Condos for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (331 Rentals) Page 5 of 7

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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

16 Gerald Rd
BostonMA02135
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

16 Gerald Rd
BostonMA02135
property at 209 Chestnut Hill Ave

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

209 Chestnut Hill Ave, Unit 1

209 Chestnut Hill Ave
BostonMA02135
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

16 Gerald Rd
BostonMA02135
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 Condo for Rent

Available Now

6 Lothian Rd, Unit 2

6 Lothian 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

93 Undine Rd
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

95 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, Unit 93

95 Undine Rd
BostonMA02135
property at 16 Malbert Rd

$5,995

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,995

Total Monthly Price
$5,995

6 Bedroom, 2 Bath Condo for Rent

Available Now

16 Malbert Rd, Unit 6-bed 2-bath

16 Malbert 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

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

289 Foster St
BostonMA02135
property at 25 Kirkwood Rd

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

5 Bedroom, 2 Bath Condo for Rent

Available Now

25 Kirkwood Rd, Unit 1##

25 Kirkwood Rd
BostonMA02135
property at 288 Foster St

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

4 Bedroom, 1 Bath Condo for Rent

Available Now

288 Foster St, Unit 1

288 Foster St
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 Condo for Rent

Available Now

1 Glenley Terrace, Unit 1

1 Glenley Terrace
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

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 Dec 1

29 Gerald Rd, Unit 2##

29 Gerald Rd
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, Unit 1

29 Gerald Rd
BostonMA02135
property at 15 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 Sep 1

15 Glenmont Rd, Unit 2

15 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

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

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

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

14 Glenmont Rd
BostonMA02135
property at 18 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

18 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

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

14 Glenmont Rd
BostonMA02135
property at 10 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

10 Glenmont Rd, Unit 2

10 Glenmont Rd
BostonMA02135
property at 2 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 15

2 Portina Rd

BostonMA02135
property at 2 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

2 Portina Rd, Unit 1

2 Portina Rd
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

10 Portina Rd
BostonMA02135
property at 2 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 15

2 Portina Rd

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 Aug 31

235 Chestnut Hill Ave, Unit 1

235 Chestnut Hill Ave
BostonMA02135
property at 2021 Commonwealth Ave

$7,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,600

Total Monthly Price
$7,600

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2021 Commonwealth Ave, Unit 2

2021 Commonwealth Ave
BostonMA02135
property at 2021 Commonwealth Ave

$8,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,750

Total Monthly Price
$8,750

5 Bedroom, 2.5 Bath Condo for Rent

Available Now

2021 Commonwealth Ave, Unit D

2021 Commonwealth Ave
BostonMA02135
property at 116 Lake St

$9,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,000

Total Monthly Price
$9,000

6 Bedroom, 4 Bath Condo for Rent

Available Now

116 Lake St, Unit 1

116 Lake St
BostonMA02135
property at 44 Kirkwood Rd

$9,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,600

Total Monthly Price
$9,600

4 Bedroom, 2 Bath Condo for Rent

Available Aug 31

44 Kirkwood Rd, Unit 1

44 Kirkwood Rd
BostonMA02135
property at 44 Kirkwood Rd

$9,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,600

Total Monthly Price
$9,600

4 Bedroom, 2 Bath Condo for Rent

Available Aug 31

44 Kirkwood Rd

BostonMA02135
property at 44 Greycliff Rd

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500

Total Monthly Price
$10,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 31

44 Greycliff Rd, Unit 1

44 Greycliff Rd
BostonMA02135
property at 44 Greycliff Rd

$12,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$12,000

Total Monthly Price
$12,000

6 Bedroom, 3 Bath Condo for Rent

Available Now

44 Greycliff Rd, Unit 2

44 Greycliff Rd
BostonMA02135
property at 44 Greycliff Rd

$12,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$12,400

Total Monthly Price
$12,400

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31, 2027

44 Greycliff Rd, Unit #2

44 Greycliff Rd
BostonMA02135
property at 16 Gerald Rd

$13,500

Total Monthly Price12 Month Lease Term

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, Unit 2

16 Gerald Rd
BostonMA02135

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 535 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $17,000. There are also 453 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $825 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 $825 to $17,500 with an average monthly rent of $5,626.

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 $2,500 to $6,750, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,100 to $6,500. Four Bedroom Single-Family rentals are also available starting from $980 and Four Bedroom Apartments start at $3,200.

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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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.