
Luxury Homes for Rent in Chestnut Hill Neighborhood of Boston, MA (422 Rentals)
The most luxurious Homes in the Chestnut Hill area of Boston with high-end amenities, features, and finishes.


7 Sutherland Rd

1982 Commonwealth Ave

247 Chestnut Hill Ave

1872 Commonwealth Ave

4 Chiswick Rd

48 Strathmore Rd, Unit 26

90 Kilsyth Rd, Unit #43

1872 Commonwealth Ave, Unit 7

46 Chiswick Rd, Unit 5
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164 Strathmore Rd, Unit 25

2039 Commonwealth Ave, Unit 11

9 Braemore Rd, Unit 1A

7 Lothian Rd, Unit 1

9 Braemore Rd, Unit 12

39 South St

1933 Commonwealth Ave, Unit #405a

9 Braemore Rd, Unit 12

26 Chiswick Rd

59 Lanark Rd, Unit 12
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Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

59 Lanark Rd, Unit 12

12 Kilsyth Ter, Unit 24

2 Braemore Rd, Unit 1

1933 Commonwealth Ave, Unit 504

276 Chestnut Hill Ave

2 Braemore Rd, Unit A

63 Selkirk Rd

67 Chiswick Rd

67 Chiswick Rd

59 Lanark Rd, Unit 2
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30 Kinross Rd, Unit 2##

37 Radnor Rd

3 Sutherland Rd

132 Chiswick Rd, Unit 1B

2 Sutherland Rd

116 Sutherland Rd

2012 Commonwealth Ave, Unit BE

276 Chestnut Hill Ave, Unit 26

24 Chiswick Rd

1933 Commonwealth Ave, Unit #-
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1868 Commonwealth Ave, Unit 5

1999 Commonwealth Ave, Unit 4

1880 Commonwealth Ave, Unit 5

8 Selkirk Rd

72 Strathmore Rd

2001 Commonwealth Ave, Unit 16

39 Englewood Ave, Unit 12

79 Sutherland Rd, Unit 4

2009 Commonwealth Ave, Unit 20

15 South St, Unit 6
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Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.
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 | $3,171 | $2,125 | $4,800 |
| Chestnut Hill 3 Bedroom Homes for Rent | $3,870 | $2,500 | $6,500 |
| Chestnut Hill 4 Bedroom Homes for Rent | $5,606 | $1,100 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $6,437 | $4,700 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,219 | $1,175 | $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 422 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 394 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,050 to $10,250. There are also 538 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 $5,075.
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 $8,030, 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
Written by: Amelia Ramstead
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.