Luxury Homes for Rent in Chestnut Hill, MA (2,812 Rentals) Page 12 of 57

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

property at 13 Union St

13 Union St

WatertownMA02472
property at 38 Allston St

38 Allston St, Unit 16

38 Allston St
BostonMA02134
property at 35 Mount Hood Rd

35 Mount Hood Rd, Unit 6

35 Mount Hood Rd
BostonMA02135
property at 8 Selkirk Rd

8 Selkirk Rd

BostonMA02135
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3688 Washington St
$2,990
Total Monthly Price

Total Monthly Price

Base Rent
$2,620
Required Monthly Fees
$370

Total Monthly Price
$2,990
1 Bedroom Apartments Available Apr 2, 2026

3688 Washington St

3688 Washington StBoston, MA 02130
Furnished
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161 Washington St
$2,990
Total Monthly Price

Total Monthly Price

Base Rent
$2,550
Required Monthly Fees
$440

Total Monthly Price
$2,990
2 Bedroom Apartments Available Nov 16

161 Washington St

161 Washington StBoston, MA 02135
Furnished
property at 11 Fairfield St

11 Fairfield St, Unit 1

11 Fairfield St
WatertownMA02472
property at 1531 Beacon St

1531 Beacon St, Unit 16

1531 Beacon St
BrooklineMA02446
property at 42 Brackett St

42 Brackett St, Unit 44-2

42 Brackett St
BostonMA02135
property at 1522 VFW Pkwy

1522 VFW Pkwy, Unit 204

1522 VFW Pkwy
BostonMA02132
property at 316 Tappan St

316 Tappan St, Unit 1B

316 Tappan St
BrooklineMA02445
property at 70 Saint Paul St

70 Saint Paul St, Unit 6

70 Saint Paul St
BrooklineMA02446
property at 12 Ransom Rd

12 Ransom Rd, Unit 12A

12 Ransom Rd
BostonMA02135
property at 319 Belgrade Ave

319 Belgrade Ave, Unit 303

319 Belgrade Ave
BostonMA02131
property at 22 School St

22 School St

NewtonMA02458
property at 240 Kelton St

240 Kelton St, Unit 7

240 Kelton St
BostonMA02134
property at 11 Fairfield St

11 Fairfield St, Unit 2

11 Fairfield St
WatertownMA02472
property at 240 Kelton St

240 Kelton St, Unit 16

240 Kelton St
BostonMA02134
property at 49 Prince St

49 Prince St, Unit 1

49 Prince St
BrooklineMA02445
property at 15 Scottfield Rd

15 Scottfield Rd, Unit 16

15 Scottfield Rd
BostonMA02134
property at 51 Montfern Ave

51 Montfern Ave, Unit 1

51 Montfern Ave
BostonMA02135
property at 147 Kelton St

147 Kelton St, Unit 311

147 Kelton St
BostonMA02134
property at 1662 Commonwealth Ave

1662 Commonwealth Ave, Unit 41

1662 Commonwealth Ave
BostonMA02135
property at 116 Englewood Ave

116 Englewood Ave, Unit 25

116 Englewood Ave
BostonMA02135
property at 2035 Commonwealth Ave

2035 Commonwealth Ave, Unit 9

2035 Commonwealth Ave
BostonMA02135
property at 86 Beechcroft St

86 Beechcroft St, Unit 2

86 Beechcroft St
BostonMA02135
property at 1263 Commonwealth Ave

1263 Commonwealth Ave, Unit 8

1263 Commonwealth Ave
BostonMA02134
property at 49 Montfern Ave

49 Montfern Ave, Unit 1

49 Montfern Ave
BostonMA02135
property at 35 Coolidge Hill Rd

35 Coolidge Hill Rd, Unit 29-3

35 Coolidge Hill Rd
WatertownMA02472
property at 71 Brighton Ave

71 Brighton Ave, Unit 4

71 Brighton Ave
BostonMA02134
property at 4 Centre Ln

4 Centre Ln, Unit T

4 Centre Ln
BostonMA02132
property at 66 Harvard Ave

66 Harvard Ave, Unit 4

66 Harvard Ave
BostonMA02134
property at 1758 Commonwealth Ave

1758 Commonwealth Ave, Unit 1

1758 Commonwealth Ave
BostonMA02135
property at 24 Hibbard Rd

24 Hibbard Rd, Unit 1

24 Hibbard Rd
NewtonMA02458
property at 94 Beechcroft St

94 Beechcroft St, Unit 2

94 Beechcroft St
BostonMA02135
property at 1450 Beacon St

1450 Beacon St, Unit 203

1450 Beacon St
BrooklineMA02446
property at 41 Colborne Rd

41 Colborne Rd, Unit 6

41 Colborne Rd
BostonMA02135
property at 96 Winthrop Rd

96 Winthrop Rd, Unit 1

96 Winthrop Rd
BrooklineMA02445
property at 70 Union St

70 Union St, Unit 2

70 Union St
BostonMA02135
property at 1666 Commonwealth Ave

1666 Commonwealth Ave, Unit 32

1666 Commonwealth Ave
BostonMA02135
property at 2001 Commonwealth Ave

2001 Commonwealth Ave, Unit 16

2001 Commonwealth Ave
BostonMA02135
property at 1082 Commonwealth Ave

1082 Commonwealth Ave, Unit 503

1082 Commonwealth Ave
BostonMA02215
property at 59 Lanark Rd

59 Lanark Rd, Unit 12

59 Lanark Rd
BostonMA02135
property at 10 Scottfield Rd

10 Scottfield Rd, Unit 13

10 Scottfield Rd
BostonMA02134

Frequently Asked Questions about Chestnut Hill

What type of rentals are currently available in Chestnut Hill?

There are currently 3985 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $14,200. There are also 3352 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

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Apartment Common Area Rules: What Renters Need to Know

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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.