Luxury Homes for Rent in Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (503 Rentals) Page 2 of 11

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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 91 Wallingford Rd

91 Wallingford Rd, Unit 3

91 Wallingford Rd
BostonMA02135
property at 31 Lake Shore Ct

31 Lake Shore Ct, Unit 3

31 Lake Shore Ct
BostonMA02135
property at 51 Lake Shore Ct

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 51 Lake Shore Ct

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 39 Foster St

39 Foster St, Unit 1

39 Foster St
BostonMA02135
property at 159 Foster St

159 Foster St, Unit 1

159 Foster St
BostonMA02135
property at 51 Lake Shore Ct

51 Lake Shore Ct, Unit 1

51 Lake Shore Ct
BostonMA02135
property at 19 Beecher Ter

19 Beecher Ter

NewtonMA02459
property at 35 Foster St

35 Foster St, Unit 1

35 Foster St
BostonMA02135
property at 135 Chiswick Rd

135 Chiswick Rd, Unit 6

135 Chiswick Rd
BostonMA02135
property at 19 Chestnut Hill Ave

19 Chestnut Hill Ave, Unit 1

19 Chestnut Hill Ave
BostonMA02135
property at 2012 Commonwealth Ave

2012 Commonwealth Ave, Unit BE

2012 Commonwealth Ave
BostonMA02135
property at 43 N Crescent Circuit

43 N Crescent Circuit, Unit 1

43 N Crescent Circuit
BostonMA02135
property at 249 Chestnut Hill Ave

249 Chestnut Hill Ave, Unit 1

249 Chestnut Hill Ave
BostonMA02135
property at 29 Eastburn St

29 Eastburn St, Unit 2

29 Eastburn St
BostonMA02135
property at 14 Lyne Rd

14 Lyne Rd, Unit 1

14 Lyne Rd
BostonMA02135
property at 211 Lake Shore Rd

211 Lake Shore Rd, Unit 2

211 Lake Shore Rd
BostonMA02135
property at 1880 Commonwealth Ave

1880 Commonwealth Ave, Unit 12

1880 Commonwealth Ave
BostonMA02135
property at 35 Commonwealth Ave

35 Commonwealth Ave, Unit U201-1-bed

35 Commonwealth Ave
Chestnut HillMA02467
property at 440 Washington St

440 Washington St, Unit 3

440 Washington St
BostonMA02135
property at 440 Washington St

440 Washington St, Unit 3

440 Washington St
BostonMA02135
property at 440 Washington St

440 Washington St, Unit 3

440 Washington St
BostonMA02135
property at 440 Washington St

440 Washington St, Unit 3

440 Washington St
BostonMA02135
property at 8 Mt Vernon St

8 Mt Vernon St

BostonMA02135
property at 21 Chestnut Hill Ave

21 Chestnut Hill Ave, Unit 1

21 Chestnut Hill Ave
BostonMA02135
property at 2001 Commonwealth Ave

2001 Commonwealth Ave, Unit 16

2001 Commonwealth Ave
BostonMA02135
property at 295 Commonwealth Ave

295 Commonwealth Ave, Unit H-18

295 Commonwealth Ave
Chestnut HillMA02467
property at 288 Foster St

288 Foster St, Unit 2

288 Foster St
BostonMA02135
property at 2035 Commonwealth Ave

2035 Commonwealth Ave, Unit 9

2035 Commonwealth Ave
BostonMA02135
property at 2 Portina Rd

2 Portina Rd, Unit 2

2 Portina Rd
BostonMA02135
property at 92 Langley Rd

92 Langley Rd, Unit 2

92 Langley Rd
NewtonMA02459
property at 99 Chestnut Hill Ave

99 Chestnut Hill Ave, Unit 313

99 Chestnut Hill Ave
BostonMA02135
property at 99 Chestnut Hill Ave

99 Chestnut Hill Ave, Unit 313

99 Chestnut Hill Ave
BostonMA02135
property at 55 Chestnut Hill Ave

55 Chestnut Hill Ave, Unit 313

55 Chestnut Hill Ave
BostonMA02135
property at 247 Chestnut Hill Ave

247 Chestnut Hill Ave, Unit 3

247 Chestnut Hill Ave
BostonMA02135
property at 27 Brock St

27 Brock St, Unit 1

27 Brock St
BostonMA02135
property at 16 Brock St

16 Brock St, Unit 1

16 Brock St
BostonMA02135
property at 1 Oneil Pl

1 Oneil Pl, Unit 1

1 Oneil Pl
BostonMA02135
property at 6 Leicester St

6 Leicester St, Unit 1

6 Leicester St
BostonMA02135
property at 183 Chestnut Hill Ave

183 Chestnut Hill Ave, Unit 6

183 Chestnut Hill Ave
BostonMA02135
property at 2009 Commonwealth Ave

2009 Commonwealth Ave, Unit 20

2009 Commonwealth Ave
BostonMA02135
property at 550 Washington St

550 Washington St, Unit 1

550 Washington St
BostonMA02135
property at 505 Washington St

505 Washington St, Unit 3

505 Washington St
BostonMA02135
property at 541 Washington St

541 Washington St, Unit 1

541 Washington St
BostonMA02135
property at 2016 Commonwealth Ave
property at 276 Chestnut Hill Ave

276 Chestnut Hill Ave, Unit 25

276 Chestnut Hill Ave
BostonMA02135
property at 58 Winship St

58 Winship St

BostonMA02135
property at 16 Chestnut Hill Ave

16 Chestnut Hill Ave, Unit 3

16 Chestnut Hill Ave
BostonMA02135
property at 1933 Commonwealth Ave

1933 Commonwealth Ave, Unit 12

1933 Commonwealth Ave
BostonMA02135

Frequently Asked Questions about Chestnut Hill Middlesex

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

There are currently 716 Apartments for Rent in Chestnut Hill Middlesex, MA with pricing that ranges from $1,850 to $17,000. There are also 588 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill Middlesex ranging from $950 to $40,000.

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 $950 to $40,000 with an average monthly rent of $5,829.

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 $6,260, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,550 to $6,900. Four Bedroom Single-Family rentals are also available starting from $1,025 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 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.

decorative image for The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro article

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

decorative image for Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting article

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.