
Luxury Homes for Rent in the Chestnut Hill Neighborhood of Boston, MA (289 Rentals) Page 2 of 6
The most luxurious Homes in the Chestnut Hill area of Boston with high-end amenities, features, and finishes.


370 Chestnut Hill Ave, Unit 34

65 Chiswick Rd, Unit 4

95 Kilsyth Rd, Unit 2

35 South St, Unit 8

22 Chiswick Rd, Unit 18

1778 Commonwealth Ave, Unit 1

106 Strathmore Rd, Unit 3

Total Monthly Price
109 Strathmore Rd, Unit SI FL2-ID1564668P

288 Chestnut Hill Ave, Unit #14
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Total Monthly Price
109 Strathmore Rd, Unit SI FL2-ID1564691P

Total Monthly Price
109 Strathmore Rd, Unit SI FL2-ID1564676P

Total Monthly Price
109 Strathmore Rd, Unit SI FL2-ID1564682P

Total Monthly Price
109 Strathmore Rd, Unit SI FL2-ID1564692P

100 Kilsyth Rd, Unit 5

115 Kilsyth Rd, Unit 3

34 Orkney Rd, Unit 2

61 Selkirk Rd, Unit 1

61 Selkirk Rd, Unit 11

28 Sidlaw Rd, Unit 6
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26 Chiswick Rd, Unit 8

63 Selkirk Rd, Unit 7

65 Chiswick Rd, Unit 2

63 Selkirk Rd, Unit 2

63 Selkirk Rd, Unit 3

63 Selkirk Rd, Unit 6

2018 Commonwealth Ave, Unit 36

65 Chiswick Rd, Unit 1

2018 Commonwealth Ave, Unit 47

1874 Commonwealth Ave, Unit 1
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19 South St, Unit 1

286 Chestnut Hill Ave, Unit 5

65 Chiswick Rd, Unit 5

63 Selkirk Rd, Unit 8

65 Chiswick Rd, Unit 6

288 Chestnut Hill Ave, Unit 14

67 Chiswick Rd, Unit 2

63 Selkirk Rd, Unit 4

65 Chiswick Rd, Unit 3

2017 Commonwealth Ave, Unit 6
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67 Chiswick Rd, Unit 1

50 Englewood Ave, Unit 1

39 Strathmore Rd, Unit 2

276 Chestnut Hill Ave, Unit 19

45 Radnor Rd, Unit 1

20 South St, Unit 1

20 South St, Unit 2

45 Radnor Rd, Unit 2

2017 Commonwealth Ave, Unit 6

2018 Commonwealth Ave, Unit 45
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Chestnut Hill, Boston, MA Local Guide

How much does it cost to rent a home in Chestnut Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Chestnut Hill 2 Bedroom Homes for Rent | $3,070 | $2,300 | $4,375 |
| Chestnut Hill 3 Bedroom Homes for Rent | $3,785 | $2,800 | $6,500 |
| Chestnut Hill 4 Bedroom Homes for Rent | $5,507 | $1,280 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $6,929 | $5,000 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,286 | $1,050 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $10,500 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 289 rentals with your search options within a 1 mile radius of the Chestnut Hill Neighborhood of Boston, MA.
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Frequently Asked Questions about Chestnut Hill
What type of rentals are currently available in Chestnut Hill?
There are currently 218 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,350 to $10,500. There are also 379 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $1,050 to $12,500.
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 $1,050 to $12,500 with an average monthly rent of $3,514.
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 $2,695 to $7,790, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $6,500. Four Bedroom Single-Family rentals are also available starting from $1,280 and Four Bedroom Apartments start at $1,350.
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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First Apartment Regrets: Real Renters Share What They'd Do Differently
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