49 Englewood Ave
BostonMA02135
Homes for Rent in Chestnut Hill, MA Under $5,500 (3,605 Rentals) Page 20 of 73
1650 Commonwealth Ave
BostonMA02135
1137 Commonwealth Ave
BostonMA02215
193 Winthrop Rd
BrooklineMA02445
55 Brighton Ave, Unit 202
55 Brighton Ave
BostonMA02134
19 Pond St, Unit 2
19 Pond St
BostonMA02130
46 Leo M Birmingham Pky, Unit 408
46 Leo M Birmingham Pky
BostonMA02135
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$4,090
Total Monthly Price
2 Bedroom Apartments Available Jan 1, 2026Total Monthly Price
Base Rent
$4,090
Total Monthly Price
$4,090
1284 Beacon St
1284 Beacon StBrookline, MA 02446
99 Chestnut Hill Ave, Unit 317
99 Chestnut Hill Ave
BostonMA02135
1131 Commonwealth Ave
BostonMA02134
56 Winship St
BostonMA02135
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$4,037
Total Monthly Price
2 Bedroom Apartments Available Nov 16Total Monthly Price
Base Rent
$4,037
Total Monthly Price
$4,037
175 Freeman St
175 Freeman StBrookline, MA 02446
20 Stearns Rd, Unit 54
20 Stearns Rd
BrooklineMA02446
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$4,000
Total Monthly Price
3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$4,000
Total Monthly Price
$4,000
1801 Beacon St
1801 Beacon StBrookline, MA 02445
1945 Commonwealth Ave, Unit 13C
1945 Commonwealth Ave
BostonMA02135
38 Newton St, Unit 2
38 Newton St
BostonMA02135
5 Turner Ter, Unit 1
5 Turner Ter
NewtonMA02460
48 Cameron St, Unit 2
48 Cameron St
BrooklineMA02445
162 Kelton St, Unit 2
162 Kelton St
BostonMA02134
56 Hobson St, Unit 2
56 Hobson St
BostonMA02135
128 Washington St, Unit T
128 Washington St
BostonMA02135
1729 Commonwealth Ave, Unit 89-3
1729 Commonwealth Ave
BostonMA02135
35 Chiswick Rd, Unit 4
35 Chiswick Rd
BostonMA02135
33 Pond Ave, Unit 723B
33 Pond Ave
BrooklineMA02445
37 Egremont Rd, Unit 5
37 Egremont Rd
BostonMA02135
24 Glenville Ave, Unit 3
24 Glenville Ave
BostonMA02134
14 Glenville Ave, Unit 2
14 Glenville Ave
BostonMA02134
137 Chiswick Terrace, Unit 5
137 Chiswick Terrace
BostonMA02135
12 Glenville Terrace, Unit 2
12 Glenville Terrace
BostonMA02134
87 Gardner St, Unit 1
87 Gardner St
BostonMA02134
66 Parsons St, Unit 2
66 Parsons St
BostonMA02135
12 Glenville Ave, Unit 3
12 Glenville Ave
BostonMA02134
16 Glenville Ave, Unit 3
16 Glenville Ave
BostonMA02134
162 Kelton St, Unit 2
162 Kelton St
BostonMA02134
20 Alton Pl, Unit 4
20 Alton Pl
BrooklineMA02446
36 Brainerd Rd, Unit 2
36 Brainerd Rd
BostonMA02134
135 Nonantum St, Unit 1
135 Nonantum St
BostonMA02135
128 Washington St, Unit 2
128 Washington St
BostonMA02135
2 Colliston Rd, Unit B
2 Colliston Rd
BostonMA02135
216 Arlington St, Unit 2
216 Arlington St
WatertownMA02472
216 Arlington St, Unit 2
216 Arlington St
WatertownMA02472
38 Newton St, Unit 2
38 Newton St
BostonMA02135
26 Holly Ln, Unit 2
26 Holly Ln
BrooklineMA02467
27 Pratt St, Unit 2
27 Pratt St
BostonMA02134
49 Bennett St, Unit 2
49 Bennett St
BostonMA02135
31 Justin Rd, Unit 2
31 Justin Rd
BostonMA02135
1 Everett St, Unit 201
1 Everett St
BostonMA02134
97 Kilsyth Rd, Unit 3
97 Kilsyth Rd
BostonMA02135
89 Perthshire Rd
BostonMA02135
76 Easton St, Unit 4
76 Easton St
BostonMA02134
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 | $3,242 | $1,200 | $9,500 |
| Chestnut Hill 3 Bedroom Homes for Rent | $3,992 | $950 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $4,633 | $900 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $5,783 | $850 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,808 | $950 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $2,319 | $925 | $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 5067 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $17,000. There are also 4197 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $850 to $40,000.
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 $850 to $40,000 with an average monthly rent of $4,113.
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 $1,000 to $14,817, while Three Bedroom Homes, Condos, and Townhomes for rent range from $950 to $12,000. Four Bedroom Single-Family rentals are also available starting from $900 and Four Bedroom Apartments start at $1,400.
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.
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.
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.