Homes for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (485 Rentals)

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property at 60 Undine Rd

$1,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,250

Total Monthly Price
$1,250

6 Bedroom, 2 Bath Home for Rent

Available Sep 1

60 Undine Rd

BostonMA02135
property at 17 Fairbanks St

$2,190

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,190

Total Monthly Price
$2,190

1 Bedroom, 1 Bath Home for Rent

Available Now

17 Fairbanks St

BostonMA02135
property at 51 Algonquin Rd

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

51 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 51 Algonquin Rd

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

51 Algonquin Rd

Chestnut HillMA02467
property at 14 Caltha Rd

$2,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

2 Bedroom, 1 Bath Condo for Rent

Available Now

14 Caltha Rd, Unit 1P

14 Caltha Rd
BostonMA02135
property at 515 Heath St

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 1 Bath Home for Rent

Available Jan 1, 2027

515 Heath St

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 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 Sep 1

73 Undine Rd

BostonMA02135
property at 2035 Commonwealth Ave

$2,045 - $2,350

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,045 - $2,350

Total Monthly Price
$2,045 - $2,350

Studio To 1 Bedroom Condos for Rent

Available Sep 1

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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 Sep 1, 2028

12 Gerald Rd

BostonMA02135
property at 2 Hammond Pond Pky

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

2 Hammond Pond Pky, Unit 604

2 Hammond Pond Pky
Chestnut HillMA02467
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 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 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 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 2009 Commonwealth Ave

$2,425

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,425

Total Monthly Price
$2,425

1 Bedroom, 1 Bath Condo for Rent

Available Now

property at 292 Foster St

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1

292 Foster St, Unit 2

292 Foster St
BostonMA02135
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

2 Bedroom, 1 Bath Condo for Rent

Available Now

2009 Commonwealth Ave, Unit 20

2009 Commonwealth Ave
BostonMA02135
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

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

property at 29 Gerald Rd

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31, 2027

29 Gerald Rd, Unit 1

29 Gerald Rd
BostonMA02135
property at 1999 Commonwealth Ave

$2,045 - $4,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,045 - $4,250

Total Monthly Price
$2,045 - $4,250

Studio To 2 Bedroom Condos for Rent

Available Sep 1

property at 1999 Commonwealth Ave

$2,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,450

Total Monthly Price
$2,450

1 Bedroom, 1 Bath Condo for Rent

Available Sep 1

1999 Commonwealth Ave, Unit 11

1999 Commonwealth Ave
BostonMA02135
property at 2001 Commonwealth Ave

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 1 Bath Condo for Rent

Available Now

2001 Commonwealth Ave, Unit 34

2001 Commonwealth Ave
BostonMA02135
property at 1999 Commonwealth Ave

$3,200 - $4,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200 - $4,200

Total Monthly Price
$3,200 - $4,200

2 To 3 Bedroom Condos for Rent

Available Sep 1

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 204 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 Sep 1

204 Lake Shore Rd, Unit 3

204 Lake Shore Rd
BostonMA02135
property at 178 Lake Shore Rd

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom, 2 Bath Condo for Rent

Available Sep 1

178 Lake Shore Rd, Unit 4

178 Lake Shore Rd
BostonMA02135
property at 35 Lake Shore Ct

$3,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650

Total Monthly Price
$3,650

3 Bedroom, 2 Bath Condo for Rent

Available Sep 1

35 Lake Shore Ct, Unit 1

35 Lake Shore Ct
BostonMA02135
property at 44 Greycliff Rd

$11,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 30, 2027

44 Greycliff Rd, Unit 1

44 Greycliff Rd
BostonMA02135

Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

property at 44 Greycliff Rd

$12,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$12,400

Total Monthly Price
$12,400

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31, 2027

44 Greycliff Rd, Unit #2

44 Greycliff Rd
BostonMA02135
property at 37 Radnor Rd

$2,600 - $3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600 - $3,500

Total Monthly Price
$2,600 - $3,500

2 To 3 Bedroom Condos for Rent

Available Now

37 Radnor Rd

BostonMA02135
property at 2003 Commonwealth Ave

$3,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,250

Total Monthly Price
$3,250

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

2003 Commonwealth Ave, Unit 20

2003 Commonwealth Ave
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 1933 Commonwealth Ave

$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 Sep 1

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

1933 Commonwealth Ave
BostonMA02135
property at 539 Commonwealth Ave

$5,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

4 Bedroom, 3 Bath Condo for Rent

Available Now

539 Commonwealth Ave, Unit 2

539 Commonwealth Ave
NewtonMA02459
property at 25 Kirkwood Rd

$9,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,900

Total Monthly Price
$9,900

4 Bedroom, 2 Bath Condo for Rent

Available Aug 31, 2027

25 Kirkwood Rd

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 Sep 1

140 Kenrick St, Unit Apt 23

140 Kenrick St
BostonMA02135
property at 15 South 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

15 South St, Unit 15 South

15 South St
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 30 Lake Shore Ct

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 2 Bath Condo for Rent

Available Now

30 Lake Shore Ct, Unit 1

30 Lake Shore Ct
BostonMA02135
property at 235 Chestnut Hill Ave

$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

235 Chestnut Hill Ave, Unit 1

235 Chestnut Hill Ave
BostonMA02135
property at 247 Chestnut Hill Ave

$2,350 - $3,125

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,350 - $3,125

Total Monthly Price
$2,350 - $3,125

Studio To 2 Bedroom Condos for Rent

Available Now

property at 142 Kenrick St

$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

142 Kenrick St, Unit 38

142 Kenrick St
BostonMA02135
property at 12 Louise Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

12 Louise Rd

Chestnut HillMA02467
property at 225 Chestnut Hill Ave

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 1 Bath Condo for Rent

Available Now

225 Chestnut Hill Ave, Unit 1

225 Chestnut Hill Ave
BostonMA02135
property at 46 Kirkwood Rd

$12,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$12,200

Total Monthly Price
$12,200

6 Bedroom, 3 Bath Home for Rent

Available Sep 1, 2028

46 Kirkwood Rd

BostonMA02135
property at 14 Louise Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

14 Louise Rd, Unit 1

14 Louise Rd
Chestnut HillMA02467
property at 120 Kenrick St

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

120 Kenrick St, Unit 1

120 Kenrick St
BostonMA02135
property at 120 Kenrick St

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

4 Bedroom, 2 Bath Condo for Rent

Available Now

120 Kenrick St, Unit 5

120 Kenrick 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.

Chestnut Hill Middlesex, Boston College, MA Local Guide

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

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

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

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

Read Article
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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
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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.

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Pet Friendly Lifestyle
Chestnut Hill Middlesex, Chestnut Hill, MA

Ranked #2

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 319 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $960 to $13,500. There are also 480 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,075 to $16,800.

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 $1,075 to $16,800 with an average monthly rent of $5,194.

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 $1,300 to $7,420, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,495 to $6,900. Four Bedroom Single-Family rentals are also available starting from $2,900 and Four Bedroom Apartments start at $2,400.

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 Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention   article

Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.