Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (412 Rentals) Page 4 of 9

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539 Washington St, Unit 2
$3,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400
3 Bedroom Apartment Available Sep 1

539 Washington St, Unit 2

539 Washington StBoston, MA 02135
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25 Undine Rd, Unit 25 a
$7,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,800

Total Monthly Price
$7,800
4 Bedroom Apartment Available Sep 1

25 Undine Rd, Unit 25 a

25 Undine RdBoston, MA 02135
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58 Tremont St
$3,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300
3 Bedroom Apartment Available Sep 1

58 Tremont St

58 Tremont StBoston, MA 02135
Cost Per Sq.Ft.
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7 Winship St, Unit 1
$2,395
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,395

Total Monthly Price
$2,395
1 Bedroom Apartment Available Sep 1

7 Winship St, Unit 1

7 Winship StBoston, MA 02135
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80 Langley Rd
$2,400 - $2,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400 - $2,500

Total Monthly Price
$2,400 - $2,500
3 Bedroom Apartment Available Jul 31

80 Langley Rd

80 Langley RdBoston, MA 02135
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461 Washington St
$2,934 - $5,434
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,934 - $5,434

Total Monthly Price
$2,934 - $5,434
Studio to 2 Bedroom Apartment Available Jul 31

461 Washington St

461 Washington StBoston, MA 02135
Affordability
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31 Willoughby St
$2,725 - $3,225
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,725 - $3,225

Total Monthly Price
$2,725 - $3,225
3 to 4 Bedroom Apartment Available Jul 31

31 Willoughby St

31 Willoughby StBoston, MA 02135
Affordability
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566 Washington St, Unit 14
$1,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,800

Total Monthly Price
$1,800
1 Bedroom Apartment Available Now

566 Washington St, Unit 14

566 Washington StBoston, MA 02135
Affordability
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2 O'Neil Pl, Unit 1
$3,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200
2 Bedroom Apartment Available Sep 1

2 O'Neil Pl, Unit 1

2 O'Neil PlBoston, MA 02135
Cost Per Sq.Ft.
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328 Washington St, Unit 2c
$4,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200
4 Bedroom Apartment Available Sep 1

328 Washington St, Unit 2c

328 Washington StBoston, MA 02135
Cost Per Sq.Ft.
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31 Willoughby St, Unit 1
$3,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300
3 Bedroom Apartment Available Now

31 Willoughby St, Unit 1

31 Willoughby StBoston, MA 02135
Cost Per Sq.Ft.
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31 N Crescent Circuit, Unit 1z
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

31 N Crescent Circuit, Unit 1z

31 N Crescent CircuitBoston, MA 02135
Cost Per Sq.Ft.
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26 Lake Shore Ter, Unit 2
$1,350
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,350

Total Monthly Price
$1,350
3 Bedroom Apartment Available Sep 1

26 Lake Shore Ter, Unit 2

26 Lake Shore TerBoston, MA 02135
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58 Tremont St
$3,500 - $3,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500 - $3,800

Total Monthly Price
$3,500 - $3,800
3 Bedroom Apartment Available Soon

58 Tremont St

58 Tremont StBoston, MA 02135
Cost Per Sq.Ft.
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3 Winship Pl, Unit 1
$1,350
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,350

Total Monthly Price
$1,350
2 Bedroom Apartment Available Sep 1

3 Winship Pl, Unit 1

3 Winship PlBoston, MA 02135
Affordability
  • Smoke Free

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, July 29, 2026, there are currently 412 available Chestnut Hill Middlesex apartments priced from $960 to $14,300, with an average monthly rent of $3,402.

How much are Studio apartments in Chestnut Hill Middlesex?

There are currently 53 Studio Apartments in Chestnut Hill Middlesex with rent ranges from $1,800 to $4,230 with an average price of $2,343.

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 $960 to $7,399 with an average monthly rent of $2,635.

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 $1,350 to $5,434. Today's average rental price for Two Bedrooms here is $3,386.

How expensive are Chestnut Hill Middlesex Three Bedroom Apartments?

There are currently 104 Three Bedroom Apartments listings available in Chestnut Hill Middlesex on ApartmentHomeLiving.com. The pricing ranges from $1,350 to $7,999 - averaging $3,785 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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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.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

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There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

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Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.