2 Bedroom Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (119 Rentals)

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31-35 South Street
Rent Specials
$3,100
Total Monthly Price

Total Monthly Price

Base Rent
$3,000 - $3,600

Total Monthly Price
$3,000 - $3,600
2 Bedroom Apartments Available Jan 1, 2026

31-35 South Street

31 South StBrighton, MA 02135
Student Housing
  • Verified
  • Utilities Included
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286 & 288 Chestnut Hill Avenue
Rent Specials
$2,875
Total Monthly Price

Total Monthly Price

Base Rent
$2,100 - $3,100

Total Monthly Price
$2,100 - $3,100
2 Bedroom Apartments Available Now

286 & 288 Chestnut Hill Avenue

286-288 Chestnut Hill AveBrighton, MA 02135
Student Housing
  • Verified
  • Customer Reviewed
  • Utilities Included
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2016 Commonwealth Ave, Unit F
$4,850
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,850

Total Monthly Price
$4,850
2 Bedroom Apartment Available Sep 1, 2026

2016 Commonwealth Ave, Unit F

2016 Commonwealth AveBoston, MA 02135
Affordability

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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2021 Commonwealth Ave, Unit S
$4,750
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,750

Total Monthly Price
$4,750
2 Bedroom Apartment Available Sep 1, 2026

2021 Commonwealth Ave, Unit S

2021 Commonwealth AveBoston, MA 02135
Affordability
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117 Lake Shore Rd, Unit #1
$2,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400
2 Bedroom Apartment Available Now

117 Lake Shore Rd, Unit #1

117 Lake Shore RdBoston, MA 02135
Affordability
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1874 Commonwealth Ave, Unit 1
$3,354
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,354

Total Monthly Price
$3,354
2 Bedroom Apartment Available Sep 1, 2026

1874 Commonwealth Ave, Unit 1

1874 Commonwealth AveBoston, MA 02135
Cost Per Sq.Ft.
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1870 Commonwealth Ave, Unit 12A
$4,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500
2 Bedroom Apartment Available Now

1870 Commonwealth Ave, Unit 12A

1870 Commonwealth AveBoston, MA 02135
Affordability
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1870 Commonwealth Ave, Unit 3
$3,354
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,354

Total Monthly Price
$3,354
2 Bedroom Apartment Available Sep 1, 2026

1870 Commonwealth Ave, Unit 3

1870 Commonwealth AveBoston, MA 02135
Cost Per Sq.Ft.
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163 Chestnut Hill Ave, Unit 202
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

163 Chestnut Hill Ave, Unit 202

163 Chestnut Hill AveBoston, MA 02135
Affordability
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163 Chestnut Hill Ave, Unit 202
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

163 Chestnut Hill Ave, Unit 202

163 Chestnut Hill AveBoston, MA 02135
Affordability

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.

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1870 Commonwealth Ave, Unit 12A
$4,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500
2 Bedroom Apartment Available Now

1870 Commonwealth Ave, Unit 12A

1870 Commonwealth AveBoston, MA 02135
Affordability
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1959 Commonwealth Ave, Unit 2
$2,350
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,350

Total Monthly Price
$2,350
2 Bedroom Apartment Available Now

1959 Commonwealth Ave, Unit 2

1959 Commonwealth AveBoston, MA 02135
Affordability
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16 South St, Unit 12
$3,700
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700
2 Bedroom Apartment Available Now

16 South St, Unit 12

16 South StBoston, MA 02135
Affordability
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99 Chestnut Hill Ave, Unit 313
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000
2 Bedroom Apartment Available Now

99 Chestnut Hill Ave, Unit 313

99 Chestnut Hill AveBoston, MA 02135
Affordability
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136 Chiswick Rd, Unit #6
$2,950
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950
2 Bedroom Apartment Available Now

136 Chiswick Rd, Unit #6

136 Chiswick RdBoston, MA 02135
Cost Per Sq.Ft.

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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.

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6 South St
$3,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600
2 Bedroom Apartment Available Now

6 South St

6 South StBoston, MA 02135
Affordability
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144 Lake Shore Rd, Unit 1
$2,650
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650
2 Bedroom Apartment Available Now

144 Lake Shore Rd, Unit 1

144 Lake Shore RdBoston, MA 02135
Affordability
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19 Chestnut Hill Ave
$2,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800
2 Bedroom Apartment Available Now

19 Chestnut Hill Ave

19 Chestnut Hill AveBoston, MA 02135
Affordability
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144 Lake Shore Rd
$2,650
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650
2 Bedroom Apartment Available Now

144 Lake Shore Rd

144 Lake Shore RdBoston, MA 02135
Affordability

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.

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315 Foster St, Unit 2017 COMM AVE
$3,175
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,175

Total Monthly Price
$3,175
2 Bedroom Apartment Available Now

315 Foster St, Unit 2017 COMM AVE

315 Foster StBoston, MA 02135
Affordability
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25 South St, Unit #31 - B2
$3,650
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650

Total Monthly Price
$3,650
2 Bedroom Apartment Available Now

25 South St, Unit #31 - B2

25 South StBoston, MA 02135
Affordability
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120 Foster Ter
$3,550
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,550

Total Monthly Price
$3,550
2 Bedroom Apartment Available Now

120 Foster Ter

120 Foster TerBoston, MA 02135
Affordability
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249 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 Apartment Available Now

249 Chestnut Hill Ave

249 Chestnut Hill AveBoston, MA 02135
Affordability

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.

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.

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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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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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Getting Around the Chestnut Hill Middlesex Neighborhood in Chestnut Hill, MA

Walk Score®

59 / 100

Somewhat Walkable

Some errands can be accomplished on foot

Bike Score®

47 / 100

Somewhat Bikeable

Minimal bike infrastructure

Transit Score®

53 / 100

Good Transit

Many nearby public transportation options

Frequently Asked Questions about 2 Bedroom Chestnut Hill Middlesex Apartments

What is the Cheapest apartment in Chestnut Hill Middlesex with 2 Bedroom?

Currently the most affordable 2 Bedroom in Chestnut Hill Middlesex is at listed at $1,850.

How much is the average rent for a 2 Bedroom Chestnut Hill Middlesex Apartment?

The average rent for a 2 Bedroom Apartment in Chestnut Hill Middlesex is $2,572.

What is the largest available 2 Bedroom Chestnut Hill Middlesex Apartment for rent?

Today's apartment with the most square footage in Chestnut Hill Middlesex is a square feet unit at .

What is the average size for Chestnut Hill Middlesex 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Chestnut Hill Middlesex is currently sq ft.

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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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.

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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.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.