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

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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 140 Kenrick St

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

140 Kenrick St, Unit Apt 23

140 Kenrick St
BostonMA02135
property at 1840 Commonwealth Ave

$2,175 - $2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,175 - $2,650

Total Monthly Price
$2,175 - $2,650

Studio To 1 Bedroom Condos for Rent

Available Sep 1

property at 1872 Commonwealth Ave

$2,295 - $3,795

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,295 - $3,795

Total Monthly Price
$2,295 - $3,795

1 To 4 Bedroom Condos for Rent

Available Sep 1

property at 1982 Commonwealth Ave

$2,300 - $3,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,300 - $3,300

Total Monthly Price
$2,300 - $3,300

1 To 3 Bedroom Condos for Rent

Available Sep 1

property at 99 Chestnut Hill Ave

$2,300 - $3,325

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,300 - $3,325

Total Monthly Price
$2,300 - $3,325

Studio To 2 Bedroom Condos for Rent

Available Now

property at 247 Chestnut Hill Ave

$2,350 - $3,125

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,350 - $3,125

Total Monthly Price
$2,350 - $3,125

Studio To 2 Bedroom Condos for Rent

Available Now

property at 4 Chiswick Rd

$2,400 - $2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400 - $2,500

Total Monthly Price
$2,400 - $2,500

Studio To 1 Bedroom Condos for Rent

Available Aug 1

4 Chiswick Rd

BostonMA02135
property at 302 Washington St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

302 Washington St, Unit 4

302 Washington St
BostonMA02135
property at 185 Chestnut Hill Ave

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

Studio, 1 Bath Condo for Rent

Available Now

185 Chestnut Hill Ave, Unit 6

185 Chestnut Hill Ave
BostonMA02135
property at 34 Foster St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

34 Foster St, Unit 1

34 Foster St
BostonMA02135

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property at 85 Wallingford Rd

$2,525 - $2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,525 - $2,950

Total Monthly Price
$2,525 - $2,950

1 To 2 Bedroom Condos for Rent

Available Now

85 Wallingford Rd

BostonMA02135
property at 142 Kenrick St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Now

142 Kenrick St, Unit 38

142 Kenrick St
BostonMA02135
property at 2 Hammond Pond Pky

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

2 Hammond Pond Pky, Unit 604

2 Hammond Pond Pky
Chestnut HillMA02467
property at 27 South St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 Bedroom, 1 Bath Condo for Rent

Available Now

27 South St, Unit #B3

27 South St
BostonMA02135
property at 2 Braemore Rd

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 Bedroom, 1 Bath Condo for Rent

Available Jul 1

2 Braemore Rd, Unit A

2 Braemore Rd
BostonMA02135
property at 2039 Commonwealth Ave

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 Bedroom, 1 Bath Condo for Rent

Available Sep 1

2039 Commonwealth Ave, Unit 11

2039 Commonwealth Ave
BostonMA02135
property at 164 Strathmore Rd

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 Bedroom, 1 Bath Condo for Rent

Available Sep 1

164 Strathmore Rd, Unit 25

164 Strathmore Rd
BostonMA02135
property at 9 Braemore Rd

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

1 Bedroom, 1 Bath Condo for Rent

Available Now

9 Braemore Rd, Unit 12

9 Braemore Rd
BostonMA02135
property at 9 Braemore Rd

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

9 Braemore Rd, Unit 1A

9 Braemore Rd
BostonMA02135
property at 137 Chiswick Rd

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Aug 31

137 Chiswick Rd, Unit 114

137 Chiswick Rd
BostonMA02135

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Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

