Homes for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (462 Rentals)

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property at 150 Kenrick St
$2,900

Total Monthly Price

Base Rent$2,900

Total Monthly Price$2,900
12 Month Lease Term
3 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

150 Kenrick St, Unit 4

150 Kenrick St
BostonMA02135
  • Smoke Free
property at 17 Fairbanks St
$1,985

Total Monthly Price

Base Rent$1,985

Total Monthly Price$1,985
12 Month Lease Term
1 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

17 Fairbanks St

BostonMA02135
  • Smoke Free
property at 51 Algonquin Rd
$3,800

Total Monthly Price

Base Rent$3,800

Total Monthly Price$3,800
12 Month Lease Term
3 Bedroom, 1 Bath Townhome for Rent
Available Now

51 Algonquin Rd

Chestnut HillMA02467
property at 51 Algonquin Rd
$3,950

Total Monthly Price

Base Rent$3,950

Total Monthly Price$3,950
12 Month Lease Term
3 Bedroom, 1 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

51 Algonquin Rd

Chestnut HillMA02467
property at 51 Algonquin Rd
$4,000

Total Monthly Price

Base Rent$4,000

Total Monthly Price$4,000
12 Month Lease Term
3 Bedroom, 1 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

51 Algonquin Rd

Chestnut HillMA02467
property at 90 Boylston St
$2,950

Total Monthly Price

Base Rent$2,950

Total Monthly Price$2,950
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Furnished

90 Boylston St, Unit 4

90 Boylston St
Chestnut HillMA02467
property at 50 Undine Rd
$3,400

Total Monthly Price

Base Rent$3,400

Total Monthly Price$3,400
12 Month Lease Term
3 Bedroom, 2.5 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

50 Undine Rd, Unit 5

50 Undine Rd
BostonMA02135
  • Smoke Free
property at 515 Heath St
$3,600

Total Monthly Price

Base Rent$3,600

Total Monthly Price$3,600
3 Bedroom, 1 Bath Home for Rent
Available Jan 1, 2027
Furnished

515 Heath St

BrooklineMA02467
  • Smoke Free
property at 73 Undine Rd
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
12 Month Lease Term
4 Bedroom, 2.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

73 Undine Rd

BostonMA02135
property at 60 Undine Rd
$1,000

Total Monthly Price

Base Rent$1,000

Total Monthly Price$1,000
12 Month Lease Term
6 Bedroom, 2 Bath Home for Rent
Available Nov 1
Affordability

60 Undine Rd

BostonMA02135
  • Smoke Free

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

property at 2035 Commonwealth Ave
$2,395 - $3,895

Total Monthly Price

Base Rent$2,395 - $3,895

Total Monthly Price$2,395 - $3,895
12 Month Lease Term
1 To 2 Bedroom Condos for Rent
Available Now
property at 2031 Commonwealth Ave
$2,695

Total Monthly Price

Base Rent$2,695

Total Monthly Price$2,695
12 Month Lease Term
1 Bedroom, 1 Bath Condo for Rent
Available Oct 1
Affordability

2031 Commonwealth Ave, Unit 16

2031 Commonwealth Ave
BostonMA02135
property at 12 Gerald Rd
$10,500

Total Monthly Price

Base Rent$10,500

Total Monthly Price$10,500
12 Month Lease Term
5 Bedroom, 3 Bath Home for Rent
Available Sep 1, 2027
Luxury

12 Gerald Rd

BostonMA02135
  • Smoke Free
property at 2 Hammond Pond Pky
$2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
12 Month Lease Term
2 Bedroom, 1.5 Bath Condo for Rent
Available Now
Affordability

2 Hammond Pond Pky, Unit 604

2 Hammond Pond Pky
Chestnut HillMA02467
property at 25 Greycliff Rd
$4,650

Total Monthly Price

Base Rent$4,650

Total Monthly Price$4,650
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
  • Smoke Free
property at 2021 Commonwealth Ave
$7,600

Total Monthly Price

Base Rent$7,600

Total Monthly Price$7,600
12 Month Lease Term
5 Bedroom, 2 Bath Condo for Rent
Available Now

2021 Commonwealth Ave, Unit 2

2021 Commonwealth Ave
BostonMA02135
  • Smoke Free
property at 1988 Commonwealth Ave
$2,350

Total Monthly Price

Base Rent$2,350

Total Monthly Price$2,350
12 Month Lease Term
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

