29 Brainerd Rd, Unit 305
29 Brainerd Rd
BostonMA02134
Homes for Rent in Chestnut Hill, MA Under $4,500 (3,066 Rentals) Page 32 of 62
98 Robinwood Ave, Unit 4
98 Robinwood Ave
BostonMA02130
29 Brainerd Rd, Unit 305
29 Brainerd Rd
BostonMA02134
29 Brainerd Rd, Unit 305
29 Brainerd Rd
BostonMA02134
141 Coolidge Ave, Unit 415
141 Coolidge Ave
WatertownMA02472
38 Juniper St, Unit 112
38 Juniper St
BrooklineMA02445
64 Brooks St
BostonMA02135
15 North Beacon St, Unit 405
15 North Beacon St
BostonMA02134
2 Imrie Rd, Unit 1
2 Imrie Rd
BostonMA02134
42 Hano St
BostonMA02134
1607 Commonwealth Ave, Unit 9
1607 Commonwealth Ave
BostonMA02135
6 Leicester St, Unit 1
6 Leicester St
BostonMA02135
1404 Commonwealth Ave, Unit 5
1404 Commonwealth Ave
BostonMA02135
23 Allston St, Unit 1
23 Allston St
BostonMA02134
23 Allston St, Unit 1
23 Allston St
BostonMA02134
317 Summit Ave, Unit 5
317 Summit Ave
BostonMA02135
71 Turner St, Unit 3
71 Turner St
BostonMA02135
2009 Commonwealth Ave, Unit 20
2009 Commonwealth Ave
BostonMA02135
21 Westbourne Ter, Unit 6
21 Westbourne Ter
BrooklineMA02446
550 Washington St, Unit 1
550 Washington St
BostonMA02135
6 Sutherland Rd, Unit 3
6 Sutherland Rd
BostonMA02135
62 Litchfield St
BostonMA02135
29 Brainerd Rd, Unit 305
29 Brainerd Rd
BostonMA02134
8 Adella Pl, Unit 2
8 Adella Pl
BostonMA02134
62 Litchfield St
BostonMA02135
close
View Me
$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
close
View Me
$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
50 Leo M Birmingham Pkwy
BostonMA02135
close
View Me
$3,100
Total Monthly Price
3 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
62 Union St
62 Union StBoston, MA 02135
29 Blaine St
BostonMA02134
172 Fuller St, Unit 3
172 Fuller St
BrooklineMA02446
53 Manchester Rd, Unit 5
53 Manchester Rd
BrooklineMA02446
80 St Paul St
BrooklineMA02446
55 Manchester Rd
BrooklineMA02446
57 Manchester Rd
BrooklineMA02446
59 Manchester Rd, Unit 6
59 Manchester Rd
BrooklineMA02446
59 Manchester Rd, Unit 6
59 Manchester Rd
BrooklineMA02446
59 Manchester Rd, Unit 6
59 Manchester Rd
BrooklineMA02446
close
View Me
$3,090
Total Monthly Price
2 Bedroom Apartments Available Dec 11Total Monthly Price
Base Rent
$3,090
Total Monthly Price
$3,090
161 Washington St
161 Washington StBoston, MA 02135
close
View Me
$3,085
Total Monthly Price
1 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,085
Total Monthly Price
$3,085
50 Gerry Rd
50 Gerry RdBrookline, MA 02467
close
View Me
$3,085
Total Monthly Price
1 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,085
Total Monthly Price
$3,085
71 Kilsyth Rd
71 Kilsyth RdBoston, MA 02135
1186 Commonwealth Ave
BostonMA02134
159-201 Washington St
BostonMA02135
61 Adamson St
BostonMA02134
63 Adamson St
BostonMA02134
53 Manchester Rd, Unit 5
53 Manchester Rd
BrooklineMA02446
14 Westford St, Unit 8
14 Westford St
BostonMA02134
close
View Me
$3,075
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,075
Total Monthly Price
$3,075
53 Manchester Rd
53 Manchester RdBrookline, MA 02446
close
View Me
$3,070
Total Monthly Price
1 Bedroom Apartments Available Mar 22, 2026Total Monthly Price
Base Rent
$3,070
Total Monthly Price
$3,070
60 Brainerd Rd
60 Brainerd RdBoston, MA 02134
close
View Me
$3,065
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,065
Total Monthly Price
$3,065
38 School St
38 School StBoston, MA 02135
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 | $3,239 | $1,200 | $9,500 |
| Chestnut Hill 3 Bedroom Homes for Rent | $4,001 | $950 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $4,659 | $900 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $5,798 | $850 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,791 | $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.
Browse Top Homes for Rent in Chestnut Hill
Explore Chestnut Hill
Let everyone know!
Do you know the Chestnut Hill area?
If you’re an expert on all things Chestnut Hill, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Frequently Asked Questions about Chestnut Hill
What type of rentals are currently available in Chestnut Hill?
There are currently 5029 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $17,000. There are also 4140 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 $4,075.
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 $1,550.
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.
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.