Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (517 Rentals)

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property at 27 Crosby Rd

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

2 Bedroom, 2 Bath Home for Rent

Available Sep 1

27 Crosby Rd

Chestnut HillMA02467
property at 25 Crosby Rd

$3,500 - $6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500 - $6,000

Total Monthly Price
$3,500 - $6,000

2 To 4 Bedroom Condos for Rent

Available Now

25 Crosby Rd

Chestnut HillMA02467
property at 25 Crosby Rd

$6,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,300

Total Monthly Price
$6,300

4 Bedroom, 2 Bath Home for Rent

Available Sep 1

25 Crosby Rd

Chestnut HillMA02467
property at 68 Manet Rd

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

4 Bedroom, 3 Bath Condo for Rent

Available Sep 1

68 Manet Rd, Unit 1

68 Manet Rd
Chestnut HillMA02467
property at 235 Commonwealth Ave

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800

4 Bedroom, 2 Bath Home for Rent

Available Aug 31

235 Commonwealth Ave

Chestnut HillMA02467
property at 28 Manet Rd

$4,800 - $5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800 - $5,800

Total Monthly Price
$4,800 - $5,800

4 To 5 Bedroom Condos for Rent

Available Now

28 Manet Rd

Chestnut HillMA02467
property at 28 Manet Rd

$5,400 - $6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,400 - $6,500

Total Monthly Price
$5,400 - $6,500

4 To 5 Bedroom Condos for Rent

Available Sep 1

28 Manet Rd

Chestnut HillMA02467
property at 295 Commonwealth Ave

$2,550 - $3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550 - $3,000

Total Monthly Price
$2,550 - $3,000

Studio, 1 Bath Condo for Rent

Available Now

295 Commonwealth Ave

Chestnut HillMA02467
property at 136 Middlesex Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Now

136 Middlesex Rd, Unit 2

136 Middlesex Rd
Chestnut HillMA02467

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 47 Algonquin Rd

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

47 Algonquin Rd, Unit 2

47 Algonquin Rd
Chestnut HillMA02467
property at 47 Algonquin Rd

$5,700 - $5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,700 - $5,800

Total Monthly Price
$5,700 - $5,800

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

47 Algonquin Rd

Chestnut HillMA02467
property at 51 Algonquin Rd

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

51 Algonquin Rd

Chestnut HillMA02467
property at 26 Holly Ln

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

26 Holly Ln, Unit 2

26 Holly Ln
BrooklineMA02467
property at 199 Boylston St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 3.5 Bath Condo for Rent

Available Now

199 Boylston St, Unit 1

199 Boylston St
Chestnut HillMA02467
property at 199 Boylston St

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

4 Bedroom, 3.5 Bath Home for Rent

Available Sep 1

199 Boylston St

Chestnut HillMA02467
property at 25 Wade St

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 3.5 Bath Home for Rent

Available Now

25 Wade St

BostonMA02135
property at 31 Hammond Pond Pky

$2,900

Total Monthly Price5 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

31 Hammond Pond Pky, Unit #2

31 Hammond Pond Pky
Chestnut HillMA02467
property at 508 Heath St

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

3 Bedroom, 2 Bath Condo for Rent

Available Now

508 Heath St, Unit 1

508 Heath St
BrooklineMA02467
property at 73 Undine Rd

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

4 Bedroom, 2.5 Bath Home for Rent

Available Now

73 Undine Rd

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 476 Heath St

$15,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$15,000

Total Monthly Price
$15,000

6 Bedroom, 6.5 Bath Home for Rent

Available Now

476 Heath St

Chestnut HillMA02467
property at 60 Undine Rd

$1,050

Total Monthly Price3 Month Lease Term

Total Monthly Price

Base Rent
$1,050

Total Monthly Price
$1,050

6 Bedroom, 2 Bath Home for Rent

Available Jun 1

60 Undine Rd

BostonMA02135
property at 11 Hammond Pond Pky

$2,600 - $3,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600 - $3,450

Total Monthly Price
$2,600 - $3,450

Studio To 2 Bedroom Condos for Rent

Available Now

11 Hammond Pond Pky

Chestnut HillMA02467
property at 95 Undine Rd

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800

4 Bedroom, 2 Bath Condo for Rent

Available Now

95 Undine Rd, Unit 95

95 Undine Rd
BostonMA02135
property at 93 Undine Rd

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800

4 Bedroom, 2 Bath Condo for Rent

Available Now

93 Undine Rd, Unit 93

93 Undine Rd
BostonMA02135
property at 95 Undine Rd

$5,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,900

Total Monthly Price
$5,900

4 Bedroom, 2 Bath Condo for Rent

Available Aug 30

95 Undine Rd

BostonMA02135
property at 20 Hammond Pond Pky

$3,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,450

Total Monthly Price
$3,450

2 Bedroom, 2 Bath Condo for Rent

Available Now

20 Hammond Pond Pky, Unit 305

20 Hammond Pond Pky
Chestnut HillMA02467
property at 2045 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 Sep 1

2045 Commonwealth Ave, Unit 31-16

2045 Commonwealth Ave
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 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 Now

