Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA with Hardwood Floors (158 Rentals) Page 2 of 4

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property at 35 Winship St

$4,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,600
Total Monthly Price
$4,600

4 Bedroom, 2 Bath Condo for Rent

Available Now

35 Winship St, Unit 2, Unit 2

35 Winship St
BostonMA02135
property at 1999 Commonwealth Ave

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650
Total Monthly Price
$4,650

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

1999 Commonwealth Ave, Unit 12, Unit 12

1999 Commonwealth Ave
BostonMA02135
property at 35 Foster St

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800
Total Monthly Price
$4,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

35 Foster St, Unit 1, Unit 1

35 Foster St
BostonMA02135
property at 4 Chestnut Pl

$4,890

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,890
Total Monthly Price
$4,890

4 Bedroom, 4 Bath Condo for Rent

Available Sep 1

4 Chestnut Pl

BostonMA02135
property at 209 Chestnut Hill Ave

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000
Total Monthly Price
$5,000

4 Bedroom, 2 Bath Condo for Rent

Available Now

209 Chestnut Hill Ave, Unit 2, Unit 2

209 Chestnut Hill Ave
BostonMA02135
property at 6 Lothian Rd

$5,200 - $5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200 - $5,800
Total Monthly Price
$5,200 - $5,800

4 To 5 Bedroom Condos for Rent

Available Now

6 Lothian Rd

BostonMA02135
property at 49 Breck Ave

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200
Total Monthly Price
$5,200

5 Bedroom, 2 Bath Home for Rent

Available Now

49 Breck Ave

BostonMA02135
property at 49 Breck Ave

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200
Total Monthly Price
$5,200

5 Bedroom, 2 Bath Home for Rent

Available Now

49 Breck Ave

BostonMA02135
property at 91 Wallingford Rd

$5,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,400
Total Monthly Price
$5,400

4 Bedroom, 2 Bath Townhome for Rent

Available Sep 1

91 Wallingford Rd

BostonMA02135
property at 225 Chestnut Hill Ave

$5,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,400
Total Monthly Price
$5,400

4 Bedroom, 1 Bath Condo for Rent

Available Sep 1

225 Chestnut Hill Ave, Unit 3, Unit 3

225 Chestnut Hill Ave
BostonMA02135
property at 16 Foster St

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600
Total Monthly Price
$5,600

5 Bedroom, 3 Bath Townhome for Rent

Available Now

16 Foster St

BostonMA02135
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 Home for Rent

Available Now

6 Lothian Rd

BostonMA02135
property at 29 Gerald Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000
Total Monthly Price
$6,000

3 Bedroom, 1 Bath Condo for Rent

Available Now

29 Gerald 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 Home for Rent

Available Now

1 Glenley Terrace

BostonMA02135
property at 16 Gerald Rd

$6,200 - $13,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200 - $13,500
Total Monthly Price
$6,200 - $13,500

3 To 6 Bedroom Condos for Rent

Available Sep 1, 2027

16 Gerald Rd

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

153 Foster St, Unit 1, Unit 1

153 Foster St
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 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

29 Gerald Rd, Unit 2##, Unit 2##

29 Gerald Rd
BostonMA02135
property at 1 Glenley Terrace

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000
Total Monthly Price
$7,000

6 Bedroom, 3 Bath Condo for Rent

Available Sep 1

1 Glenley Terrace, Unit 1, Unit 1

1 Glenley Terrace
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 Townhome for Rent

Available Now

52 Lane Park, Unit 1, Unit 1

52 Lane Park
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

$9,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,900
Total Monthly Price
$9,900

4 Bedroom, 2 Bath Condo for Rent

Available Aug 30, 2027

44 Kirkwood Rd, Unit 2, Unit 2

44 Kirkwood Rd
BostonMA02135
property at 44 Greycliff Rd

$11,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,000
Total Monthly Price
$11,000

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 30, 2027

44 Greycliff Rd, Unit 1, Unit 1

44 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 Aug 31

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
Showing Results 51-100, Page 2 of 4

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 493 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $17,000. There are also 603 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $800 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 $800 to $17,500 with an average monthly rent of $6,124.

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 $8,997, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,700 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,030 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

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Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

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What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

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Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

decorative image for 18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property article

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.