Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (457 Rentals) Page 4 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 3 Glenley Ter

$5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,800
Total Monthly Price
$5,800

6 Bedroom, 3 Bath Home for Rent

Available Sep 1

3 Glenley Ter

BostonMA02135
property at 26 Tanglewood Rd

$5,995

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,995
Total Monthly Price
$5,995

3 Bedroom, 3 Bath Townhome for Rent

Available Jul 1

26 Tanglewood Rd

NewtonMA02459
property at 199 Boylston St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000
Total Monthly Price
$6,000

4 Bedroom, 3.5 Bath Condo for Rent

Available Now

199 Boylston St, Unit 1

199 Boylston St
Chestnut HillMA02467
property at 153 Foster St

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200
Total Monthly Price
$6,200

4 Bedroom, 2 Bath Townhome for Rent

Available Sep 1

153 Foster St, Unit 1

153 Foster St
BostonMA02135
property at 29 Gerald Rd

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200
Total Monthly Price
$6,200

3 Bedroom, 1 Bath Condo for Rent

Available Aug 31, 2027

29 Gerald Rd, Unit 1

29 Gerald Rd
BostonMA02135
property at 235 Chestnut Hill Ave

$6,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,700
Total Monthly Price
$6,700

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

235 Chestnut Hill Ave, Unit 1

235 Chestnut Hill Ave
BostonMA02135
property at 235 Chestnut Hill Ave

$6,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,700
Total Monthly Price
$6,700

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

235 Chestnut Hill Ave, Unit 1

235 Chestnut Hill Ave
BostonMA02135
property at 64 Langley Rd

$6,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,900
Total Monthly Price
$6,900

5 Bedroom, 3.5 Bath Home for Rent

Available Now

64 Langley Rd, Unit 1

64 Langley Rd
BostonMA02135
property at 1 Glenley Terrace

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000
Total Monthly Price
$7,000

6 Bedroom, 3 Bath Condo for Rent

Available Sep 1

1 Glenley Terrace, Unit 1

1 Glenley Terrace
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 52 Lane Park

$8,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,800
Total Monthly Price
$8,800

6 Bedroom, 2.5 Bath Home for Rent

Available Now

52 Lane Park

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 12 Gerald Rd

$9,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,500
Total Monthly Price
$9,500

5 Bedroom, 3 Bath Home for Rent

Available Now

12 Gerald 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, Unit 1

44 Kirkwood Rd
BostonMA02135
property at 25 Kirkwood Rd

$9,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,900
Total Monthly Price
$9,900

4 Bedroom, 2 Bath Condo for Rent

Available Aug 31, 2027

25 Kirkwood Rd

BostonMA02135
property at 52 Bostonia Ave

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500
Total Monthly Price
$10,500

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31

52 Bostonia Ave, Unit 1

52 Bostonia Ave
BrightonMA02135
property at 44 Bostonia Ave

$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 Bostonia Ave, Unit 1

44 Bostonia Ave
BrightonMA02135
property at 52 Greycliff Rd

$10,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500
Total Monthly Price
$10,500

6 Bedroom, 3 Bath Home for Rent

Available Sep 1

52 Greycliff Rd

BostonMA02135
property at 44 Greycliff Rd

$10,500 - $12,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,500 - $12,000
Total Monthly Price
$10,500 - $12,000

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31

44 Greycliff Rd

BrightonMA02135
property at 44 Greycliff Rd

$11,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,000
Total Monthly Price
$11,000

6 Bedroom, 2.5 Bath Condo for Rent

Available Aug 30, 2027

44 Greycliff Rd, Unit 1

44 Greycliff Rd
BostonMA02135
property at 1860 Commonwealth Ave

$11,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,000
Total Monthly Price
$11,000

6 Bedroom, 4.5 Bath Home for Rent

Available Sep 1

1860 Commonwealth Ave

BostonMA02135
property at 52 Greycliff Rd

$11,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,100
Total Monthly Price
$11,100

6 Bedroom, 3 Bath Home for Rent

Available Aug 31

52 Greycliff Rd

BostonMA02135
property at 46 Kirkwood Rd

$11,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,200
Total Monthly Price
$11,200

6 Bedroom, 3 Bath Home for Rent

Available Sep 1

46 Kirkwood Rd

BostonMA02135
property at 46 Bostonia Ave

$11,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,200
Total Monthly Price
$11,200

6 Bedroom, 3 Bath Condo for Rent

Available Aug 31

46 Bostonia Ave, Unit 1

46 Bostonia Ave
BrightonMA02135
Showing Results 151-200, Page 4 of 10

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 408 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $960 to $17,000. There are also 574 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $1,100 to $16,800.

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 $1,100 to $16,800 with an average monthly rent of $5,647.

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 $1,350 to $8,370, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,700 to $8,000. Four Bedroom Single-Family rentals are also available starting from $2,900 and Four Bedroom Apartments start at $1,050.

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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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.