Luxury Homes for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (354 Rentals) Page 5 of 8

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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 21 Wiltshire Rd
$4,200

Total Monthly Price

Base Rent$4,200

Total Monthly Price$4,200
3 Bedroom, 1 Bath Rentals
Available Now
Affordability

21 Wiltshire Rd, Unit 2

21 Wiltshire Rd
BostonMA02135
property at 437 Washington St
$2,900

Total Monthly Price

Base Rent$2,900

Total Monthly Price$2,900
3 Bedroom, 1 Bath Rentals
Available Now
Affordability

437 Washington St, Unit 2

437 Washington St
BostonMA02135
property at 124 Kenrick St
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
4 Bedroom, 3 Bath Rentals
Available Now
Affordability

124 Kenrick St, Unit 6

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

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
4 Bedroom, 3 Bath Rentals
Available Now
Affordability

124 Kenrick St, Unit 5

124 Kenrick St
BostonMA02135
property at 39 Foster St
$3,300

Total Monthly Price

Base Rent$3,300

Total Monthly Price$3,300
3 Bedroom, 1 Bath Rentals
Available Now
Affordability

39 Foster St, Unit 1

39 Foster St
BostonMA02135
property at 437 Washington St
$2,900

Total Monthly Price

Base Rent$2,900

Total Monthly Price$2,900
3 Bedroom, 1 Bath Rentals
Available Now
Affordability

437 Washington St, Unit 1

437 Washington St
BostonMA02135
property at 20 Lyne Rd
$3,600

Total Monthly Price

Base Rent$3,600

Total Monthly Price$3,600
3 Bedroom, 1 Bath Rentals
Available Now
Affordability

20 Lyne Rd

BostonMA02135
property at 2 O'Neil Pl
$2,750

Total Monthly Price

Base Rent$2,750

Total Monthly Price$2,750
2 Bedroom, 1 Bath Rentals
Available Now
Affordability

2 Oneil Pl. 2, Unit 2

2 O'Neil Pl
BostonMA02135
property at 15-17-17 Belmont Rd
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
12 Month Lease Term
2 Bedroom, 1 Bath Townhome for Rent
Available Now
Affordability

15-17-17 Belmont Rd

BrooklineMA02467
property at 2020 Commonwealth Ave
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability
property at 20 Sidlaw Rd
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

20 Sidlaw Rd

BostonMA02135
property at 2016 Commonwealth Ave
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
1 Bedroom, 1 Bath Condo for Rent
Available Sep 10
Affordability
property at 202 Chestnut Hill Ave
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
1 Bedroom Rentals
Available Now
Affordability
property at 290 Chestnut Hill Ave
$2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability
property at 545 Washington St
$2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

545 Washington St

BostonMA02135
property at 9 Embassy Rd
$2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

9 Embassy Rd

BostonMA02135
property at 2 Lothian Rd
$2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

2 Lothian Rd

BostonMA02135
property at 288 Chestnut Hill Ave
$2,600 - $3,125

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
Studio To 2 Bedroom Rentals
Available Now
Affordability
property at 36 Dighton St
$2,500 - $2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
2 Bedroom Rentals
Available Now
Affordability

36 Dighton St

BostonMA02135
property at 145 Englewood Ave
$2,600 - $4,000

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
1 To 2 Bedroom Rentals
Available Now
Affordability

145 Englewood Ave

BostonMA02135
property at 272 Chestnut Hill Ave
$2,615

Total Monthly Price

Base Rent$2,615

Total Monthly Price$2,615
1 Bedroom, 1 Bath Home for Rent
Available Now
Affordability
property at 1990 Commonwealth Ave
$2,650 - $5,040

Total Monthly Price

Base Rent$2,650

Total Monthly Price$2,650
1 To 3 Bedroom Rentals
Available Now
Affordability
property at 24 Brock St
$2,700

Total Monthly Price

Base Rent$2,700

Total Monthly Price$2,700
2 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

24 Brock St

BostonMA02135
property at 118 Strathmore Rd
$2,700

Total Monthly Price

Base Rent$2,700

Total Monthly Price$2,700
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

118 Strathmore Rd

BostonMA02135
property at 133 Lake Shore Rd
$2,700

Total Monthly Price

Base Rent$2,700

Total Monthly Price$2,700
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

133 Lake Shore Rd

BostonMA02135
property at 41 South St
$2,700

Total Monthly Price

Base Rent$2,700

Total Monthly Price$2,700
2 Bedroom Rentals
Available Now
Affordability

41 South St

BostonMA02135
property at 30 Beecher Pl
$2,750

Total Monthly Price

Base Rent$2,750

Total Monthly Price$2,750
1 Bedroom, 1 Bath Townhome for Rent
Available Now
Affordability

30 Beecher Pl

NewtonMA02459
property at 141 Chiswick Rd
$2,750

Total Monthly Price

Base Rent$2,750

Total Monthly Price$2,750
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

141 Chiswick Rd

BostonMA02135

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

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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.