Ave, Unit 1

44 Bostonia Ave
BrightonMA02135
property at 43 N Crescent Circuit

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

43 N Crescent Circuit, Unit 1

43 N Crescent Circuit
BostonMA02135

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 409 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.