Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA with Hardwood Floors (110 Rentals) Page 2 of 3

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property at 6 Lothian Rd

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800
Total Monthly Price
$5,800

5 Bedroom, 2 Bath Condo for Rent

Available Now

6 Lothian Rd, Unit 2

6 Lothian Rd
BostonMA02135
property at 64 Langley Rd

$5,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,950
Total Monthly Price
$5,950

4 Bedroom, 2.5 Bath Home for Rent

Available Now

64 Langley Rd

BostonMA02135
property at 16 Malbert Rd

$5,995

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,995
Total Monthly Price
$5,995

6 Bedroom, 2 Bath Condo for Rent

Available Now

16 Malbert Rd, Unit 6-bed 2-bath

16 Malbert Rd
BostonMA02135
property at 1 Glenley Terrace

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200
Total Monthly Price
$6,200

6 Bedroom, 3 Bath Condo for Rent

Available Now

1 Glenley Terrace, Unit 1

1 Glenley Terrace
BostonMA02135
property at 1 Glenley Terrace

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200
Total Monthly Price
$6,200

6 Bedroom, 3 Bath Home for Rent

Available Now

1 Glenley Terrace

BostonMA02135
property at 153 Foster St

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200
Total Monthly Price
$6,200

4 Bedroom, 2 Bath Townhome for Rent

Available Sep 1, 2026

153 Foster St, Unit 1

153 Foster St
BostonMA02135
property at 29 Gerald Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500
Total Monthly Price
$6,500

3 Bedroom, 1 Bath Condo for Rent

Available Dec 1, 2026

29 Gerald Rd, Unit 2##

29 Gerald Rd
BostonMA02135
property at 120 Lake St

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500
Total Monthly Price
$6,500

6 Bedroom, 3 Bath Townhome for Rent

Available Now

120 Lake St

BostonMA02135
property at 116 Lake St

$8,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,400
Total Monthly Price
$8,400

6 Bedroom, 4 Bath Home for Rent

Available Now

116 Lake St

BostonMA02135
property at 52 Lane Park

$8,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,800
Total Monthly Price
$8,800

6 Bedroom, 2.5 Bath Home for Rent

Available Now

52 Lane Park

BostonMA02135
property at 12 Gerald Rd

$9,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,500
Total Monthly Price
$9,500

5 Bedroom, 3 Bath Home for Rent

Available Now

12 Gerald Rd

BostonMA02135
property at 12 Gerald Rd

$9,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,500
Total Monthly Price
$9,500

5 Bedroom, 3 Bath Home for Rent

Available Now

12 Gerald Rd

BostonMA02135
property at 44 Kirkwood Rd

$9,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,600
Total Monthly Price
$9,600

4 Bedroom, 2 Bath Townhome for Rent

Available Sep 1, 2026

44 Kirkwood Rd

BostonMA02135
property at 52 Greycliff Rd

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500
Total Monthly Price
$10,500

6 Bedroom, 3 Bath Home for Rent

Available Sep 1, 2026

52 Greycliff Rd

BostonMA02135
property at 52 Greycliff Rd

$11,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,100
Total Monthly Price
$11,100

6 Bedroom, 3 Bath Home for Rent

Available Sep 1, 2027

52 Greycliff Rd

BostonMA02135
property at 46 Kirkwood Rd

$11,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,200
Total Monthly Price
$11,200

6 Bedroom, 3 Bath Home for Rent

Available Sep 1, 2026

46 Kirkwood 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
Showing Results 51-100, Page 2 of 3

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 409 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.