1988 Commonwealth Ave, Unit 62

1988 Commonwealth Ave
BostonMA02135
property at 2009 Commonwealth Ave
$2,425

Total Monthly Price

Base Rent$2,425

Total Monthly Price$2,425
12 Month Lease Term
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability
  • Smoke Free
property at 2009 Commonwealth Ave
$3,100

Total Monthly Price

Base Rent$3,100

Total Monthly Price$3,100
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

2009 Commonwealth Ave, Unit 20

2009 Commonwealth Ave
BostonMA02135
property at 29 Gerald Rd
$6,200

Total Monthly Price

Base Rent$6,200

Total Monthly Price$6,200
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Aug 31, 2027

29 Gerald Rd, Unit 1

29 Gerald Rd
BostonMA02135

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

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

property at 1999 Commonwealth Ave
$2,300

Total Monthly Price

Base Rent$2,300

Total Monthly Price$2,300
12 Month Lease Term
1 Bedroom, 1 Bath Condo for Rent
Available Oct 1
Affordability

1999 Commonwealth Ave, Unit 11

1999 Commonwealth Ave
BostonMA02135
  • Smoke Free
property at 2001 Commonwealth Ave
$2,395

Total Monthly Price

Base Rent$2,395

Total Monthly Price$2,395
12 Month Lease Term
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

2001 Commonwealth Ave, Unit 1

2001 Commonwealth Ave
BostonMA02135
property at 1999 Commonwealth Ave
$2,700 - $3,800

Total Monthly Price

Base Rent$2,700 - $3,800

Total Monthly Price$2,700 - $3,800
12 Month Lease Term
2 To 3 Bedroom Condos for Rent
Available Now
Affordability
property at 1999 Commonwealth Ave
$3,895

Total Monthly Price

Base Rent$3,895

Total Monthly Price$3,895
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

1999 Commonwealth Ave, Unit 7

1999 Commonwealth Ave
BostonMA02135
property at 39 South St
$2,600 - $4,600

Total Monthly Price

Base Rent$2,600 - $4,600

Total Monthly Price$2,600 - $4,600
12 Month Lease Term
1 To 3 Bedroom Condos for Rent
Available Now

39 South St

BostonMA02135
  • Smoke Free
property at 41 South St
$2,700

Total Monthly Price

Base Rent$2,700

Total Monthly Price$2,700
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

41 South St, Unit 6

41 South St
BostonMA02135
  • Smoke Free
property at 51 Lake Shore Ct
$2,900

Total Monthly Price

Base Rent$2,900

Total Monthly Price$2,900
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 35 Lake Shore Ct
$3,000

Total Monthly Price

Base Rent$3,000

Total Monthly Price$3,000
12 Month Lease Term
3 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

35 Lake Shore Ct, Unit 1

35 Lake Shore Ct
BostonMA02135
property at 207 Lake Shore Rd
$3,400

Total Monthly Price

Base Rent$3,400

Total Monthly Price$3,400
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

207 Lake Shore Rd, Unit 2

207 Lake Shore Rd
BostonMA02135
property at 44 Greycliff Rd
$12,400

Total Monthly Price

Base Rent$12,400

Total Monthly Price$12,400
12 Month Lease Term
6 Bedroom, 3 Bath Condo for Rent
Available Aug 31, 2027

44 Greycliff Rd, Unit #2

44 Greycliff Rd
BostonMA02135

Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

property at 44 Greycliff Rd
$10,500 - $12,000

Total Monthly Price

Base Rent$10,500 - $12,000

Total Monthly Price$10,500 - $12,000
12 Month Lease Term
6 Bedroom, 3 Bath Condo for Rent
Available Now

44 Greycliff Rd

BrightonMA02135
property at 52 Greycliff Rd
$11,100

Total Monthly Price

Base Rent$11,100

Total Monthly Price$11,100
12 Month Lease Term
6 Bedroom, 3 Bath Home for Rent
Available Sep 1, 2027

52 Greycliff Rd

BostonMA02135
property at 37 Radnor Rd
$2,600 - $3,500

Total Monthly Price

Base Rent$2,600 - $3,500

Total Monthly Price$2,600 - $3,500
12 Month Lease Term
2 To 3 Bedroom Condos for Rent
Available Now
Affordability

37 Radnor Rd

BostonMA02135
property at 37 Radnor Rd
$9,800

Total Monthly Price

Base Rent$9,800

Total Monthly Price$9,800
12 Month Lease Term
6 Bedroom, 3 Bath Condo for Rent
Available Aug 22, 2027
Cost Per Sq.Ft.

