
Luxury Homes for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (354 Rentals) Page 2 of 8
The most luxurious Homes in the Chestnut Hill Middlesex area of Chestnut Hill with high-end amenities, features, and finishes.


145 Englewood Ave, Unit 4

110 Academy Hill Rd, Unit 1

1872 Commonwealth Ave, Unit 408

21 Wiltshire Rd, Unit 2

73 Undine Rd

120 Kenrick St, Unit 1

25 Greycliff Rd, Unit 1

24 Tremont St

225 Chestnut Hill Ave, Unit 1
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

6 Lothian Rd, Unit 3

7 Lothian Rd, Unit 3

91 Wallingford Rd

539 Commonwealth Ave, Unit 2

110 Kenrick St

235 Chestnut Hill Ave, Unit 1

49 Radnor Rd, Unit 2

53 Radnor Rd, Unit 2

29 Gerald Rd, Unit 1

153 Foster St, Unit 1

2021 Commonwealth Ave, Unit 2

16 South St, Unit 1

126 Lake St

116 Lake St

37 Radnor Rd, Unit 1

53 Radnor Rd, Unit 1

25 Kirkwood Rd

44 Greycliff Rd

12 Gerald Rd

1860 Commonwealth Ave

52 Greycliff Rd

44 Greycliff Rd, Unit #2

Total Monthly Price
160 Boylston St, Unit SI FL3-ID6526A

Total Monthly Price
160 Boylston St, Unit SI FL1-ID6519A

35 South St, Unit 8

219 Commonwealth Ave, Unit 25

219 Commonwealth Ave, Unit 15

91 Academy Hill Rd

62 Algonquin Rd, Unit 1

42 Fairbanks St, Unit 1

15 Moody St

8 Hammondswood Rd

44 Winship St, Unit 2

42 Winship St, Unit 1

44 Winship St

Total Monthly Price
160 Boylston St, Unit SI FL3-ID4144A

207 Lake Shore Rd, Unit 2

173 Warren St

365 Washington St, Unit 303A

175 Warren St
Chestnut Hill Middlesex, Boston College, MA Local Guide
How much does it cost to rent a home in Chestnut Hill Middlesex?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Chestnut Hill Middlesex 2 Bedroom Homes for Rent | $3,119 | $2,300 | $6,000 |
| Chestnut Hill Middlesex 3 Bedroom Homes for Rent | $3,743 | $2,250 | $7,250 |
| Chestnut Hill Middlesex 4 Bedroom Homes for Rent | $5,614 | $1,160 | $10,000+ |
| Chestnut Hill Middlesex 5 Bedroom Homes for Rent | $6,222 | $1,210 | $10,000+ |
| Chestnut Hill Middlesex 6 Bedroom Homes for Rent | $7,614 | $1,000 | $10,000+ |
| Chestnut Hill Middlesex 7 Bedroom Homes for Rent | $9,466 | $6,600 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 354 rentals with your search options within a 2 mile radius of the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA.
Explore Chestnut Hill
Frequently Asked Questions about Chestnut Hill Middlesex
What type of rentals are currently available in Chestnut Hill Middlesex?
There are currently 274 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,000 to $13,500. There are also 462 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,000 to $16,000.
What is the current price range for Rental Homes in Chestnut Hill Middlesex?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestnut Hill Middlesex ranges from $1,000 to $16,000 with an average monthly rent of $3,744.
How much are larger Three and Four Bedroom Rentals in Chestnut Hill Middlesex?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestnut Hill Middlesex range from $1,000 to $7,640, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,250 to $7,250. Four Bedroom Single-Family rentals are also available starting from $1,160 and Four Bedroom Apartments start at $1,350.
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.
Articles, How-To's, and Tips

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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.