10 Hammond Pond Pky, Unit 304

10 Hammond Pond Pky
Chestnut HillMA02467

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 250 Hammond Pond Pky

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

250 Hammond Pond Pky, Unit 1203N

250 Hammond Pond Pky
Chestnut HillMA02467
property at 2016 Commonwealth Ave

$4,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,850

Total Monthly Price
$4,850

2 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1

2016 Commonwealth Ave, Unit 5

2016 Commonwealth Ave
BostonMA02135
property at 12 Gerald Rd

$9,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,500

Total Monthly Price
$9,500

5 Bedroom, 3 Bath Home for Rent

Available Now

12 Gerald 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

2031 Commonwealth Ave, Unit 12

2031 Commonwealth Ave
BostonMA02135
property at 25 Greycliff Rd

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650

3 Bedroom, 1 Bath Condo for Rent

Available Now

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
property at 25 Greycliff Rd

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
property at 16 Gerald Rd

$5,600 - $11,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600 - $11,200

Total Monthly Price
$5,600 - $11,200

3 To 6 Bedroom Condos for Rent

Available Aug 31

16 Gerald Rd

BostonMA02135
property at 16 Gerald Rd

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31

16 Gerald Rd, Unit 1

16 Gerald Rd
BostonMA02135
property at 16 Gerald Rd

$5,600 - $6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600 - $6,500

Total Monthly Price
$5,600 - $6,500

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31

16 Gerald Rd

BostonMA02135
property at 16 Gerald Rd

$6,200 - $13,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200 - $13,500

Total Monthly Price
$6,200 - $13,500

3 To 6 Bedroom Condos for Rent

Available Sep 1, 2027

16 Gerald Rd

BostonMA02135
property at 321 Hammond Pond Pky

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

321 Hammond Pond Pky, Unit 301

321 Hammond Pond Pky
Chestnut HillMA02467
property at 2021 Commonwealth Ave

$2,295

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,295

Total Monthly Price
$2,295

1 Bedroom, 1 Bath Condo for Rent

Available Now

2021 Commonwealth Ave, Unit 2001-2

2021 Commonwealth Ave
BostonMA02135
property at 2017 Commonwealth Ave

$4,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,450

Total Monthly Price
$4,450

2 Bedroom, 1 Bath Condo for Rent

Available Now

2017 Commonwealth Ave, Unit #1

2017 Commonwealth Ave
BostonMA02135
property at 2021 Commonwealth Ave

$7,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,600

Total Monthly Price
$7,600

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2021 Commonwealth Ave, Unit 2

2021 Commonwealth Ave
BostonMA02135
property at 2021 Commonwealth Ave

$8,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,750

Total Monthly Price
$8,750

5 Bedroom, 2.5 Bath Condo for Rent

Available Now

2021 Commonwealth Ave, Unit D

2021 Commonwealth Ave
BostonMA02135
property at 1982 Commonwealth Ave

$2,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,300

Total Monthly Price
$2,300

1 Bedroom, 1 Bath Condo for Rent

Available Now

1982 Commonwealth Ave, Unit 9

1982 Commonwealth Ave
BostonMA02135
property at 2 Hammond Pond Pky

$2,900

Total Monthly Price24 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

1 Bedroom, 1 Bath Condo for Rent

Available Now

2 Hammond Pond Pky, Unit 203

2 Hammond Pond Pky
Chestnut HillMA02467
property at 2009 Commonwealth Ave

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom, 1 Bath Condo for Rent

Available Now

2009 Commonwealth Ave, Unit 20

2009 Commonwealth Ave
BostonMA02135
property at 320 Hammond Pond Pky

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 2 Bath Condo for Rent

Available Now

320 Hammond Pond Pky

Chestnut HillMA02467
property at 320 Hammond Pond Pkwy

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

2 Bedroom, 2 Bath Condo for Rent

Available Now

320 Hammond Pond Pkwy, Unit 104

320 Hammond Pond Pkwy
NewtonMA02467

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
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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
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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.

Read Article
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How a Move-In Inspection Can Protect Your Security Deposit

Learn How a Move-In Inspection Can Protect Your Security Deposit from the Renter University at AparmentHomeLiving.com.

Read Article
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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

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Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 543 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $17,000. There are also 517 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $830 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 $830 to $17,500 with an average monthly rent of $6,368.

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 $11,215, 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 $830 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 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.

decorative image for 18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property article

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

decorative image for A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment article

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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.