Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (409 Rentals) Page 5 of 9

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property at 85 Brayton Rd

$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

85 Brayton Rd, Unit 2

85 Brayton Rd
BostonMA02135
property at 41 North Crescent Circuit

$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

41 North Crescent Circuit, Unit 2

41 North Crescent Circuit
BostonMA02135
property at 89 Brayton Rd

$4,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

89 Brayton Rd, Unit 2

89 Brayton Rd
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 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 7 North Crescent Circuit

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Townhome for Rent

Available Now

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 124 Academy Hill Rd

$2,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,100

Total Monthly Price
$2,100

1 Bedroom, 1 Bath Condo for Rent

Available Now

124 Academy Hill Rd, Unit B

124 Academy Hill Rd
BostonMA02135
property at 161 Brayton 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

161 Brayton Rd, Unit 1

161 Brayton Rd
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 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 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 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 64 Langley Rd

$5,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,950

Total Monthly Price
$5,950

4 Bedroom, 2.5 Bath Home for Rent

Available Now

64 Langley Rd

BostonMA02135
property at 64 Langley Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 2.5 Bath Condo for Rent

Available Now

64 Langley Rd, Unit 64

64 Langley Rd
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 64 Langley Rd

$6,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,900

Total Monthly Price
$6,900

5 Bedroom, 3.5 Bath Home for Rent

Available Now

64 Langley Rd, Unit 1

64 Langley Rd
BostonMA02135
property at 96 Chestnut Hill Ave

$5,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,300

Total Monthly Price
$5,300

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

96 Chestnut Hill Ave, Unit 2

96 Chestnut Hill Ave
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 14 Langley Rd

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 1 Bath Condo for Rent

Available Now

14 Langley Rd, Unit 2

14 Langley Rd
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 84 Wallingford Rd

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

3 Bedroom, 2 Bath Condo for Rent

Available Now

84 Wallingford Rd, Unit 1

84 Wallingford Rd
BostonMA02135
property at 80 Wallingford Rd

$4,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,450

Total Monthly Price
$4,450

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

80 Wallingford Rd, Unit 1

80 Wallingford Rd
BostonMA02135
property at 91 Wallingford Rd

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

91 Wallingford Rd, Unit 2

91 Wallingford Rd
BostonMA02135
property at 91 Wallingford Rd

$2,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

3 Bedroom, 1 Bath Condo for Rent

Available Now

91 Wallingford Rd, Unit 3

91 Wallingford Rd
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 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 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 91 Wallingford Rd

$5,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,400

Total Monthly Price
$5,400

4 Bedroom, 2 Bath Townhome for Rent

Available Sep 1, 2026

91 Wallingford Rd

BostonMA02135
property at 22 Shanley 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

22 Shanley 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 20 Shanley 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

20 Shanley St, Unit 1R

20 Shanley St
BostonMA02135
property at 8 Mt Vernon St

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 1 Bath Home for Rent

Available Now

8 Mt Vernon St

BostonMA02135
property at 19 Turner 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

19 Turner St, Unit 1

19 Turner St
BostonMA02135
property at 29 Mount Vernon St

$4,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,400

Total Monthly Price
$4,400

4 Bedroom, 2 Bath Condo for Rent

Available Now

29 Mount Vernon St, Unit 2

29 Mount Vernon St
BostonMA02135
property at 29 Eastburn St

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Now

29 Eastburn St, Unit 2

29 Eastburn 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 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 15 Beechcroft St

$2,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,100

Total Monthly Price
$2,100

1 Bedroom, 1 Bath Condo for Rent

Available Now

15 Beechcroft St

BostonMA02135
property at 16 Priscilla Rd

$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

16 Priscilla Rd, Unit 2

16 Priscilla Rd
BostonMA02135
property at 16 Priscilla Rd

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

5 Bedroom, 2 Bath Condo for Rent

Available Now

16 Priscilla Rd, Unit 2

16 Priscilla Rd
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 55 Chestnut Hill Ave

$6,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,400

Total Monthly Price
$6,400

6 Bedroom, 3 Bath Condo for Rent

Available Now

55 Chestnut Hill Ave, Unit 2

55 Chestnut Hill Ave
BostonMA02135
property at 14 Lyne Rd

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Now

14 Lyne Rd, Unit 1

14 Lyne Rd
BostonMA02135
property at 440 Washington St

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

440 Washington St, Unit 3

440 Washington St
BostonMA02135
property at 440 Washington St

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

440 Washington St, Unit 3

440 Washington St
BostonMA02135
property at 440 Washington St

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

440 Washington St, Unit 3

440 Washington St
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 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

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.