
Cheap Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $900 (92 Rentals)
Search the lowest-cost Apartments available for rent right now in the Chestnut Hill Middlesex area of Chestnut Hill.


Furnished Bedroom with Private Ensuite Bath in Brighton!

Total Monthly Price
193 Strathmore Rd

Total Monthly Price
2018 Commonwealth Avenue

Total Monthly Price
3 Lothian Rd

Total Monthly Price
2016 Commonwealth Ave

Total Monthly Price
14 Beechcroft St, Unit B1, Unit B1

2018 Commonwealth Ave, Unit 24

Total Monthly Price
2018 Commonwealth Ave

Total Monthly Price
258 Chestnut Hill Ave, Unit 1, Unit 1
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.

Total Monthly Price
152 Strathmore Rd, Unit 1, Unit 1

Total Monthly Price
28 Sidlaw Rd, Unit 6, Unit 6

Total Monthly Price
7 North Crescent Circuit, Unit 1, Unit 1

Total Monthly Price
49 Winship St

Total Monthly Price
4 Chiswick Rd, Unit 24, Unit 24

Total Monthly Price
193 Strathmore Rd, Unit 10, Unit 10

2018 Commonwealth Ave, Unit 3

Total Monthly Price
12 Brock St, Unit #4, Unit #4

Total Monthly Price
2005 Commonwealth Ave, Unit 27, Unit 27

Total Monthly Price
110 Strathmore Rd
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.

Total Monthly Price
286 & 288 Chestnut Hill Avenue

10 Lothian Rd, Unit 14

Total Monthly Price
31-35 South Street

Total Monthly Price
42 Kirkwood Rd

Total Monthly Price
1997 Commonwealth Ave, Unit 27, Unit 27

125 Chiswick Rd, Unit 309

Total Monthly Price
38 Kirkwood Rd

125 Chiswick Rd, Unit 312

Total Monthly Price
7 Lothian Rd, Unit 3, Unit 3

Total Monthly Price
383 Langley Rd, Unit 3831, Unit 3831
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.

199 Strathmore Rd, Unit 4

125 Chiswick Rd, Unit 310

Total Monthly Price
566 Washington St, Unit 1, Unit 1

Total Monthly Price
5 Pama Gdns, Unit 4, Unit 4

10 Lothian Rd, Unit 7

10 Lothian Rd, Unit 12

Total Monthly Price
11 Beechcroft St, Unit 4, Unit 4

10 Lothian Rd, Unit 5

Total Monthly Price
1875 Commonwealth Ave

Total Monthly Price
10 Hammond Pond Pkwy, Unit 106, Unit 106
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.

286 Chestnut Hill Ave, Unit 11

Total Monthly Price
391 Langley Rd, Unit 2, Unit 2

Total Monthly Price
18 Malbert Rd, Unit 1, Unit 1

Total Monthly Price
28 Sidlaw Rd

Total Monthly Price
461 Washington St

10 Lothian Rd, Unit 10

Total Monthly Price
258 Chestnut Hill Ave

Total Monthly Price
260 Chestnut Hill Ave

10 Lothian Rd, Unit 2

Total Monthly Price
39 South St, Unit 62, Unit 62
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.
Chestnut Hill Middlesex, Boston College, MA Local Guide

How much does it cost to rent an apartment in Chestnut Hill Middlesex?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Chestnut Hill Middlesex Studio Apartments | $2,395 | $1,900 | $4,090 |
| Chestnut Hill Middlesex 1 Bedroom Apartments | $2,570 | $1,050 | $4,645 |
| Chestnut Hill Middlesex 2 Bedroom Apartments | $3,409 | $2,000 | $5,640 |
| Chestnut Hill Middlesex 3 Bedroom Apartments | $3,903 | $2,550 | $8,997 |
| Chestnut Hill Middlesex 4 Bedroom Apartments | $5,188 | $3,200 | $9,600 |
| Chestnut Hill Middlesex 5 Bedroom Apartments | $6,584 | $4,300 | $9,000 |
| Chestnut Hill Middlesex 6 Bedroom Apartments | $10,247 | $5,800 | $10,000+ |
Browse Apartments in this Neighborhood
There are currently 92 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
- Nearby Chestnut Hill neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Chestnut Hill Middlesex Apartments for Rent
 | Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 286 & 288 Chestnut Hill Avenue | Studio | Studio,1BA | $2,100 |
Best Value Apartments for Rent in Chestnut Hill Middlesex, MA
As of April 29, 2026 the best value apartment in the Chestnut Hill Middlesex area is the $0.20 price per square foot 49 Winship St Model at 49 Winship St in the in the St. Elizabeth's neighborhood starting from $2,000. The second greatest value Chestnut Hill Middlesex apartment is the 28 Sidlaw Rd Model at 28 Sidlaw Rd, Unit 6 starting at $2,000 with a $0.20 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 49 Winship St | 49 Winship St | Studio ,1BA | $0.20 |
| 28 Sidlaw Rd, Unit 6 | 28 Sidlaw Rd | 1BR,1BA | $0.20 |
| 193 Strathmore Rd, Unit 10 | 193 Strathmore Rd | 1BR,1BA | $0.20 |
| 152 Strathmore Rd, Unit 1 | 152 Strathmore Rd | 1BR,1BA | $0.20 |
| 12 Brock St, Unit #4 | 12 Brock St | 1BR,1BA | $0.21 |
| 5 Pama Gdns, Unit 4 | 5 Pama Gdns | 1BR,1BA | $0.22 |
| 7 Lothian Rd, Unit 3 | 7 Lothian Rd | 1BR,1BA | $0.22 |
| 12 Gerald Rd, Unit 24 | 12 Gerald Rd | 1BR,1BA | $0.24 |
| 198 Strathmore Rd, Unit 3 | 198 Strathmore Rd | 1BR,1BA | $0.24 |
| 249 Chestnut Hill Ave, Unit 32 | 249 Chestnut Hill Ave | 2BR,1BA | $0.24 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read ArticleDon'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 ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash 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.
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.
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 Cheap Chestnut Hill Middlesex Apartments
What is the Cheapest Studio apartment in Chestnut Hill Middlesex?
Currently the most affordable Cheap Studio Apartment in Chestnut Hill Middlesex is at 286 & 288 Chestnut Hill Avenue listed at $2,100.
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

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.