Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (319 Rentals) Page 5 of 7

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property at 150 Nonantum St
$3,500

Total Monthly Price

Base Rent$3,500
Total Monthly Price$3,500
3 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

150 Nonantum St

BostonMA02135
property at 37 Rogers Park Ave
$3,900

Total Monthly Price

Base Rent$3,900
Total Monthly Price$3,900
4 Bedroom, 1.5 Bath Home for Rent
Available Now
Affordability

37 Rogers Park Ave

BostonMA02135
property at 10 Dighton St
$4,250

Total Monthly Price

Base Rent$4,250
Total Monthly Price$4,250
4 Bedroom, 2 Bath Home for Rent
Available Oct 1
Affordability

10 Dighton St

BostonMA02135
property at 1940 Commonwealth Ave
$2,575

Total Monthly Price

Base Rent$2,575
Total Monthly Price$2,575
2 Bedroom, 1 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

1940 Commonwealth Ave

BostonMA02135
property at 91 Wallingford Rd
$3,495

Total Monthly Price

Base Rent$3,495
Total Monthly Price$3,495
3 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

91 Wallingford Rd

BostonMA02135
property at 229 Chapel St
$3,400

Total Monthly Price

Base Rent$3,400
Total Monthly Price$3,400
3 Bedroom, 1.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

229 Chapel St

NewtonMA02458
property at 1840 Commonwealth Ave
$2,050

Total Monthly Price

Base Rent$2,050
Total Monthly Price$2,050
1 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

1840 Commonwealth Ave

BostonMA02135
property at 11 Travis Dr
$2,200

Total Monthly Price

Base Rent$2,200
Total Monthly Price$2,200
1 Bedroom Rentals
Available Now
Affordability

11 Travis Dr

NewtonMA02467
property at 36 Undine Rd
$4,200

Total Monthly Price

Base Rent$4,200
Total Monthly Price$4,200
3 Bedroom, 2 Bath Home for Rent
Available Now
Affordability

36 Undine Rd

BostonMA02135
property at 1949 Commonwealth Ave
$1,975

Total Monthly Price

Base Rent$1,975
Total Monthly Price$1,975
Studio, 1 Bath Home for Rent
Available Now
Affordability

1949 Commonwealth Ave

BostonMA02135
property at 90 Undine Rd
$4,000

Total Monthly Price

Base Rent$4,000
Total Monthly Price$4,000
3 Bedroom, 2 Bath Home for Rent
Available Now
Affordability

90 Undine Rd

BostonMA02135
property at 54 Crosby Rd
$4,500

Total Monthly Price

Base Rent$4,500
Total Monthly Price$4,500
3 Bedroom, 1 Bath Home for Rent
Available Now

54 Crosby Rd

NewtonMA02467
property at 36 Gerald Rd
$3,000 - $3,500

Total Monthly Price

Base Rent$3,000
Total Monthly Price$3,000
1 To 2 Bedroom Rentals
Available Now
Affordability

36 Gerald Rd

BostonMA02135
property at 26-28-28 Tip Top St
$3,400

Total Monthly Price

Base Rent$3,400
Total Monthly Price$3,400
3 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

26-28-28 Tip Top St

BostonMA02135
property at 386 Market St
$3,050 - $4,100

Total Monthly Price

Base Rent$3,050
Total Monthly Price$3,050
1 To 2 Bedroom Rentals
Available Now
Affordability

386 Market St

BostonMA02135
property at 48 Trapelo St
$2,399 - $3,900

Total Monthly Price

Base Rent$2,399
Total Monthly Price$2,399
2 To 4 Bedroom Rentals
Available Now
Affordability

48 Trapelo St

BostonMA02135
property at 23 Parsons St
$1,950

Total Monthly Price

Base Rent$1,950
Total Monthly Price$1,950
Studio, 1 Bath Home for Rent
Available Now
Affordability

23 Parsons St

BostonMA02135
property at 5 Braemore Rd
$2,100

Total Monthly Price

Base Rent$2,100
Total Monthly Price$2,100
1 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

5 Braemore Rd

BostonMA02135
property at 28 Academy Hill Rd
$1,800

Total Monthly Price

Base Rent$1,800
Total Monthly Price$1,800
Studio, 1 Bath Home for Rent
Available Now
Affordability

28 Academy Hill Rd

BostonMA02135
property at 1959 Commonwealth Ave
$2,695

Total Monthly Price

Base Rent$2,695
Total Monthly Price$2,695
3 Bedroom, 1 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

1959 Commonwealth Ave

BostonMA02135
property at 36 Dickinson Rd
$3,450

Total Monthly Price

Base Rent$3,450
Total Monthly Price$3,450
3 Bedroom, 1.5 Bath Home for Rent
Available Now
Affordability

36 Dickinson Rd

BostonMA02135
property at 84 Brayton Rd
$2,950

Total Monthly Price

Base Rent$2,950
Total Monthly Price$2,950
2 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

84 Brayton Rd

BostonMA02135
property at 27 Langley Rd
$3,400

Total Monthly Price

Base Rent$3,400
Total Monthly Price$3,400
3 Bedroom, 1 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

27 Langley Rd

BostonMA02135
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Imperial Towers
1 Bedroom Apartments

Imperial Towers

280 Boylston StChestnut Hill, MA 02467
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120 Kenrick
Studio Apartments

120 Kenrick

120 Kenrick StBrighton, MA 02135
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Hampton Place
Studio Apartments

Hampton Place

77-79 Florence StChestnut Hill, MA 02467
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19 Braemore Rd
Studio Apartments

19 Braemore Rd

19 Braemore RdBrighton, MA 02135
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100 Suffolk Rd
1 Bedroom Apartments

100 Suffolk Rd

100 Suffolk RdChestnut Hill, MA 02467
Showing Results 201-250, Page 5 of 7

Frequently Asked Questions about Chestnut Hill Middlesex

What is the current pricing and availability for apartments for rent in the Chestnut Hill Middlesex area of Chestnut Hill, MA?

As of today, September 12, 2026, there are currently 319 available Chestnut Hill Middlesex apartments priced from $1,000 to $13,500, with an average monthly rent of $3,865.

How much are Studio apartments in Chestnut Hill Middlesex?

There are currently 46 Studio Apartments in Chestnut Hill Middlesex with rent ranges from $1,800 to $4,320 with an average price of $2,410.

What is the current price range for One Bedroom Chestnut Hill Middlesex Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Chestnut Hill Middlesex ranges from $1,800 to $4,841 with an average monthly rent of $2,576.

What does renting a Two Bedroom Apartment in Chestnut Hill Middlesex cost?

The monthly rent prices of Two Bedroom Apartments currently available in Chestnut Hill Middlesex range from $2,350 to $6,120. Today's average rental price for Two Bedrooms here is $3,531.

How expensive are Chestnut Hill Middlesex Three Bedroom Apartments?

There are currently 75 Three Bedroom Apartments listings available in Chestnut Hill Middlesex on ApartmentHomeLiving.com. The pricing ranges from $1,000 to $7,790 - averaging $3,946 for the location.

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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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.