5 Bedroom Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (24 Rentals)

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153 Foster St, Unit 1
$9,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,000

Total Monthly Price
$9,000
5 Bedroom Apartment Available Now

153 Foster St, Unit 1

153 Foster StBoston, MA 02135
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288 Foster St, Unit #2
$7,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000
5 Bedroom Apartment Available Now

288 Foster St, Unit #2

288 Foster StBoston, MA 02135
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2021 Commonwealth Avenue, Unit D
$8,750
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,750

Total Monthly Price
$8,750
5 Bedroom Apartment Available Now

2021 Commonwealth Avenue, Unit D

2021 Commonwealth AvenueBoston, MA 02135
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163 Foster St, Unit 153 #1
$8,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,600

Total Monthly Price
$8,600
5 Bedroom Apartment Available Now

163 Foster St, Unit 153 #1

163 Foster StBoston, MA 02135
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28 Manet Rd
$5,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800
5 Bedroom Apartment Available Now

28 Manet Rd

28 Manet RdChestnut Hill, MA 02467
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28 Manet Rd, Unit 1
$6,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500
5 Bedroom Apartment Available Sep 1, 2026

28 Manet Rd, Unit 1

28 Manet RdChestnut Hill, MA 02467
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153 Foster St
$9,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,000

Total Monthly Price
$9,000
5 Bedroom Apartment Available Now

153 Foster St

153 Foster StBoston, MA 02135

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.

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200 Commonwealth Ave, Unit 1
$7,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,500

Total Monthly Price
$7,500
5 Bedroom Apartment Available Aug 23, 2026

200 Commonwealth Ave, Unit 1

200 Commonwealth AveChestnut Hill, MA 02467
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69 Breck Ave
$4,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300
5 Bedroom Apartment Available Now

69 Breck Ave

69 Breck AveBoston, MA 02135
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2 Lothian Rd, Unit 6-2
$5,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500
5 Bedroom Apartment Available Sep 1, 2026

2 Lothian Rd, Unit 6-2

2 Lothian RdBoston, MA 02135
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9 Radnor Rd, Unit 1
$5,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000
5 Bedroom Apartment Available Now

9 Radnor Rd, Unit 1

9 Radnor RdBoston, MA 02135
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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.

property at 62 Algonquin Rd

62 Algonquin Rd

NewtonMA02467
property at 6 Lothian Rd

6 Lothian Rd

BostonMA02135
property at 25 Kirkwood Rd

25 Kirkwood Rd

BostonMA02135

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

Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

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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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The 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.

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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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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

Frequently Asked Questions about Chestnut Hill Middlesex

How much are Studio apartments in Chestnut Hill Middlesex?

There are currently 49 Studio Apartments in Chestnut Hill Middlesex with rent ranges from $1,950 to $3,730 with an average price of $2,523.

What is the current price range for One Bedroom Chestnut Hill Middlesex Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Chestnut Hill Middlesex ranges from $1,050 to $4,500 with an average monthly rent of $2,492.

What does renting a Two Bedroom Apartment in Chestnut Hill Middlesex cost?

The monthly rent prices of Two Bedroom Apartments currently available in Chestnut Hill Middlesex range from $2,000 to $5,200. Today's average rental price for Two Bedrooms here is $3,437.

How expensive are Chestnut Hill Middlesex Three Bedroom Apartments?

There are currently 111 Three Bedroom Apartments listings available in Chestnut Hill Middlesex on ApartmentHomeLiving.com. The pricing ranges from $2,550 to $5,970 - averaging $3,942 for the location.

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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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.