Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (358 Rentals) Page 5 of 8

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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 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 Crosby Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 2 Bath Condo for Rent

Available Now

25 Crosby Rd, Unit 2

25 Crosby Rd
Chestnut HillMA02467
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 47 Crosby Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

47 Crosby Rd, Unit 2

47 Crosby Rd
Chestnut HillMA02467
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 64 Langley Rd

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

4 Bedroom, 2.5 Bath Home for Rent

Available Now

64 Langley Rd

BostonMA02135
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, 2026

153 Foster St, Unit 1

153 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 Home for Rent

Available Now

1 Glenley Terrace

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 66 Kirkwood Rd

$6,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,200

Total Monthly Price
$6,200

4 Bedroom, 1 Bath Home for Rent

Available Now

66 Kirkwood Rd

BostonMA02135
property at 55 Chestnut Hill Ave

$6,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,400

Total Monthly Price
$6,400

6 Bedroom, 3 Bath Condo for Rent

Available Now

55 Chestnut Hill Ave, Unit 2

55 Chestnut Hill Ave
BostonMA02135
property at 25 Wade St

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 3.5 Bath Home for Rent

Available Now

25 Wade St

BostonMA02135
property at 120 Lake St

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

6 Bedroom, 3 Bath Townhome for Rent

Available Now

120 Lake St

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, 2026

29 Gerald Rd, Unit 1

29 Gerald Rd
BostonMA02135
property at 20 Manet Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1, 2026

20 Manet Rd, Unit 1

20 Manet Rd
Chestnut HillMA02467
property at 28 Manet Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1, 2026

28 Manet Rd, Unit 1

28 Manet Rd
Chestnut HillMA02467
property at 36 Manet Rd

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 1.5 Bath Condo for Rent

Available Sep 1, 2026

36 Manet Rd, Unit #1

36 Manet Rd
Chestnut HillMA02467
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, 2026

29 Gerald Rd, Unit 2##

29 Gerald Rd
BostonMA02135
property at 25 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, 2026

25 Gerald Rd, Unit 1

25 Gerald Rd
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 5 Radnor Rd

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

4 Bedroom, 1 Bath Condo for Rent

Available Aug 30, 2026

5 Radnor Rd, Unit 2

5 Radnor Rd
BostonMA02135
property at 68 Manet Rd

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

4 Bedroom, 3 Bath Condo for Rent

Available Sep 1, 2026

68 Manet Rd, Unit 1

68 Manet Rd
Chestnut HillMA02467
property at 288 Foster St

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

5 Bedroom, 2 Bath Condo for Rent

Available Now

288 Foster St, Unit 2

288 Foster St
BostonMA02135
property at 289 Foster St

$7,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,500

Total Monthly Price
$7,500

4 Bedroom, 1 Bath Townhome for Rent

Available Now

289 Foster St, Unit #1

289 Foster St
BostonMA02135
property at 44 Kirkwood Rd

$7,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,500

Total Monthly Price
$7,500

5 Bedroom, 2 Bath Condo for Rent

Available Jan 1, 2026

44 Kirkwood Rd, Unit X

44 Kirkwood Rd
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, 2026

2021 Commonwealth Ave, Unit 2

2021 Commonwealth Ave
BostonMA02135
property at 116 Lake St

$8,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,400

Total Monthly Price
$8,400

6 Bedroom, 4 Bath Home for Rent

Available Now

116 Lake St

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 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 27 Bostonia Ave

$9,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,500

Total Monthly Price
$9,500

6 Bedroom, 2.5 Bath Condo for Rent

Available Now

27 Bostonia Ave

BrightonMA02135
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 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, 2026

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 Townhome for Rent

Available Sep 1, 2026

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 Home for Rent

Available Aug 31, 2026

44 Kirkwood Rd

BostonMA02135
property at 46 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 Sep 1, 2026

46 Kirkwood Rd, Unit #1

46 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, 2026

44 Kirkwood Rd, Unit 1

44 Kirkwood Rd
BostonMA02135
property at 64 Greycliff Rd

$10,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$10,000

Total Monthly Price
$10,000

1 Bedroom, 1 Bath Townhome for Rent

Available Now

64 Greycliff Rd, Unit 1

64 Greycliff Rd
BostonMA02135
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, 2026

52 Greycliff 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, 2026

44 Greycliff Rd, Unit 1

44 Greycliff Rd
BostonMA02135
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, 2026

52 Greycliff 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, 2026

44 Greycliff Rd, Unit 1

44 Greycliff Rd
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, 2026

44 Bostonia Ave, Unit 1

44 Bostonia Ave
BrightonMA02135
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, 2026

52 Bostonia Ave, Unit 1

52 Bostonia Ave
BrightonMA02135
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, 2026

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 Sep 1, 2027

52 Greycliff 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, 2026

46 Bostonia Ave, Unit 1

46 Bostonia Ave
BrightonMA02135
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, 2026

46 Kirkwood Rd

BostonMA02135

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 452 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $14,300. There are also 415 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $760 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 $760 to $17,500 with an average monthly rent of $7,073.

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 $2,550 to $6,285, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $7,000. Four Bedroom Single-Family rentals are also available starting from $860 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

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

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.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.