Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (604 Rentals) Page 2 of 13

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property at 320 Hammond Pond Pky

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 2 Bath Condo for Rent

Available Now

320 Hammond Pond Pky

Chestnut HillMA02467
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, Unit 104

320 Hammond Pond Pkwy
NewtonMA02467
property at 288 Foster St

$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 Sep 1

288 Foster St, Unit 1, Unit 1

288 Foster St
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

BostonMA02135
property at 29 Gerald Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

29 Gerald Rd

BostonMA02135
property at 288 Foster St

$6,200 - $7,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200 - $7,200

Total Monthly Price
$6,200 - $7,200

4 To 5 Bedroom Condos for Rent

Available Now

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

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

29 Gerald Rd, Unit 2##, Unit 2##

29 Gerald Rd
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, 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, Unit 16

2001 Commonwealth Ave
BostonMA02135
property at 1999 Commonwealth Ave

$3,650 - $4,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650 - $4,900

Total Monthly Price
$3,650 - $4,900

2 To 3 Bedroom Condos for Rent

Available Jun 1

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, 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

1999 Commonwealth Ave, Unit 12, Unit 12

1999 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

1999 Commonwealth Ave, Unit 2, Unit 2

1999 Commonwealth Ave
BostonMA02135
property at 25 Moody St

$4,995

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,995

Total Monthly Price
$4,995

3 Bedroom, 1.5 Bath Home for Rent

Available Now

25 Moody St

Chestnut HillMA02467
property at 9 Radnor Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

4 Bedroom, 2 Bath Condo for Rent

Available Aug 30

9 Radnor Rd, Unit 1, Unit 1

9 Radnor Rd
BostonMA02135
property at 39 South St

$2,750 - $4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,750 - $4,800

Total Monthly Price
$2,750 - $4,800

1 To 3 Bedroom Condos for Rent

Available Jun 1

39 South St

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, 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, Unit 2

211 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, Unit 2

215 Lake Shore Rd
BostonMA02135
property at 162 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 Sep 1

162 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, Unit 1

204 Lake Shore Rd
BostonMA02135
property at 153 Lake Shore Rd

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 2 Bath Condo for Rent

Available Aug 1

153 Lake Shore Rd, Unit 1, Unit 1

153 Lake Shore Rd
BostonMA02135
property at 166 Lake Shore Rd

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 2 Bath Condo for Rent

Available Aug 1

166 Lake Shore Rd, Unit 1L, Unit 1L

166 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

44 Greycliff Rd, Unit 1, Unit 1

44 Greycliff Rd
BostonMA02135
property at 44 Greycliff Rd

$10,500 - $12,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500 - $12,000

Total Monthly Price
$10,500 - $12,000

6 Bedroom, 3 Bath Condo for Rent

Available Now

44 Greycliff Rd

BostonMA02135
property at 44 Greycliff Rd

$11,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 30, 2027

44 Greycliff Rd, Unit 1, Unit 1

44 Greycliff Rd
BostonMA02135
property at 44 Greycliff Rd

$12,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$12,400

Total Monthly Price
$12,400

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31, 2027

44 Greycliff Rd, Unit #2, Unit #2

44 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

52 Greycliff Rd

BostonMA02135
property at 44 Greycliff Rd

$10,500 - $12,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500 - $12,000

Total Monthly Price
$10,500 - $12,000

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31

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 Aug 31

52 Greycliff Rd

BostonMA02135
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 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, 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, Unit 1

289 Foster St
BostonMA02135
property at 64 Greycliff Rd

$6,250 - $11,000

Total Monthly Price4 Month Lease Term

Total Monthly Price

Base Rent
$6,250 - $11,000

Total Monthly Price
$6,250 - $11,000

1 To 4 Bedroom Townhomes for Rent

Available Now

64 Greycliff Rd

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

BostonMA02135
property at 37 Radnor Rd

$2,840 - $4,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,840 - $4,850

Total Monthly Price
$2,840 - $4,850

2 To 3 Bedroom Condos for Rent

Available Now

37 Radnor 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, Unit 13C

1945 Commonwealth Ave
BostonMA02135
property at 2003 Commonwealth Ave

$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

2003 Commonwealth Ave, Unit A, Unit A

2003 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, Unit #B3

27 South St
BostonMA02135
property at 1933 Commonwealth Ave

$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

1933 Commonwealth Ave, Unit 504, Unit 504

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

1 To 2 Bedroom Condos 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 493 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $17,000. There are also 603 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $800 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 $800 to $17,500 with an average monthly rent of $6,124.

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 $8,997, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,700 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,030 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

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Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

decorative image for 18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property article

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.