Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (498 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 7 Lothian Rd

$2,000 - $2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000 - $2,800

Total Monthly Price
$2,000 - $2,800

Studio To 3 Bedroom Condos for Rent

Available Now

7 Lothian Rd

BostonMA02135
property at 1840 Commonwealth Ave

$2,250 - $2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,250 - $2,650

Total Monthly Price
$2,250 - $2,650

Studio To 1 Bedroom Condos for Rent

Available Sep 1

property at 1982 Commonwealth Ave

$2,300 - $3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,300 - $3,300

Total Monthly Price
$2,300 - $3,300

1 To 3 Bedroom Condos for Rent

Available Sep 1

property at 247 Chestnut Hill Ave

$2,300 - $2,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,300 - $2,850

Total Monthly Price
$2,300 - $2,850

Studio To 1 Bedroom Condos for Rent

Available Jun 1

property at 99 Chestnut Hill Ave

$2,300 - $3,325

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,300 - $3,325

Total Monthly Price
$2,300 - $3,325

Studio To 2 Bedroom Condos for Rent

Available Jun 1

property at 1872 Commonwealth Ave

$2,350 - $2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,350 - $2,950

Total Monthly Price
$2,350 - $2,950

1 To 2 Bedroom Condos for Rent

Available Sep 1

property at 7 Lothian Rd

$2,350 - $2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,350 - $2,800

Total Monthly Price
$2,350 - $2,800

Studio To 2 Bedroom Condos for Rent

Available Jun 1

7 Lothian Rd

BostonMA02135
property at 4 Chiswick Rd

$2,400 - $2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400 - $2,500

Total Monthly Price
$2,400 - $2,500

Studio To 1 Bedroom Condos for Rent

Available Aug 1

4 Chiswick Rd

BostonMA02135
property at 35 Foster St

$2,500 - $4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500 - $4,800

Total Monthly Price
$2,500 - $4,800

1 To 4 Bedroom Condos for Rent

Available Sep 1

35 Foster St

BostonMA02135
property at 189 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 Sep 1

189 Chestnut Hill Ave, Unit 15, Unit 15

189 Chestnut Hill Ave
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 185 Chestnut Hill Ave

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

Studio, 1 Bath Condo for Rent

Available Now

185 Chestnut Hill Ave, Unit 6, Unit 6

185 Chestnut Hill 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, Unit 6

28 Sidlaw 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, Unit #B3

27 South St
BostonMA02135
property at 9 Braemore Rd

$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

9 Braemore Rd, Unit 12, Unit 12

9 Braemore Rd
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 Now

7 Lothian Rd, Unit 1, Unit 1

7 Lothian Rd
BostonMA02135
property at 155 Strathmore Rd

$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

155 Strathmore Rd, Unit 2, Unit 2

155 Strathmore Rd
BostonMA02135
property at 276 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

276 Chestnut Hill Ave, Unit #12A, Unit #12A

276 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 9 Braemore Rd

$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 Sep 1

9 Braemore Rd, Unit 1A, Unit 1A

9 Braemore Rd
BostonMA02135
property at 1986 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 May 31

1986 Commonwealth Ave, Unit 4, Unit 4

1986 Commonwealth Ave
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, Unit 1

2 Braemore Rd
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 Jun 1

2 Braemore Rd, Unit A, Unit A

2 Braemore Rd
BostonMA02135
property at 1933 Commonwealth Ave

$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

1933 Commonwealth Ave, Unit 504, Unit 504

1933 Commonwealth 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, Unit 4

140 Kenrick St
BostonMA02135
property at 39 South St

$2,750 - $4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,750 - $4,800

Total Monthly Price
$2,750 - $4,800

1 To 3 Bedroom Condos for Rent

Available Jun 1

39 South St

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, 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 29 Eastburn St

$2,800 - $2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800 - $2,950

Total Monthly Price
$2,800 - $2,950

2 Bedroom, 1 Bath Condo for Rent

Available Now

29 Eastburn St

BostonMA02135
property at 137 Chiswick 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 Jun 1

137 Chiswick Rd, Unit 6, Unit 6

137 Chiswick Rd
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, Unit 2

50 Larch St
BostonMA02135
property at 37 Radnor Rd

$2,840 - $4,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,840 - $4,850

Total Monthly Price
$2,840 - $4,850

2 To 3 Bedroom Condos for Rent

Available Now

37 Radnor Rd

BostonMA02135
property at 96 Chestnut Hill Ave

$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

96 Chestnut Hill Ave, Unit 5, Unit 5

96 Chestnut Hill Ave
BostonMA02135
property at 29 Wiltshire 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 Sep 1

29 Wiltshire Rd, Unit 1, Unit 1

29 Wiltshire Rd
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, 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, Unit BE

2012 Commonwealth Ave
BostonMA02135
property at 135 Chiswick Rd

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

3 Bedroom, 1 Bath Condo for Rent

Available Now

135 Chiswick Rd, Unit 6, Unit 6

135 Chiswick Rd
BostonMA02135
property at 1868 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 Sep 1

1868 Commonwealth Ave, Unit 5, Unit 5

1868 Commonwealth Ave
BostonMA02135
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, Unit 12

1880 Commonwealth Ave
BostonMA02135
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 Sep 1

1880 Commonwealth Ave, Unit 5, Unit 5

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, 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, Unit 2

211 Lake Shore Rd
BostonMA02135
property at 21 Chestnut Hill 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

21 Chestnut Hill Ave, Unit 1, Unit 1

21 Chestnut Hill Ave
BostonMA02135

Chestnut Hill Middlesex, Boston College, MA Local Guide

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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

3.5
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 471 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 575 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $950 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 $950 to $17,500 with an average monthly rent of $5,752.

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 $8,997, while Three Bedroom Homes, Condos, and Townhomes for rent range from $950 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,130 and Four Bedroom Apartments start at $3,100.

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 A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back article

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

decorative image for Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts  article

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.