Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (415 Rentals) Page 2 of 9

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
close
View Me
148 Strathmore Rd, Unit 1
$4,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100
4 Bedroom Apartment Available Now

148 Strathmore Rd, Unit 1

148 Strathmore RdBoston, MA 02135
Affordability
close
View Me
210 Chestnut Hill Ave, Unit 6
$4,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000
3 Bedroom Apartment Available Aug 31

210 Chestnut Hill Ave, Unit 6

210 Chestnut Hill AveBoston, MA 02135
Affordability
close
View Me
16 Gerald Rd, Unit 1
$6,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200
3 Bedroom Apartment Available Sep 1

16 Gerald Rd, Unit 1

16 Gerald RdBoston, MA 02135
  • Smoke Free
close
View Me
15 Moody St, Unit 1
$6,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,900

Total Monthly Price
$6,900
3 Bedroom Apartment Available Sep 1

15 Moody St, Unit 1

15 Moody StChestnut Hill, MA 02467
Cost Per Sq.Ft.
close
View Me
2 Braemore Rd, Unit 1
$2,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600
1 Bedroom Apartment Available Now

2 Braemore Rd, Unit 1

2 Braemore RdBoston, MA 02135
Affordability
close
View Me
16 Dighton St, Unit 2
$3,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400
4 Bedroom Apartment Available Now

16 Dighton St, Unit 2

16 Dighton StBoston, MA 02135
Cost Per Sq.Ft.
close
View Me
260 Chestnut Hill Ave
$2,600 - $3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600 - $3,100

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

260 Chestnut Hill Ave

260 Chestnut Hill AveBoston, MA 02135
Affordability
close
View Me
16 Gerald Rd, Unit 1
$6,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200
3 Bedroom Apartment Available Aug 30, 2027

16 Gerald Rd, Unit 1

16 Gerald RdBoston, MA 02135
close
View Me
71 Chestnut Hill Ave, Unit 73
$3,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800
4 Bedroom Apartment Available Sep 1

71 Chestnut Hill Ave, Unit 73

71 Chestnut Hill AveBoston, MA 02135
Affordability
close
View Me
65 Strathmore Rd
$3,595 - $4,700
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,595 - $4,700

Total Monthly Price
$3,595 - $4,700
1 to 4 Bedroom Apartment Available Sep 1

65 Strathmore Rd

65 Strathmore RdBoston, MA 02135
Affordability
close
View Me
558 Washington St, Unit 2
$3,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500
3 Bedroom Apartment Available Now

558 Washington St, Unit 2

558 Washington StBoston, MA 02135
Affordability
close
View Me
16 Gerald Rd, Unit 1
$6,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200
3 Bedroom Apartment Available Aug 30, 2027

16 Gerald Rd, Unit 1

16 Gerald RdBoston, MA 02135
close
View Me
2025 Commonwealth Ave, Unit 7
$3,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400
2 Bedroom Apartment Available Now

2025 Commonwealth Ave, Unit 7

2025 Commonwealth AveBoston, MA 02135
Affordability
close
View Me
9 Montfern Ave, Unit 9A
$3,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200
2 Bedroom Apartment Available Now

9 Montfern Ave, Unit 9A

9 Montfern AveBoston, MA 02135
Affordability
close
View Me
435 Market St, Unit 301
$3,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600
2 Bedroom Apartment Available Now

435 Market St, Unit 301

435 Market StBoston, MA 02135
Affordability
close
View Me
225 Chestnut Hill Ave, Unit 1
$4,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,400

Total Monthly Price
$4,400
4 Bedroom Apartment Available Sep 1

225 Chestnut Hill Ave, Unit 1

225 Chestnut Hill AveBoston, MA 02135
Furnished
  • Smoke Free
close
View Me
209 Chestnut Hill Ave, Unit 1
$5,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200
4 Bedroom Apartment Available Sep 1

209 Chestnut Hill Ave, Unit 1

209 Chestnut Hill AveBoston, MA 02135
Affordability
  • Smoke Free
close
View Me
19 Chestnut Hill Ave, Unit 1
$2,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900
2 Bedroom Apartment Available Sep 1

19 Chestnut Hill Ave, Unit 1

19 Chestnut Hill AveBoston, 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 415 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

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention   article

Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

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.

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

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

Written by: Robin Stewart

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.

decorative image for Pet-Friendly Renting: Everything You Need to Know Before You Move article

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.