Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (498 Rentals) Page 10 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 570 Washington St

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

4 Bedroom, 1 Bath Condo for Rent

Available Now

570 Washington St

BostonMA02135
property at 22 N Crescent Circuit

$3,850

Total Monthly Price

Total Monthly Price

Base Rent
$3,850

Total Monthly Price
$3,850

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

property at 37 N Crescent Circuit

$3,850

Total Monthly Price

Total Monthly Price

Base Rent
$3,850

Total Monthly Price
$3,850

3 Bedroom, 1 Bath Home for Rent

Available Sep 1

property at 3 Glenley Terrace

$3,900

Total Monthly Price

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 3 Bath Townhome for Rent

Available Now

3 Glenley Terrace

BostonMA02135
property at 3 A Glenley Terrace

$3,900

Total Monthly Price

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 3 Bath Condo for Rent

Available Sep 1

3 A Glenley Terrace

BostonMA01718
property at 46 Brackett St

$3,900

Total Monthly Price

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 1 Bath Condo for Rent

Available Now

46 Brackett St

BrightonMA02134
property at 30 Bentley St

$3,900

Total Monthly Price

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 3.5 Bath Home for Rent

Available Now

30 Bentley St

BostonMA02135
property at 5 Glenley Terrace

$3,700 - $5,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 To 6 Bedroom Rentals

