Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (483 Rentals)

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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 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 27 Commonwealth Ave

$3,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,250

Total Monthly Price
$3,250

1 Bedroom, 1 Bath Condo for Rent

Available Now

27 Commonwealth Ave, Unit 6

27 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
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 1195 Boylston St

$3,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

1195 Boylston St, Unit 1195

1195 Boylston St
Chestnut HillMA02467
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 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

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 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 60 Undine Rd

$1,100

Total Monthly Price3 Month Lease Term

Total Monthly Price

Base Rent
$1,100

Total Monthly Price
$1,100

6 Bedroom, 2 Bath Home for Rent

Available Now

60 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

$3,300

Total Monthly Price24 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 1 Bath Condo for Rent

Available Aug 1

20 Hammond Pond Pky, Unit 206

20 Hammond Pond Pky
Chestnut HillMA02467
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 2035 Commonwealth Ave

$2,295 - $2,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,295 - $2,450

Total Monthly Price
$2,295 - $2,450

Studio To 1 Bedroom Condos for Rent

Available Sep 1

property at 2039 Commonwealth Ave

$2,465

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,465

Total Monthly Price
$2,465

1 Bedroom, 1 Bath Condo for Rent

Available Sep 1

2039 Commonwealth Ave, Unit 22

2039 Commonwealth Ave
BostonMA02135
property at 2039 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

2039 Commonwealth Ave, Unit 11

2039 Commonwealth Ave
BostonMA02135
property at 2035 Commonwealth Ave

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

2035 Commonwealth Ave, Unit 2

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

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 2016 Commonwealth Ave

$4,695

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,695

Total Monthly Price
$4,695

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

2016 Commonwealth Ave, Unit 4

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 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 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

$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

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 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
property at 29 Gerald Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

29 Gerald Rd

BostonMA02135
property at 29 Gerald Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

3 Bedroom, 1 Bath Condo for Rent

Available Dec 1

29 Gerald Rd, Unit 2##

29 Gerald Rd
BostonMA02135
property at 1999 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

1999 Commonwealth Ave, Unit 24

1999 Commonwealth Ave
BostonMA02135
property at 1999 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

1999 Commonwealth Ave, Unit 4

1999 Commonwealth Ave
BostonMA02135
property at 2001 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

2001 Commonwealth Ave, Unit 16

2001 Commonwealth Ave
BostonMA02135
property at 1999 Commonwealth Ave

$3,650 - $4,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650 - $4,900

Total Monthly Price
$3,650 - $4,900

2 To 3 Bedroom Condos for Rent

Available Now

property at 25 Moody St

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

3 Bedroom, 1.5 Bath Home for Rent

Available Now

25 Moody St

Chestnut HillMA02467
property at 39 South St

$2,600 - $4,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600 - $4,600

Total Monthly Price
$2,600 - $4,600

1 To 3 Bedroom Condos for Rent

Available Now

39 South St

BostonMA02135
property at 103 Lake Shore Rd

$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 Aug 1

103 Lake Shore Rd, Unit 3

103 Lake Shore 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

51 Lake Shore Ct
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 100 Lake Shore Rd

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 2 Bath Condo for Rent

Available Sep 1

100 Lake Shore Rd

BostonMA02135
property at 129 Lake Shore 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 Sep 2

129 Lake Shore Rd, Unit 2A

129 Lake Shore Rd
BostonMA02135
property at 215 Lake Shore 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

215 Lake Shore Rd, Unit 2

215 Lake Shore Rd
BostonMA02135
property at 153 Lake Shore Rd

$3,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,750

Total Monthly Price
$3,750

3 Bedroom, 2 Bath Condo for Rent

Available Sep 1

153 Lake Shore Rd, Unit 3

153 Lake Shore Rd
BostonMA02135
property at 204 Lake Shore Rd

$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

204 Lake Shore Rd, Unit 1

204 Lake Shore Rd
BostonMA02135
property at 166 Lake Shore Rd

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 2 Bath Condo for Rent

Available Aug 1

166 Lake Shore Rd, Unit 1L

166 Lake Shore Rd
BostonMA02135
property at 44 Greycliff Rd

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500

Total Monthly Price
$10,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 31

44 Greycliff Rd, Unit 1

44 Greycliff Rd
BostonMA02135

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 #1

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

Pet Friendliness Lifestyle Score

3.5
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 407 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,000 to $17,000. There are also 488 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,050 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 $1,050 to $16,800 with an average monthly rent of $5,690.

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 $8,030, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,700 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,180 and Four Bedroom Apartments start at $1,050.

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

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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.

decorative image for Creative Ways Developers Reimagine Retail Spaces as Residential Units  article

Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

decorative image for Neighborhood and Market Insights: How to Choose the Right Area to Rent   article

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

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.

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.