Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (480 Rentals) Page 10 of 10

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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 7 Glenley Terrace

$3,900 - $4,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 To 4 Bedroom Rentals

Available Sep 1

7 Glenley Terrace

BostonMA02135
property at 3 Glenley Terrace

$3,800 - $4,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 To 4 Bedroom Rentals

Available Now

3 Glenley Terrace

BostonMA02135
property at 3 A Glenley Terrace

$3,900

Total Monthly Price

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom Rentals

Available Sep 1

3 A Glenley Terrace

BostonMA01718
property at 37 N Crescent Circuit

$3,950

Total Monthly Price

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 1 Bath Home for Rent

Available Sep 1

property at 41 N Crescent Circuit

$3,500 - $3,950

Total Monthly Price

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom Rentals

Available Now

property at 368 Chestnut Hill Ave

$4,500

Total Monthly Price

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

3 Bedroom, 1 Bath Condo for Rent

Available Aug 1

property at 5 Glenley Terrace

$4,800

Total Monthly Price

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

5 Glenley Terrace

BostonMA02135
property at 2 Glenley Terrace

$4,800

Total Monthly Price

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2 Glenley Terrace

BostonMA02135
property at 8 Lothian Rd

$5,200

Total Monthly Price

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

8 Lothian Rd

BostonMA02135
property at 70 Larch St

$5,250

Total Monthly Price

Total Monthly Price

Base Rent
$5,250

Total Monthly Price
$5,250

5 Bedroom, 2 Bath Home for Rent

Available Now

70 Larch St

BostonMA02135
property at 124 Kenrick St

$5,400

Total Monthly Price

Total Monthly Price

Base Rent
$5,400

Total Monthly Price
$5,400

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

124 Kenrick St

BostonMA02135
property at 1793 Commonwealth Ave

$5,400

Total Monthly Price

Total Monthly Price

Base Rent
$5,400

Total Monthly Price
$5,400

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

property at 66 Lothian Rd

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

5 Bedroom, 2 Bath Home for Rent

Available Sep 1

66 Lothian Rd

BostonMA02135
property at 2 Lothian Rd

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2 Lothian Rd

BostonMA02135
property at 21 Hamlet St

$5,700

Total Monthly Price

Total Monthly Price

Base Rent
$5,700

Total Monthly Price
$5,700

3 Bedroom, 2.5 Bath Townhome for Rent

Available Now

21 Hamlet St

NewtonMA02459
property at 200 Commonwealth Ave

$6,100

Total Monthly Price

Total Monthly Price

Base Rent
$6,100

Total Monthly Price
$6,100

5 Bedroom, 2.5 Bath Home for Rent

Available Aug 23

property at 43 Greycliff Rd

$6,200

Total Monthly Price

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

3 Bedroom, 1.5 Bath Condo for Rent

Available Aug 24, 2027

43 Greycliff Rd

BostonMA02135
property at 35 Winship St

$6,200

Total Monthly Price

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

4 Bedroom, 2 Bath Condo for Rent

Available Now

35 Winship St

BostonMA02135
property at 16 Foster St

$6,500

Total Monthly Price

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 3 Bath Townhome for Rent

Available Now

16 Foster St

BostonMA02135
property at 39 Winship St

$6,600

Total Monthly Price

Total Monthly Price

Base Rent
$6,600

Total Monthly Price
$6,600

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

39 Winship St

BostonMA02135
property at 11 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 Home for Rent

Available Sep 1

11 Glenley Terrace

BostonMA02135
property at 48 Greycliff Rd

$11,000

Total Monthly Price

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 31, 2027

48 Greycliff Rd

BostonMA02135
property at 52 Greycliff Rd

$11,000

Total Monthly Price

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31

52 Greycliff Rd

BostonMA02135
property at 1773 Commonwealth Ave

$11,000

Total Monthly Price

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

7 Bedroom, 7 Bath Condo for Rent

Available Aug 15

property at 82 Louise Rd

$11,000

Total Monthly Price

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

4 Bedroom, 4 Bath Townhome for Rent

Available Now

82 Louise Rd

NewtonMA02467
property at 225 Kenrick St

$12,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$12,500

Total Monthly Price
$12,500

5 Bedroom, 3.5 Bath Home for Rent

Available Now

225 Kenrick St

NewtonMA02458
property at 16 Gerald Rd

$13,500

Total Monthly Price

Total Monthly Price

Base Rent
$13,500

Total Monthly Price
$13,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 31

16 Gerald Rd

BostonMA02135
property at 1789 Commonwealth Ave

$3,975 - $13,600

Total Monthly Price

Total Monthly Price

Base Rent
$13,600

Total Monthly Price
$13,600

Studio To 8 Bedroom Rentals

Available Now

property at 132 Yarmouth Rd

$15,000

Total Monthly Price

Total Monthly Price

Base Rent
$15,000

Total Monthly Price
$15,000

4 Bedroom, 5 Bath Home for Rent

Available Now

132 Yarmouth Rd

BrooklineMA02467
property at 476 Heath St

$15,000

Total Monthly Price

Total Monthly Price

Base Rent
$15,000

Total Monthly Price
$15,000

9 Bedroom, 5.5 Bath Home for Rent

Available Now

476 Heath St

BrooklineMA02467
property at 29 Merrill Rd

$17,500

Total Monthly Price

Total Monthly Price

Base Rent
$17,500

Total Monthly Price
$17,500

5 Bedroom Rentals

Available Now

29 Merrill Rd

NewtonMA02459

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 533 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 555 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $775 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 $775 to $17,500 with an average monthly rent of $7,055.

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 $9,323, 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 $980 and Four Bedroom Apartments start at $3,000.

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 Maximizing Your Refund: Essential Tax Tips for Renters article

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.

decorative image for A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment article

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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.