37 Radnor Rd, Unit 1

37 Radnor Rd
BostonMA02135
property at 2003 Commonwealth Avenue
$2,250

Total Monthly Price

Base Rent$2,250

Total Monthly Price$2,250
12 Month Lease Term
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

2003 Commonwealth Avenue, Unit 9

2003 Commonwealth Avenue
BostonMA02135
  • Smoke Free
property at 2003 Commonwealth Ave
$3,250

Total Monthly Price

Base Rent$3,250

Total Monthly Price$3,250
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

2003 Commonwealth Ave, Unit 20

2003 Commonwealth Ave
BostonMA02135
property at 27 South St
$2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
12 Month Lease Term
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

27 South St, Unit #B3

27 South St
BostonMA02135
property at 1933 Commonwealth Ave
$2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
12 Month Lease Term
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability
property at 1933 Commonwealth Ave
$2,700

Total Monthly Price

Base Rent$2,700

Total Monthly Price$2,700
12 Month Lease Term
1 Bedroom, 1 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

1933 Commonwealth Ave, Unit 504

1933 Commonwealth Ave
BostonMA02135
property at 539 Commonwealth Ave
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
12 Month Lease Term
4 Bedroom, 3 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

539 Commonwealth Ave, Unit 2

539 Commonwealth Ave
NewtonMA02459

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 49 Radnor Rd
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Aug 22, 2027

49 Radnor Rd, Unit 2

49 Radnor Rd
BostonMA02135
property at 25 Kirkwood Rd
$9,900

Total Monthly Price

Base Rent$9,900

Total Monthly Price$9,900
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Aug 31, 2027

25 Kirkwood Rd

BostonMA02135
property at 26 Lake Shore Ct
$2,595

Total Monthly Price

Base Rent$2,595

Total Monthly Price$2,595
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Oct 1
Affordability

26 Lake Shore Ct, Unit 1P

26 Lake Shore Ct
BostonMA02135
property at 53 Radnor Rd
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Aug 22, 2027
Cost Per Sq.Ft.

53 Radnor Rd, Unit 2

53 Radnor Rd
BostonMA02135
property at 16 South St
$7,700

Total Monthly Price

Base Rent$7,700

Total Monthly Price$7,700
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Sep 1, 2027

16 South St, Unit 1

16 South St
BostonMA02135
property at 53 Radnor Rd
$9,800

Total Monthly Price

Base Rent$9,800

Total Monthly Price$9,800
12 Month Lease Term
6 Bedroom, 3 Bath Condo for Rent
Available Aug 22, 2027
Cost Per Sq.Ft.

53 Radnor Rd, Unit 1

53 Radnor Rd
BostonMA02135
property at 116 Lake St
$8,200

Total Monthly Price

Base Rent$8,200

Total Monthly Price$8,200
12 Month Lease Term
6 Bedroom, 4 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

116 Lake St

BostonMA02135
property at 30 Lake Shore Ct
$3,400

Total Monthly Price

Base Rent$3,400

Total Monthly Price$3,400
12 Month Lease Term
3 Bedroom, 2 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

30 Lake Shore Ct, Unit 1

30 Lake Shore Ct
BostonMA02135
property at 235 Chestnut Hill Ave
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now

235 Chestnut Hill Ave, Unit 1

235 Chestnut Hill Ave
BostonMA02135
property at 247 Chestnut Hill Ave
$2,400 - $3,100

Total Monthly Price

Base Rent$2,400 - $3,100

Total Monthly Price$2,400 - $3,100
12 Month Lease Term
Studio To 2 Bedroom Condos for Rent
Available Now
Affordability

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.

Chestnut Hill Middlesex, Boston College, MA Local Guide

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

Read Article
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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

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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.

Read Article

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

Read Article
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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.

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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

3.5
Pet Friendly

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Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 274 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,000 to $13,500. There are also 462 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,000 to $16,000.

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 $1,000 to $16,000 with an average monthly rent of $3,744.

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 $1,000 to $7,640, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,250 to $7,250. Four Bedroom Single-Family rentals are also available starting from $1,160 and Four Bedroom Apartments start at $1,350.

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 Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My! article

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.

decorative image for Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags   article

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.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

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.

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.