
Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (723 Rentals)
The most luxurious Homes in the Chestnut Hill Middlesex area of Chestnut Hill with high-end amenities, features, and finishes.


24 Wallingford Rd, Unit 2

25 South St, Unit 5

2018 Commonwealth Ave, Unit 45

2045 Commonwealth Ave, Unit M-46

209 Chestnut Hill Ave, Unit 9

140 Kenrick St, Unit 4

84 Boylston St, Unit 2

1933 Commonwealth Ave

155 Strathmore Rd, Unit 2
The Art of the Rental Viewing: What to look for during a property tour
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.

65 Strathmore Rd, Unit 5

145 Englewood Ave, Unit 43

1933 Commonwealth Ave, Unit 611

29 Wiltshire Rd, Unit 1

1845 Commonwealth Ave, Unit 29

1795 Commonwealth Ave

2012 Commonwealth 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.

185 Chestnut Hill Ave, Unit 09

133 Chiswick Rd, Unit 207

27 South St, Unit #B3

39 Commonwealth Ave, Unit 22

36 Dighton St, Unit 14

1880 Commonwealth Ave, Unit 15

135 Chiswick Rd, Unit 207

370 Chestnut Hill Ave, Unit 1

135 Chiswick Rd, Unit 408

5 Braemore Rd, Unit 1-15

1160 Boylston St, Unit 31

140 Kenrick St

1933 Commonwealth Ave, Unit 111
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.

140 Kenrick St, Unit 4

140 Kenrick St, Unit #4

100 Kenrick St

80 Chestnut Hill Ave, Unit 1

140 Kenrick St, Unit 4

249 Chestnut Hill Ave, Unit 51

2 Braemore Rd, Unit 1

181 Washington St, Unit 3338

5 Braemore Rd, Unit 8

1860 Commonwealth Ave, Unit 1

13 Winship St

110 Strathmore Rd, Unit 204

2012 Commonwealth Ave

24 Wallingford Rd, Unit 5

20 Shanley St

20 Shanley St

20 Shanley St, Unit 2R

7 Lothian Rd, Unit 8

20 Shanley St, Unit 2R

22 Shanley St
Chestnut Hill Middlesex, Boston College, MA Local Guide

How much does it cost to rent a home in Chestnut Hill Middlesex?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Chestnut Hill Middlesex 2 Bedroom Homes for Rent | $3,266 | $2,400 | $5,200 |
Chestnut Hill Middlesex 3 Bedroom Homes for Rent | $3,894 | $2,550 | $8,000 |
Chestnut Hill Middlesex 4 Bedroom Homes for Rent | $5,038 | $950 | $9,600 |
Chestnut Hill Middlesex 5 Bedroom Homes for Rent | $6,577 | $1,000 | $10,000+ |
Chestnut Hill Middlesex 6 Bedroom Homes for Rent | $9,108 | $1,150 | $10,000+ |
Chestnut Hill Middlesex 7 Bedroom Homes for Rent | $11,200 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 723 rentals with your search options within a 2 mile radius of the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA.
Explore Chestnut Hill
Chestnut Hill Middlesex, Boston College, MA Local Guide
- Nearby Chestnut Hill neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
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.
Frequently Asked Questions about Chestnut Hill Middlesex
What type of rentals are currently available in Chestnut Hill Middlesex?
There are currently 1075 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,150 to $23,500. There are also 844 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $950 to $40,000.
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 $950 to $40,000 with an average monthly rent of $5,984.
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 $2,550 to $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,550 to $8,000. Four Bedroom Single-Family rentals are also available starting from $950 and Four Bedroom Apartments start at $1,150.
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.

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.