Cheap Homes for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $1,000 (67 Rentals)

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Search the lowest-cost Homes available for rent right now in the Chestnut Hill Middlesex area of Chestnut Hill.

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

Rent According to Income: A Look at Income-Restricted Rentals

Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.

property at 32 Sidlaw Rd
$1,700

Total Monthly Price

Base Rent$1,700

Total Monthly Price$1,700
Studio, 1 Bath Condo for Rent
Available Now
Affordability

32 Sidlaw Rd

BostonMA02135
property at 2001 Commonwealth Ave
$1,700 - $3,150

Total Monthly Price

Base Rent$1,700

Total Monthly Price$1,700
Studio To 2 Bedroom Rentals
Available Now
Affordability
property at 17 Fairbanks St
$1,750

Total Monthly Price

Base Rent$1,750

Total Monthly Price$1,750
12 Month Lease Term
1 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

17 Fairbanks St

BostonMA02135
  • Smoke Free
property at 247 Chestnut Hill Ave
$1,795

Total Monthly Price

Base Rent$1,795

Total Monthly Price$1,795
Studio, 1 Bath Condo for Rent
Available Now
Affordability

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 555 Washington St
$1,850

Total Monthly Price

Base Rent$1,850

Total Monthly Price$1,850
1 Bedroom, 1 Bath Rentals
Available Now
Affordability

555 Washington St, Unit 1

555 Washington St
BostonMA02135
property at 1840 Commonwealth Ave
$1,895 - $2,395

Total Monthly Price

Base Rent$1,895 - $2,395

Total Monthly Price$1,895 - $2,395
12 Month Lease Term
Studio To 2 Bedroom Condos for Rent
Available Now
Affordability
property at 227 Chestnut Hill Ave
$1,900

Total Monthly Price

Base Rent$1,900

Total Monthly Price$1,900
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability
property at 206 Chestnut Hill Ave
$1,900 - $2,500

Total Monthly Price

Base Rent$1,900

Total Monthly Price$1,900
Studio To 1 Bedroom Rentals
Available Now
Affordability
property at 228 Chestnut Hill Ave
$1,950

Total Monthly Price

Base Rent$1,950

Total Monthly Price$1,950
Studio, 1 Bath Condo for Rent
Available Now
Affordability
property at 201 Strathmore Rd
$1,950

Total Monthly Price

Base Rent$1,950

Total Monthly Price$1,950
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

201 Strathmore 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 199 Strathmore Rd
$1,995 - $2,050

Total Monthly Price

Base Rent$1,995

Total Monthly Price$1,995
Studio To 1 Bedroom Rentals
Available Now
Affordability

199 Strathmore Rd

BostonMA02135
property at 4 Chiswick Rd
$2,000 - $2,200

Total Monthly Price

Base Rent$2,000 - $2,200

Total Monthly Price$2,000 - $2,200
12 Month Lease Term
Studio To 1 Bedroom Condos for Rent
Available Now
Affordability

4 Chiswick Rd

BostonMA02135
property at 20-20 Brock St
$2,100

Total Monthly Price

Base Rent$2,100

Total Monthly Price$2,100
1 Bedroom, 1 Bath Home for Rent
Available Sep 15
Affordability

20-20 Brock St

BostonMA02135
property at 22 Brock St
$2,150

Total Monthly Price

Base Rent$2,150

Total Monthly Price$2,150
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

22 Brock St

BostonMA02135

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

property at 190 Chestnut Hill Ave
$2,150

Total Monthly Price

Base Rent$2,150

Total Monthly Price$2,150
Studio, 1 Bath Condo for Rent
Available Now
Affordability
property at 208 Chestnut Hill Ave
$2,150

Total Monthly Price

Base Rent$2,150

Total Monthly Price$2,150
Studio Rentals
Available Now
Affordability
property at 23 Brock St
$2,200

Total Monthly Price

Base Rent$2,200

Total Monthly Price$2,200
1 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

23 Brock St

BostonMA02135
property at 18 Brock St
$2,200

Total Monthly Price

Base Rent$2,200

Total Monthly Price$2,200
1 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

18 Brock St

BostonMA02135
property at 30 Brock St
$2,200

Total Monthly Price

Base Rent$2,200

Total Monthly Price$2,200
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

30 Brock St

BostonMA02135
property at 20 Brock St
$2,200 - $2,250

Total Monthly Price

Base Rent$2,200

Total Monthly Price$2,200
1 Bedroom Rentals
Available Now
Affordability

20 Brock St

BostonMA02135
property at 7 Lothian Rd
$2,200 - $5,300

Total Monthly Price

Base Rent$2,200

Total Monthly Price$2,200
1 To 5 Bedroom Rentals
Available Now
Affordability

7 Lothian 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

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

Chestnut Hill Middlesex, Boston College, MA Local Guide

Cheapest Available Chestnut Hill Middlesex Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
286 & 288 Chestnut Hill AvenueStudioStudio,1BA$2,100

Best Value Apartments for Rent in Chestnut Hill Middlesex, MA

As of September 12, 2026 the best value apartment in the Chestnut Hill Middlesex area is the $0.18 price per square foot 141 Englewood Model at 141 Englewood, Unit 2 in the in the Chestnut Hill neighborhood starting from $1,800. The second greatest value Chestnut Hill Middlesex apartment is the 193 Strathmore Rd Model at 193 Strathmore Rd starting at $1,900 with a $0.19 price per square foot in the Chestnut Hill neighborhood. Here is today’s list of the best values for Chestnut Hill Middlesex apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
141 Englewood, Unit 2141 EnglewoodStudio ,1BA$0.18
193 Strathmore Rd193 Strathmore Rd1BR,1BA$0.19
193 Strathmore Rd, Unit 10193 Strathmore Rd1BR,1BA$0.20
2 Chestnut Hill Ave, Unit 42 Chestnut Hill AveStudio ,1BA$0.20
7 Lothian Rd, Unit 37 Lothian Rd1BR,1BA$0.22
198 Strathmore Rd, Unit 3198 Strathmore Rd1BR,1BA$0.23
141 Englewood Ave, Unit 38141 Englewood Ave1BR,1BA$0.25
2 Oneil Pl, Unit 22 Oneil Pl2BR,1BA$0.28
6 Gerald Rd, Unit A6 Gerald Rd2BR,1BA$0.29
57 Breck Ave, Unit #257 Breck Ave3BR,1BA$0.30

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
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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 263 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,000 to $13,500. There are also 412 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 $3,605.

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 $7,790, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,495 to $6,900. 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

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Rent According to Income: A Look at Income-Restricted Rentals

Written by: Robin Stewart

The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.

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.