Luxury Homes for Rent in Chestnut Hill Neighborhood of Boston, MA (546 Rentals)

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Higher End Luxurious Homes in the Chestnut Hill area of Boston.

property at 27 Orkney Rd

27 Orkney Rd, Unit 1

27 Orkney Rd
BostonMA02135
property at 27 Orkney Rd

27 Orkney Rd, Unit 1

27 Orkney Rd
BostonMA02135
property at 12 Gerald Rd

12 Gerald Rd

BostonMA02135
property at 37 Radnor Rd

37 Radnor Rd, Unit 1

37 Radnor Rd
BostonMA02135
property at 49 Radnor Rd

49 Radnor Rd, Unit 1

49 Radnor Rd
BostonMA02135
property at 45 Radnor Rd

45 Radnor Rd

BostonMA02135

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

property at 117 Sutherland Rd

117 Sutherland Rd

BostonMA02135
property at 25 Wade St

25 Wade St

BostonMA02135
property at 129 Sutherland Rd

129 Sutherland Rd

BostonMA02135

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

property at 45 Radnor Rd

45 Radnor Rd, Unit 2

45 Radnor Rd
BostonMA02135
property at 53 Radnor Rd

53 Radnor Rd, Unit 2

53 Radnor Rd
BostonMA02135
property at 1914 Beacon St

1914 Beacon St

BostonMA02135

Boston's Best Affordable Neighborhoods

Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

property at 6 Lothian Rd

6 Lothian Rd, Unit 2

6 Lothian Rd
BostonMA02135
property at 154 Kilsyth Rd

154 Kilsyth Rd

BostonMA02135
property at 47 Orkney Rd

47 Orkney Rd, Unit 2

47 Orkney Rd
BostonMA02135
property at 27 Orkney Rd

27 Orkney Rd, Unit 2

27 Orkney Rd
BostonMA02135
property at 47 Orkney Rd

47 Orkney Rd, Unit 2

47 Orkney Rd
BostonMA02135
property at 27 Orkney Rd

27 Orkney Rd

BostonMA02135
property at 45 Orkney Rd

45 Orkney Rd, Unit 3

45 Orkney Rd
BostonMA02135
property at 7 Kilsyth Ter

7 Kilsyth Ter

BostonMA02135

Chestnut Hill, Boston, MA Local Guide

Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

decorative image of people with a giant lease agreement

Frequently Asked Questions about Chestnut Hill

What type of rentals are currently available in Chestnut Hill?

There are currently 749 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $950 to $25,723. There are also 663 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $1,750 to $15,000.

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 $1,750 to $15,000 with an average monthly rent of $4,847.

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 $8,655, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,895 to $7,500. Four Bedroom Single-Family rentals are also available starting from $3,525 and Four Bedroom Apartments start at $1,025.

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.

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

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.

decorative image for Navigating the Rental Market: Tips for First-Time Renters article

Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.

decorative image for Rise of Digital Nomads: Remote Work Tips for Apartment Renters article

Rise of Digital Nomads: Remote Work Tips for Apartment Renters

Written by: Brandie Parton

As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.

decorative image for Know Your Rights - How Discrimination Laws Impact Landlords and Tenants article

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Written by: Christine Leonard, Esq.

Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.