Condos for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (321 Rentals)

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.
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
property at 10 Hammond Pond Pky

$2,500

Total Monthly Price24 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Feb 1, 2026

10 Hammond Pond Pky, Unit 304

10 Hammond Pond Pky
Chestnut HillMA02467
property at 295 Commonwealth Ave

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

Studio, 1 Bath Condo for Rent

Available Now

295 Commonwealth Ave, Unit H-18

295 Commonwealth Ave
Chestnut HillMA02467
property at 35 Commonwealth Ave

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

1 Bedroom, 1 Bath Condo for Rent

Available Now

35 Commonwealth Ave, Unit U201-1-bed

35 Commonwealth Ave
Chestnut HillMA02467
property at 320 Hammond Pond Pky

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 2 Bath Condo for Rent

Available Now

320 Hammond Pond Pky

Chestnut HillMA02467
property at 11 Hammond Pond Pky

$3,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,450

Total Monthly Price
$3,450

2 Bedroom, 2 Bath Condo for Rent

Available Now

11 Hammond Pond Pky, Unit 203

11 Hammond Pond Pky
Chestnut HillMA02467
property at 136 Middlesex Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Now

136 Middlesex Rd, Unit 2

136 Middlesex Rd
Chestnut HillMA02467
property at 25 Crosby Rd

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

2 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

25 Crosby Rd

Chestnut HillMA02467
property at 47 Algonquin Rd

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

47 Algonquin Rd, Unit 2

47 Algonquin Rd
Chestnut HillMA02467
property at 250 Hammond Pond Pky

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

250 Hammond Pond Pky, Unit 1203N

250 Hammond Pond Pky
Chestnut HillMA02467
property at 321 Hammond Pond Pky

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

321 Hammond Pond Pky, Unit 301

321 Hammond Pond Pky
Chestnut HillMA02467

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

property at 28 Manet Rd

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

4 Bedroom, 1 Bath Condo for Rent

Available Now

28 Manet Rd, Unit 2

28 Manet Rd
Chestnut HillMA02467
property at 47 Algonquin Rd

$5,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,700

Total Monthly Price
$5,700

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

47 Algonquin Rd, Unit 1

47 Algonquin Rd
Chestnut HillMA02467
property at 47 Crosby Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

47 Crosby Rd, Unit 2

47 Crosby Rd
Chestnut HillMA02467
property at 25 Crosby Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 2 Bath Condo for Rent

Available Now

25 Crosby Rd, Unit 2

25 Crosby Rd
Chestnut HillMA02467
property at 199 Boylston St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 3.5 Bath Condo for Rent

Available Now

199 Boylston St, Unit 1

199 Boylston St
Chestnut HillMA02467
property at 20 Manet Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1, 2026

20 Manet Rd, Unit 1

20 Manet Rd
Chestnut HillMA02467
property at 28 Manet Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1, 2026

28 Manet Rd, Unit 1

28 Manet Rd
Chestnut HillMA02467
property at 68 Manet Rd

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

4 Bedroom, 3 Bath Condo for Rent

Available Sep 1, 2026

68 Manet Rd, Unit 1

68 Manet Rd
Chestnut HillMA02467
property at 384 Langley Rd

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 1 Bath Condo for Rent

Available Now

384 Langley Rd, Unit 384

384 Langley Rd
NewtonMA02459
property at 320 Hammond Pond Pkwy

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

2 Bedroom, 2 Bath Condo for Rent

Available Now

320 Hammond Pond Pkwy, Unit 104

320 Hammond Pond Pkwy
NewtonMA02467

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

property at 201 Langley Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Now

201 Langley Rd, Unit 201

201 Langley Rd
NewtonMA02459
property at 26 Holly Ln

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

26 Holly Ln, Unit 2

26 Holly Ln
BrooklineMA02467
property at 508 Heath St

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

3 Bedroom, 2 Bath Condo for Rent

Available Now

508 Heath St, Unit 1

508 Heath St
BrooklineMA02467
property at 27 Bostonia Ave

$9,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,500

Total Monthly Price
$9,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Now

27 Bostonia Ave

BrightonMA02135
property at 44 Greycliff Rd

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500

Total Monthly Price
$10,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 31, 2026

44 Greycliff Rd, Unit 1

44 Greycliff Rd
BrightonMA02135
property at 44 Bostonia Ave

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500

Total Monthly Price
$10,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 31, 2026

