Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (498 Rentals) Page 3 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 22 Eastburn St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1.5 Bath Townhome for Rent

Available Now

22 Eastburn St

BostonMA02135
property at 71 Foster St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

71 Foster St, Unit 1, Unit 1

71 Foster St
BostonMA02135
property at 7 North Crescent Circuit

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Townhome for Rent

Available Now

property at 152 Lake St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

152 Lake St, Unit 1, Unit 1

152 Lake St
BostonMA02135
property at 370 Chestnut Hill Ave

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

370 Chestnut Hill Ave, Unit 35, Unit 35

370 Chestnut Hill Ave
BostonMA02135
property at 7 Lothian Rd

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Condo for Rent

Available Aug 1

7 Lothian Rd, Unit 18, Unit 18

7 Lothian Rd
BostonMA02135
property at 25 Crosby Rd

$3,500 - $6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500 - $6,000

Total Monthly Price
$3,500 - $6,000

2 To 4 Bedroom Condos for Rent

Available Now

25 Crosby Rd

Chestnut HillMA02467
property at 16 Gerald Rd

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Home for Rent

Available Now

16 Gerald Rd

BostonMA02135
property at 99 Union St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 2 Bath Townhome for Rent

Available Now

99 Union St

BostonMA02135
property at 27 S Crescent Circuit

$3,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,550

Total Monthly Price
$3,550

3 Bedroom, 2 Bath Condo for Rent

Available Now

property at 27 South Crescent Circuit

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

27 South Crescent Circuit, Unit A, Unit A

27 South Crescent Circuit
BostonMA02135
property at 215 Lake Shore Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Now

