
Cheap Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $900 (157 Rentals)
Search the lowest-cost Apartments available for rent right now in the Chestnut Hill Middlesex area of Chestnut Hill.


163 Strathmore Rd, Unit #23

65 Strathmore Rd, Unit 7
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.

160 Strathmore Rd, Unit 5

258 Chestnut Hill Ave, Unit 1

2016 Commonwealth Ave, Unit 2

65 Strathmore Rd, Unit 33

19 Chestnut Hill Ave, Unit 3

19 Chestnut Hill Ave, Unit 3

249 Chestnut Hill Ave, Unit #1
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.

141 Englewood Ave, Unit 2

5 Chestnut Hill Ave, Unit 2-4

5 Chestnut Hill Ave, Unit 2-4

2000 Commonwealth Ave, Unit #23
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.

497 Boylston St, Unit 003

545 Washington St, Unit 3

114 Strathmore Rd, Unit #203

28 Academy Hill Rd

19 Beechcroft St, Unit 4

124 Academy Hill Rd, Unit B

288 Chestnut Hill Ave

2045 Commonwealth Ave
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.

193 Strathmore Rd, Unit 10

1999 Commonwealth Ave, Unit #21

Chiswick Building

549 Washington St, Unit 1

136B Chiswick Rd, Unit 15

19 Chestnut Hill Ave, Unit 3
Chestnut Hill Middlesex, Boston College, MA Local Guide

How much does it cost to rent an apartment in Chestnut Hill Middlesex?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Chestnut Hill Middlesex Studio Apartments | $2,220 | $1,795 | $3,800 |
Chestnut Hill Middlesex 1 Bedroom Apartments | $2,568 | $975 | $4,500 |
Chestnut Hill Middlesex 2 Bedroom Apartments | $3,374 | $2,010 | $5,270 |
Chestnut Hill Middlesex 3 Bedroom Apartments | $3,730 | $2,500 | $6,900 |
Chestnut Hill Middlesex 4 Bedroom Apartments | $5,323 | $3,200 | $10,000+ |
Chestnut Hill Middlesex 5 Bedroom Apartments | $7,209 | $4,200 | $10,000+ |
Chestnut Hill Middlesex 6 Bedroom Apartments | $10,125 | $4,500 | $10,000+ |
Browse Apartments in this Neighborhood
There are currently 157 rentals with your search options within a 2 mile radius of the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA.
See all Apartments in Chestnut HillExplore Chestnut Hill
Chestnut Hill Middlesex, Boston College, MA Local Guide
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Best Value Apartments for Rent in Chestnut Hill Middlesex, MA
As of July 11, 2025 the best value apartment in the Chestnut Hill Middlesex area is the $0.19 price per square foot 30 Bentley St Model at 30 Bentley St, Unit 3 in the in the St. Elizabeth's neighborhood starting from $1,900. The second greatest value Chestnut Hill Middlesex apartment is the 5 Chestnut Hill Ave Model at 5 Chestnut Hill Ave, Unit 2-4 starting at $2,000 with a $0.20 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. |
---|---|---|---|
30 Bentley St, Unit 3 | 30 Bentley St | Studio ,1BA | $0.19 |
5 Chestnut Hill Ave, Unit 2-4 | 5 Chestnut Hill Ave | Studio ,1BA | $0.20 |
5 Chestnut Hill Ave, Unit 2-4 | 5 Chestnut Hill Ave | Studio ,1BA | $0.20 |
549 Washington St, Unit 1 | 549 Washington St | 1BR,1BA | $0.22 |
19 Chestnut Hill Ave, Unit 3 | 19 Chestnut Hill Ave | Studio ,1BA | $0.22 |
1933 Commonwealth Ave, Unit 17 | 1933 Commonwealth Ave | 1BR,1BA | $0.23 |
183 Strathmore Rd, Unit 2 | 183 Strathmore Rd | 2BR,1BA | $0.23 |
30 Academy Hill Rd, Unit 2 | 30 Academy Hill Rd | 1BR,1BA | $0.24 |
2000 Commonwealth Ave, Unit 2018-01 | 2000 Commonwealth Ave | 1BR,1BA | $0.24 |
2000 Commonwealth Ave, Unit 2018-1 | 2000 Commonwealth Ave | 1BR,1BA | $0.24 |
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.
Pet Friendly LifestyleChestnut Hill Middlesex, Chestnut Hill, MA
Ranked #2
Among neighborhoods in Chestnut Hill, MA for Apartment listings with Pet Friendly Amenities
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Getting Around the Chestnut Hill Middlesex Neighborhood in Chestnut Hill, MA
Walk Score®
59 / 100
Somewhat Walkable
Some errands can be accomplished on foot
Bike Score®
47 / 100
Somewhat Bikeable
Minimal bike infrastructure
Transit Score®
53 / 100
Good Transit
Many nearby public transportation options
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Chestnut Hill Middlesex Apartments
How much is rent for a Cheap One Bedroom Chestnut Hill Middlesex Apartment?
The lowest price for a Cheap One Bedroom Chestnut Hill Middlesex Apartment is $2,195 at 31-35 South Street.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.