
Luxury Homes for Rent in Chestnut Hill Neighborhood of Boston, MA (431 Rentals) Page 3 of 9
The most luxurious Homes in the Chestnut Hill area of Boston with high-end amenities, features, and finishes.


39 Englewood Ave, Unit 1

43 Selkirk Rd

129 Sutherland
1914 Beacon St, Unit 2

11 Kinross Rd, Unit 2

129 Sutherland Rd

235 Chestnut Hill Ave, Unit 1

235 Chestnut Hill Ave, Unit 1

23 Orkney Rd, Unit 2

2021 Commonwealth Ave, Unit 2

12 Gerald Rd

1860 Commonwealth Ave

32 Orkney Rd, Unit 2

2018 Commonwealth Ave, Unit 35

1820 Commonwealth Ave, Unit 2

123 Sutherland Rd, Unit L

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

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

Total Monthly Price
109 Strathmore Rd, Unit SI FL2-ID1564685P

286 Chestnut Hill Ave, Unit 4

374 Chestnut Hill Ave, Unit 52

47 Englewood Ave, Unit 2

1932 Beacon St, Unit 5

1950 Beacon St, Unit 3A

286 Chestnut Hill Ave, Unit 16

4 Ayr Rd, Unit 41

115 Kilsyth Rd, Unit 2

100 Kilsyth Rd, Unit 27

100 Kilsyth Rd, Unit 5

100 Kilsyth Rd, Unit 26

100 Kilsyth Rd, Unit 21

115 Kilsyth Rd, Unit 3

3 Sutherland Rd, Unit 2

1950 Beacon St, Unit 1Z

1932 Beacon St, Unit 5A

286 Chestnut Hill Ave, Unit #16

31 South St, Unit B2

1933 Commonwealth Ave, Unit 505

31 South St, Unit 6

34 Orkney Rd, Unit 2

34 Orkney Rd, Unit 1

31 South St, Unit 12

41 Orkney Rd, Unit 3

143 Kilsyth Rd, Unit 1

32 Orkney Rd, Unit 3

2017 Commonwealth Ave, Unit 4

35 South St, Unit 1

61 Selkirk Rd, Unit 1

61 Selkirk Rd, Unit 11
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 | $3,176 | $2,250 | $4,800 |
| Chestnut Hill 3 Bedroom Homes for Rent | $3,891 | $2,500 | $6,500 |
| Chestnut Hill 4 Bedroom Homes for Rent | $5,633 | $1,100 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $6,377 | $4,700 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,252 | $1,200 | $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 431 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 398 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,050 to $10,250. There are also 560 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $1,100 to $14,500.
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 $1,100 to $14,500 with an average monthly rent of $5,080.
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 $2,500 to $8,350, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $6,500. Four Bedroom Single-Family rentals are also available starting from $1,100 and Four Bedroom Apartments start at $1,050.
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

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.

A Local Experts Guide to the Top Boston Neighborhoods for College Renters
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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!

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.

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

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.