Luxury Homes for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (355 Rentals)

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The most luxurious Homes in the Chestnut Hill Middlesex area of Chestnut Hill with high-end amenities, features, and finishes.

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 99 Chestnut Hill Ave
$2,300 - $3,325

Total Monthly Price

Base Rent$2,300 - $3,325

Total Monthly Price$2,300 - $3,325
12 Month Lease Term
Studio To 2 Bedroom Condos for Rent
Available Now
Affordability
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
Affordability
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
property at 185 Chestnut Hill Ave
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
12 Month Lease Term
Studio, 1 Bath Condo for Rent
Available Now
Affordability

185 Chestnut Hill Ave, Unit 6

185 Chestnut Hill Ave
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 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 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 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 142 Kenrick St
$2,600

Total Monthly Price

Base Rent$2,600

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

142 Kenrick St, Unit 38

142 Kenrick St
BostonMA02135

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

Looking for the perfect rental? From apartments and condos to lofts and single family rentals, explore the unique pros and cons of each rental type to help you land in your perfect new place.

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 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
Affordability

39 South St

BostonMA02135
  • Smoke Free
property at 137 Chiswick Rd
$2,650

Total Monthly Price

Base Rent$2,650

Total Monthly Price$2,650
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

137 Chiswick Rd, Unit 114

137 Chiswick Rd
BostonMA02135
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 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 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 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 1872 Commonwealth Ave
$2,750

Total Monthly Price

Base Rent$2,750

Total Monthly Price$2,750
12 Month Lease Term
2 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

1872 Commonwealth Ave, Unit A

1872 Commonwealth Ave
BostonMA02135
  • Smoke Free
property at 13 Winship St
$2,795

Total Monthly Price

Base Rent$2,795

Total Monthly Price$2,795
12 Month Lease Term
3 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

13 Winship St

BostonMA02135
property at 137 Chiswick Rd
$2,800

Total Monthly Price

Base Rent$2,800

Total Monthly Price$2,800
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

137 Chiswick Rd, Unit 3

137 Chiswick Rd
BostonMA02135

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 22 Shanley St
$2,800

Total Monthly Price

Base Rent$2,800

Total Monthly Price$2,800
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

22 Shanley St

BostonMA02135
  • Smoke Free
property at 132 Chiswick Rd
$2,850

Total Monthly Price

Base Rent$2,850

Total Monthly Price$2,850
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

132 Chiswick Rd, Unit 1B

132 Chiswick Rd
BostonMA02135
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 1868 Commonwealth Ave
$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

1868 Commonwealth Ave, Unit 5DW

1868 Commonwealth Ave
BostonMA02135
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 1880 Commonwealth Ave
$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
Affordability

1880 Commonwealth Ave, Unit 5

1880 Commonwealth Ave
BostonMA02135
property at 137 Chiswick Rd
$3,000 - $3,005

Total Monthly Price

Base Rent$3,000 - $3,005

Total Monthly Price$3,000 - $3,005
12 Month Lease Term
3 To 4 Bedroom Condos for Rent
Available Now
Affordability

137 Chiswick Rd

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 129 Chiswick Rd
$3,050

Total Monthly Price

Base Rent$3,050

Total Monthly Price$3,050
12 Month Lease Term
2 Bedroom, 1 Bath Townhome for Rent
Available Now
Affordability

129 Chiswick Rd

BostonMA02135
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

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 276 Chestnut Hill Ave
$3,125

Total Monthly Price

Base Rent$3,125

Total Monthly Price$3,125
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

276 Chestnut Hill Ave, Unit 5

276 Chestnut Hill Ave
BostonMA02135
property at 2 Priscilla Rd
$3,200

Total Monthly Price

Base Rent$3,200

Total Monthly Price$3,200
12 Month Lease Term
2 Bedroom, 1.5 Bath Condo for Rent
Available Now
Affordability

2 Priscilla Rd, Unit 1

2 Priscilla Rd
BostonMA02135
property at 148 Strathmore Rd
$3,250

Total Monthly Price

Base Rent$3,250

Total Monthly Price$3,250
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

148 Strathmore Rd, Unit 21

148 Strathmore Rd
BostonMA02135
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 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 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 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 7 Lothian Rd
$3,450

Total Monthly Price

Base Rent$3,450

Total Monthly Price$3,450
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

7 Lothian Rd, Unit 3

7 Lothian Rd
BostonMA02135
property at 101 Nonantum St
$3,500

Total Monthly Price

Base Rent$3,500

Total Monthly Price$3,500
12 Month Lease Term
4 Bedroom, 1.5 Bath Townhome for Rent
Available Sep 11
Affordability

101 Nonantum St

BostonMA02135
property at 12 Louise Rd
$3,500

Total Monthly Price

Base Rent$3,500

Total Monthly Price$3,500
12 Month Lease Term
3 Bedroom, 1 Bath Townhome for Rent
Available Now
Luxury

12 Louise Rd

Chestnut HillMA02467

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.

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 145 Chiswick Rd
$3,600

Total Monthly Price

Base Rent$3,600

Total Monthly Price$3,600
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

145 Chiswick Rd, Unit 8

145 Chiswick Rd
BostonMA02135
property at 135 Chiswick Rd
$3,600

Total Monthly Price

Base Rent$3,600

Total Monthly Price$3,600
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

135 Chiswick Rd, Unit 4

135 Chiswick Rd
BostonMA02135
property at 210 Chestnut Hill Ave
$3,700

Total Monthly Price

Base Rent$3,700

Total Monthly Price$3,700
12 Month Lease Term
3 Bedroom, 2 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

210 Chestnut Hill Ave, Unit 6

210 Chestnut Hill Ave
BostonMA02135
property at 71-73 Chestnut Hill Ave
$3,800

Total Monthly Price

Base Rent$3,800

Total Monthly Price$3,800
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

71-73 Chestnut Hill Ave, Unit 2

71-73 Chestnut Hill Ave
BostonMA02135
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 96 Chestnut Hill Ave
$3,800

Total Monthly Price

Base Rent$3,800

Total Monthly Price$3,800
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

96 Chestnut Hill Ave, Unit 73

96 Chestnut Hill Ave
BostonMA02135
property at 195 Lake St
$3,800 - $4,500

Total Monthly Price

Base Rent$3,800 - $4,500

Total Monthly Price$3,800 - $4,500
12 Month Lease Term
4 To 5 Bedroom Condos for Rent
Available Now
Cost Per Sq.Ft.

195 Lake St

BostonMA02135
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 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

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.

Chestnut Hill Middlesex, Boston College, MA Local Guide

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.

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

3.5
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 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.