close
View Me
$1,0001 Bedroom Apartments Available Sep 1
14 Wallingford Rd, Unit 1
14 Wallingford RdBoston, MA 02135
Cheap Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $1,100 (104 Rentals)
Search the lowest-cost Homes available for rent right now in the Chestnut Hill Middlesex area of Chestnut Hill.
close
View Me
$1,0001 Bedroom Apartments Available Aug 1
14 Wallingford Rd, Unit 2
14 Wallingford RdBoston, MA 02135
close
View Me
$1,0001 Bedroom Apartments Available Sep 1
14 Wallingford Rd, Unit 2
14 Wallingford RdBoston, MA 02135
close
View Me
$1,0001 Bedroom Apartments Available Sep 1
14 Wallingford Rd, Unit 1
14 Wallingford RdBoston, MA 02135
Room in Shared 6 bed/4 bath home, Unit C
104 Academy Hill Rd
BostonMA02135
60 Undine Rd
BostonMA02135
Room in Shared 5 bed/1.5 bath home, Unit A
490 Washington St
BostonMA02135
Room in Shared 4 bed/1.5 bath home, Unit A
490 Washington St
BostonMA02135
Room in Shared 6 bed/2 bath home, Unit 3F
132 Chiswick Rd
BostonMA02135
Room in Shared 6 bed/2 bath home, Unit 2B
132 Chiswick Rd
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.
Room in Shared 6 bed/4 bath home, Unit F
104 Academy Hill Rd
BostonMA02135
Room in Shared 5 bed/1.5 bath home, Unit C
490 Washington St
BostonMA02135
Room in Shared 5 bed/2 bath home, Unit B
129 Chiswick Rd
BostonMA02135
Room in Shared 6 bed/4 bath home, Unit E
104 Academy Hill Rd
BostonMA02135
Room in Shared 6 bed/4 bath home, Unit A
104 Academy Hill Rd
BostonMA02135
Room in Shared 5 bed/2 bath home, Unit E
129 Chiswick Rd
BostonMA02135
Room in Shared 6 bed/2 bath home, Unit 2D
132 Chiswick Rd
BostonMA02135
Room in Shared 6 bed/2 bath home, Unit 2C
132 Chiswick Rd
BostonMA02135
Room in Shared 5 bed/1.5 bath home, Unit E
490 Washington St
BostonMA02135
Room in Shared 5 bed/2 bath home, Unit A
129 Chiswick Rd
BostonMA02135
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.
Room in Shared 6 bed/4 bath home, Unit B
104 Academy Hill Rd
BostonMA02135
86 Academy Hill Rd
BostonMA02135
280 Boylston St
NewtonMA02467
close
View Me
$1,9751 Bedroom Apartments Available Aug 1
6 Beechcroft St, Unit 4
6 Beechcroft StBoston, MA 02135
2 Chestnut Hill Ave, Unit 4
2 Chestnut Hill Ave
BostonMA02135
close
View Me
$2,000Studio Apartments Available Jul 1
2 Chestnut Hill Ave, Unit 4
2 Chestnut Hill AveBoston, MA 02135
19 Chestnut Hill Ave, Unit 3
19 Chestnut Hill Ave
BostonMA02135
4 Chiswick Rd, Unit 24
4 Chiswick Rd
BostonMA02135
7 Lothian Rd
BostonMA02135
2 Chestnut Hill Ave, Unit 4
2 Chestnut Hill Ave
BostonMA02135
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.
65 Strathmore Rd
BostonMA02135
173 Chiswick Rd, Unit 29
173 Chiswick Rd
BostonMA02135
2001 Commonwealth Ave, Unit 12
2001 Commonwealth Ave
BostonMA02135
2001 Commonwealth Ave, Unit 12
2001 Commonwealth Ave
BostonMA02135
2001 Commonwealth Ave
BostonMA02135
555 Washington St, Unit 1
555 Washington St
BostonMA02135
16 Chestnut Hill Ave, Unit 3
16 Chestnut Hill Ave
BostonMA02135
2018 Commonwealth Ave, Unit 31
2018 Commonwealth Ave
BostonMA02135
close
View Me
$2,1501 Bedroom Apartments Available Sep 1
10 Lothian Rd, Unit 14
10 Lothian RdBoston, MA 02135
21 Chestnut Hill Ave, Unit 3
21 Chestnut Hill Ave
BostonMA02135
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
204 Chestnut Hill Ave
BostonMA02135
208 Chestnut Hill Ave
BostonMA02135
206 Chestnut Hill Ave
BostonMA02135
1840 Commonwealth Ave
BostonMA02135
383 Langley Rd, Unit apt 5 a
383 Langley Rd
NewtonMA02459
2018 Commonwealth Ave, Unit 23
2018 Commonwealth Ave
BostonMA02135
125 Chiswick Rd, Unit 311
125 Chiswick Rd
BostonMA02135
21 Chestnut Hill Ave, Unit 3
21 Chestnut Hill Ave
BostonMA02135
close
View Me
$2,200Studio Apartments Available Now
2018 Commonwealth Ave, Unit 23
2018 Commonwealth AveBoston, MA 02135
199 Strathmore Rd, Unit 2
199 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.