Available Sep 1

5 Glenley Terrace

BostonMA02135
property at 134 Englewood Ave

$3,945

Total Monthly Price

Total Monthly Price

Base Rent
$3,945

Total Monthly Price
$3,945

3 Bedroom Rentals

Available Sep 1

134 Englewood Ave

BostonMA02135
property at 41 N Crescent Circuit

$3,950

Total Monthly Price

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

property at 210 Chestnut Hill Ave

$4,000

Total Monthly Price

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

3 Bedroom, 2 Bath Condo for Rent

Available Now

property at 110 Kenrick St

$4,200

Total Monthly Price

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

4 Bedroom, 2 Bath Townhome for Rent

Available Now

110 Kenrick St

BostonMA02135
property at 162 Lake Shore Rd

$4,200

Total Monthly Price

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

3 Bedroom, 2 Bath Condo for Rent

Available Now

162 Lake Shore Rd

BostonMA02135
property at 558 Washington St

$4,200

Total Monthly Price

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

558 Washington St

BostonMA02135
property at 195 Lake St

$4,200

Total Monthly Price

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

4 Bedroom, 2 Bath Home for Rent

Available Now

195 Lake St

BostonMA02135
property at 30 Beecher Pl

$4,200

Total Monthly Price

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

3 Bedroom, 2 Bath Condo for Rent

Available Now

30 Beecher Pl

NewtonMA02459
property at 5 Glenmont Rd

$4,220

Total Monthly Price

Total Monthly Price

Base Rent
$4,220

Total Monthly Price
$4,220

4 Bedroom, 2 Bath Home for Rent

Available Now

5 Glenmont Rd

BostonMA02135
property at 126 Carlisle St

$4,300

Total Monthly Price

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

4 Bedroom, 2.5 Bath Townhome for Rent

Available Now

126 Carlisle St

NewtonMA02459
property at 148 Strathmore Rd

$4,300

Total Monthly Price

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

4 Bedroom, 2 Bath Condo for Rent

Available Now

148 Strathmore Rd

BostonMA02135
property at 35 South St

$4,450

Total Monthly Price

Total Monthly Price

Base Rent
$4,450

Total Monthly Price
$4,450

3 Bedroom, 1 Bath Condo for Rent

Available Now

35 South St

BostonMA02135
property at 56 Moody St

$4,495

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,495

Total Monthly Price
$4,495

3 Bedroom, 1.5 Bath Home for Rent

Available Now

56 Moody St

NewtonMA02467
property at 368 Chestnut Hill Ave

$4,500

Total Monthly Price

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

3 Bedroom, 1 Bath Condo for Rent

Available Aug 1

property at 40 Lake Shore Rd

$4,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,750

Total Monthly Price
$4,750

3 Bedroom, 21.5 Bath Home for Rent

Available Now

40 Lake Shore Rd

BostonMA02135
property at 2 Glenley Terrace

$4,800

Total Monthly Price

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2 Glenley Terrace

BostonMA02135
property at 91 Academy Hill Rd

$4,800

Total Monthly Price

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

4 Bedroom, 2 Bath Condo for Rent

Available Now

91 Academy Hill Rd

BostonMA02135
property at 7 Glenley Terrace

$4,800

Total Monthly Price

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

4 Bedroom, 2 Bath Townhome for Rent

Available Sep 1

7 Glenley Terrace

BostonMA02135
property at 2031 Commonwealth Ave

$4,950

Total Monthly Price

Total Monthly Price

Base Rent
$4,950

Total Monthly Price
$4,950

3 Bedroom, 1 Bath Condo for Rent

Available Now

property at 8 Lothian Rd

$5,200

Total Monthly Price

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

8 Lothian Rd

BostonMA02135
property at 70 Larch St

$5,250

Total Monthly Price

Total Monthly Price

Base Rent
$5,250

Total Monthly Price
$5,250

5 Bedroom Rentals

Available Now

70 Larch St

BostonMA02135
property at 124 Kenrick St

$5,400

Total Monthly Price

Total Monthly Price

Base Rent
$5,400

Total Monthly Price
$5,400

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

124 Kenrick St

BostonMA02135
property at 66 Lothian Rd

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

5 Bedroom, 2 Bath Home for Rent

Available Sep 1

66 Lothian Rd

BostonMA02135
property at 2 Lothian Rd

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2 Lothian Rd

BostonMA02135
property at 127 Nonantum St

$5,700 - $5,900

Total Monthly Price

Total Monthly Price

Base Rent
$5,700

Total Monthly Price
$5,700

4 To 5 Bedroom Rentals

Available Now

127 Nonantum St

BostonMA02135
property at 68 Bow Rd

$5,800

Total Monthly Price

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800

3 Bedroom, 2.5 Bath Home for Rent

Available Now

68 Bow Rd

NewtonMA02459
property at 16 Foster St

$6,300

Total Monthly Price

Total Monthly Price

Base Rent
$6,300

Total Monthly Price
$6,300

5 Bedroom, 3 Bath Townhome for Rent

Available Now

16 Foster St

BostonMA02135
property at 39 Winship St

$6,600

Total Monthly Price

Total Monthly Price

Base Rent
$6,600

Total Monthly Price
$6,600

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

39 Winship St

BostonMA02135
property at 11 Glenley Terrace

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

6 Bedroom, 3 Bath Home for Rent

Available Sep 1

11 Glenley Terrace

BostonMA02135
property at 35 John St

$10,000

Total Monthly Price

Total Monthly Price

Base Rent
$10,000

Total Monthly Price
$10,000

4 Bedroom, 4 Bath Townhome for Rent

Available Now

35 John St

NewtonMA02459
property at 52 Greycliff Rd

$11,000

Total Monthly Price

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31

52 Greycliff Rd

BostonMA02135
property at 478 Clinton Rd

$11,000

Total Monthly Price

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

5 Bedroom, 3.5 Bath Home for Rent

Available Now

478 Clinton Rd

BrooklineMA02467
property at 30 Greycliff Rd

$11,000

Total Monthly Price

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 31, 2027

30 Greycliff Rd

BostonMA02135
property at 16 Gerald Rd

$13,500

Total Monthly Price

Total Monthly Price

Base Rent
$13,500

Total Monthly Price
$13,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Now

16 Gerald Rd

BostonMA02135
property at 1789 Commonwealth Ave

$13,600

Total Monthly Price

Total Monthly Price

Base Rent
$13,600

Total Monthly Price
$13,600

8 Bedroom, 9 Bath Condo for Rent

Available Now

property at 132 Yarmouth Rd

$15,000

Total Monthly Price

Total Monthly Price

Base Rent
$15,000

Total Monthly Price
$15,000

4 Bedroom, 5 Bath Home for Rent

Available Now

132 Yarmouth Rd

BrooklineMA02467
property at 29 Merrill Rd

$17,500

Total Monthly Price

Total Monthly Price

Base Rent
$17,500

Total Monthly Price
$17,500

5 Bedroom, 8 Bath Condo for Rent

Available Now

29 Merrill Rd

NewtonMA02459
property at 53 Breck Ave

$4,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,900

Total Monthly Price
$4,900

3 Bedroom, 2 Bath Home for Rent

Available Now

53 Breck Ave

BostonMA02135
property at 12 Braemore Rd

$7,400

Total Monthly Price

Total Monthly Price

Base Rent
$7,400

Total Monthly Price
$7,400

6 Bedroom, 4 Bath Home for Rent

Available Now

12 Braemore Rd

BostonMA02135
property at 110 Strathmore Rd

$3,700

Total Monthly Price

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

2 Bedroom, 2 Bath Condo for Rent

Available Now

110 Strathmore Rd, Unit 401, Unit 401

110 Strathmore Rd
BostonMA02135
property at 72 S Crescent Circuit

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 1 Bath Condo 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 471 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 571 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

decorative image for A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back article

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.

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

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.