property at 140 Kenrick St

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Condo for Rent

Available Now

140 Kenrick St, Unit #4

140 Kenrick St
BostonMA02135
property at 308 Washington St

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

308 Washington St, Unit 5

308 Washington St
BostonMA02135
property at 1933 Commonwealth Ave

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

1 Bedroom, 1 Bath Condo for Rent

Available Now

1933 Commonwealth Ave, Unit 504

1933 Commonwealth Ave
BostonMA02135
property at 145 Chiswick Rd

$2,700 - $3,450

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700 - $3,450

Total Monthly Price
$2,700 - $3,450

3 Bedroom, 1 Bath Condo for Rent

Available Aug 1

145 Chiswick Rd

BostonMA02135
property at 2 Braemore Rd

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

1 Bedroom, 1 Bath Condo for Rent

Available Now

2 Braemore Rd, Unit 1

2 Braemore Rd
BostonMA02135
property at 14 Caltha Rd

$2,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

2 Bedroom, 1 Bath Condo for Rent

Available Now

14 Caltha Rd, Unit 1P

14 Caltha Rd
BostonMA02135
property at 50 Radnor Rd

$2,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

50 Radnor Rd, Unit 1A

50 Radnor Rd
BostonMA02135
property at 137 Chiswick Rd

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

3 Bedroom, 1 Bath Condo for Rent

Available Now

137 Chiswick Rd, Unit 3

137 Chiswick Rd
BostonMA02135
property at 22 Shanley St

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

22 Shanley St

BostonMA02135
property at 29 Wiltshire Rd

$2,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

3 Bedroom, 1 Bath Condo for Rent

Available Sep 1

29 Wiltshire Rd, Unit 1

29 Wiltshire Rd
BostonMA02135

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property at 9R Winship St

$2,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

2 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

9R Winship St

BostonMA02135
property at 386 Market St

$2,850 - $3,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,850 - $3,600

Total Monthly Price
$2,850 - $3,600

1 To 2 Bedroom Condos for Rent

Available Sep 1

386 Market St

BostonMA02135
property at 132 Chiswick Rd

$2,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

2 Bedroom, 1 Bath Condo for Rent

Available Now

132 Chiswick Rd, Unit 1B

132 Chiswick Rd
BostonMA02135
property at 51 Lake Shore Ct

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 2012 Commonwealth Ave

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

2012 Commonwealth Ave, Unit BE

2012 Commonwealth Ave
BostonMA02135
property at 16 Dighton St

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

4 Bedroom, 2 Bath Condo for Rent

Available Now

16 Dighton St, Unit 2

16 Dighton St
BostonMA02135
property at 135 Chiswick Rd

$2,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

3 Bedroom, 1 Bath Condo for Rent

Available Now

135 Chiswick Rd, Unit 6

135 Chiswick Rd
BostonMA02135
property at 1868 Commonwealth Ave

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

1868 Commonwealth Ave, Unit 5

1868 Commonwealth Ave
BostonMA02135
property at 14 Lyne Rd

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Now

14 Lyne Rd, Unit 1

14 Lyne Rd
BostonMA02135
property at 1880 Commonwealth Ave

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Now

1880 Commonwealth Ave, Unit 12

1880 Commonwealth 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 1880 Commonwealth Ave

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

1880 Commonwealth Ave, Unit 5

1880 Commonwealth Ave
BostonMA02135
property at 1999 Commonwealth Ave

$2,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Condo for Rent

Available Aug 29

1999 Commonwealth Ave, Unit 4

1999 Commonwealth Ave
BostonMA02135
property at 24 Wallingford Rd

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

24 Wallingford Rd, Unit 5

24 Wallingford Rd
BostonMA02135
property at 21 Chestnut Hill Ave

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

21 Chestnut Hill Ave, Unit 1

21 Chestnut Hill Ave
BostonMA02135
property at 2001 Commonwealth Ave

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 1 Bath Condo for Rent

Available Now

2001 Commonwealth Ave, Unit 16

2001 Commonwealth Ave
BostonMA02135
property at 137 Chiswick Rd

$3,000 - $3,005

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000 - $3,005

Total Monthly Price
$3,000 - $3,005

3 To 4 Bedroom Condos for Rent

Available Now

137 Chiswick Rd

BostonMA02135
property at 161 Lake Shore Rd

$3,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

3 Bedroom, 2 Bath Condo for Rent

Available Now

161 Lake Shore Rd, Unit 2A

161 Lake Shore Rd
BostonMA02135
property at 129 Chiswick Rd

$3,050

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,050

Total Monthly Price
$3,050

2 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

129 Chiswick Rd

BostonMA02135
property at 550 Washington St

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom, 1 Bath Condo for Rent

Available Now

550 Washington St, Unit 1

550 Washington St
BostonMA02135

Chestnut Hill Middlesex, Boston College, MA Local Guide

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

Read Article
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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

decorative image of people with a giant lease agreement

Pet Friendly Lifestyle
Chestnut Hill Middlesex, Chestnut Hill, MA

Ranked #1

Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

3.5
Pet Friendly

decorative image of woman handing cat to small boy

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 411 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $960 to $17,000. There are also 568 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.

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.

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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.