Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (457 Rentals) Page 3 of 10

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 99 Union St

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 2 Bath Townhome for Rent

Available Now

99 Union St, Unit 3bd

99 Union St
BostonMA02135
property at 204 Lake Shore Rd

$3,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

3 Bedroom, 2 Bath Condo for Rent

Available Now

204 Lake Shore Rd, Unit 1

204 Lake Shore Rd
BostonMA02135
property at 51 Algonquin Rd

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

51 Algonquin Rd

Chestnut HillMA02467
property at 225 Chestnut Hill Ave

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

4 Bedroom, 1 Bath Condo for Rent

Available Now

225 Chestnut Hill Ave, Unit 2

225 Chestnut Hill Ave
BostonMA02135
property at 41 North Crescent Circuit

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

41 North Crescent Circuit, Unit 2

41 North Crescent Circuit
BostonMA02135
property at 43 N Crescent Circuit

$3,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

43 N Crescent Circuit, Unit 2

43 N Crescent Circuit
BostonMA02135
property at 250 Hammond Pond Pky

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

250 Hammond Pond Pky, Unit 1203N

250 Hammond Pond Pky
Chestnut HillMA02467
property at 26 Holly Ln

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

26 Holly Ln, Unit 2

26 Holly Ln
BrooklineMA02467
property at 409 Washington St

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

409 Washington St, Unit 401

409 Washington St
BostonMA02135
property at 51 Algonquin Rd

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

51 Algonquin Rd

Chestnut HillMA02467
property at 145 Englewood Ave

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

145 Englewood Ave, Unit 4

145 Englewood Ave
BostonMA02135
property at 9 Oak Square Ave

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

4 Bedroom, 2 Bath Condo for Rent

Available Now

9 Oak Square Ave, Unit 2

9 Oak Square Ave
BostonMA02135
property at 84 Wallingford Rd

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

3 Bedroom, 2 Bath Condo for Rent

Available Now

84 Wallingford Rd, Unit 1

84 Wallingford Rd
BostonMA02135
property at 110 Academy Hill Rd

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

5 Bedroom, 2 Bath Condo for Rent

Available Now

110 Academy Hill Rd, Unit 1

110 Academy Hill Rd
BostonMA02135
property at 110 Kenrick St

$4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

110 Kenrick St, Unit 1

110 Kenrick St
BostonMA02135
property at 1872 Commonwealth Ave

$4,150

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,150

Total Monthly Price
$4,150

2 Bedroom, 2 Bath Condo for Rent

Available Now

1872 Commonwealth Ave, Unit 408

1872 Commonwealth Ave
BostonMA02135
property at 191 Kenrick St

$4,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

4 Bedroom, 2 Bath Condo for Rent

Available Now

191 Kenrick St, Unit 1

191 Kenrick St
BostonMA02135
property at 1870 Commonwealth Ave

$4,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

2 Bedroom, 1 Bath Condo for Rent

Available Now

1870 Commonwealth Ave, Unit 12A

1870 Commonwealth Ave
BostonMA02135
property at 89 Brayton Rd

$4,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

89 Brayton Rd, Unit 2

89 Brayton Rd
BostonMA02135
property at 328 Washington St

$4,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

4 Bedroom, 2 Bath Condo for Rent

Available Now

328 Washington St, Unit 1

328 Washington St
BostonMA02135
property at 25 Embassy Rd

$4,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,300

Total Monthly Price
$4,300

4 Bedroom, 2 Bath Home for Rent

Available Now

25 Embassy Rd

BostonMA02135
property at 91 Academy Hill Rd

$4,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,400

Total Monthly Price
$4,400

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

91 Academy Hill Rd, Unit 91

91 Academy Hill Rd
BostonMA02135
property at 195 Lake St

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

4 Bedroom, 2 Bath Condo for Rent

Available Now

195 Lake St, Unit 2

195 Lake St
BostonMA02135
property at 91 Wallingford Rd

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

91 Wallingford Rd, Unit 1

91 Wallingford Rd
BostonMA02135
property at 73 Undine Rd

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

4 Bedroom, 2.5 Bath Home for Rent

Available Now

73 Undine Rd

BostonMA02135
property at 35 South St

$4,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,600

Total Monthly Price
$4,600

3 Bedroom, 1 Bath Condo for Rent

Available Now

35 South St, Unit 10

35 South St
BostonMA02135
property at 1999 Commonwealth Ave

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

1999 Commonwealth Ave, Unit 12

1999 Commonwealth Ave
BostonMA02135
property at 25 Greycliff Rd

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
property at 25 Greycliff Rd

