Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (324 Rentals) Page 2 of 7

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148 Strathmore Rd, Unit 1
$4,100

Total Monthly Price

Base Rent$4,100

Total Monthly Price$4,100
12 Month Lease Term
4 Bedroom Apartment Available Now

148 Strathmore Rd, Unit 1

148 Strathmore RdBoston, MA 02135
Affordability
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16 Gerald Rd, Unit 1
$6,200

Total Monthly Price

Base Rent$6,200

Total Monthly Price$6,200
12 Month Lease Term
3 Bedroom Apartment Available Now

16 Gerald Rd, Unit 1

16 Gerald RdBoston, MA 02135
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260 Chestnut Hill Ave
$2,600 - $3,100

Total Monthly Price

Base Rent$2,600 - $3,100

Total Monthly Price$2,600 - $3,100
12 Month Lease Term
Studio to 2 Bedroom Apartment Available Now

260 Chestnut Hill Ave

260 Chestnut Hill AveBoston, MA 02135
Affordability
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16 Gerald Rd, Unit 1
$6,200

Total Monthly Price

Base Rent$6,200

Total Monthly Price$6,200
12 Month Lease Term
3 Bedroom Apartment Available Aug 30, 2027

16 Gerald Rd, Unit 1

16 Gerald RdBoston, MA 02135
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44 Kirkwood Rd, Unit 1
$9,900

Total Monthly Price

Base Rent$9,900

Total Monthly Price$9,900
12 Month Lease Term
4 Bedroom Apartment Available Aug 30, 2027

44 Kirkwood Rd, Unit 1

44 Kirkwood RdBoston, MA 02135
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21 Boylston St, Unit #1,
$4,950

Total Monthly Price

Base Rent$4,950

Total Monthly Price$4,950
12 Month Lease Term
2 Bedroom Apartment Available Now

21 Boylston St, Unit #1,

21 Boylston StChestnut Hill, MA 02467
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65 Strathmore Rd
$4,900

Total Monthly Price

Base Rent$4,900

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

65 Strathmore Rd

65 Strathmore RdBoston, MA 02135
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558 Washington St, Unit 2
$3,500

Total Monthly Price

Base Rent$3,500

Total Monthly Price$3,500
12 Month Lease Term
3 Bedroom Apartment Available Now

558 Washington St, Unit 2

558 Washington StBoston, MA 02135
Affordability
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9 Montfern Ave, Unit 9A
$3,200

Total Monthly Price

Base Rent$3,200

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

9 Montfern Ave, Unit 9A

9 Montfern AveBoston, MA 02135
Affordability
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39 Commonwealth Avenue, Unit 12
$2,800

Total Monthly Price

Base Rent$2,800

Total Monthly Price$2,800
12 Month Lease Term
2 Bedroom Apartment Available Now

39 Commonwealth Avenue, Unit 12

39 Commonwealth AvenueNewton, MA 02467
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2025 Commonwealth Ave, Unit 7
$3,400

Total Monthly Price

Base Rent$3,400

Total Monthly Price$3,400
12 Month Lease Term
2 Bedroom Apartment Available Now

2025 Commonwealth Ave, Unit 7

2025 Commonwealth AveBoston, MA 02135
Affordability
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435 Market St, Unit 301
$3,600

Total Monthly Price

Base Rent$3,600

Total Monthly Price$3,600
12 Month Lease Term
2 Bedroom Apartment Available Now

435 Market St, Unit 301

435 Market StBoston, MA 02135
Affordability
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225 Chestnut Hill Ave, Unit 1
$4,400

Total Monthly Price

Base Rent$4,400

Total Monthly Price$4,400
12 Month Lease Term
4 Bedroom Apartment Available Now

225 Chestnut Hill Ave, Unit 1

225 Chestnut Hill AveBoston, MA 02135
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16 Gerald Rd, Unit 1
$6,200

Total Monthly Price

Base Rent$6,200

Total Monthly Price$6,200
12 Month Lease Term
3 Bedroom Apartment Available Aug 30, 2027

16 Gerald Rd, Unit 1

16 Gerald RdBoston, MA 02135
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209 Chestnut Hill Ave, Unit 1
$5,200

Total Monthly Price

Base Rent$5,200

Total Monthly Price$5,200
12 Month Lease Term
4 Bedroom Apartment Available Now

209 Chestnut Hill Ave, Unit 1

209 Chestnut Hill AveBoston, MA 02135
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19 Chestnut Hill Ave, Unit 1
$2,900

Total Monthly Price

Base Rent$2,900

Total Monthly Price$2,900
12 Month Lease Term
2 Bedroom Apartment Available Now

19 Chestnut Hill Ave, Unit 1

19 Chestnut Hill AveBoston, MA 02135
Affordability
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16 South St, Unit 12
$3,700

Total Monthly Price

Base Rent$3,700

Total Monthly Price$3,700
12 Month Lease Term
2 Bedroom Apartment Available Now

16 South St, Unit 12

16 South StBoston, MA 02135
Affordability
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94 Undine Rd, Unit 100
$3,600

Total Monthly Price

Base Rent$3,600

Total Monthly Price$3,600
12 Month Lease Term
3 Bedroom Apartment Available Now

94 Undine Rd, Unit 100

94 Undine RdBoston, MA 02135
Cost Per Sq.Ft.
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23 Willoughby St, Unit 2
$3,300

Total Monthly Price

Base Rent$3,300

Total Monthly Price$3,300
12 Month Lease Term
3 Bedroom Apartment Available Now

23 Willoughby St, Unit 2

23 Willoughby StBoston, MA 02135
Cost Per Sq.Ft.
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58 Tremont St
$3,500 - $3,800

Total Monthly Price

Base Rent$3,500 - $3,800

Total Monthly Price$3,500 - $3,800
12 Month Lease Term
3 Bedroom Apartment Available Now

58 Tremont St

58 Tremont StBoston, MA 02135
Cost Per Sq.Ft.
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22 Lyne Rd, Unit 1
$3,600

Total Monthly Price

Base Rent$3,600

Total Monthly Price$3,600
12 Month Lease Term
3 Bedroom Apartment Available Now

22 Lyne Rd, Unit 1

22 Lyne RdBoston, MA 02135
Cost Per Sq.Ft.
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288 Foster St, Unit #2
$7,000

Total Monthly Price

Base Rent$7,000

Total Monthly Price$7,000
12 Month Lease Term
5 Bedroom Apartment Available Now

288 Foster St, Unit #2

288 Foster StBoston, MA 02135
Cost Per Sq.Ft.
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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
Cost Per Sq.Ft.
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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
Affordability

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 324 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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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

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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

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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

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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.