Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (403 Rentals) Page 3 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 54 Tremont St

54 Tremont St, Unit 3

54 Tremont St
BostonMA02135
property at 85 Brayton Rd

85 Brayton Rd, Unit 2

85 Brayton Rd
BostonMA02135
property at 320 Hammond Pond Pkwy

320 Hammond Pond Pkwy, Unit 104

320 Hammond Pond Pkwy
NewtonMA02467
property at 36 Colwell Ave

36 Colwell Ave, Unit 1

36 Colwell Ave
BostonMA02135
property at 11 Hammond Pond Pky

11 Hammond Pond Pky, Unit 203

11 Hammond Pond Pky
Chestnut HillMA02467
property at 7 Lothian Rd

7 Lothian Rd, Unit 11

7 Lothian Rd
BostonMA02135
property at 39 Foster St

39 Foster St, Unit 1a

39 Foster St
BostonMA02135
property at 39 Foster St

39 Foster St, Unit 1

39 Foster St
BostonMA02135
property at 22 Eastburn St

22 Eastburn St

BostonMA02135
property at 27 South Crescent Circuit

27 South Crescent Circuit, Unit A

27 South Crescent Circuit
BostonMA02135
property at 505 Washington St

505 Washington St, Unit 1

505 Washington St
BostonMA02135
property at 71 Foster St

71 Foster St, Unit 1

71 Foster St
BostonMA02135
property at 16 Dighton St

16 Dighton St, Unit 1

16 Dighton St
BostonMA02135
property at 7 North Crescent Circuit
property at 152 Lake St

152 Lake St, Unit 1

152 Lake St
BostonMA02135
property at 6 South St

6 South St, Unit uni3 2-bed 1-bath

6 South St
BostonMA02135
property at 41 North Crescent Circuit

41 North Crescent Circuit, Unit 2

41 North Crescent Circuit
BostonMA02135
property at 22 Eastburn St

22 Eastburn St

BostonMA02135
property at 321 Hammond Pond Pky

321 Hammond Pond Pky, Unit 106

321 Hammond Pond Pky
Chestnut HillMA02467
property at 27 S Crescent Circuit

27 S Crescent Circuit, Unit B

27 S Crescent Circuit
BostonMA02135
property at 27 South Crescent Circuit

27 South Crescent Circuit, Unit A

27 South Crescent Circuit
BostonMA02135
property at 386 Market St

386 Market St, Unit 2

386 Market St
BostonMA02135
property at 201 Langley Rd

201 Langley Rd, Unit 201

201 Langley Rd
NewtonMA02459
property at 136 Middlesex Rd

136 Middlesex Rd, Unit 2

136 Middlesex Rd
Chestnut HillMA02467
property at 215 Lake Shore Rd

215 Lake Shore Rd, Unit 2

215 Lake Shore Rd
BostonMA02135
property at 20 Anselm Ter

20 Anselm Ter, Unit 1

20 Anselm Ter
BostonMA02135
property at 96 Brayton Rd

96 Brayton Rd

BostonMA02135
property at 231 Chestnut Hill Ave

231 Chestnut Hill Ave, Unit 3

231 Chestnut Hill Ave
BostonMA02135
property at 27 Willoughby St

27 Willoughby St, Unit 1

27 Willoughby St
BostonMA02135
property at 161 Brayton Rd

161 Brayton Rd, Unit 1

161 Brayton Rd
BostonMA02135
property at 133 Chiswick Rd

133 Chiswick Rd, Unit B

133 Chiswick Rd
BostonMA02135
property at 104 Strathmore Rd

104 Strathmore Rd, Unit 1

104 Strathmore Rd
BostonMA02135
property at 133 Chiswick Rd

133 Chiswick Rd

BostonMA02135
property at 2 Chestnut Pl

2 Chestnut Pl, Unit 1

2 Chestnut Pl
BostonMA02135
property at 5 Glenley Terrace

5 Glenley Terrace, Unit 1

5 Glenley Terrace
BostonMA02135
property at 163 Chestnut Hill Ave
property at 58 Winship St

58 Winship St

BostonMA02135
property at 1999 Commonwealth Ave

1999 Commonwealth Ave, Unit 12

1999 Commonwealth Ave
BostonMA02135
property at 99 Chestnut Hill Ave

99 Chestnut Hill Ave, Unit 316

99 Chestnut Hill Ave
BostonMA02135
property at 56 Winship St

56 Winship St, Unit 102

56 Winship St
BostonMA02135
property at 517 Washington St

517 Washington St, Unit 2

517 Washington St
BostonMA02135
property at 204 Lake Shore Rd

204 Lake Shore Rd, Unit 1

204 Lake Shore Rd
BostonMA02135
property at 25 Crosby Rd

25 Crosby Rd

Chestnut HillMA02467
property at 51 Algonquin Rd

51 Algonquin Rd

Chestnut HillMA02467
property at 51 Algonquin Rd

51 Algonquin Rd

Chestnut HillMA02467
property at 1945 Commonwealth Ave

1945 Commonwealth Ave, Unit 13C

1945 Commonwealth Ave
BostonMA02135
property at 47 Algonquin Rd

47 Algonquin Rd, Unit 2

47 Algonquin Rd
Chestnut HillMA02467
property at 26 Holly Ln

26 Holly Ln, Unit 2

26 Holly Ln
BrooklineMA02467
property at 250 Hammond Pond Pky

250 Hammond Pond Pky, Unit 1203N

250 Hammond Pond Pky
Chestnut HillMA02467
property at 47 Algonquin Rd

47 Algonquin Rd, Unit 2

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 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 $980 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 $980 to $36,000 with an average monthly rent of $6,807.

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 $3,150.

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.