Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (457 Rentals) Page 2 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 178 Lake Shore Rd

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom, 2 Bath Condo for Rent

Available Sep 1

178 Lake Shore Rd, Unit 4

178 Lake Shore Rd
BostonMA02135
property at 2009 Commonwealth Ave

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

2 Bedroom, 1 Bath Condo for Rent

Available Now

2009 Commonwealth Ave, Unit 20

2009 Commonwealth Ave
BostonMA02135
property at 15 South St

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

2 Bedroom, 1 Bath Condo for Rent

Available Now

15 South St, Unit 6

15 South St
BostonMA02135
property at 2 Priscilla Rd

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

2 Priscilla Rd, Unit 1

2 Priscilla Rd
BostonMA02135
property at 27 Commonwealth Ave

$3,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,250

Total Monthly Price
$3,250

1 Bedroom, 1 Bath Condo for Rent

Available Now

27 Commonwealth Ave, Unit 6

27 Commonwealth Ave
Chestnut HillMA02467
property at 148 Strathmore Rd

$3,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,250

Total Monthly Price
$3,250

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

148 Strathmore Rd, Unit 21

148 Strathmore Rd
BostonMA02135
property at 2003 Commonwealth Ave

$3,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,250

Total Monthly Price
$3,250

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

2003 Commonwealth Ave, Unit 20

2003 Commonwealth Ave
BostonMA02135
property at 130 Englewood Ave

$3,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,250

Total Monthly Price
$3,250

2 Bedroom, 1 Bath Condo for Rent

Available Now

130 Englewood Ave, Unit 4

130 Englewood Ave
BostonMA02135
property at 8 Oakland St

$3,300 - $3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300 - $3,500

Total Monthly Price
$3,300 - $3,500

3 Bedroom, 1 Bath Condo for Rent

Available Now

8 Oakland St

BostonMA02135
property at 541 Washington St

$3,300 - $3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300 - $3,400

Total Monthly Price
$3,300 - $3,400

3 Bedroom, 1 Bath Condo for Rent

Available Now

541 Washington St

BostonMA02135
property at 145 Chiswick Rd

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

3 Bedroom, 1 Bath Condo for Rent

Available Now

145 Chiswick Rd, Unit 8

145 Chiswick Rd
BostonMA02135
property at 20 Hammond Pond Pky

$3,300

Total Monthly Price24 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

2 Bedroom, 1 Bath Condo for Rent

Available Aug 1

20 Hammond Pond Pky, Unit 206

20 Hammond Pond Pky
Chestnut HillMA02467
property at 1933 Commonwealth Ave

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

1 Bedroom, 1 Bath Condo for Rent

Available Now

1933 Commonwealth Ave, Unit 47

1933 Commonwealth Ave
BostonMA02135
property at 231 Chestnut Hill Ave

$3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

3 Bedroom, 2 Bath Home for Rent

Available Now

property at 91 Wallingford Rd

$3,350

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,350

Total Monthly Price
$3,350

3 Bedroom, 1 Bath Condo for Rent

Available Now

91 Wallingford Rd, Unit 3

91 Wallingford Rd
BostonMA02135
property at 7 Winship St

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

4 Bedroom, 2 Bath Condo for Rent

Available Now

7 Winship St, Unit 2

7 Winship St
BostonMA02135
property at 66 Foster St

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

2 Bedroom, 2 Bath Condo for Rent

Available Sep 1

66 Foster St, Unit 1

66 Foster St
BostonMA02135
property at 320 Hammond Pond Pkwy

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

2 Bedroom, 2 Bath Condo for Rent

Available Now

320 Hammond Pond Pkwy, Unit 104

320 Hammond Pond Pkwy
NewtonMA02467
property at 29 Mt Vernon St

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

4 Bedroom, 2 Bath Condo for Rent

Available Now

29 Mt Vernon St, Unit 2A

29 Mt Vernon St
BostonMA02135
property at 20 Greymere Rd

$3,400

Total Monthly Price19 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

3 Bedroom, 1 Bath Condo for Rent

Available Now

20 Greymere Rd, Unit B

20 Greymere Rd
BostonMA02135
property at 54 Tremont St

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

3 Bedroom, 1 Bath Condo for Rent

Available Aug 1

54 Tremont St, Unit 3

54 Tremont St
BostonMA02135
property at 370 Chestnut Hill Ave

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

1 Bedroom, 1 Bath Condo for Rent

Available Now

