Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (358 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

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

property at 2045 Commonwealth Ave

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Now

2045 Commonwealth Ave, Unit M-46

2045 Commonwealth Ave
BostonMA02135
property at 145 Chiswick Rd

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

145 Chiswick Rd, Unit B

145 Chiswick Rd
BostonMA02135
property at 247 Chestnut Hill Ave

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

247 Chestnut Hill Ave, Unit 5

247 Chestnut Hill Ave
BostonMA02135
property at 1933 Commonwealth Ave

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

1933 Commonwealth Ave, Unit 108

1933 Commonwealth Ave
BostonMA02135
property at 28 Sidlaw Rd

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Now

28 Sidlaw Rd, Unit 6

28 Sidlaw Rd
BostonMA02135
property at 133 Chiswick Rd

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

133 Chiswick Rd, Unit B

133 Chiswick Rd
BostonMA02135
property at 142 Kenrick St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Mar 1, 2026

142 Kenrick St, Unit 24

142 Kenrick St
BostonMA02135
property at 10 Hammond Pond Pky

$2,500

Total Monthly Price24 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

1 Bedroom, 1 Bath Condo for Rent

Available Feb 1, 2026

10 Hammond Pond Pky, Unit 304

10 Hammond Pond Pky
Chestnut HillMA02467
property at 19 South St

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1 Bath Condo for Rent

Available Now

19 South St, Unit 11

19 South St
BostonMA02135
property at 91 Wallingford Rd

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

91 Wallingford Rd, Unit 2

91 Wallingford Rd
BostonMA02135

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

property at 135 Chiswick Rd

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

1 Bedroom, 1 Bath Condo for Rent

Available Now

135 Chiswick Rd, Unit 512

135 Chiswick Rd
BostonMA02135
property at 145 Englewood Ave

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

1 Bedroom, 1 Bath Condo for Rent

Available Now

145 Englewood Ave, Unit 43

145 Englewood Ave
BostonMA02135
property at 29 Wiltshire Rd

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

3 Bedroom, 1 Bath Condo for Rent

Available Now

29 Wiltshire Rd, Unit 1

29 Wiltshire Rd
BostonMA02135
property at 27 South St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 Bedroom, 1 Bath Condo for Rent

Available Now

27 South St, Unit #B3

27 South St
BostonMA02135
property at 185 Chestnut Hill Ave

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Now

185 Chestnut Hill Ave, Unit 09

185 Chestnut Hill Ave
BostonMA02135
property at 7 Lothian Rd

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

7 Lothian Rd, Unit 3

7 Lothian Rd
BostonMA02135
property at 18 Embassy Rd

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

18 Embassy Rd, Unit 37

18 Embassy Rd
BostonMA02135
property at 19 South St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

19 South St, Unit 11

19 South St
BostonMA02135
property at 1933 Commonwealth Ave

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

1 Bedroom, 1 Bath Condo for Rent

Available Now

1933 Commonwealth Ave, Unit 108

1933 Commonwealth Ave
BostonMA02135
property at 370 Chestnut Hill Ave

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

1 Bedroom, 1 Bath Condo for Rent

Available Now

370 Chestnut Hill Ave, Unit 1

370 Chestnut Hill Ave
BostonMA02135

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.

