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$2,750
Plus Fees
1 Bedroom Apartments Available Now288 Chestnut Hill Ave
288 Chestnut Hill AveBoston, MA 02135
Luxury Homes for Rent in Chestnut Hill, MA (2,669 Rentals) Page 8 of 54
The most luxurious Homes in Chestnut Hill with high-end amenities, features, and finishes.
99 Pond Ave, Unit 902
99 Pond Ave
BrooklineMA02445
319 Belgrade Ave, Unit 303
319 Belgrade Ave
BostonMA02131
9 Rice St, Unit 5
9 Rice St
BrooklineMA02445
20 Watertown St
WatertownMA02472
63 Selkirk Rd, Unit 1
63 Selkirk Rd
BostonMA02135
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$2,760
Total Monthly Price
2 Bedroom Apartments Available Jan 1, 2026Total Monthly Price
Base Rent
$2,320
Required Monthly Fees
$440
Total Monthly Price
$2,760
139 Washington St
139 Washington StBoston, MA 02135
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18-20 Kelley Ct, Unit 20
18-20 Kelley Ct
BostonMA02135
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$2,780
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,340
Required Monthly Fees
$440
Total Monthly Price
$2,780
1284 Beacon St
1284 Beacon StBrookline, MA 02446
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$2,780
Total Monthly Price
2 Bedroom Apartments Available Jan 1, 2026Total Monthly Price
Base Rent
$2,340
Required Monthly Fees
$440
Total Monthly Price
$2,780
139 Washington St
139 Washington StBoston, MA 02135
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$2,780
Plus Fees
2 Bedroom Apartments Available Now1189 Commonwealth Ave
1189 Commonwealth AveBoston, MA 02134
11 Camelot Ct
BostonMA02135
125 Guest St
BostonMA02135
8 Vinal St
BostonMA02135
248 Kelton St, Unit 3
248 Kelton St
BostonMA02134
15 Green, Unit 1
15 Green
BrooklineMA02446
20 John St, Unit 6
20 John St
BrooklineMA02446
1693 Commonwealth Ave, Unit 18
1693 Commonwealth Ave
BostonMA02135
96 Linden St, Unit 1A
96 Linden St
BostonMA02134
24 Ransom Rd, Unit 3
24 Ransom Rd
BostonMA02135
1121 Commonwealth Ave, Unit B1
1121 Commonwealth Ave
BostonMA02215
6 Sutherland Rd, Unit 43
6 Sutherland Rd
BostonMA02135
1161 Commonwealth Ave
BostonMA02134
71 Gardner St, Unit 33
71 Gardner St
BostonMA02134
26 Bigelow St, Unit 1
26 Bigelow St
BostonMA02135
58 Raymond St, Unit 58
58 Raymond St
BostonMA02134
66 Murdock St, Unit 1
66 Murdock St
BostonMA02135
158 Kelton St, Unit 5
158 Kelton St
BostonMA02134
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$2,800
Plus Fees
2 Bedroom Apartments Available Now1193 Commonwealth Ave
1193 Commonwealth AveBoston, MA 02134
121 Tremont St, Unit 4
121 Tremont St
BostonMA02135
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$2,800
Plus Fees
2 Bedroom Apartments Available Now1189 Commonwealth Ave
1189 Commonwealth AveBoston, MA 02134
21 Vershire St
BostonMA02132
1148 Commonwealth Ave, Unit 41
1148 Commonwealth Ave
AllstonMA02134
1161 Commonwealth Ave, Unit 23
1161 Commonwealth Ave
BostonMA02134
110 Strathmore Rd, Unit 204
110 Strathmore Rd
BostonMA02135
336 Lagrange
BostonMA02132
1688 Beacon St, Unit 18
1688 Beacon St
BrooklineMA02445
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$2,800
Plus Fees
2 Bedroom Apartments Available Now1197 Commonwealth Ave
1197 Commonwealth AveBoston, MA 02134
158 Kelton St, Unit 1
158 Kelton St
BostonMA02134
120 Warren St, Unit 6
120 Warren St
BostonMA02135
15 Barrows St, Unit 3
15 Barrows St
BostonMA02134
14 Heron St
BostonMA02132
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116 Floral St
NewtonMA02461
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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 | $3,169 | $910 | $8,500 |
| Chestnut Hill 3 Bedroom Homes for Rent | $3,928 | $925 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $4,566 | $725 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $5,593 | $730 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,959 | $750 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $3,653 | $775 | $10,000+ |
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
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Frequently Asked Questions about Chestnut Hill
What type of rentals are currently available in Chestnut Hill?
There are currently 4124 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $21,050. There are also 3255 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $725 to $38,000.
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 $725 to $38,000 with an average monthly rent of $8,086.
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 $725 and Four Bedroom Apartments start at $1,225.
Expert Rental Resources
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.
Helpful Local Expert Guides
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.
A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips
How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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!