4 Bedroom Condos for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (35 Rentals)

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property at 137 Chiswick Rd

$3,005

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000 - $3,005

Total Monthly Price
$3,000 - $3,005

4 Bedroom Condos for Rent

Available Now

137 Chiswick Rd

BostonMA02135
property at 71-73 Chestnut Hill Ave

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

71-73 Chestnut Hill Ave, Unit 2

71-73 Chestnut Hill Ave
BostonMA02135
property at 96 Chestnut Hill Ave

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

96 Chestnut Hill Ave, Unit 73

96 Chestnut Hill Ave
BostonMA02135
property at 91 Academy Hill Rd

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

91 Academy Hill Rd, Unit 91

91 Academy Hill Rd
BostonMA02135
property at 195 Lake St

$3,800 - $4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800 - $4,500

Total Monthly Price
$3,800 - $4,500

4, 5 Bedroom Condos for Rent

Available Aug 30

195 Lake St

BostonMA02135
property at 120 Kenrick St

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

120 Kenrick St, Unit 1

120 Kenrick St
BostonMA02135
property at 225 Chestnut Hill Ave

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 1 Bath Condo for Rent

Available Now

225 Chestnut Hill Ave, Unit 1

225 Chestnut Hill Ave
BostonMA02135
property at 120 Kenrick St

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

120 Kenrick St, Unit 1

120 Kenrick St
BostonMA02135

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 539 Commonwealth Ave

$5,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

4 Bedroom, 3 Bath Condo for Rent

Available Now

539 Commonwealth Ave, Unit 2

539 Commonwealth Ave
NewtonMA02459
property at 110 Kenrick St

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

4 Bedroom, 2 Bath Condo for Rent

Available Now

110 Kenrick St

BostonMA02135
property at 153 Foster St

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

153 Foster St, Unit 2A

153 Foster St
BostonMA02135
property at 199 Boylston St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 3.5 Bath Condo for Rent

Available Now

199 Boylston St, Unit 1

199 Boylston St
Chestnut HillMA02467
property at 235 Chestnut Hill Ave

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

235 Chestnut Hill Ave, Unit 1

235 Chestnut Hill Ave
BostonMA02135
property at 25 Kirkwood Rd

$9,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,900

Total Monthly Price
$9,900

4 Bedroom, 2 Bath Condo for Rent

Available Aug 31, 2027

25 Kirkwood Rd

BostonMA02135
property at 33R Winship Pl

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

4 Bedroom, 1 Bath Rentals

Available Aug 1

33R Winship Pl

BostonMA02135
property at 124 Kenrick St

$5,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

4 Bedroom, 3 Bath Rentals

Available Aug 1

124 Kenrick St, Unit 5

124 Kenrick St
BostonMA02135

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.

property at 124 Kenrick St

$5,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

4 Bedroom, 3 Bath Rentals

Available Aug 1

124 Kenrick St, Unit 6

124 Kenrick St
BostonMA02135
property at 120 Kenrick St

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

4 Bedroom, 2 Bath Rentals

Available Sep 1

120 Kenrick St, Unit 5

120 Kenrick St
BostonMA02135
property at 33R Winship Pl

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

4 Bedroom, 1 Bath Rentals

Available Sep 1

33R Winship Pl

BostonMA02135
property at 24 Eastburn St

$3,600

Total Monthly Price

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

4 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1

24 Eastburn St

BostonMA02135
property at 558 Washington St

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

4 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1

558 Washington St

BostonMA02135
property at 199 Lake St

$4,200

Total Monthly Price

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

199 Lake St

BostonMA02135
property at 91 Academy Hill Rd

$4,200

Total Monthly Price

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

91 Academy Hill 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 148 Strathmore Rd

$4,300

Total Monthly Price

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

4 Bedroom, 2 Bath Condo for Rent

Available Now

148 Strathmore Rd

BostonMA02135
property at 2 Glenley Terrace

$4,800

Total Monthly Price

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2 Glenley Terrace

BostonMA02135
property at 6 Lothian Rd

$5,050 - $5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,050

Total Monthly Price
$5,050

4 Bedroom Rentals

Available Sep 1

6 Lothian Rd

BostonMA02135
property at 120 Kenrick St

$5,000 - $5,200

Total Monthly Price

Total Monthly Price

Base Rent
$5,175

Total Monthly Price
$5,175

4 Bedroom Rentals

Available Now

120 Kenrick St

BostonMA02135
property at 8 Lothian Rd

$5,200

Total Monthly Price

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

8 Lothian Rd

BostonMA02135
property at 147 Kenrick St

$5,200

Total Monthly Price

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

147 Kenrick St

BostonMA02135
property at 127 Nonantum St

$5,100 - $5,565

Total Monthly Price

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom Rentals

Available Now

127 Nonantum St

BostonMA02135
property at 23 Winship St

$5,700

Total Monthly Price

Total Monthly Price

Base Rent
$5,700

Total Monthly Price
$5,700

4 Bedroom, 2.5 Bath Condo for Rent

Available Aug 1

23 Winship St

BostonMA02135

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.

property at 143 Kenrick St

$5,900

Total Monthly Price

Total Monthly Price

Base Rent
$5,900

Total Monthly Price
$5,900

4 Bedroom, 3 Bath Condo for Rent

Available Aug 1

143 Kenrick St

BostonMA02135
property at 126 Kenrick St

$5,900

Total Monthly Price

Total Monthly Price

Base Rent
$5,900

Total Monthly Price
$5,900

4 Bedroom, 3 Bath Condo for Rent

Available Aug 1

126 Kenrick St

BostonMA02135
property at 47 Winship St

$3,800 - $6,600

Total Monthly Price

Total Monthly Price

Base Rent
$6,600

Total Monthly Price
$6,600

4 Bedroom Rentals

Available Aug 1

47 Winship St

BostonMA02135

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
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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.

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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 309 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,000 to $14,300. There are also 462 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,130 to $13,500.

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 $1,130 to $13,500 with an average monthly rent of $4,467.

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 $1,350 to $7,999, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,495 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,005 and Four Bedroom Apartments start at $2,400.

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

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

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

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

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