Cheap Homes for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $1,100 (101 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

$1,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,250
Total Monthly Price
$1,250

6 Bedroom, 2 Bath Home for Rent

Available Sep 1

60 Undine Rd

BostonMA02135
property at 2001 Commonwealth Ave

$1,795 - $3,150

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,795
Total Monthly Price
$1,795

Studio To 2 Bedroom Rentals

Available Now

2001 Commonwealth Ave

BostonMA02135

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.

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property at 1872 Commonwealth Ave

$1,865 - $3,195

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,865 - $3,195
Total Monthly Price
$1,865 - $3,195

Studio To 3 Bedroom Condos for Rent

Available Sep 1

1872 Commonwealth Ave

BostonMA02135
property at 8 Chiswick Rd

$1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900
Total Monthly Price
$1,900

Studio, 1 Bath Condo for Rent

Available Sep 1

8 Chiswick Rd

BostonMA02135
property at 555 Washington St

$1,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,950
Total Monthly Price
$1,950

1 Bedroom, 1 Bath Rentals

Available Sep 1

555 Washington St, Unit 1

555 Washington St
BostonMA02135
property at 7 Lothian Rd

$2,000 - $2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000 - $2,800
Total Monthly Price
$2,000 - $2,800

Studio To 3 Bedroom Condos for Rent

Available Now

7 Lothian Rd

BostonMA02135
property at 4 Chiswick Rd

$2,000 - $2,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000 - $2,200
Total Monthly Price
$2,000 - $2,200

Studio To 1 Bedroom Condos for Rent

Available Sep 1

4 Chiswick Rd

BostonMA02135
property at 1840 Commonwealth Ave

$2,000 - $2,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000 - $2,450
Total Monthly Price
$2,000 - $2,450

Studio To 1 Bedroom Condos for Rent

Available Sep 1

1840 Commonwealth Ave

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.

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property at 21 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 Rentals

Available Now

21 Chestnut Hill Ave, Unit 3

21 Chestnut Hill Ave
BostonMA02135
property at 32 Sidlaw Rd

$2,000 - $2,450

Total Monthly Price

Total Monthly Price

Base Rent
$2,000
Total Monthly Price
$2,000

Studio To 1 Bedroom Rentals

Available Aug 1

32 Sidlaw Rd

BostonMA02135
property at 1999 Commonwealth Ave

$2,045 - $4,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,045 - $4,250
Total Monthly Price
$2,045 - $4,250

Studio To 2 Bedroom Condos for Rent

Available Sep 1

1999 Commonwealth Ave

BostonMA02135
property at 2035 Commonwealth Ave

$2,045 - $3,545

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,045 - $3,545
Total Monthly Price
$2,045 - $3,545

Studio To 2 Bedroom Condos for Rent

Available Now

2035 Commonwealth Ave

BostonMA02135
property at 2045 Commonwealth Ave

$2,045 - $2,425

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,045
Total Monthly Price
$2,045

Studio To 1 Bedroom Rentals

Available Sep 1

2045 Commonwealth Ave

BostonMA02135
property at 201 Strathmore Rd

$2,050

Total Monthly Price

Total Monthly Price

Base Rent
$2,050
Total Monthly Price
$2,050

1 Bedroom, 1 Bath Condo for Rent

Available Sep 1

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.

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property at 385 Washington 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 Sep 1

385 Washington St, Unit 4

385 Washington 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.

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property at 141 Englewood Ave

$2,150

Total Monthly Price

Total Monthly Price

Base Rent
$2,150
Total Monthly Price
$2,150

Studio, 1 Bath Condo for Rent

Available Sep 1

141 Englewood Ave

BostonMA02135
property at 216 Chestnut Hill Ave

$2,150 - $2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,150
Total Monthly Price
$2,150

Studio To 1 Bedroom Rentals

Available Now

216 Chestnut Hill Ave

BostonMA02135
property at 208 Chestnut Hill Ave

$2,150

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,150
Total Monthly Price
$2,150

Studio Rentals

Available Sep 1

208 Chestnut Hill Ave

BostonMA02135
property at 10 Lothian Rd

$2,150 - $2,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,150
Total Monthly Price
$2,150

1 Bedroom Rentals

Available Now

10 Lothian Rd

BostonMA02135
property at 206 Chestnut Hill Ave

$2,150 - $2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,150
Total Monthly Price
$2,150

Studio To 1 Bedroom Rentals

Available Now

206 Chestnut Hill Ave

BostonMA02135
property at 17 Fairbanks St

$2,170

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,170
Total Monthly Price
$2,170

1 Bedroom, 1 Bath Home for Rent

Available Now

17 Fairbanks St

BostonMA02135
property at 383 Langley Rd

$2,195

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,195
Total Monthly Price
$2,195

Studio, 1 Bath Condo for Rent

Available Sep 1

383 Langley Rd, Unit apt 5 a

383 Langley Rd
NewtonMA02459

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.

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Showing Results 1-50, Page 1 of 3

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 July 29, 2026 the best value apartment in the Chestnut Hill Middlesex area is the $0.30 price per square foot 31 N Crescent Circuit Model at 31 N Crescent Circuit, Unit 1z in the in the St. Elizabeth's neighborhood starting from $3,000. The second greatest value Chestnut Hill Middlesex apartment is the 31 Willoughby St Model at 31 Willoughby St, Unit 1 starting at $3,300 with a $0.33 price per square foot in the St. Elizabeth's 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.
31 N Crescent Circuit, Unit 1z31 N Crescent Circuit2BR,1BA$0.30
31 Willoughby St, Unit 131 Willoughby St3BR,1BA$0.33
58 Tremont St58 Tremont St3BR,1BA$0.35
23 Willoughby St, Unit 223 Willoughby St3BR,1BA$0.33
7 Lothian Rd, Unit 37 Lothian Rd1BR,1BA$0.22
198 Strathmore Rd, Unit 3198 Strathmore Rd1BR,1BA$0.23
258 Chestnut Hill Ave, Unit 1258 Chestnut Hill AveStudio ,1BA$0.22
193 Strathmore Rd, Unit 10193 Strathmore Rd1BR,1BA$0.20
2 Chestnut Hill Ave, Unit 42 Chestnut Hill AveStudio ,1BA$0.20
15 South St, Unit 615 South St2BR,1BA$0.28

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.

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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 305 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $960 to $14,300. There are also 464 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,130 to $15,000.

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 $1,130 to $15,000 with an average monthly rent of $4,614.

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 $1,350 to $7,999, 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 $3,005 and Four Bedroom Apartments start at $2,400.

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

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 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.