Luxury Homes for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (354 Rentals) Page 7 of 8

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

The most luxurious Homes in the Chestnut Hill Middlesex area of Chestnut Hill with high-end amenities, features, and finishes.

property at 3 Glenley Terrace
$3,900

Total Monthly Price

Base Rent$3,900

Total Monthly Price$3,900
12 Month Lease Term
3 Bedroom, 3 Bath Townhome for Rent
Available Now
Affordability

3 Glenley Terrace

BostonMA02135
property at 41 N Crescent Circuit
$3,900

Total Monthly Price

Base Rent$3,900

Total Monthly Price$3,900
3 Bedroom, 1 Bath Home for Rent
Available Now
Affordability
property at 19 Lyne Rd
$3,900

Total Monthly Price

Base Rent$3,900

Total Monthly Price$3,900
3 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

19 Lyne Rd

BostonMA02135
property at 46 Brackett St
$3,900

Total Monthly Price

Base Rent$3,900

Total Monthly Price$3,900
3 Bedroom, 1 Bath Condo for Rent
Available Now

46 Brackett St

BrightonMA02134
property at 1-40 Turner St
$3,900

Total Monthly Price

Base Rent$3,900

Total Monthly Price$3,900
3 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

1-40 Turner St

BostonMA02135
property at 85 Academy Hill Rd
$3,900

Total Monthly Price

Base Rent$3,900

Total Monthly Price$3,900
4 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

85 Academy Hill Rd

BostonMA02135
property at 3 Portina Rd
$4,000

Total Monthly Price

Base Rent$4,000

Total Monthly Price$4,000
4 Bedroom, 1 Bath Townhome for Rent
Available Now
Affordability

3 Portina Rd

BostonMA02135
property at 70 Larch St
$4,100

Total Monthly Price

Base Rent$4,100

Total Monthly Price$4,100
5 Bedroom, 2 Bath Home for Rent
Available Now
Affordability

70 Larch St

BostonMA02135
property at 161 Brayton Rd
$3,800 - $4,100

Total Monthly Price

Base Rent$4,100

Total Monthly Price$4,100
3 Bedroom Rentals
Available Now
Affordability

161 Brayton Rd

BostonMA02135
property at 191 Kenrick St
$4,150

Total Monthly Price

Base Rent$4,150

Total Monthly Price$4,150
4 Bedroom, 2 Bath Home for Rent
Available Now
Affordability

191 Kenrick St

BostonMA02135
property at 40 Lake Shore Rd
$4,200

Total Monthly Price

Base Rent$4,200

Total Monthly Price$4,200
3 Bedroom, 1.5 Bath Home for Rent
Available Now
Affordability

40 Lake Shore Rd

BostonMA02135
property at 199 Lake St
$4,200

Total Monthly Price

Base Rent$4,200

Total Monthly Price$4,200
4 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

199 Lake St

BostonMA02135
property at 83 Brayton Rd
$4,200

Total Monthly Price

Base Rent$4,200

Total Monthly Price$4,200
5 Bedroom, 2 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

83 Brayton Rd

BostonMA02135
property at 5 Glenley Terrace
$4,200

Total Monthly Price

Base Rent$4,200

Total Monthly Price$4,200
3 Bedroom, 3 Bath Condo for Rent
Available Now
Affordability

5 Glenley Terrace

BostonMA02135
property at 99 Chestnut Hill Ave
$2,300 - $4,200

Total Monthly Price

Base Rent$4,200

Total Monthly Price$4,200
Studio To 2 Bedroom Rentals
Available Now
Affordability
property at 12 Hammondswood Rd
$4,250

Total Monthly Price

Base Rent$4,250

Total Monthly Price$4,250
3 Bedroom, 2 Bath Townhome for Rent
Available Now

12 Hammondswood Rd

NewtonMA02467
property at 2017 Commonwealth Ave
$4,250 - $4,675

Total Monthly Price

Base Rent$4,295

Total Monthly Price$4,295
2 Bedroom Rentals
Available Now
Affordability
property at 132 Middlesex Rd
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
3 Bedroom, 2 Bath Condo for Rent
Available Now

132 Middlesex Rd

BrooklineMA02467
property at 69 Undine Rd
$4,600

Total Monthly Price

Base Rent$4,600

Total Monthly Price$4,600
12 Month Lease Term
5 Bedroom, 1.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

69 Undine Rd

BostonMA02135
property at 148 Strathmore Rd
$3,250 - $4,800

Total Monthly Price

Base Rent$4,800

Total Monthly Price$4,800
2 To 4 Bedroom Rentals
Available Now
Affordability

148 Strathmore Rd

BostonMA02135
property at 1 Glenley Terrace
$4,900 - $5,800

Total Monthly Price

Base Rent$4,900

Total Monthly Price$4,900
6 Bedroom Rentals
Available Now
Affordability

1 Glenley Terrace

BostonMA02135
property at 45 Henshaw St
$4,950

Total Monthly Price

Base Rent$4,950

Total Monthly Price$4,950
3 Bedroom, 2 Bath Home for Rent
Available Now
Affordability

45 Henshaw St

BostonMA02135
property at 215 Chestnut Hill Ave
$5,000

Total Monthly Price

Base Rent$5,000

Total Monthly Price$5,000
4 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability
property at 108 Kenrick St
$5,000

Total Monthly Price

Base Rent$5,000

Total Monthly Price$5,000
4 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

108 Kenrick St

BostonMA02135
property at 7 Gem Ave
$5,000

Total Monthly Price

Base Rent$5,000

Total Monthly Price$5,000
3 Bedroom, 2.5 Bath Townhome for Rent
Available Oct 1
Cost Per Sq.Ft.

