Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (407 Rentals) Page 6 of 9

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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 52 Lane Park

52 Lane Park

BostonMA02135
property at 116 Lake St

116 Lake St, Unit 1

116 Lake St
BostonMA02135
property at 116 Lake St

116 Lake St

BostonMA02135
property at 12 Gerald Rd

12 Gerald Rd

BostonMA02135
property at 12 Gerald Rd

12 Gerald Rd

BostonMA02135
property at 44 Kirkwood Rd

44 Kirkwood Rd, Unit 1

44 Kirkwood Rd
BostonMA02135
property at 44 Kirkwood Rd

44 Kirkwood Rd

BostonMA02135
property at 44 Kirkwood Rd

44 Kirkwood Rd

BostonMA02135
property at 46 Kirkwood Rd

46 Kirkwood Rd, Unit #1

46 Kirkwood Rd
BostonMA02135
property at 44 Kirkwood Rd

44 Kirkwood Rd

BostonMA02135
property at 49 Radnor Rd

49 Radnor Rd, Unit 1

49 Radnor Rd
BostonMA02135
property at 37 Radnor Rd

37 Radnor Rd, Unit 1

37 Radnor Rd
BostonMA02135
property at 64 Greycliff Rd

64 Greycliff Rd, Unit 1

64 Greycliff Rd
BostonMA02135
property at 44 Greycliff Rd

44 Greycliff Rd, Unit 1

44 Greycliff Rd
BrightonMA02135
property at 52 Greycliff Rd

52 Greycliff Rd, Unit T

52 Greycliff Rd
BostonMA02135
property at 44 Bostonia Ave

44 Bostonia Ave, Unit 1

44 Bostonia Ave
BrightonMA02135
property at 52 Greycliff Rd

52 Greycliff Rd

BostonMA02135
property at 52 Greycliff Rd

52 Greycliff Rd

BostonMA02135
property at 44 Greycliff Rd

44 Greycliff Rd, Unit 1

44 Greycliff Rd
BostonMA02135
property at 44 Greycliff Rd

44 Greycliff Rd, Unit 1

44 Greycliff Rd
BostonMA02135
property at 1860 Commonwealth Ave
property at 46 Kirkwood Rd

46 Kirkwood Rd

BostonMA02135
property at 44 Greycliff Rd

44 Greycliff Rd, Unit 2

44 Greycliff Rd
BostonMA02135
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35 South St
$3,050
Total Monthly Price

Total Monthly Price

Base Rent
$2,610
Required Monthly Fees
$440

Total Monthly Price
$3,050
2 Bedroom Apartments Available Jan 18, 2026

35 South St

35 South StBoston, MA 02135
Furnished
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181 Washington St
$3,105
Total Monthly Price

Total Monthly Price

Base Rent
$2,740
Required Monthly Fees
$365

Total Monthly Price
$3,105
Studio Apartments Available Jan 18, 2026

181 Washington St

181 Washington StBoston, MA 02135
Furnished
property at 181 Washington St

181 Washington St

BostonMA02135
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181 Washington St
$3,135
Total Monthly Price

Total Monthly Price

Base Rent
$2,780
Required Monthly Fees
$355

Total Monthly Price
$3,135
1 Bedroom Apartments Available Nov 22

181 Washington St

181 Washington StBoston, MA 02135
Furnished
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181 Washington St
$3,165
Total Monthly Price

Total Monthly Price

Base Rent
$2,820
Required Monthly Fees
$345

Total Monthly Price
$3,165
Studio Apartments Available May 2, 2026

181 Washington St

181 Washington StBoston, MA 02135
Furnished
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181 Washington St
$3,325
Total Monthly Price

Total Monthly Price

Base Rent
$2,890
Required Monthly Fees
$435

Total Monthly Price
$3,325
2 Bedroom Apartments Available Dec 21

181 Washington St

181 Washington StBoston, MA 02135
Furnished
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181 Washington St
$4,025
Total Monthly Price

Total Monthly Price

Base Rent
$3,590
Required Monthly Fees
$435

Total Monthly Price
$4,025
2 Bedroom Apartments Available Jan 1, 2026

181 Washington St

181 Washington StBoston, MA 02135
Furnished

Frequently Asked Questions about Chestnut Hill Middlesex

What type of rentals are currently available in Chestnut Hill Middlesex?

There are currently 430 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $13,500. There are also 472 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $850 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 $850 to $36,000 with an average monthly rent of $7,107.

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 $3,200.

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.