
Luxury Homes for Rent in Chestnut Hill, MA (3,332 Rentals) Page 35 of 67
The most luxurious Homes in Chestnut Hill with high-end amenities, features, and finishes.


251 Winchester St

210 Chestnut Hill Ave, Unit 6

35 Waverly St, Unit 2

29 Cummings Rd

99 Gardner St

136 Kenrick St

51 Brighton Ave

38 Chester St

1323 Commonwealth Ave

21 Lothrop St

101-199 Gardner St

59 Brighton Ave, Unit B

6 Primrose St, Unit 1

29 Perthshire Rd

21 Gibbs St, Unit 2

199 Gardner St, Unit 403

128 Kenrick St

1325 Commonwealth Ave

18 Ashford St

27 Lothrop St

81 Brighton Ave

99 Needham St, Unit 2235

55 Gerry Rd

6 Glencoe St

8-10 Glencoe St

175 Freeman St, Unit 604

175 Freeman St, Unit 602

175 Freeman St, Unit 621
1485 Beacon St, Unit 708

527 VFW Parkway, Unit V-527

18 Glencoe St

1573 Centre St

42 Longwood Ave, Unit 4

1729 Commonwealth Ave

31 Harris St

54 Harvard St, Unit 3

75 Beechcroft St, Unit 1

45 Ashford St, Unit 3
1618 Beacon St

11 Royal St, Unit 3

38 Turner St, Unit 1

18 Alton Pl, Unit 4

36 Turner St, Unit 1

62 Union St

175 Freeman St, Unit 313

27 Sherman Rd

5 Washington St, Unit 425

28 Park Vale Ave

19 Gerry Rd
Chestnut Hill, 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 | $3,291 | $2,150 | $10,000+ |
| Chestnut Hill 3 Bedroom Homes for Rent | $3,969 | $900 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $4,882 | $1,175 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $5,894 | $975 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,653 | $1,000 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $3,574 | $1,110 | $10,000+ |
Browse Top Homes for Rent in Chestnut Hill
Explore Chestnut Hill
Frequently Asked Questions about Chestnut Hill
What type of rentals are currently available in Chestnut Hill?
There are currently 2391 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $800 to $13,500. There are also 4045 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $900 to $24,000.
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 $900 to $24,000 with an average monthly rent of $3,536.
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 $1,495 to $12,773, while Three Bedroom Homes, Condos, and Townhomes for rent range from $900 to $12,600. Four Bedroom Single-Family rentals are also available starting from $1,175 and Four Bedroom Apartments start at $1,300.
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

Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.

What It Really Costs to Live in Boston: A Local Renter's Guide
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.

Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!

Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!
Articles, How-To's, and Tips

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.