Luxury Homes for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (354 Rentals) Page 2 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 51 Algonquin Rd
$4,000

Total Monthly Price

Base Rent$4,000

Total Monthly Price$4,000
12 Month Lease Term
3 Bedroom, 1 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

51 Algonquin Rd

Chestnut HillMA02467
property at 145 Englewood Ave
$4,000

Total Monthly Price

Base Rent$4,000

Total Monthly Price$4,000
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Furnished

145 Englewood Ave, Unit 4

145 Englewood Ave
BostonMA02135
property at 110 Academy Hill Rd
$4,100

Total Monthly Price

Base Rent$4,100

Total Monthly Price$4,100
12 Month Lease Term
5 Bedroom, 2 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

110 Academy Hill Rd, Unit 1

110 Academy Hill Rd
BostonMA02135
property at 1872 Commonwealth Ave
$4,150

Total Monthly Price

Base Rent$4,150

Total Monthly Price$4,150
12 Month Lease Term
2 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

1872 Commonwealth Ave, Unit 408

1872 Commonwealth Ave
BostonMA02135
property at 21 Wiltshire Rd
$4,200

Total Monthly Price

Base Rent$4,200

Total Monthly Price$4,200
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Oct 1
Affordability

21 Wiltshire Rd, Unit 2

21 Wiltshire Rd
BostonMA02135
property at 73 Undine Rd
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
12 Month Lease Term
4 Bedroom, 2.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

73 Undine Rd

BostonMA02135
property at 120 Kenrick St
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

120 Kenrick St, Unit 1

120 Kenrick St
BostonMA02135
property at 25 Greycliff Rd
$4,650

Total Monthly Price

Base Rent$4,650

Total Monthly Price$4,650
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
  • Smoke Free
property at 24 Tremont St
$4,800

Total Monthly Price

Base Rent$4,800

Total Monthly Price$4,800
12 Month Lease Term
4 Bedroom, 2.5 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

24 Tremont St

BostonMA02135
property at 225 Chestnut Hill Ave
$5,200

Total Monthly Price

Base Rent$5,200

Total Monthly Price$5,200
12 Month Lease Term
4 Bedroom, 1 Bath Condo for Rent
Available Now
Furnished

225 Chestnut Hill Ave, Unit 1

225 Chestnut Hill Ave
BostonMA02135

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

property at 6 Lothian Rd
$5,250

Total Monthly Price

Base Rent$5,250

Total Monthly Price$5,250
12 Month Lease Term
5 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

6 Lothian Rd, Unit 3

6 Lothian Rd
BostonMA02135
property at 7 Lothian Rd
$5,300

Total Monthly Price

Base Rent$5,300

Total Monthly Price$5,300
12 Month Lease Term
5 Bedroom, 2 Bath Condo for Rent
Available Now
Affordability

7 Lothian Rd, Unit 3

7 Lothian Rd
BostonMA02135
property at 91 Wallingford Rd
$5,400

Total Monthly Price

Base Rent$5,400

Total Monthly Price$5,400
12 Month Lease Term
4 Bedroom, 2 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

91 Wallingford Rd

BostonMA02135
property at 539 Commonwealth Ave
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
12 Month Lease Term
4 Bedroom, 3 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

539 Commonwealth Ave, Unit 2

539 Commonwealth Ave
NewtonMA02459
property at 110 Kenrick St
$5,600

Total Monthly Price

Base Rent$5,600

Total Monthly Price$5,600
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

110 Kenrick St

BostonMA02135
  • Smoke Free
property at 235 Chestnut Hill Ave
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now

235 Chestnut Hill Ave, Unit 1

235 Chestnut Hill Ave
BostonMA02135
property at 49 Radnor Rd
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Aug 22, 2027

49 Radnor Rd, Unit 2

49 Radnor Rd
BostonMA02135
property at 53 Radnor Rd
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Aug 22, 2027
Cost Per Sq.Ft.

