Luxury Homes for Rent in Chestnut Hill, MA (2,795 Rentals) Page 16 of 56

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The most luxurious Homes in Chestnut Hill with high-end amenities, features, and finishes.

property at 1607 Commonwealth Ave

1607 Commonwealth Ave, Unit 9

1607 Commonwealth Ave
BostonMA02135
property at 2025 Commonwealth Ave
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1440 Beacon St
$3,120
Total Monthly Price

Total Monthly Price

Base Rent
$2,760
Required Monthly Fees
$360

Total Monthly Price
$3,120
Studio Apartments Available Aug 4, 2026

1440 Beacon St

1440 Beacon StBrookline, MA 02446
Furnished
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1440 Beacon St
$3,120
Total Monthly Price

Total Monthly Price

Base Rent
$2,760
Required Monthly Fees
$360

Total Monthly Price
$3,120
Studio Apartments Available Aug 4, 2026

1440 Beacon St

1440 Beacon StBrookline, MA 02446
Furnished
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12 Elko St
$3,125
Total Monthly Price

Total Monthly Price

Base Rent
$2,710
Required Monthly Fees
$415

Total Monthly Price
$3,125
2 Bedroom Apartments Available Mar 25, 2026

12 Elko St

12 Elko StBoston, MA 02135
Furnished
property at 322 Tappan St

322 Tappan St, Unit 1b

322 Tappan St
BrooklineMA02445
property at 309 Tappan St

309 Tappan St, Unit #1B

309 Tappan St
BrooklineMA02445
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3686 Washington St
$3,135
Total Monthly Price

Total Monthly Price

Base Rent
$2,780
Required Monthly Fees
$355

Total Monthly Price
$3,135
1 Bedroom Apartments Available May 7, 2026

3686 Washington St

3686 Washington StBoston, MA 02130
Furnished
property at 22 Eulita Ter

22 Eulita Ter, Unit 22##

22 Eulita Ter
BostonMA02135
property at 1950 Beacon St

1950 Beacon St, Unit 1

1950 Beacon St
BostonMA02135
property at 1400 Commonwealth Ave

1400 Commonwealth Ave, Unit 6

1400 Commonwealth Ave
BostonMA02134
property at 1412 Commonwealth Avenue

1412 Commonwealth Avenue, Unit 19A

1412 Commonwealth Avenue
BostonMA02135
property at 505 Washington St

505 Washington St, Unit 3

505 Washington St
BostonMA02135
property at 79 Sutherland Rd

79 Sutherland Rd, Unit 7

79 Sutherland Rd
BostonMA02135
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181 Washington St
$3,165
Total Monthly Price

Total Monthly Price

Base Rent
$2,820
Required Monthly Fees
$345

Total Monthly Price
$3,165
Studio Apartments Available May 2, 2026

181 Washington St

181 Washington StBoston, MA 02135
Furnished
property at 192 Allston St

192 Allston St, Unit 2-bed 1-bath

192 Allston St
BostonMA02134
property at 108 Hyde Park Ave

108 Hyde Park Ave, Unit 2

108 Hyde Park Ave
BostonMA02130
property at 19 Lancaster Ter

19 Lancaster Ter, Unit 103

19 Lancaster Ter
BrooklineMA02446
property at 104 Warren St

104 Warren St, Unit 5

104 Warren St
BostonMA02135
property at 33 Shannon St

33 Shannon St, Unit 3

33 Shannon St
BostonMA02135
property at 16 Glenville Ave

16 Glenville Ave, Unit 8

16 Glenville Ave
BostonMA02134
property at 104 Warren St

104 Warren St, Unit 5

104 Warren St
BostonMA02135
property at 306 Tappan St

306 Tappan St, Unit 103

306 Tappan St
BrooklineMA02445
property at 1254 Commonwealth Ave

1254 Commonwealth Ave, Unit 3

1254 Commonwealth Ave
BostonMA02134
property at 365 Western Ave

365 Western Ave

BostonMA02135
property at 85 Brainerd Rd

85 Brainerd Rd, Unit 303

85 Brainerd Rd
BostonMA02134
property at 369 Tappan St

369 Tappan St, Unit 12

369 Tappan St
BrooklineMA02445
property at 1850 Beacon St

1850 Beacon St

BrooklineMA02445

Frequently Asked Questions about Chestnut Hill

What type of rentals are currently available in Chestnut Hill?

There are currently 3978 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $14,200. There are also 3358 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $750 to $22,000.

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 $750 to $22,000 with an average monthly rent of $4,883.

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 $925 to $22,000. Four Bedroom Single-Family rentals are also available starting from $830 and Four Bedroom Apartments start at $1,068.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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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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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.