7 Gem Ave

BostonMA02135
property at 120 Kenrick St
$4,500 - $5,200

Total Monthly Price

Base Rent$5,000

Total Monthly Price$5,000
4 Bedroom Rentals
Available Now
Affordability

120 Kenrick St

BostonMA02135
property at 147 Kenrick St
$5,200

Total Monthly Price

Base Rent$5,200

Total Monthly Price$5,200
4 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

147 Kenrick St

BostonMA02135
property at 66 Lothian Rd
$5,200

Total Monthly Price

Base Rent$5,200

Total Monthly Price$5,200
4 Bedroom, 2 Bath Home for Rent
Available Now
Affordability

66 Lothian Rd

BostonMA02135
property at 8 Lothian Rd
$5,200 - $5,500

Total Monthly Price

Base Rent$5,200

Total Monthly Price$5,200
4 To 5 Bedroom Rentals
Available Now
Affordability

8 Lothian Rd

BostonMA02135
property at 6 Lothian Rd
$5,200 - $5,800

Total Monthly Price

Base Rent$5,200

Total Monthly Price$5,200
12 Month Lease Term
4 To 5 Bedroom Rentals
Available Now
Affordability

6 Lothian Rd

BostonMA02135
property at 1793 Commonwealth Ave
$5,400

Total Monthly Price

Base Rent$5,400

Total Monthly Price$5,400
5 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability
property at 12 Lothian Rd
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
5 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

12 Lothian Rd

BostonMA02135
property at 28 Lothian Rd
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
5 Bedroom, 2 Bath Home for Rent
Available Now
Affordability

28 Lothian Rd

BostonMA02135
property at 126 Kenrick St
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
4 Bedroom, 3 Bath Condo for Rent
Available Now

126 Kenrick St

BostonMA02135
property at 6-124 Kenrick St
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
4 Bedroom, 3 Bath Home for Rent
Available Now
Affordability

6-124 Kenrick St

BostonMA02135
property at 122 Kenrick St
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
4 Bedroom Rentals
Available Now
Affordability

122 Kenrick St

BostonMA02135
property at 23 Winship St
$5,700

Total Monthly Price

Base Rent$5,700

Total Monthly Price$5,700
4 Bedroom, 2.5 Bath Condo for Rent
Available Now

23 Winship St

BostonMA02135
property at 27 Maplewood Ave
$5,800

Total Monthly Price

Base Rent$5,800

Total Monthly Price$5,800
4 Bedroom, 2 Bath Home for Rent
Available Now

27 Maplewood Ave

NewtonMA02459
property at 1 Jackson St
$3,800 - $6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
2 Bedroom Rentals
Available Now

1 Jackson St

NewtonMA02459
property at 47 Winship St
$6,600

Total Monthly Price

Base Rent$6,600

Total Monthly Price$6,600
4 Bedroom, 2 Bath Condo for Rent
Available Now

47 Winship St

BostonMA02135
property at 16 Cabot St
$6,900

Total Monthly Price

Base Rent$6,900

Total Monthly Price$6,900
3 Bedroom, 2.5 Bath Home for Rent
Available Now

16 Cabot St

NewtonMA02458
property at 151 Foster St
$8,000

Total Monthly Price

Base Rent$8,000

Total Monthly Price$8,000
5 Bedroom, 2 Bath Condo for Rent
Available Now

151 Foster St

BostonMA02135
property at 4 Knowles St
$9,800

Total Monthly Price

Base Rent$9,800

Total Monthly Price$9,800
12 Month Lease Term
4 Bedroom, 4.5 Bath Townhome for Rent
Available Sep 15

4 Knowles St

NewtonMA02459
property at 132 Yarmouth Rd
$11,000

Total Monthly Price

Base Rent$11,000

Total Monthly Price$11,000
4 Bedroom, 5 Bath Home for Rent
Available Now
Outdoors

132 Yarmouth Rd

BrooklineMA02467
property at 225 Kenrick St
$12,000

Total Monthly Price

Base Rent$12,000

Total Monthly Price$12,000
5 Bedroom, 3.5 Bath Home for Rent
Available Nov 1
Outdoors

225 Kenrick St

NewtonMA02458
property at 50 Greycliff Rd
$12,300

Total Monthly Price

Base Rent$12,300

Total Monthly Price$12,300
7 Bedroom, 3 Bath Condo for Rent
Available Aug 24, 2027

50 Greycliff Rd

BostonMA02135
property at 16 Gerald Rd
$13,500

Total Monthly Price

Base Rent$13,500

Total Monthly Price$13,500
6 Bedroom, 2.5 Bath Condo for Rent
Available Sep 1, 2027

16 Gerald Rd

BostonMA02135
property at 1789 Commonwealth Ave
$13,600

Total Monthly Price

Base Rent$13,600

Total Monthly Price$13,600
8 Bedroom, 9 Bath Condo for Rent
Available Now
property at 17 Montrose St
$16,000

Total Monthly Price

Base Rent$16,000

Total Monthly Price$16,000
12 Month Lease Term
5 Bedroom, 6 Bath Home for Rent
Available Now

17 Montrose St

NewtonMA02458
property at 394 Hammond St
$22,000

Total Monthly Price

Base Rent$22,000

Total Monthly Price$22,000
9 Bedroom, 5.5 Bath Home for Rent
Available Oct 1

394 Hammond St

NewtonMA02467

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 274 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,000 to $13,500. There are also 462 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,000 to $16,000.

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 $1,000 to $16,000 with an average monthly rent of $3,744.

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 $1,000 to $7,640, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,250 to $7,250. Four Bedroom Single-Family rentals are also available starting from $1,160 and Four Bedroom Apartments start at $1,350.

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 Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My! article

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

decorative image for Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags   article

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.