44 Bostonia Ave, Unit 1

44 Bostonia Ave
BrightonMA02135
property at 52 Bostonia Ave

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500

Total Monthly Price
$10,500

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31, 2026

52 Bostonia Ave, Unit 1

52 Bostonia Ave
BrightonMA02135
property at 46 Bostonia Ave

$11,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,200

Total Monthly Price
$11,200

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31, 2026

46 Bostonia Ave, Unit 1

46 Bostonia Ave
BrightonMA02135
property at 141 Englewood Ave

$1,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,850

Total Monthly Price
$1,850

Studio, 1 Bath Condo for Rent

Available Now

141 Englewood Ave, Unit 1

141 Englewood Ave
BostonMA02135
property at 4 Chiswick Rd

$1,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,950

Total Monthly Price
$1,950

1 Bedroom, 1 Bath Condo for Rent

Available Now

4 Chiswick Rd, Unit 5

4 Chiswick Rd
BostonMA02135

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

property at 1999 Commonwealth Ave

$1,999

Total Monthly Price10 Month Lease Term

Total Monthly Price

Base Rent
$1,999

Total Monthly Price
$1,999

1 Bedroom, 1 Bath Condo for Rent

Available Now

1999 Commonwealth Ave, Unit 01-2

1999 Commonwealth Ave
BostonMA02135
property at 4 Chiswick Rd

$2,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

Studio, 1 Bath Condo for Rent

Available Now

4 Chiswick Rd, Unit 24

4 Chiswick Rd
BostonMA02135
property at 19 Chestnut Hill Ave

$2,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

Studio, 1 Bath Condo for Rent

Available Now

19 Chestnut Hill Ave, Unit 3

19 Chestnut Hill Ave
BostonMA02135
property at 1872 Commonwealth Ave

$2,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

1 Bedroom, 1 Bath Condo for Rent

Available Now

1872 Commonwealth Ave, Unit 6

1872 Commonwealth Ave
BostonMA02135
property at 155 Strathmore Rd

$2,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

1 Bedroom, 1 Bath Condo for Rent

Available Now

155 Strathmore Rd, Unit 1

155 Strathmore Rd
BostonMA02135
property at 160 Strathmore Rd

$2,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

1 Bedroom, 1 Bath Condo for Rent

Available Feb 1, 2026

160 Strathmore Rd, Unit 5

160 Strathmore Rd
BostonMA02135
property at 173 Chiswick Rd

$2,045

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,045

Total Monthly Price
$2,045

2 Bedroom, 1 Bath Condo for Rent

Available Now

173 Chiswick Rd, Unit 29

173 Chiswick Rd
BostonMA02135
property at 124 Academy Hill Rd

$2,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,100

Total Monthly Price
$2,100

1 Bedroom, 1 Bath Condo for Rent

Available Now

124 Academy Hill Rd, Unit B

124 Academy Hill Rd
BostonMA02135
property at 15 Beechcroft St

$2,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,100

Total Monthly Price
$2,100

1 Bedroom, 1 Bath Condo for Rent

Available Now

15 Beechcroft St

BostonMA02135
property at 10 Lothian Rd

$2,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,200

Total Monthly Price
$2,200

1 Bedroom, 1 Bath Condo for Rent

Available Now

10 Lothian Rd, Unit 7

10 Lothian Rd
BostonMA02135
property at 2021 Commonwealth Ave

$2,295

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,295

Total Monthly Price
$2,295

1 Bedroom, 1 Bath Condo for Rent

Available Now

2021 Commonwealth Ave, Unit 2001-2

2021 Commonwealth Ave
BostonMA02135
property at 1868 Commonwealth Ave

$2,295

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,295

Total Monthly Price
$2,295

1 Bedroom, 1 Bath Condo for Rent

Available Now

1868 Commonwealth Ave, Unit 2

1868 Commonwealth Ave
BostonMA02135
property at 2009 Commonwealth Ave

$2,295

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,295

Total Monthly Price
$2,295

1 Bedroom, 1 Bath Condo for Rent

Available Now

property at 1965 Commonwealth Ave

$2,325

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,325

Total Monthly Price
$2,325

1 Bedroom, 1 Bath Condo for Rent

Available Now

1965 Commonwealth Ave, Unit 31

1965 Commonwealth Ave
BostonMA02135
property at 1870 Commonwealth Ave

$2,350

Total Monthly Price18 Month Lease Term

Total Monthly Price

Base Rent
$2,350

Total Monthly Price
$2,350

1 Bedroom, 1 Bath Condo for Rent

Available Mar 15, 2026

1870 Commonwealth Ave, Unit 7

1870 Commonwealth Ave
BostonMA02135
property at 114 Strathmore Rd

$2,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

1 Bedroom, 1 Bath Condo for Rent

Available Now

114 Strathmore Rd, Unit 406

114 Strathmore Rd
BostonMA02135
property at 1999 Commonwealth Ave

$2,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

1 Bedroom, 1 Bath Condo for Rent

Available Now

1999 Commonwealth Ave, Unit 24

1999 Commonwealth Ave
BostonMA02135
property at 2016 Commonwealth Ave

$2,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

1 Bedroom, 1 Bath Condo for Rent

Available Now

2016 Commonwealth Ave, Unit 48

2016 Commonwealth Ave
BostonMA02135
property at 2 Lothian Rd

$2,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

2 Bedroom, 1 Bath Condo for Rent

Available Now

2 Lothian Rd, Unit 1

2 Lothian Rd
BostonMA02135
property at 140 Kenrick St

$2,400

Total Monthly Price9 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

1 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

140 Kenrick St, Unit 25

140 Kenrick St
BostonMA02135

Chestnut Hill Middlesex, Boston College, MA Local Guide

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

Read Article
Decorative image

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

Read Article
Decorative image

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

Read Article
Decorative image

Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

decorative image of people with a giant lease agreement

Pet Friendly Lifestyle
Chestnut Hill Middlesex, Chestnut Hill, MA

Ranked #1

Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

decorative image of woman handing cat to small boy

Frequently Asked Questions about Chestnut Hill Middlesex

What type of rentals are currently available in Chestnut Hill Middlesex?

There are currently 467 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $17,000. There are also 421 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $730 to $17,500.

What is the current price range for Rental Homes in Chestnut Hill Middlesex?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestnut Hill Middlesex ranges from $730 to $17,500 with an average monthly rent of $6,426.

How much are larger Three and Four Bedroom Rentals in Chestnut Hill Middlesex?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestnut Hill Middlesex range from $2,550 to $6,320, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $7,000. Four Bedroom Single-Family rentals are also available starting from $860 and Four Bedroom Apartments start at $3,200.

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 How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips article

How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips

Written by: Justin Habersaat

Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!