Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (409 Rentals)

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property at 47 Crosby Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

47 Crosby Rd, Unit 2

47 Crosby Rd
Chestnut HillMA02467
property at 25 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 Condo for Rent

Available Sep 1, 2026

25 Crosby Rd

Chestnut HillMA02467
property at 25 Crosby Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 2 Bath Condo for Rent

Available Now

25 Crosby Rd, Unit 2

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, 2026

68 Manet Rd, Unit 1

68 Manet Rd
Chestnut HillMA02467
property at 28 Manet Rd

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

4 Bedroom, 1 Bath Condo for Rent

Available Now

28 Manet Rd, Unit 2

28 Manet Rd
Chestnut HillMA02467
property at 28 Manet Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1, 2026

28 Manet Rd, Unit 1

28 Manet Rd
Chestnut HillMA02467
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
property at 20 Manet Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1, 2026

20 Manet Rd, Unit 1

20 Manet Rd
Chestnut HillMA02467
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 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

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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 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

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,700

Total Monthly Price
$5,700

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

47 Algonquin Rd, Unit 1

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, 2026

51 Algonquin Rd

Chestnut HillMA02467
property at 515 Heath St

$3,400

Total Monthly Price

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

3 Bedroom, 1 Bath Home for Rent

Available Now

515 Heath St

BrooklineMA02467
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 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 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
property at 11 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

11 Hammond Pond Pky, Unit 203

11 Hammond Pond Pky
Chestnut HillMA02467

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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 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

$5,800

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 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, 2026

95 Undine Rd, Unit 93

95 Undine Rd
BostonMA02135
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 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 2016 Commonwealth Ave

$2,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

1 Bedroom, 1 Bath Condo for Rent

Available Now

2016 Commonwealth Ave, Unit 48

2016 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 Feb 1, 2026

10 Hammond Pond Pky, Unit 304

10 Hammond Pond Pky
Chestnut HillMA02467
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 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, 2026

2016 Commonwealth Ave, Unit 5

2016 Commonwealth Ave
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 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 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, 2026

2031 Commonwealth Ave, Unit 12

2031 Commonwealth Ave
BostonMA02135
property at 16 Gerald Rd

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Home for Rent

Available Now

16 Gerald 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 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

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, 2026

16 Gerald Rd, Unit 1

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, 2026

16 Gerald Rd, Unit 1

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, 2026

16 Gerald Rd, Unit 1

16 Gerald Rd
BostonMA02135
property at 16 Gerald Rd

$13,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$13,500

Total Monthly Price
$13,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Sep 1, 2027

16 Gerald Rd, Unit 2

16 Gerald Rd
BostonMA02135

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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 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 2000 Commonwealth Ave

$5,040

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,040

Total Monthly Price
$5,040

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

2000 Commonwealth Ave, Unit 5

2000 Commonwealth Ave
BostonMA02135
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

$5,040

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,040

Total Monthly Price
$5,040

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1, 2026

2021 Commonwealth Ave, Unit 5

2021 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, 2026

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 2009 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

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

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.

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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.

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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

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 452 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 409 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 $7,073.

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 $860 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.