Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (358 Rentals) Page 6 of 8

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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 44 Greycliff Rd

$12,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$12,000
Total Monthly Price
$12,000

6 Bedroom, 3 Bath Condo for Rent

Available Now

44 Greycliff Rd, Unit 2

44 Greycliff Rd
BostonMA02135
property at 16 Gerald Rd

$13,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$13,500
Total Monthly Price
$13,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Sep 1, 2027

16 Gerald Rd, Unit 2

16 Gerald Rd
BostonMA02135
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181 Washington St
$3,155
Total Monthly Price

Total Monthly Price

Base Rent
$2,790
Required Monthly Fees
$365
Total Monthly Price
$3,155
Studio Apartments Available Jan 18, 2026

181 Washington St

181 Washington StBoston, MA 02135
Furnished
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181 Washington St
$2,655
Total Monthly Price

Total Monthly Price

Base Rent
$2,220
Required Monthly Fees
$435
Total Monthly Price
$2,655
2 Bedroom Apartments Available Dec 23

181 Washington St

181 Washington StBoston, MA 02135
Furnished
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181 Washington St
$3,035
Total Monthly Price

Total Monthly Price

Base Rent
$2,690
Required Monthly Fees
$345
Total Monthly Price
$3,035
Studio Apartments Available May 2, 2026

181 Washington St

181 Washington StBoston, MA 02135
Furnished
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35 South St
$3,290
Total Monthly Price

Total Monthly Price

Base Rent
$2,850
Required Monthly Fees
$440
Total Monthly Price
$3,290
2 Bedroom Apartments Available May 1, 2026

35 South St

35 South StBoston, MA 02135
Furnished
Showing Results 251-300, Page 6 of 8

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 452 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 415 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $760 to $17,500.

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 $760 to $17,500 with an average monthly rent of $7,073.

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 $6,285, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $7,000. Four Bedroom Single-Family rentals are also available starting from $860 and Four Bedroom Apartments start at $3,200.

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

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.

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.