370 Chestnut Hill Ave, Unit 34

370 Chestnut Hill Ave
BostonMA02135
property at 85 Brayton Rd

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

3 Bedroom, 1 Bath Condo for Rent

Available Now

85 Brayton Rd, Unit 2

85 Brayton Rd
BostonMA02135
property at 7 Lothian Rd

$3,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,450

Total Monthly Price
$3,450

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

7 Lothian Rd, Unit 3

7 Lothian Rd
BostonMA02135
property at 505 Washington St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

505 Washington St, Unit 1

505 Washington St
BostonMA02135
property at 25 Crosby Rd

$3,500 - $6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500 - $6,000

Total Monthly Price
$3,500 - $6,000

2 To 4 Bedroom Condos for Rent

Available Now

25 Crosby Rd

Chestnut HillMA02467
property at 22 Eastburn St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1.5 Bath Townhome for Rent

Available Now

22 Eastburn St

BostonMA02135
property at 7 Trapelo St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

7 Trapelo St

BostonMA02135
property at 68 Foster St

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 2 Bath Condo for Rent

Available Sep 1

68 Foster St, Unit 1

68 Foster St
BostonMA02135
property at 145 Chiswick Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 1 Bath Condo for Rent

Available Now

145 Chiswick Rd, Unit 8

145 Chiswick Rd
BostonMA02135
property at 8 Louise Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Sep 1

8 Louise Rd, Unit 2

8 Louise Rd
Chestnut HillMA02467
property at 135 Chiswick Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

135 Chiswick Rd, Unit 4

135 Chiswick Rd
BostonMA02135
property at 14 Louise Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

14 Louise Rd, Unit 1

14 Louise Rd
Chestnut HillMA02467
property at 215 Lake Shore Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Now

215 Lake Shore Rd, Unit 2

215 Lake Shore Rd
BostonMA02135
property at 20 Anselm Ter

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Now

20 Anselm Ter, Unit 1

20 Anselm Ter
BostonMA02135
property at 136 Middlesex Rd

$3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Condo for Rent

Available Now

136 Middlesex Rd, Unit 2

136 Middlesex Rd
Chestnut HillMA02467
property at 27 Willoughby St

$3,650 - $4,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650 - $4,100

Total Monthly Price
$3,650 - $4,100

3 To 4 Bedroom Condos for Rent

Available Now

27 Willoughby St

BostonMA02135
property at 206 Chestnut Hill Ave

$3,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650

Total Monthly Price
$3,650

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

206 Chestnut Hill Ave, Unit 8

206 Chestnut Hill Ave
BostonMA02135
property at 161 Brayton Rd

$3,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,650

Total Monthly Price
$3,650

3 Bedroom, 1 Bath Condo for Rent

Available Now

161 Brayton Rd, Unit 1

161 Brayton Rd
BostonMA02135
property at 5 Glenley Terrace

$3,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

3 Bedroom, 2 Bath Condo for Rent

Available Sep 1

5 Glenley Terrace, Unit 1

5 Glenley Terrace
BostonMA02135
property at 71-73 Chestnut Hill Ave

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

71-73 Chestnut Hill Ave, Unit 2

71-73 Chestnut Hill Ave
BostonMA02135
property at 51 Algonquin Rd

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

51 Algonquin Rd

Chestnut HillMA02467
property at 195 Lake St

$3,800 - $4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800 - $4,500

Total Monthly Price
$3,800 - $4,500

4 To 5 Bedroom Condos for Rent

Available Aug 30

195 Lake St

BostonMA02135
property at 96 Chestnut Hill Ave

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1

96 Chestnut Hill Ave, Unit 73

96 Chestnut Hill Ave
BostonMA02135
property at 27 Bostonia Ave

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

4 Bedroom, 1 Bath Condo for Rent

Available Sep 1

27 Bostonia Ave

BostonMA02135
property at 210 Chestnut Hill Ave

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 2 Bath Condo for Rent

Available Sep 1

210 Chestnut Hill Ave, Unit 6

210 Chestnut Hill Ave
BostonMA02135
property at 135 Chiswick Rd

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1

135 Chiswick Rd, Unit 3

135 Chiswick Rd
BostonMA02135
property at 30 Lake Shore Ct

$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

30 Lake Shore Ct, Unit 1

30 Lake Shore Ct
BostonMA02135

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.