Homes for Rent by Owner in Chestnut Hill, MA (20 Rentals)

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property at 23 Westgate Rd

$2,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,300

Total Monthly Price
$2,300

1 Bedroom, 1 Bath Condo for Rent

Available Now

23 Westgate Rd, Unit 6

23 Westgate Rd
Boston CollegeMA02467
property at 369 Tappan St

$3,000

Total Monthly Price9 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

1 Bedroom, 1 Bath Condo for Rent

Available Now

369 Tappan St, Unit 12

369 Tappan St
BrooklineMA02445
property at 515 Heath St

$3,400

Total Monthly Price

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

3 Bedroom, 1 Bath Home for Rent

Available Now

515 Heath St

BrooklineMA02467
property at 1793 Beacon St

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

1793 Beacon St, Unit 5

1793 Beacon St
BrooklineMA02445
property at 10 Juniper St

$3,799

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,799

Total Monthly Price
$3,799

3 Bedroom, 1 Bath Condo for Rent

Available Now

10 Juniper St, Unit 35

10 Juniper St
BrooklineMA02445
property at 55 Presentation Rd

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 1.5 Bath Townhome for Rent

Available Now

55 Presentation Rd, Unit 1

55 Presentation Rd
BrightonMA02135

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Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.

property at 628 Boylston St

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom, 1 Bath Home for Rent

Available Jan 1, 2026

628 Boylston St

NewtonMA02459
property at 39 Parkton Rd

$1,298

Total Monthly Price8 Month Lease Term

Total Monthly Price

Base Rent
$1,298

Total Monthly Price
$1,298

3 Bedroom, 1 Bath Condo for Rent

Available Now

39 Parkton Rd, Unit 1

39 Parkton Rd
BostonMA02130
property at 1870 Commonwealth Ave

$2,350

Total Monthly Price18 Month Lease Term

Total Monthly Price

Base Rent
$2,350

Total Monthly Price
$2,350

1 Bedroom, 1 Bath Condo for Rent

Available Mar 15, 2026

1870 Commonwealth Ave, Unit 7

1870 Commonwealth Ave
BostonMA02135
property at 90 Kilsyth Rd

$2,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

1 Bedroom, 1 Bath Condo for Rent

Available Jan 15, 2026

90 Kilsyth Rd, Unit 24

90 Kilsyth Rd
BostonMA02135
property at 100 Summer St

$2,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

2 Bedroom, 1 Bath Condo for Rent

Available Now

100 Summer St, Unit 1-2

100 Summer St
WatertownMA02472
property at 142 Kenrick St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Mar 1, 2026

142 Kenrick St, Unit 24

142 Kenrick St
BostonMA02135

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property at 39 South St

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

39 South St, Unit 4

39 South St
BostonMA02135
property at 226 Jamaicaway

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

property at 1868 Commonwealth Ave

$3,354

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,354

Total Monthly Price
$3,354

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

1868 Commonwealth Ave, Unit 5

1868 Commonwealth Ave
BostonMA02135
property at 96 Brayton Rd

$3,600

Total Monthly Price9 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2.5 Bath Condo for Rent

Available Now

96 Brayton Rd, Unit 1

96 Brayton Rd
BostonMA02135
property at 14 Union St

$3,800

Total Monthly Price3 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

4 Bedroom, 2 Bath Home for Rent

Available Dec 31

14 Union St

BostonMA02135
property at 9 Gardner Ter

$4,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,400

Total Monthly Price
$4,400

4 Bedroom, 2 Bath Condo for Rent

Available Now

9 Gardner Ter, Unit 3

9 Gardner Ter
BostonMA02134

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property at 32 Long Ave

$6,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,600

Total Monthly Price
$6,600

6 Bedroom, 3 Bath Condo for Rent

Available Now

32 Long Ave, Unit 1

32 Long Ave
BostonMA02134

Chestnut Hill, MA Local Guide

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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Top Neighborhoods Near Boston Colleges and Universities

Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chestnut Hill, MA Rentals by Map

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Frequently Asked Questions about Chestnut Hill

What type of rentals are currently available in Chestnut Hill?

There are currently 4165 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $21,050. There are also 3609 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $725 to $38,000.

What is the current price range for Rental Homes in Chestnut Hill?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestnut Hill ranges from $725 to $38,000 with an average monthly rent of $7,459.

How much are larger Three and Four Bedroom Rentals in Chestnut Hill?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestnut Hill range from $950 to $12,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $850 to $22,000. Four Bedroom Single-Family rentals are also available starting from $725 and Four Bedroom Apartments start at $1,225.

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.

Helpful Local Expert Guides

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The 10 Best Affordable Neighborhoods in Boston, MA

Written by: Amelia Ramstead

Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

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A Local Experts Guide to the Top Boston Neighborhoods for College Renters

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Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!

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Explore Like a Local: The Insider's Guide to Boston

Written by: Amelia Ramstead

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Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street

Written by: Amelia Ramstead

Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.

Articles, How-To's, and Tips

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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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.