Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (404 Rentals)

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The most luxurious Homes in the Chestnut Hill Middlesex area of Chestnut Hill with high-end amenities, features, and finishes.

property at 35 Dickinson Rd

35 Dickinson Rd, Unit Unit 33

35 Dickinson Rd
BostonMA02135
property at 515 Heath St

515 Heath St

BrooklineMA02467
property at 461 Washington St

461 Washington St, Unit 305

461 Washington St
BostonMA02135
property at 155 Strathmore Rd

155 Strathmore Rd, Unit 2

155 Strathmore Rd
BostonMA02135
property at 247 Chestnut Hill Ave

247 Chestnut Hill Ave, Unit 4

247 Chestnut Hill Ave
BostonMA02135
property at 91 Wallingford Rd

91 Wallingford Rd, Unit 1

91 Wallingford Rd
BostonMA02135
property at 1933 Commonwealth Ave

1933 Commonwealth Ave, Unit 111

1933 Commonwealth Ave
BostonMA02135
property at 140 Kenrick St

140 Kenrick St, Unit 4

140 Kenrick St
BostonMA02135
property at 2045 Commonwealth Ave

2045 Commonwealth Ave, Unit M-46

2045 Commonwealth Ave
BostonMA02135
property at 209 Chestnut Hill Ave

209 Chestnut Hill Ave, Unit 9

209 Chestnut Hill Ave
BostonMA02135

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.

property at 29 Wiltshire Rd

29 Wiltshire Rd, Unit 1

29 Wiltshire Rd
BostonMA02135
property at 145 Englewood Ave

145 Englewood Ave, Unit 43

145 Englewood Ave
BostonMA02135
property at 153 Lake Shore Rd

153 Lake Shore Rd, Unit 3

153 Lake Shore Rd
BostonMA02135
property at 148 Strathmore Rd

148 Strathmore Rd, Unit 6

148 Strathmore Rd
BostonMA02135
property at 63 Breck Ave

63 Breck Ave

BostonMA02135
property at 27 South St

27 South St, Unit #B3

27 South St
BostonMA02135
property at 185 Chestnut Hill Ave

185 Chestnut Hill Ave, Unit 09

185 Chestnut Hill Ave
BostonMA02135
property at 36 Dighton St

36 Dighton St, Unit 15

36 Dighton St
BostonMA02135
property at 1933 Commonwealth Ave

1933 Commonwealth Ave, Unit 401

1933 Commonwealth Ave
BostonMA02135
property at 138 Woodland Rd

138 Woodland Rd, Unit 6

138 Woodland 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 370 Chestnut Hill Ave

370 Chestnut Hill Ave, Unit 1

370 Chestnut Hill Ave
BostonMA02135
property at 5 Braemore Rd

5 Braemore Rd, Unit 1-15

5 Braemore Rd
BostonMA02135
property at 1933 Commonwealth Ave

1933 Commonwealth Ave, Unit 401

1933 Commonwealth Ave
BostonMA02135
property at 249 Chestnut Hill Ave

249 Chestnut Hill Ave, Unit 51

249 Chestnut Hill Ave
BostonMA02135
property at 2 Braemore Rd

2 Braemore Rd, Unit 1

2 Braemore Rd
BostonMA02135
property at 140 Kenrick St

140 Kenrick St, Unit 4

140 Kenrick St
BostonMA02135
property at 32 Sidlaw Rd

32 Sidlaw Rd, Unit 3

32 Sidlaw Rd
BostonMA02135
property at 5 Braemore Rd

5 Braemore Rd, Unit 8

5 Braemore Rd
BostonMA02135
property at 276 Chestnut Hill Ave

276 Chestnut Hill Ave, Unit 6

276 Chestnut Hill Ave
BostonMA02135
property at 1988 Commonwealth Ave

1988 Commonwealth Ave, Unit 9

1988 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 20 Shanley St

20 Shanley St, Unit 1R

20 Shanley St
BostonMA02135
property at 117 Lake Shore Rd

117 Lake Shore Rd, Unit 3

117 Lake Shore Rd
BostonMA02135
property at 20 Shanley St

20 Shanley St, Unit 2R

20 Shanley St
BostonMA02135
property at 22 Shanley St

22 Shanley St

BostonMA02135
property at 110 Strathmore Rd

110 Strathmore Rd, Unit 204

110 Strathmore Rd
BostonMA02135
property at 91 Wallingford Rd

91 Wallingford Rd, Unit 3

91 Wallingford Rd
BostonMA02135
property at 31 Lake Shore Ct

31 Lake Shore Ct, Unit 3

31 Lake Shore Ct
BostonMA02135
property at 91 Wallingford Rd

91 Wallingford Rd, Unit 3

91 Wallingford Rd
BostonMA02135
property at 51 Lake Shore Ct

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 2 Portina Rd

2 Portina Rd, Unit 2

2 Portina Rd
BostonMA02135

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 2 Portina Rd

2 Portina Rd

BostonMA02135
property at 19 Chestnut Hill Ave

19 Chestnut Hill Ave, Unit 1

19 Chestnut Hill Ave
BostonMA02135
property at 51 Lake Shore Ct

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 51 Lake Shore Ct

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 159 Foster St

159 Foster St, Unit 1

159 Foster St
BostonMA02135
property at 35 Foster St

35 Foster St, Unit 1

35 Foster St
BostonMA02135
property at 135 Chiswick Rd

135 Chiswick Rd, Unit 6

135 Chiswick Rd
BostonMA02135
property at 43 N Crescent Circuit

43 N Crescent Circuit, Unit 1

43 N Crescent Circuit
BostonMA02135
property at 2012 Commonwealth Ave

2012 Commonwealth Ave, Unit BE

2012 Commonwealth Ave
BostonMA02135
property at 29 Eastburn St

29 Eastburn St, Unit 2

29 Eastburn St
BostonMA02135

Chestnut Hill Middlesex, Boston College, MA Local Guide

Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

Read Article
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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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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 431 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $13,500. There are also 470 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $980 to $36,000.

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 $980 to $36,000 with an average monthly rent of $6,807.

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 $5,955, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $6,500. Four Bedroom Single-Family rentals are also available starting from $1,080 and Four Bedroom Apartments start at $3,150.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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.

decorative image for Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between article

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.