3 Bedroom Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (94 Rentals) Page 2 of 2

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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 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 51 Algonquin Rd

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1, 2026

51 Algonquin Rd

Chestnut HillMA02467
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 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 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 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 35 Henshaw St

$4,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

3 Bedroom, 4 Bath Condo for Rent

Available Now

35 Henshaw St, Unit 1ZB

35 Henshaw St
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 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 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 276 Chestnut Hill Ave

$4,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,600

Total Monthly Price
$4,600

3 Bedroom, 1.5 Bath Condo for Rent

Available Aug 2, 2026

276 Chestnut Hill Ave, Unit 9

276 Chestnut Hill Ave
BostonMA02135
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 258 Chestnut Hill Ave

$4,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,600

Total Monthly Price
$4,600

3 Bedroom, 1.5 Bath Condo for Rent

Available Aug 1, 2026

258 Chestnut Hill Ave, Unit 9

258 Chestnut Hill 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 25 Greycliff Rd

$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

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
property at 25 Greycliff Rd

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
property at 508 Heath St

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

3 Bedroom, 2 Bath Condo for Rent

Available Now

508 Heath St, Unit 1

508 Heath St
BrooklineMA02467
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 2000 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

2000 Commonwealth Ave, Unit 5

2000 Commonwealth Ave
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 2021 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

2021 Commonwealth Ave, Unit 5

2021 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 16 Gerald Rd

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31, 2026

16 Gerald Rd, Unit 1

16 Gerald Rd
BostonMA02135
property at 12 Gerald Rd

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31, 2026

12 Gerald Rd, Unit 1

12 Gerald Rd
BostonMA02135
property at 16 Gerald Rd

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31, 2026

16 Gerald Rd, Unit 1

16 Gerald Rd
BostonMA02135
property at 16 Gerald Rd

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31, 2026

16 Gerald Rd, Unit 1

16 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 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 25 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

25 Gerald Rd, Unit 1

25 Gerald Rd
BostonMA02135
property at 36 Turner St

$3,450

Total Monthly Price

Total Monthly Price

Base Rent
$3,450

Total Monthly Price
$3,450

3 Bedroom, 1 Bath Condo for Rent

Available Now

36 Turner St

BostonMA02135
property at 22 Eastburn St

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Townhome for Rent

Available Now

22 Eastburn St

BostonMA02135
property at 31 Ripley St

$4,250

Total Monthly Price

Total Monthly Price

Base Rent
$4,250

Total Monthly Price
$4,250

3 Bedroom Rentals

Available Now

31 Ripley St

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 Sep 1, 2026

property at 569 Commonwealth Ave

$5,000

Total Monthly Price

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

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

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 415 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.