Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (511 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

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 155 Strathmore Rd

155 Strathmore Rd, Unit 2

155 Strathmore Rd
BostonMA02135
property at 461 Washington St

461 Washington St, Unit 305

461 Washington St
BostonMA02135
property at 140 Kenrick St

140 Kenrick St, Unit 4

140 Kenrick St
BostonMA02135
property at 2025 Commonwealth Ave

2025 Commonwealth Ave, Unit 6

2025 Commonwealth Ave
BostonMA02135
property at 249 Chestnut Hill Ave

249 Chestnut Hill Ave, Unit 32

249 Chestnut Hill Ave
BostonMA02135
property at 6 Portina Rd

6 Portina Rd, Unit 3

6 Portina Rd
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

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.

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 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 1933 Commonwealth Ave

1933 Commonwealth Ave, Unit 108

1933 Commonwealth Ave
BostonMA02135
property at 1933 Commonwealth Ave

1933 Commonwealth Ave, Unit 108

1933 Commonwealth Ave
BostonMA02135
property at 133 Chiswick Rd

133 Chiswick Rd, Unit 207

133 Chiswick Rd
BostonMA02135
property at 63 Breck Ave

63 Breck Ave

BostonMA02135
property at 138 Woodland Rd

138 Woodland Rd, Unit 6

138 Woodland Rd
Chestnut HillMA02467
property at 370 Chestnut Hill Ave

370 Chestnut Hill Ave, Unit 1

370 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 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 1933 Commonwealth Ave

1933 Commonwealth Ave, Unit 401

1933 Commonwealth Ave
BostonMA02135
property at 153 Lake Shore Rd

153 Lake Shore Rd, Unit 3

153 Lake Shore Rd
BostonMA02135
property at 51 Lake Shore Ct

51 Lake Shore Ct, Unit #1

51 Lake Shore Ct
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 181 Washington St

181 Washington St, Unit 3338

181 Washington St
BostonMA02135
property at 140 Kenrick St

140 Kenrick St, Unit #4

140 Kenrick St
BostonMA02135
property at 100 Kenrick St

100 Kenrick St

BostonMA02135
property at 140 Kenrick St

140 Kenrick St, Unit 4

140 Kenrick 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 5 Braemore Rd

5 Braemore Rd, Unit 8

5 Braemore Rd
BostonMA02135
property at 1988 Commonwealth Ave

1988 Commonwealth Ave, Unit 9

1988 Commonwealth Ave
BostonMA02135
property at 11 Beechcroft St

11 Beechcroft St

BostonMA02135
property at 117 Lake Shore Rd

117 Lake Shore Rd, Unit 3

117 Lake Shore Rd
BostonMA02135
property at 24 Wallingford Rd

24 Wallingford Rd, Unit 5

24 Wallingford Rd
BostonMA02135
property at 110 Strathmore Rd

110 Strathmore Rd, Unit 204

110 Strathmore 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 7 Lothian Rd

7 Lothian Rd, Unit 8

7 Lothian Rd
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 276 Chestnut Hill Ave

276 Chestnut Hill Ave, Unit 11

276 Chestnut Hill Ave
BostonMA02135
property at 91 Wallingford Rd

91 Wallingford Rd, Unit 3

91 Wallingford Rd
BostonMA02135
property at 2025 Commonwealth Ave

2025 Commonwealth Ave, Unit 1

2025 Commonwealth Ave
BostonMA02135
property at 249 Chestnut Hill Ave

249 Chestnut Hill Ave, Unit 32

249 Chestnut Hill Ave
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 51 Lake Shore Ct

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
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 39 Foster St

39 Foster St, Unit 1

39 Foster St
BostonMA02135

Chestnut Hill Middlesex, Boston College, MA Local Guide

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 #2

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

Pet Friendliness Lifestyle Score

4.0
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 693 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,850 to $17,000. There are also 591 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $950 to $40,000.

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 $950 to $40,000 with an average monthly rent of $5,850.

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 $6,260, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,550 to $6,900. Four Bedroom Single-Family rentals are also available starting from $1,025 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 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.

decorative image for The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro article

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

decorative image for Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting article

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.