311 Tappan St, Unit 1
311 Tappan St
BrooklineMA02445
Luxury Homes for Rent in Chestnut Hill, MA (2,795 Rentals) Page 12 of 56
The most luxurious Homes in Chestnut Hill with high-end amenities, features, and finishes.
8 Selkirk Rd
BostonMA02135
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$2,990
Total Monthly Price
1 Bedroom Apartments Available Apr 2, 2026Total Monthly Price
Base Rent
$2,620
Required Monthly Fees
$370
Total Monthly Price
$2,990
3688 Washington St
3688 Washington StBoston, MA 02130
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$2,990
Total Monthly Price
2 Bedroom Apartments Available Nov 16Total Monthly Price
Base Rent
$2,550
Required Monthly Fees
$440
Total Monthly Price
$2,990
161 Washington St
161 Washington StBoston, MA 02135
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1531 Beacon St, Unit 16
1531 Beacon St
BrooklineMA02446
42 Brackett St, Unit 44-2
42 Brackett St
BostonMA02135
319 Belgrade Ave, Unit 303
319 Belgrade Ave
BostonMA02131
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11 Fairfield St, Unit 1
11 Fairfield St
WatertownMA02472
70 Saint Paul St, Unit 6
70 Saint Paul St
BrooklineMA02446
12 Ransom Rd, Unit 12A
12 Ransom Rd
BostonMA02135
240 Kelton St, Unit 16
240 Kelton St
BostonMA02134
240 Kelton St, Unit 7
240 Kelton St
BostonMA02134
244 Kelton St, Unit uni6 2-bed 1-bath
244 Kelton St
BostonMA02134
11 Fairfield St, Unit 2
11 Fairfield St
WatertownMA02472
22 School St
NewtonMA02458
1522 VFW Pkwy, Unit 204
1522 VFW Pkwy
BostonMA02132
316 Tappan St, Unit 1B
316 Tappan St
BrooklineMA02445
312 Tappan St
BrooklineMA02445
15 Parkton Rd, Unit #3
15 Parkton Rd
BostonMA02130
512 Centre St, Unit 2
512 Centre St
BostonMA02130
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90 Kilsyth Rd, Unit 43
90 Kilsyth Rd
BostonMA02135
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1774 Beacon St, Unit 8
1774 Beacon St
BrooklineMA02445
74 Dunboy St
BostonMA02135
147 Kelton St, Unit 501
147 Kelton St
BostonMA02134
11 Atkins St, Unit 2
11 Atkins St
BostonMA02135
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374 Chestnut Hill Ave
BostonMA02135
54 Lancaster Ter, Unit 2B
54 Lancaster Ter
BrooklineMA02446
2012 Commonwealth Ave
BostonMA02135
9 Brooksdale Rd
BostonMA02135
365 Western Ave
BostonMA02135
150 N Beacon St
BostonMA02135
163 Chestnut Hill Ave
BostonMA02135
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39 South St, Unit 4
39 South St
BostonMA02135
2001 Commonwealth Ave, Unit 16
2001 Commonwealth Ave
BostonMA02135
1666 Commonwealth Ave, Unit 32
1666 Commonwealth Ave
BostonMA02135
1082 Commonwealth Ave, Unit 503
1082 Commonwealth Ave
BostonMA02215
22 Alton Pl, Unit 6
22 Alton Pl
BrooklineMA02446
305 Allston St, Unit 2
305 Allston St
BostonMA02135
305 Summit Ave, Unit 2
305 Summit Ave
BostonMA02135
70 Union St, Unit 2
70 Union St
BostonMA02135
59 Lanark Rd, Unit 12
59 Lanark Rd
BostonMA02135
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.