Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (474 Rentals) Page 6 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 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 Home for Rent

Available Aug 31

44 Kirkwood 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 Condo for Rent

Available Aug 31

44 Kirkwood Rd, Unit 1

44 Kirkwood 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 Condo for Rent

Available Aug 31

44 Kirkwood 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 Home for Rent

Available Aug 31, 2027

44 Kirkwood Rd

BostonMA02135
property at 44 Greycliff Rd

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

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

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 31

44 Greycliff Rd, Unit 1

44 Greycliff Rd
BostonMA02135
property at 44 Bostonia Ave

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

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

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 31

44 Bostonia Ave, Unit 1

44 Bostonia Ave
BrightonMA02135
property at 44 Greycliff Rd

$10,500 - $12,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500 - $12,000
Total Monthly Price
$10,500 - $12,000

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31

44 Greycliff Rd

BrightonMA02135
property at 44 Greycliff Rd

$10,500 - $12,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500 - $12,000
Total Monthly Price
$10,500 - $12,000

6 Bedroom, 3 Bath Condo for Rent

Available Now

44 Greycliff Rd

BostonMA02135
property at 52 Bostonia Ave

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

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

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31

52 Bostonia Ave, Unit 1

52 Bostonia Ave
BrightonMA02135
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

52 Greycliff 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

52 Greycliff Rd

BostonMA02135
property at 44 Bostonia Ave

$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 Now

44 Bostonia Ave

BrightonMA02135
property at 1860 Commonwealth Ave

$11,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

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

6 Bedroom, 4.5 Bath Home for Rent

Available Sep 1

1860 Commonwealth Ave

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 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 46 Bostonia Ave

$11,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

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

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31

46 Bostonia Ave, Unit 1

46 Bostonia Ave
BrightonMA02135
property at 44 Greycliff Rd

$12,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$12,400
Total Monthly Price
$12,400

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31, 2027

44 Greycliff Rd, Unit #2

44 Greycliff Rd
BostonMA02135
property at 476 Heath St

$15,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$15,000
Total Monthly Price
$15,000

6 Bedroom, 6.5 Bath Home for Rent

Available Now

476 Heath St

Chestnut HillMA02467
Showing Results 251-300, Page 6 of 10

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 528 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 551 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 $6,534.

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 $9,111, 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.