property at 19 South St

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Now

19 South St, Unit 11

19 South St
BostonMA02135
property at 2 Braemore Rd

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

1 Bedroom, 1 Bath Condo for Rent

Available Now

2 Braemore Rd, Unit 1

2 Braemore Rd
BostonMA02135
property at 249 Chestnut Hill Ave

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Condo for Rent

Available Now

249 Chestnut Hill Ave, Unit 51

249 Chestnut Hill Ave
BostonMA02135
property at 140 Kenrick St

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Condo for Rent

Available Now

140 Kenrick St, Unit 4

140 Kenrick St
BostonMA02135
property at 5 Braemore Rd

$2,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

1 Bedroom, 1 Bath Condo for Rent

Available Now

5 Braemore Rd, Unit 8

5 Braemore Rd
BostonMA02135
property at 2031 Commonwealth Ave

$2,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

1 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

2031 Commonwealth Ave, Unit 12

2031 Commonwealth Ave
BostonMA02135
property at 50 Larch St

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

50 Larch St, Unit 2

50 Larch St
BostonMA02135
property at 22 Shanley St

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

22 Shanley St

BostonMA02135
property at 110 Strathmore Rd

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

110 Strathmore Rd, Unit 204

110 Strathmore Rd
BostonMA02135
property at 20 Shanley St

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

20 Shanley St, Unit 1R

20 Shanley St
BostonMA02135

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.

property at 91 Wallingford Rd

$2,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

3 Bedroom, 1 Bath Condo for Rent

Available Now

91 Wallingford Rd, Unit 3

91 Wallingford Rd
BostonMA02135
property at 31 Lake Shore Ct

$2,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

2 Bedroom, 1 Bath Condo for Rent

Available Now

31 Lake Shore Ct, Unit 3

31 Lake Shore Ct
BostonMA02135
property at 51 Lake Shore Ct

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 159 Foster St

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

159 Foster St, Unit 1

159 Foster St
BostonMA02135
property at 51 Lake Shore Ct

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 2012 Commonwealth Ave

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

2012 Commonwealth Ave, Unit BE

2012 Commonwealth Ave
BostonMA02135
property at 35 Foster St

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

35 Foster St, Unit 1

35 Foster St
BostonMA02135
property at 19 Chestnut Hill Ave

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

19 Chestnut Hill Ave, Unit 1

19 Chestnut Hill Ave
BostonMA02135
property at 43 N Crescent Circuit

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

43 N Crescent Circuit, Unit 1

43 N Crescent Circuit
BostonMA02135
property at 29 Eastburn St

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Now

29 Eastburn St, Unit 2

29 Eastburn St
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 1880 Commonwealth Ave

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Now

1880 Commonwealth Ave, Unit 12

1880 Commonwealth Ave
BostonMA02135
property at 14 Lyne Rd

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Now

14 Lyne Rd, Unit 1

14 Lyne Rd
BostonMA02135
property at 211 Lake Shore Rd

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Now

211 Lake Shore Rd, Unit 2

211 Lake Shore Rd
BostonMA02135
property at 440 Washington St

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

440 Washington St, Unit 3

440 Washington St
BostonMA02135
property at 440 Washington St

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

440 Washington St, Unit 3

440 Washington St
BostonMA02135
property at 35 Commonwealth Ave

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

1 Bedroom, 1 Bath Condo for Rent

Available Now

35 Commonwealth Ave, Unit U201-1-bed

35 Commonwealth Ave
Chestnut HillMA02467
property at 440 Washington St

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

440 Washington St, Unit 3

440 Washington St
BostonMA02135
property at 2035 Commonwealth Ave

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

2035 Commonwealth Ave, Unit 9

2035 Commonwealth Ave
BostonMA02135
property at 295 Commonwealth Ave

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

Studio, 1 Bath Condo for Rent

Available Now

295 Commonwealth Ave, Unit H-18

295 Commonwealth Ave
Chestnut HillMA02467

Chestnut Hill Middlesex, Boston College, MA Local Guide

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

Read Article
Decorative image

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

Read Article
Decorative image

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

Pet Friendly Lifestyle
Chestnut Hill Middlesex, Chestnut Hill, MA

Ranked #1

Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

decorative image of woman handing cat to small boy

Frequently Asked Questions about Chestnut Hill Middlesex

What type of rentals are currently available in Chestnut Hill Middlesex?

There are currently 452 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 415 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $760 to $17,500.

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 $760 to $17,500 with an average monthly rent of $7,020.

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 $6,285, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $7,000. Four Bedroom Single-Family rentals are also available starting from $1,010 and Four Bedroom Apartments start at $3,200.

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

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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.