5 Bedroom Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (46 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
property at 132 Chiswick Rd

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

5 Bedroom, 2 Bath Condo for Rent

Available Now

132 Chiswick Rd, Unit 2, Unit 2

132 Chiswick Rd
BostonMA02135
property at 28 Manet Rd

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800 - $5,800

Total Monthly Price
$4,800 - $5,800

5 Bedroom Condos for Rent

Available Now

28 Manet Rd

Chestnut HillMA02467
property at 16 Priscilla Rd

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

5 Bedroom, 2 Bath Condo for Rent

Available Now

16 Priscilla Rd, Unit 2, Unit 2

16 Priscilla Rd
BostonMA02135
property at 91 Wallingford Rd

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

91 Wallingford Rd, Unit 1, Unit 1

91 Wallingford Rd
BostonMA02135
property at 49 Breck Ave

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

5 Bedroom, 2 Bath Home for Rent

Available Now

49 Breck Ave

BostonMA02135
property at 6 Lothian Rd

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200 - $5,800

Total Monthly Price
$5,200 - $5,800

5 Bedroom Condos for Rent

Available Now

6 Lothian Rd

BostonMA02135
property at 49 Breck Ave

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

5 Bedroom, 2 Bath Home for Rent

Available Now

49 Breck Ave

BostonMA02135
property at 28 Manet Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,400 - $6,500

Total Monthly Price
$5,400 - $6,500

5 Bedroom Condos for Rent

Available Sep 1

28 Manet Rd

Chestnut HillMA02467
property at 16 Foster St

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

5 Bedroom, 3 Bath Townhome for Rent

Available Now

16 Foster St

BostonMA02135
property at 6 Lothian Rd

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800

5 Bedroom, 2 Bath Home for Rent

Available Now

6 Lothian Rd

BostonMA02135

Renting with Roommates: Realistic Expectations for Shared Lease

Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.

property at 288 Foster St

$7,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200 - $7,200

Total Monthly Price
$6,200 - $7,200

5 Bedroom Condos for Rent

Available Now

288 Foster St

BostonMA02135
property at 28 Manet Rd

$6,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,300

Total Monthly Price
$6,300

5 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1

28 Manet Rd, Unit 1, Unit 1

28 Manet Rd
Chestnut HillMA02467
property at 16 Foster St

$6,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,300

Total Monthly Price
$6,300

5 Bedroom, 3 Bath Townhome for Rent

Available Sep 1

16 Foster St

BostonMA02135
property at 16 Foster St

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 3 Bath Townhome for Rent

Available Sep 1

16 Foster St

BostonMA02135
property at 25 Wade St

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 3.5 Bath Home for Rent

Available Now

25 Wade St

BostonMA02135
property at 64 Langley Rd

$6,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,900

Total Monthly Price
$6,900

5 Bedroom, 3.5 Bath Home for Rent

Available Now

64 Langley Rd, Unit 1, Unit 1

64 Langley Rd
BostonMA02135
property at 14 Glenmont Rd

$7,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,200

Total Monthly Price
$7,200

5 Bedroom, 2 Bath Condo for Rent

Available Aug 15

14 Glenmont Rd, Unit 2, Unit 2

14 Glenmont Rd
BostonMA02135
property at 14 Glenmont Rd

$7,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,200

Total Monthly Price
$7,200

5 Bedroom, 2 Bath Townhome for Rent

Available Aug 15

14 Glenmont Rd

BostonMA02135
property at 14 Glenmont Rd

$7,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,200

Total Monthly Price
$7,200

5 Bedroom, 2 Bath Condo for Rent

Available Aug 15

14 Glenmont Rd, Unit 2, Unit 2

14 Glenmont Rd
BostonMA02135
property at 153 Foster St

$7,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,500

Total Monthly Price
$7,500

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

153 Foster St, Unit 1, Unit 1

153 Foster St
BostonMA02135

Renting Smart: Lease Basics Every Renter Needs

Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com

property at 25 Kirkwood Rd

$8,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,000

Total Monthly Price
$8,000

5 Bedroom, 2 Bath Condo for Rent

Available Now

25 Kirkwood Rd, Unit 1##, Unit 1##

25 Kirkwood Rd
BostonMA02135
property at 12 Gerald Rd

$9,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,500

Total Monthly Price
$9,500

5 Bedroom, 3 Bath Home for Rent

Available Now

12 Gerald Rd

BostonMA02135
property at 12 Gerald Rd

$9,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,500

Total Monthly Price
$9,500

5 Bedroom, 3 Bath Home for Rent

Available Now

12 Gerald Rd

BostonMA02135

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.

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.

property at 66 Lothian Rd

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

5 Bedroom, 2 Bath Home for Rent

Available Sep 1

66 Lothian Rd

BostonMA02135
property at 2 Lothian Rd

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2 Lothian Rd

BostonMA02135
property at 16 Foster St

$5,600 - $6,500

Total Monthly Price

Total Monthly Price

Base Rent
$6,300

Total Monthly Price
$6,300

5 Bedroom Rentals

Available Now

16 Foster St

BostonMA02135
property at 478 Clinton Rd

$11,000

Total Monthly Price

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

5 Bedroom, 3.5 Bath Home for Rent

Available Now

478 Clinton Rd

BrooklineMA02467
property at 29 Merrill Rd

$17,500

Total Monthly Price

Total Monthly Price

Base Rent
$17,500

Total Monthly Price
$17,500

5 Bedroom, 8 Bath Condo for Rent

Available Now

29 Merrill Rd

NewtonMA02459

Chestnut Hill Middlesex, Boston College, MA Local Guide

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 Article
Decorative image

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.

decorative image of people with a giant lease agreement

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

decorative image of woman handing cat to small boy

Frequently Asked Questions about Chestnut Hill Middlesex

What type of rentals are currently available in Chestnut Hill Middlesex?

There are currently 471 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 575 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $950 to $17,500.

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 $950 to $17,500 with an average monthly rent of $5,752.

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 $2,550 to $8,997, while Three Bedroom Homes, Condos, and Townhomes for rent range from $950 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,130 and Four Bedroom Apartments start at $3,100.

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

decorative image for A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back article

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

decorative image for Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts  article

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.

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

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.

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

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.