Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (409 Rentals) Page 2 of 9

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property at 320 Hammond Pond Pkwy

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

2 Bedroom, 2 Bath Condo for Rent

Available Now

320 Hammond Pond Pkwy, Unit 104

320 Hammond Pond Pkwy
NewtonMA02467
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 2005 Commonwealth Ave

$5,040

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,040

Total Monthly Price
$5,040

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

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 29 Gerald Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

29 Gerald Rd, Unit 1

29 Gerald Rd
BostonMA02135
property at 29 Gerald Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

3 Bedroom, 1 Bath Condo for Rent

Available Dec 1, 2026

29 Gerald Rd, Unit 2##

29 Gerald Rd
BostonMA02135
property at 288 Foster St

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

5 Bedroom, 2 Bath Condo for Rent

Available Now

288 Foster St, Unit 2

288 Foster St
BostonMA02135
property at 5 Radnor Rd

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

4 Bedroom, 1 Bath Condo for Rent

Available Aug 30, 2026

5 Radnor Rd, Unit 2

5 Radnor Rd
BostonMA02135
property at 1999 Commonwealth Ave

$1,999

Total Monthly Price10 Month Lease Term

Total Monthly Price

Base Rent
$1,999

Total Monthly Price
$1,999

1 Bedroom, 1 Bath Condo for Rent

Available Now

1999 Commonwealth Ave, Unit 01-2

1999 Commonwealth Ave
BostonMA02135
property at 1999 Commonwealth Ave

$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

1999 Commonwealth Ave, Unit 24

1999 Commonwealth Ave
BostonMA02135
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 1999 Commonwealth 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 Sep 1, 2026

1999 Commonwealth Ave, Unit 4

1999 Commonwealth Ave
BostonMA02135
property at 1997 Commonwealth 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

1997 Commonwealth Ave, Unit 7

1997 Commonwealth Ave
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 2001 Commonwealth Ave

$5,040

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,040

Total Monthly Price
$5,040

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

2001 Commonwealth Ave, Unit 12

2001 Commonwealth Ave
BostonMA02135
property at 1999 Commonwealth Ave

$5,040

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,040

Total Monthly Price
$5,040

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

1999 Commonwealth Ave, Unit 12A

1999 Commonwealth Ave
BostonMA02135
property at 1965 Commonwealth Ave

$2,325

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,325

Total Monthly Price
$2,325

1 Bedroom, 1 Bath Condo for Rent

Available Now

1965 Commonwealth Ave, Unit 31

1965 Commonwealth Ave
BostonMA02135
property at 31 Lake Shore Ct

$2,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

2 Bedroom, 1 Bath Condo for Rent

Available Now

31 Lake Shore Ct, Unit 3

31 Lake Shore Ct
BostonMA02135
property at 51 Lake Shore Ct

$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

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 51 Lake Shore Ct

$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

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 211 Lake Shore 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

211 Lake Shore Rd, Unit 2

211 Lake Shore Rd
BostonMA02135
property at 39 South 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 Condo for Rent

Available Jan 1, 2026

39 South St, Unit 4

39 South St
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 153 Lake Shore Rd

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 2 Bath Condo for Rent

Available Jan 1, 2026

153 Lake Shore Rd, Unit 3

153 Lake Shore Rd
BostonMA02135
property at 215 Lake Shore Rd

$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

215 Lake Shore Rd, Unit 2

215 Lake Shore Rd
BostonMA02135
property at 204 Lake Shore Rd

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 2 Bath Condo for Rent

Available Now

204 Lake Shore Rd, Unit 1

204 Lake Shore Rd
BostonMA02135
property at 44 Greycliff Rd

$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 Greycliff Rd, Unit 1

44 Greycliff Rd
BostonMA02135
property at 44 Greycliff Rd

$12,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$12,000

Total Monthly Price
$12,000

6 Bedroom, 3 Bath Condo for Rent

Available Now

44 Greycliff Rd, Unit 2

44 Greycliff Rd
BostonMA02135
property at 1959 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

1959 Commonwealth Ave, Unit 5

1959 Commonwealth Ave
BostonMA02135
property at 52 Greycliff Rd

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500

Total Monthly Price
$10,500

6 Bedroom, 3 Bath Home for Rent

Available Sep 1, 2026

52 Greycliff Rd

BostonMA02135
property at 52 Greycliff Rd

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500

Total Monthly Price
$10,500

6 Bedroom, 3 Bath Home for Rent

Available Sep 1, 2026

52 Greycliff Rd

BostonMA02135
property at 44 Greycliff Rd

$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 Greycliff Rd, Unit 1

44 Greycliff Rd
BrightonMA02135
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 201 Langley Rd

$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

201 Langley Rd, Unit 201

201 Langley Rd
NewtonMA02459
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 289 Foster St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 1 Bath Condo for Rent

Available Now

289 Foster St, Unit 1

289 Foster St
BostonMA02135
property at 289 Foster St

$7,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,500

Total Monthly Price
$7,500

4 Bedroom, 1 Bath Townhome for Rent

Available Now

289 Foster St, Unit #1

289 Foster St
BostonMA02135
property at 64 Greycliff Rd

$10,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,000

Total Monthly Price
$10,000

1 Bedroom, 1 Bath Townhome for Rent

Available Now

64 Greycliff Rd, Unit 1

64 Greycliff Rd
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 1933 Commonwealth Ave

$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 Jan 1, 2026

1933 Commonwealth Ave, Unit 108

1933 Commonwealth Ave
BostonMA02135
property at 27 South St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 Bedroom, 1 Bath Condo for Rent

Available Now

27 South St, Unit #B3

27 South St
BostonMA02135
property at 1933 Commonwealth Ave

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

1 Bedroom, 1 Bath Condo for Rent

Available Now

1933 Commonwealth Ave, Unit 108

1933 Commonwealth Ave
BostonMA02135
property at 1933 Commonwealth Ave

$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

1933 Commonwealth Ave, Unit 403

1933 Commonwealth Ave
BostonMA02135
property at 1933 Commonwealth Ave

$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

1933 Commonwealth Ave, Unit 1

1933 Commonwealth Ave
BostonMA02135
property at 25 Kirkwood Rd

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

5 Bedroom, 2 Bath Condo for Rent

Available Now

25 Kirkwood Rd, Unit 1##

25 Kirkwood Rd
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

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 19 South St

$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 Now

19 South St, Unit 11

19 South St
BostonMA02135
property at 19 South St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Now

19 South St, Unit 11

19 South St
BostonMA02135
property at 19 South St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

19 South St, Unit 11

19 South St
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.