
Luxury Homes for Rent in Chestnut Hill Neighborhood of Boston, MA (325 Rentals)
The most luxurious Homes in the Chestnut Hill area of Boston with high-end amenities, features, and finishes.


2045 Commonwealth Ave, Unit M-46

110 Lanark Rd, Unit 6

1933 Commonwealth Ave, Unit 108

247 Chestnut Hill Ave, Unit 5

116 Sutherland Rd, Unit 1

1933 Commonwealth Ave, Unit 108

52 Strathmore Rd

28 Sidlaw Rd, Unit 6

145 Englewood Ave, Unit 43
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117 Sutherland Rd, Unit 3

7 Lothian Rd, Unit 3

27 South St, Unit #B3

2 Ayr Rd, Unit unitB 1-bed 1-bath

370 Chestnut Hill Ave, Unit 1

19 South St, Unit 11

12 Kilsyth Ter, Unit 24

97 Strathmore Rd, Unit 8

2 Braemore Rd, Unit 1

249 Chestnut Hill Ave, Unit 51
Explore Like a Local: The Insider's Guide to Boston
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.

110 Lanark Rd, Unit 7

110 Lanark Rd, Unit 7

5 Braemore Rd, Unit 8

2031 Commonwealth Ave, Unit 12

69 Chiswick Rd, Unit 9

63 Selkirk Rd, Unit 1

46 Chiswick Rd, Unit 3

59 Lanark Rd, Unit 2

98 Strathmore Rd, Unit 2

6 Sutherland Rd, Unit 43
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Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

110 Strathmore Rd, Unit 204

39 Englewood Ave, Unit 12

30 Chiswick Rd, Unit 2

63 Selkirk Rd, Unit 3

2012 Commonwealth Ave, Unit BE

1880 Commonwealth Ave, Unit 12

8 Selkirk Rd

39 South St, Unit 4

61 Strathmore Rd, Unit 3a

2001 Commonwealth Ave, Unit 16
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2035 Commonwealth Ave, Unit 9

116 Englewood Ave, Unit 25

59 Lanark Rd, Unit 12

21 Sutherland Rd, Unit 1

39 South St, Unit 4

2009 Commonwealth Ave, Unit 10

370 Chestnut Hill Ave

2009 Commonwealth Ave, Unit 20

39 South St, Unit 2

1880 Commonwealth Ave, Unit 10
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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 | $3,178 | $2,225 | $4,850 |
| Chestnut Hill 3 Bedroom Homes for Rent | $4,275 | $2,800 | $7,700 |
| Chestnut Hill 4 Bedroom Homes for Rent | $5,196 | $900 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $7,125 | $1,000 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $7,303 | $880 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $11,700 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 325 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 450 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,150 to $14,200. There are also 388 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $880 to $17,500.
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 $880 to $17,500 with an average monthly rent of $7,650.
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 $2,700 to $6,115, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $7,700. Four Bedroom Single-Family rentals are also available starting from $900 and Four Bedroom Apartments start at $3,500.
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 to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
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.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!