Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (503 Rentals) Page 6 of 11

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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 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 116 Lake St

$9,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,000

Total Monthly Price
$9,000

6 Bedroom, 4 Bath Condo for Rent

Available Now

116 Lake St, Unit 1, Unit 1

116 Lake St
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 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

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, Unit 1

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 Condo for Rent

Available Aug 30, 2027

44 Kirkwood Rd, Unit 2, Unit 2

44 Kirkwood 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, 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 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, 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 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, Unit 1

44 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 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 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

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 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

46 Kirkwood 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, Unit 1

46 Bostonia Ave
BrightonMA02135

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 482 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 580 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $950 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 $950 to $17,500 with an average monthly rent of $5,779.

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 $7,760, while Three Bedroom Homes, Condos, and Townhomes for rent range from $950 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,160 and Four Bedroom Apartments start at $3,100.

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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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

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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.