Luxury Homes for Rent in Chestnut Hill, MA (2,787 Rentals)

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The most luxurious Homes in Chestnut Hill with high-end amenities, features, and finishes.

property at 39 Grove St

39 Grove St, Unit B

39 Grove St
Chestnut HillMA02467
property at 138 Woodland Rd

138 Woodland Rd, Unit 6

138 Woodland Rd
Chestnut HillMA02467
property at 607 Vfw Pky

607 Vfw Pky

Chestnut HillMA02467
property at 46 Gerry Rd

46 Gerry Rd

Chestnut HillMA02467
property at 295 Commonwealth Ave

295 Commonwealth Ave, Unit H-18

295 Commonwealth Ave
Chestnut HillMA02467
property at 146 Independence Dr

146 Independence Dr, Unit 1

146 Independence Dr
Chestnut HillMA02467
property at 35 Commonwealth Ave

35 Commonwealth Ave, Unit U201-1-bed

35 Commonwealth Ave
Chestnut HillMA02467
property at 79 Thornton Rd

79 Thornton Rd

Chestnut HillMA02467
property at 80 Thornton Rd

80 Thornton Rd

Chestnut HillMA02467
property at 51 Thornton Rd

51 Thornton Rd

Chestnut HillMA02467
property at 79 Thornton Rd

79 Thornton Rd, Unit 79

79 Thornton Rd
Chestnut HillMA02467
property at 194 Gerry Rd

194 Gerry Rd

Chestnut HillMA02467
property at 101 Independence Dr

101 Independence Dr, Unit 1

101 Independence Dr
Chestnut HillMA02467
property at 320 Hammond Pond Pky

320 Hammond Pond Pky

Chestnut HillMA02467
property at 1019 W Roxbury Pky

1019 W Roxbury Pky, Unit 2

1019 W Roxbury Pky
Chestnut HillMA02467
property at 231 Gerry Rd

231 Gerry Rd

Chestnut HillMA02467
property at 201 Sherman Rd

201 Sherman Rd, Unit 810

201 Sherman Rd
Chestnut HillMA02467
property at 130 Sherman Rd

130 Sherman Rd, Unit 130

130 Sherman Rd
Chestnut HillMA02467
property at 59 Thornton Rd

59 Thornton Rd

Chestnut HillMA02467
property at 527 Vfw Pky

527 Vfw Pky

Chestnut HillMA02467
property at 241 Gerry Rd

241 Gerry Rd

Chestnut HillMA02467
property at 11 Hammond Pond Pky

11 Hammond Pond Pky, Unit 203

11 Hammond Pond Pky
Chestnut HillMA02467
property at 475 Vfw Pky

475 Vfw Pky, Unit 2

475 Vfw Pky
Chestnut HillMA02467
property at 321 Hammond Pond Pky

321 Hammond Pond Pky, Unit 106

321 Hammond Pond Pky
Chestnut HillMA02467
property at 9 Sherman Rd

9 Sherman Rd

Chestnut HillMA02467
property at 136 Middlesex Rd

136 Middlesex Rd, Unit 2

136 Middlesex Rd
Chestnut HillMA02467
property at 148 Independence Dr

148 Independence Dr

Chestnut HillMA02467
property at 9 Sherman Rd

9 Sherman Rd, Unit 1

9 Sherman Rd
Chestnut HillMA02467
property at 120 Thornton Rd

120 Thornton Rd

Chestnut HillMA02467
property at 33 Gerry Rd

33 Gerry Rd

Chestnut HillMA02467
property at 136 Thornton Rd

136 Thornton Rd, Unit 1

136 Thornton Rd
Chestnut HillMA02467
property at 110 Sherman Rd

110 Sherman Rd

Chestnut HillMA02467
property at 97 Sherman Rd

97 Sherman Rd

Chestnut HillMA02467
property at 499 Vfw Pky

499 Vfw Pky

Chestnut HillMA02467
property at 29 Independence Dr

29 Independence Dr

Chestnut HillMA02467
property at 242 Gerry Rd

242 Gerry Rd

Chestnut HillMA02467
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 47 Algonquin Rd

47 Algonquin Rd, Unit 2

47 Algonquin Rd
Chestnut HillMA02467
property at 9 Reservoir Rd

9 Reservoir Rd, Unit 1

9 Reservoir Rd
Chestnut HillMA02467
property at 47 Algonquin Rd

47 Algonquin Rd, Unit 2

47 Algonquin Rd
Chestnut HillMA02467
property at 250 Hammond Pond Pky

250 Hammond Pond Pky, Unit 1203N

250 Hammond Pond Pky
Chestnut HillMA02467
property at 321 Hammond Pond Pky

321 Hammond Pond Pky, Unit 301

321 Hammond Pond Pky
Chestnut HillMA02467
property at 28 Manet Rd

28 Manet Rd, Unit 2

28 Manet Rd
Chestnut HillMA02467
property at 49 Hackensack Rd

49 Hackensack Rd, Unit 1

49 Hackensack Rd
Chestnut HillMA02467
property at 203 Ellery Ct

203 Ellery Ct, Unit T

203 Ellery Ct
Chestnut HillMA02467

Chestnut Hill, MA Local Guide

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chestnut Hill, MA Rentals by Map

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Frequently Asked Questions about Chestnut Hill

What type of rentals are currently available in Chestnut Hill?

There are currently 3969 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $14,200. There are also 3382 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $750 to $22,000.

What is the current price range for Rental Homes in Chestnut Hill?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestnut Hill ranges from $750 to $22,000 with an average monthly rent of $4,755.

How much are larger Three and Four Bedroom Rentals in Chestnut Hill?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestnut Hill range from $950 to $12,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,050 to $22,000. Four Bedroom Single-Family rentals are also available starting from $900 and Four Bedroom Apartments start at $1,068.

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 10 Best Affordable Neighborhoods in Boston, MA article

The 10 Best Affordable Neighborhoods in Boston, MA

Written by: Amelia Ramstead

Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

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.

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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.