Homes for Rent in Chestnut Hill, MA with Swimming Pool (123 Rentals)

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property at 10 Hammond Pond Pky

$2,500

Total Monthly Price24 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Feb 1, 2026

10 Hammond Pond Pky, Unit 304

10 Hammond Pond Pky
Chestnut HillMA02467
property at 607 Vfw Pky

$2,885

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,885

Total Monthly Price
$2,885

1 Bedroom, 1 Bath Townhome for Rent

Available Now

607 Vfw Pky

Chestnut HillMA02467
property at 46 Gerry Rd

$2,930

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,930

Total Monthly Price
$2,930

1 Bedroom, 1 Bath Townhome for Rent

Available Now

46 Gerry Rd

Chestnut HillMA02467
property at 79 Thornton Rd

$3,130

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,130

Total Monthly Price
$3,130

1 Bedroom, 1.5 Bath Townhome for Rent

Available Now

79 Thornton Rd, Unit 79

79 Thornton Rd
Chestnut HillMA02467
property at 194 Gerry Rd

$3,130

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,130

Total Monthly Price
$3,130

1 Bedroom, 1 Bath Townhome for Rent

Available Now

194 Gerry Rd

Chestnut HillMA02467
property at 130 Sherman Rd

$3,375

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,375

Total Monthly Price
$3,375

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

130 Sherman Rd, Unit 130

130 Sherman Rd
Chestnut HillMA02467
property at 527 Vfw Pky

$3,395

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,395

Total Monthly Price
$3,395

2 Bedroom, 1 Bath Townhome for Rent

Available Now

527 Vfw Pky

Chestnut HillMA02467
property at 59 Thornton Rd

$3,395

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,395

Total Monthly Price
$3,395

2 Bedroom, 1 Bath Townhome for Rent

Available Now

59 Thornton Rd

Chestnut HillMA02467
property at 241 Gerry Rd

$3,395

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,395

Total Monthly Price
$3,395

2 Bedroom, 1 Bath Townhome for Rent

Available Now

241 Gerry Rd

Chestnut HillMA02467
property at 148 Independence Dr

$3,645

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,645

Total Monthly Price
$3,645

2 Bedroom, 1 Bath Townhome for Rent

Available Now

148 Independence Dr

Chestnut HillMA02467

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property at 120 Thornton Rd

$3,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

120 Thornton Rd

Chestnut HillMA02467
property at 33 Gerry Rd

$3,710

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,710

Total Monthly Price
$3,710

2 Bedroom, 1 Bath Townhome for Rent

Available Jan 1, 2026

33 Gerry Rd

Chestnut HillMA02467
property at 97 Sherman Rd

$3,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,750

Total Monthly Price
$3,750

2 Bedroom, 1.5 Bath Townhome for Rent

Available Feb 1, 2026

97 Sherman Rd

Chestnut HillMA02467
property at 499 Vfw Pky

$3,760

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,760

Total Monthly Price
$3,760

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

499 Vfw Pky

Chestnut HillMA02467
property at 29 Independence Dr

$3,820

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,820

Total Monthly Price
$3,820

2 Bedroom, 1 Bath Townhome for Rent

Available Now

29 Independence Dr

Chestnut HillMA02467
property at 250 Hammond Pond Pky

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

250 Hammond Pond Pky, Unit 1203N

250 Hammond Pond Pky
Chestnut HillMA02467
property at 33 Westgate Rd

$2,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

1 Bedroom, 1 Bath Condo for Rent

Available Now

33 Westgate Rd, Unit 1

33 Westgate Rd
Boston CollegeMA02467
property at 33 Westgate Rd

$2,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,200

Total Monthly Price
$2,200

1 Bedroom, 1 Bath Condo for Rent

Available Now

33 Westgate Rd, Unit 5

33 Westgate Rd
Boston CollegeMA02467
property at 33 Westgate Rd

$2,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,200

Total Monthly Price
$2,200

1 Bedroom, 1 Bath Condo for Rent

Available Now

33 Westgate Rd, Unit 5

33 Westgate Rd
Boston CollegeMA02467
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

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property at 31 Westgate Rd

$2,695

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,695

Total Monthly Price
$2,695

2 Bedroom, 1 Bath Condo for Rent

Available Now

31 Westgate Rd, Unit 5

31 Westgate Rd
Boston CollegeMA02467
property at 589 Vfw Pky

$2,885

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,885

Total Monthly Price
$2,885

1 Bedroom, 1 Bath Townhome for Rent

Available Now

589 Vfw Pky

Boston CollegeMA02467
property at 162 Sherman Rd

$2,885

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,885

Total Monthly Price
$2,885

1 Bedroom, 1.5 Bath Townhome for Rent

Available Now

162 Sherman Rd

Boston CollegeMA02467
property at 50 Broadlawn Park

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 2 Bath Condo for Rent

Available Now

50 Broadlawn Park, Unit 410

50 Broadlawn Park
Boston CollegeMA02467
property at 50-56 Broadlawn Park

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 2 Bath Condo for Rent

Available Now

50-56 Broadlawn Park, Unit 410

50-56 Broadlawn Park
Boston CollegeMA02467
property at 60 Broadlawn Park

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 2 Bath Condo for Rent

Available Now

60 Broadlawn Park, Unit 410

60 Broadlawn Park
Boston CollegeMA02467
property at 44 Washington St

$2,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,100

Total Monthly Price
$2,100

Studio, 1 Bath Condo for Rent

Available Dec 22

44 Washington St, Unit 616

44 Washington St
BrooklineMA02445
property at 33 Pond Ave

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 Bedroom, 1 Bath Condo for Rent

