Luxury Homes for Rent in Chestnut Hill, MA (2,669 Rentals) Page 5 of 54

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

property at 20 Radcliffe Rd

$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

20 Radcliffe Rd, Unit 106

20 Radcliffe Rd
BostonMA02134
property at 1638 Commonwealth Ave

$2,625

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,625

Total Monthly Price
$2,625

1 Bedroom, 1 Bath Condo for Rent

Available Now

1638 Commonwealth Ave, Unit 3

1638 Commonwealth Ave
BostonMA02135
property at 77 Walk Hill St

$2,650

Total Monthly Price

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Townhome for Rent

Available Now

77 Walk Hill St

BostonMA02130
property at 19 South St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Now

19 South St, Unit 11

19 South St
BostonMA02135
property at 3850 Washington St

$2,650

Total Monthly Price

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

1 Bedroom, 1 Bath Townhome for Rent

Available Jan 1, 2026

3850 Washington St

BostonMA02131
property at 77 Walk Hill St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

77 Walk Hill St, Unit 1

77 Walk Hill St
BostonMA02130
property at 229 Kelton St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Now

229 Kelton St

BostonMA02134
property at 19 South St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

19 South St, Unit 11

19 South St
BostonMA02135
property at 1269 Commonwealth Ave

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Now

1269 Commonwealth Ave, Unit 2

1269 Commonwealth Ave
BostonMA02134
property at 1111 Commonwealth Ave

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

3 Bedroom, 2 Bath Condo for Rent

Available Jan 1, 2026

1111 Commonwealth Ave, Unit A

1111 Commonwealth Ave
BostonMA02215
property at 1243 Beacon St

$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

1243 Beacon St, Unit 2D

1243 Beacon St
BrooklineMA02446
property at 1243 Beacon St

$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

1243 Beacon St, Unit 1B-Brookline

1243 Beacon St
BrooklineMA02446
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 473 Arsenal St

$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

473 Arsenal St, Unit C

473 Arsenal St
WatertownMA02472
property at 9 Commonwealth Ct

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Now

9 Commonwealth Ct, Unit 13

9 Commonwealth Ct
BostonMA02135
property at 370 Chestnut Hill 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

370 Chestnut Hill Ave, Unit 1

370 Chestnut Hill Ave
BostonMA02135
property at 25 Glenville 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

25 Glenville Ave, Unit 12A

25 Glenville Ave
BostonMA02134
property at 2 Ayr Rd

$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

property at 97 Strathmore Rd

$2,675

Total Monthly Price

Total Monthly Price

Base Rent
$2,675

Total Monthly Price
$2,675

2 Bedroom, 1 Bath Condo for Rent

Available Now

97 Strathmore Rd

BostonMA02135
property at 57 Brighton Ave

$2,675

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,675

Total Monthly Price
$2,675

1 Bedroom, 1 Bath Condo for Rent

Available Now

57 Brighton Ave, Unit 2

57 Brighton Ave
BostonMA02134
property at 84 Braintree St

$2,675

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,675

Total Monthly Price
$2,675

Studio, 1 Bath Condo for Rent

Available Now

84 Braintree St, Unit 50 leo #405

84 Braintree St
BostonMA02134
property at 99 Dustin St

$2,675

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,675

Total Monthly Price
$2,675

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

99 Dustin St, Unit 34

99 Dustin St
BostonMA02135
property at 12 Kilsyth Ter

$2,675

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,675

Total Monthly Price
$2,675

1 Bedroom, 1 Bath Condo for Rent

Available Now

12 Kilsyth Ter, Unit 24

12 Kilsyth Ter
BostonMA02135
property at 97 Strathmore Rd

$2,675

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,675

Total Monthly Price
$2,675

2 Bedroom, 1 Bath Condo for Rent

Available Now

97 Strathmore Rd, Unit 8

97 Strathmore Rd
BostonMA02135
property at 1629 Commonwealth Ave

$2,675

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,675

Total Monthly Price
$2,675

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

1629 Commonwealth Ave, Unit 3

1629 Commonwealth Ave
BostonMA02135
property at 54 Vineland St

$2,685

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,685

Total Monthly Price
$2,685

2 Bedroom, 1 Bath Townhome for Rent

Available Now

54 Vineland St

BostonMA02135
property at 60 Leo M Birmingham Pky

$2,695

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,695

Total Monthly Price
$2,695

Studio, 1 Bath Condo for Rent

Available Now

60 Leo M Birmingham Pky, Unit 507

60 Leo M Birmingham Pky
BostonMA02135
property at 16 Glenville Ave

$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

16 Glenville Ave, Unit P5

16 Glenville Ave
BostonMA02134
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

Frequently Asked Questions about Chestnut Hill

What type of rentals are currently available in Chestnut Hill?

There are currently 4124 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $21,050. There are also 3255 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 $8,086.

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 $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.

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