310 Tappan St
BrooklineMA02445
Homes for Rent in Chestnut Hill, MA Under $5,500 (3,623 Rentals) Page 42 of 73
1400 Commonwealth Ave, Unit 6
1400 Commonwealth Ave
BostonMA02134
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$3,150
Total Monthly Price
1 Bedroom Apartments Available Oct 16Total Monthly Price
Base Rent
$3,150
Total Monthly Price
$3,150
181 Washington St
181 Washington StBoston, MA 02135
1788 Beacon St
BrooklineMA02445
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$3,140
Total Monthly Price
1 Bedroom Apartments Available May 20, 2026Total Monthly Price
Base Rent
$3,140
Total Monthly Price
$3,140
65 Brainerd Rd
65 Brainerd RdBoston, MA 02134
509 VFW Parkway
BrooklineMA02467
146 Independence Dr
BrooklineMA02467
146 Independence Dr
BrooklineMA02467
146 Independence Dr
BrooklineMA02467
146 Independence Dr
BrooklineMA02467
146 Independence Dr
BrooklineMA02467
298 Independence Dr
BostonMA02467
585 VFW Parkway
BrooklineMA02467
312 Tappan St
BrooklineMA02445
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$3,125
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,125
Total Monthly Price
$3,125
312 Tappan St
312 Tappan StBrookline, MA 02445
303 Tappan St, Unit 1B
303 Tappan St
BrooklineMA02445
322 Tappan St, Unit 1b
322 Tappan St
BrooklineMA02445
316 Tappan St, Unit 1B
316 Tappan St
BrooklineMA02445
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$3,125
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,125
Total Monthly Price
$3,125
312 Tappan St
312 Tappan StBrookline, MA 02445
312 Tappan St
BrooklineMA02445
398 Cambridge St
BostonMA02134
29 Brainerd Rd, Unit 305
29 Brainerd Rd
BostonMA02134
141 Coolidge Ave, Unit 415
141 Coolidge Ave
WatertownMA02472
160 Newton St
BostonMA02135
29 Elton Ave, Unit 29
29 Elton Ave
WatertownMA02472
29 Brainerd Rd, Unit 305
29 Brainerd Rd
BostonMA02134
98 Robinwood Ave, Unit 4
98 Robinwood Ave
BostonMA02130
29 Brainerd Rd, Unit 305
29 Brainerd Rd
BostonMA02134
31 Brainerd Rd
BostonMA02134
6 Litchfield St
BostonMA02135
50 Leo M Birmingham Pkwy
BostonMA02135
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$3,100
Total Monthly Price
2 Bedroom Apartments Available Sep 1, 2026Total Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
50 Jewett St
50 Jewett StBoston, MA 02131
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$3,100
Total Monthly Price
2 Bedroom Apartments Available Jan 1, 2026Total Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
154 N Beacon St
154 N Beacon StBoston, MA 02135
24 Hampstead Rd, Unit 1
24 Hampstead Rd
BostonMA02130
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$3,100
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
29 Brainerd Rd
29 Brainerd RdBoston, MA 02134
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$3,100
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
16 Westford St
16 Westford StBoston, MA 02134
6 Leicester St, Unit 1
6 Leicester St
BostonMA02135
1607 Commonwealth Ave, Unit 9
1607 Commonwealth Ave
BostonMA02135
23 Allston St, Unit 1
23 Allston St
BostonMA02134
23 Allston St, Unit 1
23 Allston St
BostonMA02134
183 Chestnut Hill Ave, Unit 6
183 Chestnut Hill Ave
BostonMA02135
1307 Commonwealth Ave, Unit 2
1307 Commonwealth Ave
BostonMA02134
1607 Commonwealth Ave, Unit 9
1607 Commonwealth Ave
BostonMA02135
1185 Commonwealth Ave, Unit 8
1185 Commonwealth Ave
BostonMA02134
1489 Beacon St, Unit 2
1489 Beacon St
BrooklineMA02446
31 Glenville Ave, Unit 1
31 Glenville Ave
BostonMA02134
1422 Commonwealth Ave, Unit 4
1422 Commonwealth Ave
BostonMA02135
66 Brooks St, Unit 3-bed 1 bath
66 Brooks St
BostonMA02135
2 Imrie Rd, Unit 1
2 Imrie Rd
BostonMA02134
42 Hano 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 | $3,236 | $1,260 | $9,500 |
| Chestnut Hill 3 Bedroom Homes for Rent | $3,998 | $950 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $4,643 | $900 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $5,779 | $825 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,784 | $950 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $1,636 | $925 | $8,500 |
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 5020 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $17,000. There are also 4194 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $825 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 $825 to $40,000 with an average monthly rent of $4,072.
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 $14,716, 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 $1,550.
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.
Kansas Citys Major Employers & the Best Places to Rent Near Them | A Local Expert Guide
Written by: Amber Kanuckel
Hey, there! I’m Amber, your ApartmentHomeLiving.com local expert for Kansas City, and I’m back with my recommendations for top employers in the area.
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.