Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (404 Rentals) Page 4 of 9

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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 137 Chiswick Terrace

137 Chiswick Terrace, Unit 5

137 Chiswick Terrace
BostonMA02135
property at 84 Wallingford Rd

84 Wallingford Rd, Unit 1

84 Wallingford Rd
BostonMA02135
property at 321 Hammond Pond Pky

321 Hammond Pond Pky, Unit 301

321 Hammond Pond Pky
Chestnut HillMA02467
property at 9 Oak Square Ave

9 Oak Square Ave, Unit 2

9 Oak Square Ave
BostonMA02135
property at 370 Chestnut Hill Ave

370 Chestnut Hill Ave, Unit 21

370 Chestnut Hill Ave
BostonMA02135
property at 96 Chestnut Hill Ave

96 Chestnut Hill Ave, Unit 2

96 Chestnut Hill Ave
BostonMA02135
property at 370 Chestnut Hill Ave

370 Chestnut Hill Ave, Unit 21

370 Chestnut Hill Ave
BostonMA02135
property at 1870 Commonwealth Ave

1870 Commonwealth Ave, Unit 12A

1870 Commonwealth Ave
BostonMA02135
property at 1997 Commonwealth Ave

1997 Commonwealth Ave, Unit 7

1997 Commonwealth Ave
BostonMA02135
property at 16 Priscilla Rd

16 Priscilla Rd, Unit 2

16 Priscilla Rd
BostonMA02135
property at 4 Langley Rd

4 Langley Rd

BostonMA02135
property at 328 Washington St

328 Washington St, Unit 1

328 Washington St
BostonMA02135
property at 89 Brayton Rd

89 Brayton Rd, Unit 2

89 Brayton Rd
BostonMA02135
property at 99 Chestnut Hill Ave

99 Chestnut Hill Ave, Unit 318

99 Chestnut Hill Ave
BostonMA02135
property at 35 Henshaw St

35 Henshaw St, Unit 1ZB

35 Henshaw St
BostonMA02135
property at 25 Embassy Rd

25 Embassy Rd

BostonMA02135
property at 83 Academy Hill Rd

83 Academy Hill Rd, Unit 1

83 Academy Hill Rd
BostonMA02135
property at 2017 Commonwealth Ave

2017 Commonwealth Ave, Unit #1

2017 Commonwealth Ave
BostonMA02135
property at 80 Wallingford Rd

80 Wallingford Rd, Unit 1

80 Wallingford Rd
BostonMA02135
property at 80 Wallingford Rd

80 Wallingford Rd, Unit 1

80 Wallingford Rd
BostonMA02135
property at 1870 Commonwealth Ave

1870 Commonwealth Ave, Unit 12A

1870 Commonwealth Ave
BostonMA02135
property at 73 Undine Rd

73 Undine Rd

BostonMA02135
property at 195 Lake St

195 Lake St, Unit 2

195 Lake St
BostonMA02135
property at 3 Glenley Ter

3 Glenley Ter

BostonMA02135
property at 35 South St

35 South St, Unit 10

35 South St
BostonMA02135
property at 276 Chestnut Hill Ave

276 Chestnut Hill Ave, Unit 9

276 Chestnut Hill Ave
BostonMA02135
property at 35 Winship St

35 Winship St, Unit 2

35 Winship St
BostonMA02135
property at 258 Chestnut Hill Ave

258 Chestnut Hill Ave, Unit 9

258 Chestnut Hill Ave
BostonMA02135
property at 25 Greycliff Rd

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
property at 25 Greycliff Rd

25 Greycliff Rd, Unit 1

25 Greycliff Rd
BostonMA02135
property at 209 Chestnut Hill Ave

209 Chestnut Hill Ave, Unit 1

209 Chestnut Hill Ave
BostonMA02135
property at 29 Mount Vernon St

29 Mount Vernon St, Unit 2

29 Mount Vernon St
BostonMA02135
property at 81 Chestnut Hill Ave

81 Chestnut Hill Ave, Unit 1

81 Chestnut Hill Ave
BostonMA02135
property at 508 Heath St

508 Heath St, Unit 1

508 Heath St
BrooklineMA02467
property at 28 Manet Rd

28 Manet Rd, Unit 2

28 Manet Rd
Chestnut HillMA02467
property at 132 Chiswick Rd

132 Chiswick Rd, Unit 2

132 Chiswick Rd
BostonMA02135
property at 27 Eulita Ter

27 Eulita Ter, Unit 2

27 Eulita Ter
BostonMA02135
property at 209 Chestnut Hill Ave

209 Chestnut Hill Ave, Unit 2

209 Chestnut Hill Ave
BostonMA02135
property at 16 Priscilla Rd

16 Priscilla Rd, Unit 2

16 Priscilla Rd
BostonMA02135
property at 209 Chestnut Hill Ave
property at 36 Kenrick St

36 Kenrick St, Unit 1

36 Kenrick St
BostonMA02135
property at 49 Breck Ave

49 Breck Ave

BostonMA02135
property at 49 Breck Ave

49 Breck Ave

BostonMA02135
property at 91 Wallingford Rd

91 Wallingford Rd

BostonMA02135
property at 28 Manet Rd

28 Manet Rd, Unit 2

28 Manet Rd
Chestnut HillMA02467
property at 120 Kenrick St

120 Kenrick St, Unit 1

120 Kenrick St
BostonMA02135
property at 16 Foster St

16 Foster St

BostonMA02135
property at 16 Gerald Rd

16 Gerald Rd, Unit 1

16 Gerald Rd
BostonMA02135
property at 16 Gerald Rd

16 Gerald Rd, Unit 1

16 Gerald Rd
BostonMA02135

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 431 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,050 to $13,500. There are also 470 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $850 to $36,000.

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 $850 to $36,000 with an average monthly rent of $7,107.

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 $5,955, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $6,500. Four Bedroom Single-Family rentals are also available starting from $1,080 and Four Bedroom Apartments start at $3,200.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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.

decorative image for Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between article

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.