53 Radnor Rd, Unit 2

53 Radnor Rd
BostonMA02135
property at 29 Gerald Rd
$6,200

Total Monthly Price

Base Rent$6,200

Total Monthly Price$6,200
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Aug 31, 2027

29 Gerald Rd, Unit 1

29 Gerald Rd
BostonMA02135
property at 153 Foster St
$6,200

Total Monthly Price

Base Rent$6,200

Total Monthly Price$6,200
12 Month Lease Term
4 Bedroom, 2 Bath Townhome for Rent
Available Now

153 Foster St, Unit 1

153 Foster St
BostonMA02135
property at 2021 Commonwealth Ave
$7,600

Total Monthly Price

Base Rent$7,600

Total Monthly Price$7,600
12 Month Lease Term
5 Bedroom, 2 Bath Condo for Rent
Available Now

2021 Commonwealth Ave, Unit 2

2021 Commonwealth Ave
BostonMA02135
  • Smoke Free
property at 16 South St
$7,700

Total Monthly Price

Base Rent$7,700

Total Monthly Price$7,700
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Sep 1, 2027

16 South St, Unit 1

16 South St
BostonMA02135
property at 126 Lake St
$8,200

Total Monthly Price

Base Rent$8,200

Total Monthly Price$8,200
12 Month Lease Term
6 Bedroom, 4 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

126 Lake St

BostonMA02135
property at 116 Lake St
$8,200

Total Monthly Price

Base Rent$8,200

Total Monthly Price$8,200
12 Month Lease Term
6 Bedroom, 4 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

116 Lake St

BostonMA02135
property at 37 Radnor Rd
$9,800

Total Monthly Price

Base Rent$9,800

Total Monthly Price$9,800
12 Month Lease Term
6 Bedroom, 3 Bath Condo for Rent
Available Aug 22, 2027
Cost Per Sq.Ft.

37 Radnor Rd, Unit 1

37 Radnor Rd
BostonMA02135
property at 53 Radnor Rd
$9,800

Total Monthly Price

Base Rent$9,800

Total Monthly Price$9,800
12 Month Lease Term
6 Bedroom, 3 Bath Condo for Rent
Available Aug 22, 2027
Cost Per Sq.Ft.

53 Radnor Rd, Unit 1

53 Radnor Rd
BostonMA02135
property at 25 Kirkwood Rd
$9,900

Total Monthly Price

Base Rent$9,900

Total Monthly Price$9,900
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Aug 31, 2027

25 Kirkwood Rd

BostonMA02135
property at 44 Greycliff Rd
$10,500 - $12,000

Total Monthly Price

Base Rent$10,500 - $12,000

Total Monthly Price$10,500 - $12,000
12 Month Lease Term
6 Bedroom, 3 Bath Condo for Rent
Available Now

44 Greycliff Rd

BrightonMA02135
property at 12 Gerald Rd
$10,500

Total Monthly Price

Base Rent$10,500

Total Monthly Price$10,500
12 Month Lease Term
5 Bedroom, 3 Bath Home for Rent
Available Sep 1, 2027
Luxury

12 Gerald Rd

BostonMA02135
  • Smoke Free
property at 1860 Commonwealth Ave
$11,000

Total Monthly Price

Base Rent$11,000

Total Monthly Price$11,000
12 Month Lease Term
6 Bedroom, 4.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.
property at 52 Greycliff Rd
$11,100

Total Monthly Price

Base Rent$11,100

Total Monthly Price$11,100
12 Month Lease Term
6 Bedroom, 3 Bath Home for Rent
Available Sep 1, 2027

52 Greycliff Rd

BostonMA02135
property at 44 Greycliff Rd
$12,400

Total Monthly Price

Base Rent$12,400

Total Monthly Price$12,400
12 Month Lease Term
6 Bedroom, 3 Bath Condo for Rent
Available Aug 31, 2027

44 Greycliff Rd, Unit #2

44 Greycliff 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.

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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.

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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.

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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.