Chestnut Hill Middlesex, Boston College, MA Local Guide
How much does it cost to rent a home in Chestnut Hill Middlesex?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Chestnut Hill Middlesex 2 Bedroom Homes for Rent | $3,176 | $2,045 | $4,695 |
| Chestnut Hill Middlesex 3 Bedroom Homes for Rent | $3,919 | $1,700 | $8,000 |
| Chestnut Hill Middlesex 4 Bedroom Homes for Rent | $5,378 | $1,410 | $10,000+ |
| Chestnut Hill Middlesex 5 Bedroom Homes for Rent | $4,895 | $1,150 | $10,000+ |
| Chestnut Hill Middlesex 6 Bedroom Homes for Rent | $7,554 | $1,100 | $10,000+ |
| Chestnut Hill Middlesex 7 Bedroom Homes for Rent | $7,000 | $7,000 | $7,000 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 104 rentals with your search options within a 2 mile radius of the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA.
Explore Chestnut Hill
Chestnut Hill Middlesex, Boston College, MA Local Guide
- Nearby Chestnut Hill neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Best Value Apartments for Rent in Chestnut Hill Middlesex, MA
As of June 13, 2026 the best value apartment in the Chestnut Hill Middlesex area is the $0.22 price per square foot 2018 Commonwealth Avenue Model at 2018 Commonwealth Avenue, Unit 23 in the in the Chestnut Hill neighborhood starting from $2,200. The second greatest value Chestnut Hill Middlesex apartment is the 153 Foster St Model at 153 Foster St, Unit 1 starting at $2,295 with a $0.23 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 2018 Commonwealth Avenue, Unit 23 | 2018 Commonwealth Avenue | Studio ,1BA | $0.22 |
| 153 Foster St, Unit 1 | 153 Foster St | 1BR,1BA | $0.23 |
| 22 Fairbanks St, Unit #6 | 22 Fairbanks St | 1BR,1BA | $0.27 |
| 48 Langley Rd, Unit 1 | 48 Langley Rd | 3BR,1BA | $0.26 |
| 7 Lothian Rd, Unit 3 | 7 Lothian Rd | 1BR,1BA | $0.22 |
| 198 Strathmore Rd, Unit 3 | 198 Strathmore Rd | 1BR,1BA | $0.23 |
| 258 Chestnut Hill Ave, Unit 1 | 258 Chestnut Hill Ave | Studio ,1BA | $0.22 |
| 193 Strathmore Rd, Unit 10 | 193 Strathmore Rd | 1BR,1BA | $0.20 |
| 46 Bostonia Ave, Unit 1 | 46 Bostonia Ave | 2BR,1BA | $0.29 |
| 49 Winship St | 49 Winship St | 2BR,1BA | $0.25 |
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
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 ArticleQuick 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.
Let everyone know!
Do you know the Chestnut Hill Middlesex area?
If you’re an expert on all things Chestnut Hill Middlesex, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Pet Friendly LifestyleChestnut Hill Middlesex, Chestnut Hill, MA
Ranked #1
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.5Pet Friendly
Frequently Asked Questions about Chestnut Hill Middlesex
What type of rentals are currently available in Chestnut Hill Middlesex?
There are currently 415 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,000 to $17,000. There are also 550 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,100 to $16,800.
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 $1,100 to $16,800 with an average monthly rent of $5,675.
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 $1,400 to $8,350, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,700 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,410 and Four Bedroom Apartments start at $1,050.
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
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.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.
Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.