Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (493 Rentals) Page 4 of 10

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The most luxurious Homes in the Chestnut Hill Middlesex area of Chestnut Hill with high-end amenities, features, and finishes.

property at 1870 Commonwealth Ave

$4,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

2 Bedroom, 1 Bath Condo for Rent

Available Now

1870 Commonwealth Ave, Unit 12A, Unit 12A

1870 Commonwealth Ave
BostonMA02135
property at 5 Glenmont Rd

$4,220

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,220

Total Monthly Price
$4,220

4 Bedroom, 2 Bath Condo for Rent

Available Jul 1

5 Glenmont Rd, Unit 1, Unit 1

5 Glenmont Rd
BostonMA02135
property at 328 Washington St

$4,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

4 Bedroom, 2 Bath Condo for Rent

Available Now

328 Washington St, Unit 1, Unit 1

328 Washington 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, Unit 2

89 Brayton Rd
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 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, Unit 1ZB

35 Henshaw St
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, Unit 1

80 Wallingford 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, Unit 2

195 Lake St
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 99 Chestnut Hill Ave

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

2 Bedroom, 2 Bath Condo for Rent

Available Sep 1

99 Chestnut Hill Ave, Unit 3, Unit 3

99 Chestnut Hill Ave
BostonMA02135
property at 73 Undine Rd

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

4 Bedroom, 2.5 Bath Home for Rent

Available Now

73 Undine Rd

BostonMA02135
property at 4 North Crescent Circuit

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

3 Bedroom, 2.5 Bath Home for Rent

Available Sep 1

4 North Crescent Circuit, Unit 1, Unit 1

4 North Crescent Circuit
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 5 Glenley Ter

$4,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,600

Total Monthly Price
$4,600

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

5 Glenley Ter

BostonMA02135
property at 35 Winship St

$4,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,600

Total Monthly Price
$4,600

4 Bedroom, 2 Bath Condo for Rent

Available Now

35 Winship St, Unit 2, Unit 2

35 Winship St
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 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 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, Unit 1

25 Greycliff Rd
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 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, Unit 1

25 Greycliff Rd
BostonMA02135
property at 2016 Commonwealth Ave

$4,695

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,695

Total Monthly Price
$4,695

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

2016 Commonwealth Ave, Unit 4, Unit 4

2016 Commonwealth Ave
BostonMA02135
property at 209 Chestnut Hill Ave

$4,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,700

Total Monthly Price
$4,700

4 Bedroom, 2 Bath Condo for Rent

Available Now

209 Chestnut Hill Ave, Unit 1, Unit 1

209 Chestnut Hill Ave
BostonMA02135
property at 3 Glenley Ter

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

4 Bedroom, 2 Bath Home for Rent

Available Sep 1

3 Glenley Ter

BostonMA02135
property at 28 Manet Rd

$4,800 - $5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800 - $5,800

Total Monthly Price
$4,800 - $5,800

4 To 5 Bedroom Condos for Rent

Available Now

28 Manet Rd

Chestnut HillMA02467
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, Unit 2

132 Chiswick 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, Unit 1

508 Heath St
BrooklineMA02467
property at 35 Foster St

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

35 Foster St, Unit 1, Unit 1

35 Foster 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, Unit 2

27 Eulita Ter
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 91 Wallingford 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 Sep 1

91 Wallingford Rd, Unit 1, Unit 1

91 Wallingford 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, Unit 2

16 Priscilla Rd
BostonMA02135
property at 209 Chestnut Hill Ave

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

4 Bedroom, 2 Bath Condo for Rent

Available Now

209 Chestnut Hill Ave, Unit 2, Unit 2

209 Chestnut Hill Ave
BostonMA02135
property at 6 Lothian Rd

$5,200 - $5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200 - $5,800

Total Monthly Price
$5,200 - $5,800

4 To 5 Bedroom Condos for Rent

Available Now

6 Lothian 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 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, Unit 1

36 Kenrick St
BostonMA02135
property at 30 Winship St

$5,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,250

Total Monthly Price
$5,250

4 Bedroom, 3 Bath Condo for Rent

Available Sep 1

30 Winship 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

91 Wallingford Rd

BostonMA02135
property at 28 Manet Rd

$5,400 - $6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,400 - $6,500

Total Monthly Price
$5,400 - $6,500

4 To 5 Bedroom Condos for Rent

Available Sep 1

28 Manet Rd

Chestnut HillMA02467
property at 225 Chestnut Hill Ave

$5,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,400

Total Monthly Price
$5,400

4 Bedroom, 1 Bath Condo for Rent

Available Sep 1

225 Chestnut Hill Ave, Unit 3, Unit 3

225 Chestnut Hill Ave
BostonMA02135
property at 120 Kenrick St

$5,500 - $5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500 - $5,600

Total Monthly Price
$5,500 - $5,600

4 Bedroom, 2 Bath Condo for Rent

Available Now

120 Kenrick St

BostonMA02135
property at 539 Commonwealth Ave

$5,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

4 Bedroom, 3 Bath Condo for Rent

Available Now

539 Commonwealth Ave, Unit 2, Unit 2

539 Commonwealth Ave
NewtonMA02459
property at 110 Kenrick St

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

4 Bedroom, 2 Bath Condo for Rent

Available Now

110 Kenrick St

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

16 Gerald Rd, Unit 1, Unit 1

16 Gerald Rd
BostonMA02135
property at 16 Foster St

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

5 Bedroom, 3 Bath Townhome for Rent

Available Now

16 Foster St

BostonMA02135
property at 16 Gerald Rd

$5,600 - $6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600 - $6,500

Total Monthly Price
$5,600 - $6,500

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31

16 Gerald Rd

BostonMA02135

Frequently Asked Questions about Chestnut Hill Middlesex

What type of rentals are currently available in Chestnut Hill Middlesex?

There are currently 471 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 575 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $950 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 $950 to $17,500 with an average monthly rent of $5,779.

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 $7,760, while Three Bedroom Homes, Condos, and Townhomes for rent range from $950 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,160 and Four Bedroom Apartments start at $3,100.

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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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

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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.

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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.