$4,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650

3 Bedroom, 1 Bath Condo for Rent

Available Now

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
property at 209 Chestnut Hill Ave

$4,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,700

Total Monthly Price
$4,700

4 Bedroom, 2 Bath Condo for Rent

Available Now

209 Chestnut Hill Ave, Unit 1

209 Chestnut Hill Ave
BostonMA02135
property at 34 Wessex Rd

$4,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,750

Total Monthly Price
$4,750

3 Bedroom, 1.5 Bath Home for Rent

Available Jul 15

34 Wessex Rd

NewtonMA02459
property at 28 Manet Rd

$4,800 - $5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800 - $5,800

Total Monthly Price
$4,800 - $5,800

4 To 5 Bedroom Condos for Rent

Available Now

28 Manet Rd

Chestnut HillMA02467
property at 132 Chiswick Rd

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

5 Bedroom, 2 Bath Condo for Rent

Available Now

132 Chiswick Rd, Unit 2

132 Chiswick Rd
BostonMA02135
property at 4 Mount Vernon St

$4,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

3 Bedroom, 3 Bath Home for Rent

Available Aug 1

4 Mount Vernon St

BostonMA02135
property at 27 Eulita Ter

$4,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,950

Total Monthly Price
$4,950

4 Bedroom, 2 Bath Condo for Rent

Available Now

27 Eulita Ter, Unit 2

27 Eulita Ter
BostonMA02135
property at 209 Chestnut Hill Ave

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

4 Bedroom, 2 Bath Condo for Rent

Available Now

209 Chestnut Hill Ave, Unit 2

209 Chestnut Hill Ave
BostonMA02135
property at 125 Nonantum St

$5,100 - $5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,100 - $5,200

Total Monthly Price
$5,100 - $5,200

4 To 5 Bedroom Condos for Rent

Available Now

125 Nonantum St

BostonMA02135
property at 225 Chestnut Hill Ave

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 1 Bath Condo for Rent

Available Now

225 Chestnut Hill Ave, Unit 1

225 Chestnut Hill Ave
BostonMA02135
property at 120 Kenrick St

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

120 Kenrick St, Unit 1

120 Kenrick St
BostonMA02135
property at 6 Lothian Rd

$5,200 - $5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200 - $5,800

Total Monthly Price
$5,200 - $5,800

4 To 5 Bedroom Condos for Rent

Available Now

6 Lothian Rd

BostonMA02135
property at 6 Lothian Rd

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

6 Lothian Rd, Unit 3

6 Lothian Rd
BostonMA02135
property at 120 Kenrick St

$5,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,200

Total Monthly Price
$5,200

4 Bedroom, 2 Bath Condo for Rent

Available Jul 1

120 Kenrick St, Unit 1

120 Kenrick St
BostonMA02135
property at 7 Lothian Rd

$5,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,300

Total Monthly Price
$5,300

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1

7 Lothian Rd, Unit 3

7 Lothian Rd
BostonMA02135
property at 91 Wallingford Rd

$5,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,400

Total Monthly Price
$5,400

4 Bedroom, 2 Bath Townhome for Rent

Available Sep 1

91 Wallingford Rd

BostonMA02135
property at 539 Commonwealth Ave

$5,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

4 Bedroom, 3 Bath Condo for Rent

Available Now

539 Commonwealth Ave, Unit 2

539 Commonwealth Ave
NewtonMA02459
property at 16 Foster St

$5,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600

Total Monthly Price
$5,600

5 Bedroom, 3 Bath Townhome for Rent

Available Now

16 Foster St

BostonMA02135
property at 110 Kenrick St

$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 Now

110 Kenrick St

BostonMA02135
property at 16 Gerald Rd

$5,600 - $11,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,600 - $11,200

Total Monthly Price
$5,600 - $11,200

3 To 6 Bedroom Condos for Rent

Available Aug 31

16 Gerald Rd

BostonMA02135
property at 47 Algonquin Rd

$5,700 - $5,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,700 - $5,800

Total Monthly Price
$5,700 - $5,800

4 Bedroom, 1.5 Bath Condo for Rent

Available Now

47 Algonquin Rd

Chestnut HillMA02467

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

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention   article

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.

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

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.

decorative image for Pet-Friendly Renting: Everything You Need to Know Before You Move article

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.

decorative image for Creative Ways Developers Reimagine Retail Spaces as Residential Units  article

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.