Cheap Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA from $900 (62 Rentals)

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

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.

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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.

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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.

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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.

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Chestnut Hill Middlesex, Boston College, MA Local Guide

Cheapest Available Chestnut Hill Middlesex Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
31-35 South StreetOne Bedroom One Bathroom1BR,1BA$2,195

Best Value Apartments for Rent in Chestnut Hill Middlesex, MA

As of June 15, 2025 the best value apartment in the Chestnut Hill Middlesex area is the $0.22 price per square foot 549 Washington St Model at 549 Washington St, Unit 1 in the in the St. Elizabeth's neighborhood starting from $2,200. The second greatest value Chestnut Hill Middlesex apartment is the 49 Winship St Model at 49 Winship St, Unit 12b starting at $2,450 with a $0.25 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.
549 Washington St, Unit 1549 Washington St1BR,1BA$0.22
49 Winship St, Unit 12b49 Winship St2BR,1BA$0.25
30 Bentley St, Unit 330 Bentley StStudio ,1BA$0.19
30 Academy Hill Rd, Unit 230 Academy Hill Rd1BR,1BA$0.24
183 Strathmore Rd, Unit 2183 Strathmore Rd2BR,1BA$0.23
5 Chestnut Hill Ave, Unit 2-45 Chestnut Hill AveStudio ,1BA$0.20
5 Chestnut Hill Ave, Unit 2-45 Chestnut Hill AveStudio ,1BA$0.20
4 Chiswick Rd, Unit 354 Chiswick Rd1BR,1BA$0.24
221 Chestnut Hill Ave, Unit 9999221 Chestnut Hill Ave1BR,1BA$0.23
1959 Commonwealth Ave, Unit 71959 Commonwealth AveStudio ,1BA$0.24

Quick Rent Budget Calculator

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Pet Friendly Lifestyle
Chestnut Hill Middlesex, Chestnut Hill, MA

Ranked #2

Among neighborhoods in Chestnut Hill, MA for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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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

What is the price of a cheap apartment in Chestnut Hill Middlesex?

The cheapest apartment in Chestnut Hill Middlesex is 31-35 South Street which is listed at $2,195, while the average apartment in Chestnut Hill Middlesex costs $23,500.

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.

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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.

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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.

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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.

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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.