Available Now

33 Pond Ave, Unit 301

33 Pond Ave
BrooklineMA02445
property at 77 Pond Ave

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

1 Bedroom, 1 Bath Condo for Rent

Available Now

77 Pond Ave, Unit 1010

77 Pond Ave
BrooklineMA02445
property at 99 Pond Ave

$2,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

1 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

99 Pond Ave, Unit 902

99 Pond Ave
BrooklineMA02445

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property at 19 Winchester St

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

1 Bedroom, 1 Bath Condo for Rent

Available Now

19 Winchester St, Unit 512

19 Winchester St
BrooklineMA02446
property at 77 Pond Ave

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

1 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

77 Pond Ave, Unit 407

77 Pond Ave
BrooklineMA02445
property at 33 Pond Ave

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

1 Bedroom, 1 Bath Condo for Rent

Available Now

33 Pond Ave, Unit 417

33 Pond Ave
BrooklineMA02445
property at 1731 Beacon St

$3,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,250

Total Monthly Price
$3,250

2 Bedroom, 1 Bath Condo for Rent

Available Now

1731 Beacon St, Unit 1213

1731 Beacon St
BrooklineMA02445
property at 1731 Beacon St

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

1 Bedroom, 1 Bath Condo for Rent

Available Now

1731 Beacon St, Unit 422

1731 Beacon St
BrooklineMA02445
property at 1731 Beacon St

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

1 Bedroom, 1 Bath Condo for Rent

Available Now

1731 Beacon St, Unit 203

1731 Beacon St
BrooklineMA02445
property at 8 Juniper St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

8 Juniper St, Unit 22

8 Juniper St
BrooklineMA02445
property at 50 Green St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 2 Bath Condo for Rent

Available Jan 1, 2026

50 Green St, Unit 411

50 Green St
BrooklineMA02446
property at 1485 Beacon St

$3,730

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,730

Total Monthly Price
$3,730

1 Bedroom, 1 Bath Condo for Rent

Available Now

1485 Beacon St, Unit 708

1485 Beacon St
BrooklineMA02446
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

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property at 50 Green St

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

2 Bedroom, 2 Bath Condo for Rent

Available Now

50 Green St, Unit 209

50 Green St
BrooklineMA02446
property at 77 Pond Ave

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

2 Bedroom, 2 Bath Condo for Rent

Available Now

77 Pond Ave, Unit 306

77 Pond Ave
BrooklineMA02445
property at 20 Webster St

$8,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,000

Total Monthly Price
$8,000

6 Bedroom, 1 Bath Condo for Rent

Available Now

20 Webster St, Unit ##

20 Webster St
BrooklineMA02446
property at 320 Hammond Pond Pkwy

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

2 Bedroom, 2 Bath Condo for Rent

Available Now

320 Hammond Pond Pkwy, Unit 104

320 Hammond Pond Pkwy
NewtonMA02467
property at 40 Puddingstone Ln

$14,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$14,000

Total Monthly Price
$14,000

6 Bedroom, 5.5 Bath Home for Rent

Available Mar 1, 2026

40 Puddingstone Ln

NewtonMA02459
property at 40 Puddingstone Ln

$14,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$14,000

Total Monthly Price
$14,000

6 Bedroom, 5.5 Bath Home for Rent

Available Mar 1, 2026

40 Puddingstone Ln

NewtonMA02459
property at 40 Puddingstone Ln

$14,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$14,750

Total Monthly Price
$14,750

6 Bedroom, 5.5 Bath Home for Rent

Available Now

40 Puddingstone Ln

NewtonMA02459
property at 110 Lanark Rd

$900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$900

Total Monthly Price
$900

4 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

110 Lanark Rd, Unit A

110 Lanark Rd
BostonMA02135
property at 124 Sutherland Rd

$2,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

Studio, 1 Bath Condo for Rent

Available Now

124 Sutherland Rd, Unit 1

124 Sutherland Rd
BostonMA02135
property at 26 Commonwealth Ter

$2,095

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,095

Total Monthly Price
$2,095

1 Bedroom, 1 Bath Condo for Rent

Available Now

26 Commonwealth Ter, Unit 3

26 Commonwealth Ter
BostonMA02135

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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.

Chestnut Hill, MA Local Guide

Boston Neighborhood Guide: Living Near UMass, MGH, and State Street

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.

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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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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

Written by: Amelia Ramstead

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

Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.

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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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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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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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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.