317 Summit Ave, Unit 5
317 Summit Ave
BostonMA02135
Luxury Homes for Rent in Chestnut Hill, MA (2,795 Rentals) Page 14 of 56
The most luxurious Homes in Chestnut Hill with high-end amenities, features, and finishes.
21 Sutherland Rd, Unit 1
21 Sutherland Rd
BostonMA02135
1788 Beacon St
BrooklineMA02445
16 Birch Rd
WatertownMA02472
1774 Beacon St
BrooklineMA02445
55 Glenellen Rd
BostonMA02132
344 Hyde Park Ave
BostonMA02131
9 Gardner St
BostonMA02134
18 Cresthill Rd
BostonMA02135
1515 Commonwealth Ave
BostonMA02135
11 Holton St, Unit 2
11 Holton St
BostonMA02134
28 Saint Paul St, Unit 1
28 Saint Paul St
BrooklineMA02446
11 Holton St, Unit 2
11 Holton St
BostonMA02134
16 Chestnut Hill Ave, Unit 3
16 Chestnut Hill Ave
BostonMA02135
32 Linden St, Unit 2
32 Linden St
BostonMA02134
202 Market St, Unit 2
202 Market St
BostonMA02135
202 Market St, Unit 2
202 Market St
BostonMA02135
15 North Beacon St, Unit 905
15 North Beacon St
BostonMA02134
15 Parkton Rd, Unit 3
15 Parkton Rd
BostonMA02130
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$3,000
Plus Fees
3 Bedroom Apartments Available Now36 Boulevard Terrace
36 Boulevard TerraceBoston, MA 02134
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50 Broadlawn Park
BostonMA02467
1774 Beacon St, Unit 6
1774 Beacon St
BrooklineMA02445
151 Coolidge Ave
WatertownMA02472
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$3,010
Total Monthly Price
2 Bedroom Apartments Available Jan 18, 2026Total Monthly Price
Base Rent
$2,570
Required Monthly Fees
$440
Total Monthly Price
$3,010
35 South St
35 South StBoston, MA 02135
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$3,020
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,580
Required Monthly Fees
$440
Total Monthly Price
$3,020
181 Washington St
181 Washington StBoston, MA 02135
67 Chiswick Rd, Unit F-1
67 Chiswick Rd
BostonMA02135
1440 Beacon St
BrooklineMA02446
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$3,040
Plus Fees
1 Bedroom Apartments Available Now270 Independence Dr
270 Independence DrBoston, MA 02467
116 Englewood Ave, Unit 13
116 Englewood Ave
BostonMA02135
100 Linden St, Unit #1
100 Linden St
BostonMA02134
1179 Commonwealth Ave, Unit 1185 #17
1179 Commonwealth Ave
BostonMA02134
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$3,050
Plus Fees
1 Bedroom Apartments Available Jan 1, 20261079 Commonwealth Ave
1079 Commonwealth AveBoston, MA 02215
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$3,050
Plus Fees
1 Bedroom Apartments Available Jan 1, 20261079 Commonwealth Ave
1079 Commonwealth AveBoston, MA 02215
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$3,075
Plus Fees
2 Bedroom Apartments Available Now53 Manchester Rd
53 Manchester RdBrookline, MA 02446
303 Tappan St, Unit 1B
303 Tappan St
BrooklineMA02445
312 Tappan St
BrooklineMA02445
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$3,080
Total Monthly Price
Studio Apartments Available Jun 1, 2026Total Monthly Price
Base Rent
$2,720
Required Monthly Fees
$360
Total Monthly Price
$3,080
1440 Beacon St
1440 Beacon StBrookline, MA 02446
1186 Commonwealth Ave
BostonMA02134
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59 Manchester Rd, Unit 6
59 Manchester Rd
BrooklineMA02446
59 Manchester Rd, Unit 6
59 Manchester Rd
BrooklineMA02446
53 Manchester Rd, Unit 5
53 Manchester Rd
BrooklineMA02446
172 Fuller St, Unit 3
172 Fuller St
BrooklineMA02446
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Chestnut Hill, MA Local Guide
How much does it cost to rent a home in Chestnut Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Chestnut Hill 2 Bedroom Homes for Rent | $3,201 | $1,080 | $9,750 |
| Chestnut Hill 3 Bedroom Homes for Rent | $3,967 | $925 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $4,514 | $830 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $5,632 | $750 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,603 | $760 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $2,352 | $825 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Frequently Asked Questions about Chestnut Hill
What type of rentals are currently available in Chestnut Hill?
There are currently 3978 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $14,200. There are also 3358 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 $4,883.
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 $925 to $22,000. Four Bedroom Single-Family rentals are also available starting from $830 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.
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.
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.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
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.