Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (328 Rentals) Page 3 of 7

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3 Glenley Terrace, Unit 1x
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
12 Month Lease Term
4 Bedroom Apartment Available Now

3 Glenley Terrace, Unit 1x

3 Glenley TerraceBoston, MA 02135
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99 Chestnut Hill Ave, Unit 313
$3,200

Total Monthly Price

Base Rent$3,200

Total Monthly Price$3,200
12 Month Lease Term
2 Bedroom Apartment Available Now

99 Chestnut Hill Ave, Unit 313

99 Chestnut Hill AveBoston, MA 02135
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39 South St, Unit 62
$2,350

Total Monthly Price

Base Rent$2,350

Total Monthly Price$2,350
12 Month Lease Term
1 Bedroom Apartment Available Now

39 South St, Unit 62

39 South StBoston, MA 02135
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16 Gerald Rd
$6,200 - $13,500

Total Monthly Price

Base Rent$6,200 - $13,500

Total Monthly Price$6,200 - $13,500
12 Month Lease Term
3 to 6 Bedroom Apartment Available Sep 1, 2027

16 Gerald Rd

16 Gerald RdBoston, MA 02135
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44 Greycliff Rd, Unit 1
$10,500

Total Monthly Price

Base Rent$10,500

Total Monthly Price$10,500
12 Month Lease Term
6 Bedroom Apartment Available Now

44 Greycliff Rd, Unit 1

44 Greycliff RdBoston, MA 02135
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44 Kirkwood Rd
$9,600 - $9,900

Total Monthly Price

Base Rent$9,600 - $9,900

Total Monthly Price$9,600 - $9,900
12 Month Lease Term
4 Bedroom Apartment Available Now

44 Kirkwood Rd

44 Kirkwood RdBoston, MA 02135
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22 Radnor Rd, Unit 1
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
12 Month Lease Term
4 Bedroom Apartment Available Aug 22, 2027

22 Radnor Rd, Unit 1

22 Radnor RdBoston, MA 02135
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276 Chestnut Hill Ave, Unit 9
$3,950

Total Monthly Price

Base Rent$3,950

Total Monthly Price$3,950
12 Month Lease Term
3 Bedroom Apartment Available Now

276 Chestnut Hill Ave, Unit 9

276 Chestnut Hill AveBoston, MA 02135
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1945 Commonwealth Ave, Unit 47
$3,200

Total Monthly Price

Base Rent$3,200

Total Monthly Price$3,200
12 Month Lease Term
1 Bedroom Apartment Available Now

1945 Commonwealth Ave, Unit 47

1945 Commonwealth AveBoston, MA 02135
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2 Oneil Pl, Unit 2
$2,750

Total Monthly Price

Base Rent$2,750

Total Monthly Price$2,750
12 Month Lease Term
2 Bedroom Apartment Available Now

2 Oneil Pl, Unit 2

2 Oneil PlBoston, MA 02135
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25 Undine Rd
$3,800 - $12,150

Total Monthly Price

Base Rent$3,800 - $12,150

Total Monthly Price$3,800 - $12,150
12 Month Lease Term
2 to 6 Bedroom Apartment Available Now

25 Undine Rd

25 Undine RdBoston, MA 02135
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3 Winship Pl, Unit 1
$1,350

Total Monthly Price

Base Rent$1,350

Total Monthly Price$1,350
12 Month Lease Term
4 Bedroom Apartment Available Now

3 Winship Pl, Unit 1

3 Winship PlBoston, MA 02135
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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 328 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.

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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.