Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (503 Rentals) Page 5 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 16 Gerald Rd

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31

16 Gerald Rd, Unit 1, Unit 1

16 Gerald Rd
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 16 Gerald Rd

$5,600 - $6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600 - $6,500

Total Monthly Price
$5,600 - $6,500

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31

16 Gerald Rd

BostonMA02135
property at 47 Algonquin Rd

$5,700 - $5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,700 - $5,800

Total Monthly Price
$5,700 - $5,800

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

47 Algonquin Rd

Chestnut HillMA02467
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 32 Gerald Rd

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800

3 Bedroom, 1 Bath Condo for Rent

Available Now

32 Gerald Rd, Unit ##1-1, Unit ##1-1

32 Gerald Rd
BostonMA02135
property at 24 Tremont St

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800

4 Bedroom, 2.5 Bath Townhome for Rent

Available Now

24 Tremont St

BostonMA02135
property at 95 Undine Rd

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800

4 Bedroom, 2 Bath Condo for Rent

Available Now

95 Undine Rd, Unit 95, Unit 95

95 Undine Rd
BostonMA02135
property at 93 Undine Rd

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800

Total Monthly Price
$5,800

4 Bedroom, 2 Bath Condo for Rent

Available Now

93 Undine Rd, Unit 93, Unit 93

93 Undine Rd
BostonMA02135
property at 95 Undine Rd

$5,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,900

Total Monthly Price
$5,900

4 Bedroom, 2 Bath Condo for Rent

Available Aug 30

95 Undine Rd

BostonMA02135
property at 64 Langley Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 2.5 Bath Condo for Rent

Available Now

64 Langley Rd, Unit 64, Unit 64

64 Langley Rd
BostonMA02135
property at 289 Foster St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 1 Bath Condo for Rent

Available Now

289 Foster St, Unit 1, Unit 1

289 Foster St
BostonMA02135
property at 199 Boylston St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 3.5 Bath Home for Rent

Available Now

199 Boylston St

Chestnut HillMA02467
property at 199 Boylston St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 3.5 Bath Condo for Rent

Available Now

199 Boylston St, Unit 1, Unit 1

199 Boylston St
Chestnut HillMA02467
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 64 Langley Rd

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

4 Bedroom, 2.5 Bath Home for Rent

Available Now

64 Langley 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 66 Kirkwood Rd

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

4 Bedroom, 1 Bath Home for Rent

Available Now

66 Kirkwood Rd

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 288 Foster St

$6,200 - $7,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200 - $7,200

Total Monthly Price
$6,200 - $7,200

4 To 5 Bedroom Condos for Rent

Available Now

288 Foster St

BostonMA02135
property at 64 Greycliff Rd

$6,250 - $11,000

Total Monthly Price4 Month Lease Term

Total Monthly Price

Base Rent
$6,250 - $11,000

Total Monthly Price
$6,250 - $11,000

1 To 4 Bedroom Townhomes for Rent

Available Now

64 Greycliff Rd

BostonMA02135
property at 28 Manet Rd

$6,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,300

Total Monthly Price
$6,300

5 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1

28 Manet Rd, Unit 1, Unit 1

28 Manet Rd
Chestnut HillMA02467
property at 16 Foster St

$6,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,300

Total Monthly Price
$6,300

5 Bedroom, 3 Bath Townhome for Rent

Available Sep 1

16 Foster St

BostonMA02135
property at 249 Chestnut Hill Ave

$6,370

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,370

Total Monthly Price
$6,370

1 Bedroom, 1 Bath Condo for Rent

Available Now

249 Chestnut Hill Ave, Unit 24, Unit 24

249 Chestnut Hill Ave
BostonMA02135
property at 229 Chestnut Hill Ave

$6,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,400

Total Monthly Price
$6,400

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

229 Chestnut Hill Ave, Unit 1, Unit 1

229 Chestnut Hill Ave
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 Sep 1

29 Gerald Rd

BostonMA02135
property at 9 Radnor Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

4 Bedroom, 2 Bath Condo for Rent

Available Aug 30

9 Radnor Rd, Unit 1, Unit 1

9 Radnor Rd
BostonMA02135
property at 16 Foster St

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 3 Bath Townhome for Rent

Available Sep 1

16 Foster St

BostonMA02135
property at 25 Wade St

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 3.5 Bath Home for Rent

Available Now

25 Wade 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 142 Jackson St

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

3 Bedroom, 1.5 Bath Home for Rent

Available Jul 1

142 Jackson St

NewtonMA02459
property at 64 Langley Rd

$6,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,900

Total Monthly Price
$6,900

5 Bedroom, 3.5 Bath Home for Rent

Available Now

64 Langley Rd, Unit 1, Unit 1

64 Langley Rd
BostonMA02135
property at 68 Manet Rd

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

4 Bedroom, 3 Bath Condo for Rent

Available Sep 1

68 Manet Rd, Unit 1, Unit 1

68 Manet Rd
Chestnut HillMA02467
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 14 Glenmont Rd

$7,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,200

Total Monthly Price
$7,200

5 Bedroom, 2 Bath Condo for Rent

Available Aug 15

14 Glenmont Rd, Unit 2, Unit 2

14 Glenmont Rd
BostonMA02135
property at 14 Glenmont Rd

$7,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,200

Total Monthly Price
$7,200

5 Bedroom, 2 Bath Condo for Rent

Available Aug 15

14 Glenmont Rd, Unit 2, Unit 2

14 Glenmont Rd
BostonMA02135
property at 14 Glenmont Rd

$7,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,200

Total Monthly Price
$7,200

5 Bedroom, 2 Bath Townhome for Rent

Available Aug 15

14 Glenmont Rd

BostonMA02135
property at 289 Foster St

$7,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,500

Total Monthly Price
$7,500

4 Bedroom, 1 Bath Townhome for Rent

Available Now

289 Foster St

BostonMA02135
property at 10 Portina Rd

$7,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,500

Total Monthly Price
$7,500

6 Bedroom, 3 Bath Condo for Rent

Available Aug 23

10 Portina Rd, Unit 1, Unit 1

10 Portina Rd
BostonMA02135
property at 153 Foster St

$7,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,500

Total Monthly Price
$7,500

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

153 Foster St, Unit 1, Unit 1

153 Foster St
BostonMA02135
property at 235 Chestnut Hill Ave

$7,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,600

Total Monthly Price
$7,600

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

235 Chestnut Hill Ave, Unit 1, Unit 1

235 Chestnut Hill Ave
BostonMA02135
property at 25 Kirkwood Rd

$8,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,000

Total Monthly Price
$8,000

5 Bedroom, 2 Bath Condo for Rent

Available Now

25 Kirkwood Rd, Unit 1##, Unit 1##

25 Kirkwood Rd
BostonMA02135
property at 159 Foster St

$8,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,200

Total Monthly Price
$8,200

6 Bedroom, 3 Bath Condo for Rent

Available Aug 28

159 Foster St, Unit 1, Unit 1

159 Foster 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 260 Foster St

$8,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,500

Total Monthly Price
$8,500

6 Bedroom, 3 Bath Condo for Rent

Available Sep 1

260 Foster St, Unit 2, Unit 2

260 Foster 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

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.

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

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.

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.