4 Bedroom Homes for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (83 Rentals)

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property at 137 Chiswick Rd
$3,005

Total Monthly Price

Base Rent$3,000 - $3,005

Total Monthly Price$3,000 - $3,005
12 Month Lease Term
4 Bedroom Condos for Rent
Available Now
Affordability

137 Chiswick Rd

BostonMA02135
property at 101 Nonantum St
$3,500

Total Monthly Price

Base Rent$3,500

Total Monthly Price$3,500
12 Month Lease Term
4 Bedroom, 1.5 Bath Townhome for Rent
Available Sep 11
Affordability

101 Nonantum St

BostonMA02135
property at 71-73 Chestnut Hill Ave
$3,800

Total Monthly Price

Base Rent$3,800

Total Monthly Price$3,800
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

71-73 Chestnut Hill Ave, Unit 2

71-73 Chestnut Hill Ave
BostonMA02135
property at 96 Chestnut Hill Ave
$3,800

Total Monthly Price

Base Rent$3,800

Total Monthly Price$3,800
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

96 Chestnut Hill Ave, Unit 73

96 Chestnut Hill Ave
BostonMA02135
property at 73 Undine Rd
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
12 Month Lease Term
4 Bedroom, 2.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

73 Undine Rd

BostonMA02135
property at 195 Lake St
$3,800 - $4,500

Total Monthly Price

Base Rent$3,800 - $4,500

Total Monthly Price$3,800 - $4,500
12 Month Lease Term
4, 5 Bedroom Condos for Rent
Available Now
Cost Per Sq.Ft.

195 Lake St

BostonMA02135
property at 120 Kenrick St
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

120 Kenrick St, Unit 1

120 Kenrick St
BostonMA02135
property at 24 Tremont St
$4,800

Total Monthly Price

Base Rent$4,800

Total Monthly Price$4,800
12 Month Lease Term
4 Bedroom, 2.5 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

24 Tremont St

BostonMA02135
property at 225 Chestnut Hill Ave
$5,200

Total Monthly Price

Base Rent$5,200

Total Monthly Price$5,200
12 Month Lease Term
4 Bedroom, 1 Bath Condo for Rent
Available Now
Furnished

225 Chestnut Hill Ave, Unit 1

225 Chestnut Hill Ave
BostonMA02135
property at 91 Wallingford Rd
$5,400

Total Monthly Price

Base Rent$5,400

Total Monthly Price$5,400
12 Month Lease Term
4 Bedroom, 2 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

91 Wallingford Rd

BostonMA02135

Exploring Rental Options: Apartments, Townhomes, and Lofts—Oh My!

Looking for the perfect rental? From apartments and condos to lofts and single family rentals, explore the unique pros and cons of each rental type to help you land in your perfect new place.

property at 539 Commonwealth Ave
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
12 Month Lease Term
4 Bedroom, 3 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

539 Commonwealth Ave, Unit 2

539 Commonwealth Ave
NewtonMA02459
property at 110 Kenrick St
$5,600

Total Monthly Price

Base Rent$5,600

Total Monthly Price$5,600
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

110 Kenrick St

BostonMA02135
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property at 235 Chestnut Hill Ave
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now

235 Chestnut Hill Ave, Unit 1

235 Chestnut Hill Ave
BostonMA02135
property at 49 Radnor Rd
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Aug 22, 2027

49 Radnor Rd, Unit 2

49 Radnor Rd
BostonMA02135
property at 53 Radnor Rd
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Aug 22, 2027
Cost Per Sq.Ft.

53 Radnor Rd, Unit 2

53 Radnor Rd
BostonMA02135
property at 153 Foster St
$6,200

Total Monthly Price

Base Rent$6,200

Total Monthly Price$6,200
12 Month Lease Term
4 Bedroom, 2 Bath Townhome for Rent
Available Now

153 Foster St, Unit 1

153 Foster St
BostonMA02135
property at 16 South St
$7,700

Total Monthly Price

Base Rent$7,700

Total Monthly Price$7,700
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Sep 1, 2027

16 South St, Unit 1

16 South St
BostonMA02135
property at 25 Kirkwood Rd
$9,900

Total Monthly Price

Base Rent$9,900

Total Monthly Price$9,900
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Aug 31, 2027

25 Kirkwood Rd

BostonMA02135

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

property at 20 South St
$7,700

Total Monthly Price

Base Rent$7,700

Total Monthly Price$7,700
4 Bedroom, 2 Bath Rentals
Available Sep 1, 2027

20 South St, Unit 1

20 South St
BostonMA02135
property at 45 Radnor Rd
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
4 Bedroom, 2 Bath Rentals
Available Aug 22, 2027

45 Radnor Rd, Unit 2

45 Radnor Rd
BostonMA02135
property at 28 Manet Rd
$5,300

Total Monthly Price

Base Rent$5,300

Total Monthly Price$5,300
4 Bedroom, 1 Bath Rentals
Available Sep 1, 2027

28 Manet Rd, Unit 2

28 Manet Rd
NewtonMA02467

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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.

Chestnut Hill Middlesex, Boston College, MA Local Guide

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.

Read Article

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
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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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Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 274 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,000 to $13,500. There are also 462 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,000 to $16,000.

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 $1,000 to $16,000 with an average monthly rent of $3,744.

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 $1,000 to $7,640, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,250 to $7,250. Four Bedroom Single-Family rentals are also available starting from $1,160 and Four Bedroom Apartments start at $1,350.

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 Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My! article

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

decorative image for Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags   article

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.