Luxury Homes for Rent in Chestnut Hill Neighborhood of Boston, MA (308 Rentals) Page 2 of 7

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The most luxurious Homes in the Chestnut Hill area of Boston with high-end amenities, features, and finishes.

property at 1933 Commonwealth Ave

1933 Commonwealth Ave, Unit 403

1933 Commonwealth Ave
BostonMA02135
property at 1933 Commonwealth Ave

1933 Commonwealth Ave, Unit 1

1933 Commonwealth Ave
BostonMA02135
property at 2 Sutherland Rd

2 Sutherland Rd, Unit 31

2 Sutherland Rd
BostonMA02135
property at 39 South St

39 South St, Unit 2

39 South St
BostonMA02135
property at 130 Englewood Ave

130 Englewood Ave, Unit 4

130 Englewood Ave
BostonMA02135
property at 10 Selkirk Rd

10 Selkirk Rd, Unit 4

10 Selkirk Rd
BostonMA02135
property at 26 Chiswick Rd

26 Chiswick Rd, Unit 13

26 Chiswick Rd
BostonMA02135
property at 141 Chiswick Rd

141 Chiswick Rd, Unit B

141 Chiswick Rd
BostonMA02135
property at 26 Chiswick Rd

26 Chiswick Rd, Unit 13

26 Chiswick Rd
BostonMA02135
property at 36 Cummings Rd

36 Cummings Rd, Unit 1

36 Cummings 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 80 Sutherland Rd

80 Sutherland Rd, Unit O-35

80 Sutherland Rd
BostonMA02135
property at 26 Chiswick Rd

26 Chiswick Rd, Unit 2

26 Chiswick Rd
BostonMA02135
property at 374 Chestnut Hill Ave

374 Chestnut Hill Ave, Unit 41

374 Chestnut Hill Ave
BostonMA02135
property at 370 Chestnut Hill Ave

370 Chestnut Hill Ave, Unit 25

370 Chestnut Hill Ave
BostonMA02135
property at 7 Lothian Rd

7 Lothian Rd, Unit 11

7 Lothian Rd
BostonMA02135
property at 1942 Beacon St

1942 Beacon St, Unit 1

1942 Beacon St
BostonMA02135
property at 48 Englewood Ave

48 Englewood Ave, Unit #2

48 Englewood Ave
BostonMA02135
property at 6 South St

6 South St, Unit uni3 2-bed 1-bath

6 South St
BostonMA02135
property at 65 Chiswick Rd

65 Chiswick Rd, Unit 3B

65 Chiswick Rd
BostonMA02135
property at 90 Kilsyth Rd

90 Kilsyth Rd, Unit 43

90 Kilsyth Rd
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 2 Sutherland Rd

2 Sutherland Rd, Unit 31

2 Sutherland Rd
BostonMA02135
property at 1942 Beacon St

1942 Beacon St, Unit 1

1942 Beacon St
BostonMA02135
property at 126 Englewood Ave

126 Englewood Ave, Unit #6

126 Englewood Ave
BostonMA02135
property at 39 Englewood Ave

39 Englewood Ave, Unit #4

39 Englewood Ave
BostonMA02135
property at 97 Kilsyth Rd

97 Kilsyth Rd, Unit 3

97 Kilsyth Rd
BostonMA02135
property at 6 Sutherland Rd

6 Sutherland Rd, Unit 31

6 Sutherland Rd
BostonMA02135
property at 6 Sutherland Rd

6 Sutherland Rd, Unit 31

6 Sutherland Rd
BostonMA02135
property at 231 Chestnut Hill Ave

231 Chestnut Hill Ave, Unit 3

231 Chestnut Hill Ave
BostonMA02135
property at 231 Chestnut Hill Ave

231 Chestnut Hill Ave, Unit 3

231 Chestnut Hill Ave
BostonMA02135
property at 104 Strathmore Rd

104 Strathmore Rd, Unit 1

104 Strathmore Rd
BostonMA02135
property at 11 Orkney Rd

11 Orkney Rd, Unit 3

11 Orkney Rd
BostonMA02135
property at 45 Englewood Ave

45 Englewood Ave, Unit 47 #6

45 Englewood Ave
BostonMA02135
property at 5 Kilsyth Ter

5 Kilsyth Ter, Unit 1

5 Kilsyth Ter
BostonMA02135
property at 1999 Commonwealth Ave

1999 Commonwealth Ave, Unit 12

1999 Commonwealth Ave
BostonMA02135
property at 6 Sutherland Rd

6 Sutherland Rd, Unit 31

6 Sutherland Rd
BostonMA02135
property at 6 Sutherland Rd

6 Sutherland Rd, Unit 31

6 Sutherland Rd
BostonMA02135
property at 6 Sutherland Rd

6 Sutherland Rd, Unit 31

6 Sutherland Rd
BostonMA02135
property at 8 Selkirk Rd

8 Selkirk Rd, Unit 2

8 Selkirk Rd
BostonMA02135
property at 99 Kilsyth Rd

99 Kilsyth Rd, Unit 2

99 Kilsyth Rd
BostonMA02135
property at 97 Kilsyth Rd

97 Kilsyth Rd, Unit 3

97 Kilsyth Rd
BostonMA02135
property at 97 Kilsyth Rd

97 Kilsyth Rd, Unit 3

97 Kilsyth Rd
BostonMA02135
property at 1945 Commonwealth Ave

1945 Commonwealth Ave, Unit 13C

1945 Commonwealth Ave
BostonMA02135
property at 97 Kilsyth Rd

97 Kilsyth Rd, Unit #2

97 Kilsyth Rd
BostonMA02135
property at 370 Chestnut Hill Ave

370 Chestnut Hill Ave, Unit 21

370 Chestnut Hill Ave
BostonMA02135
property at 1997 Commonwealth Ave

1997 Commonwealth Ave, Unit 7

1997 Commonwealth Ave
BostonMA02135
property at 1870 Commonwealth Ave

1870 Commonwealth Ave, Unit 12A

1870 Commonwealth Ave
BostonMA02135
property at 370 Chestnut Hill Ave

370 Chestnut Hill Ave, Unit 21

370 Chestnut Hill Ave
BostonMA02135
property at 370 Chestnut Hill Ave

370 Chestnut Hill Ave, Unit 21

370 Chestnut Hill Ave
BostonMA02135
property at 2 Sutherland Rd

2 Sutherland Rd, Unit 51

2 Sutherland Rd
BostonMA02135
property at 2 Sutherland Rd

2 Sutherland Rd, Unit 51

2 Sutherland Rd
BostonMA02135

Frequently Asked Questions about Chestnut Hill

What type of rentals are currently available in Chestnut Hill?

There are currently 411 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,800 to $14,200. There are also 369 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $900 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 $900 to $17,500 with an average monthly rent of $7,262.

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 $5,975, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,075 to $7,700. Four Bedroom Single-Family rentals are also available starting from $900 and Four Bedroom Apartments start at $3,600.

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.

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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 Apartment Common Area Rules: What Renters Need to Know article

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.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.