215 Lake Shore Rd, Unit 2, Unit 2

215 Lake Shore Rd
BostonMA02135
property at 20 Anselm Ter

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Now

20 Anselm Ter, Unit 1, Unit 1

20 Anselm Ter
BostonMA02135
property at 136 Middlesex Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Now

136 Middlesex Rd, Unit 2, Unit 2

136 Middlesex Rd
Chestnut HillMA02467
property at 27 Willoughby St

$3,650 - $4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650 - $4,100

Total Monthly Price
$3,650 - $4,100

3 To 4 Bedroom Condos for Rent

Available Now

27 Willoughby St

BostonMA02135
property at 161 Brayton Rd

$3,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650

Total Monthly Price
$3,650

3 Bedroom, 1 Bath Condo for Rent

Available Now

161 Brayton Rd, Unit 1, Unit 1

161 Brayton Rd
BostonMA02135
property at 133 Chiswick Rd

$3,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650

Total Monthly Price
$3,650

3 Bedroom, 1 Bath Condo for Rent

Available Now

133 Chiswick Rd, Unit B, Unit B

133 Chiswick Rd
BostonMA02135
property at 1999 Commonwealth Ave

$3,650 - $4,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650 - $4,900

Total Monthly Price
$3,650 - $4,900

2 To 3 Bedroom Condos for Rent

Available Jun 1

property at 64 Tremont St

$3,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650

Total Monthly Price
$3,650

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

64 Tremont St, Unit 1, Unit 1

64 Tremont St
BostonMA02135
property at 9 Chiswick Ter

$3,660

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,660

Total Monthly Price
$3,660

3 Bedroom, 1 Bath Condo for Rent

Available Now

9 Chiswick Ter, Unit 2, Unit 2

9 Chiswick Ter
BostonMA02135
property at 1195 Boylston St

$3,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

3 Bedroom, 1.5 Bath Condo for Rent

Available Jun 1

1195 Boylston St, Unit 1195, Unit 1195

1195 Boylston St
Chestnut HillMA02467
property at 5 Glenley Ter

$3,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

3 Bedroom, 2 Bath Condo for Rent

Available Sep 1

5 Glenley Ter

BostonMA02135
property at 5 Glenley Terrace

$3,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

3 Bedroom, 2 Bath Condo for Rent

Available Sep 1

5 Glenley Terrace, Unit 1, Unit 1

5 Glenley Terrace
BostonMA02135
property at 2 Chestnut Pl

$3,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

2 Bedroom, 2 Bath Condo for Rent

Available Now

2 Chestnut Pl, Unit 1, Unit 1

2 Chestnut Pl
BostonMA02135
property at 3 Glenley Ter

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 3 Bath Condo for Rent

Available Now

3 Glenley Ter, Unit 1, Unit 1

3 Glenley Ter
BostonMA02135
property at 51 Algonquin Rd

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

51 Algonquin Rd

Chestnut HillMA02467
property at 515 Heath St

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 1 Bath Home for Rent

Available Now

515 Heath St

BrooklineMA02467
property at 40 Glenley Ter

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 3 Bath Condo for Rent

Available Sep 1

40 Glenley Ter

BostonMA02135
property at 204 Lake Shore Rd

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 2 Bath Condo for Rent

Available Now

204 Lake Shore Rd, Unit 1, Unit 1

204 Lake Shore Rd
BostonMA02135
property at 2 Portina Rd

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 1 Bath Townhome for Rent

Available Now

2 Portina Rd

BostonMA02135
property at 27 Crosby Rd

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

2 Bedroom, 2 Bath Condo for Rent

Available Sep 1

27 Crosby Rd, Unit 3, Unit 3

27 Crosby Rd
Chestnut HillMA02467
property at 166 Lake Shore Rd

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 2 Bath Condo for Rent

Available Aug 1

166 Lake Shore Rd, Unit 1L, Unit 1L

166 Lake Shore Rd
BostonMA02135
property at 51 Algonquin Rd

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

51 Algonquin Rd

Chestnut HillMA02467
property at 153 Lake Shore Rd

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 2 Bath Condo for Rent

Available Aug 1

153 Lake Shore Rd, Unit 1, Unit 1

153 Lake Shore Rd
BostonMA02135
property at 43 N Crescent Circuit

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

43 N Crescent Circuit, Unit 2, Unit 2

43 N Crescent Circuit
BostonMA02135
property at 41 North Crescent Circuit

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

41 North Crescent Circuit, Unit 2, Unit 2

41 North Crescent Circuit
BostonMA02135
property at 48 South Crescent Circuit

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

3 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1

48 South Crescent Circuit, Unit 2, Unit 2

48 South Crescent Circuit
BostonMA02135
property at 145 Englewood Ave

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

145 Englewood Ave, Unit 4, Unit 4

145 Englewood Ave
BostonMA02135
property at 26 Holly Ln

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

26 Holly Ln, Unit 2, Unit 2

26 Holly Ln
BrooklineMA02467
property at 14 Breck Ave

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 2 Bath Condo for Rent

Available Now

14 Breck Ave, Unit 2, Unit 2

14 Breck Ave
BostonMA02135
property at 47 Algonquin Rd

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

47 Algonquin Rd, Unit 2, Unit 2

47 Algonquin Rd
Chestnut HillMA02467
property at 1945 Commonwealth Ave

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

1945 Commonwealth Ave, Unit 13C, Unit 13C

1945 Commonwealth Ave
BostonMA02135
property at 137 Chiswick Terrace

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 1 Bath Condo for Rent

Available Now

137 Chiswick Terrace, Unit 5, Unit 5

137 Chiswick Terrace
BostonMA02135
property at 409 Washington St

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

409 Washington St, Unit 401, Unit 401

409 Washington St
BostonMA02135
property at 250 Hammond Pond Pky

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

250 Hammond Pond Pky, Unit 1203N, Unit 1203N

250 Hammond Pond Pky
Chestnut HillMA02467
property at 9 Oak Square Ave

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

4 Bedroom, 2 Bath Condo for Rent

Available Now

9 Oak Square Ave, Unit 2, Unit 2

9 Oak Square Ave
BostonMA02135
property at 1872 Commonwealth Ave

$4,150

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,150

Total Monthly Price
$4,150

2 Bedroom, 2 Bath Condo for Rent

Available Now

1872 Commonwealth Ave, Unit 408, Unit 408

1872 Commonwealth Ave
BostonMA02135
property at 16 Priscilla Rd

$4,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

3 Bedroom, 1 Bath Condo for Rent

Available Now

16 Priscilla Rd, Unit 2, Unit 2

16 Priscilla Rd
BostonMA02135

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 471 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 575 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 $5,752.

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 $950 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,130 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.