
Apartments for Rent in Chestnut Hill, MA with Swimming Pool (106 Rentals)


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Avalon at Chestnut Hill

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120 Gerry Rd

Hampton Place

Chestnut Village Condominiums

Imperial Towers

Hammond Park Condominiums

The Franklin at Hancock Village

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The Aven at Newton Highlands

1443 Beacon
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Overlook at St. Gabriel's

The Charley

Reservoir Towers

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Elan Union Market

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Gables Arsenal Street

Barclay on Beacon

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Lantera at Boston Landing

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92 Gordon St, Unit 205, Unit 205

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204 Sherman Rd, Unit 829, Unit 829

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142 North Beacon St, Unit A1, Unit A1
It's time to soak up some sun!
One of the easiest and more obvious ways of enjoying the summer sun is to lounge out by your community pool. Learn a Few Rules to Keep in Mind while at the pool.

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15 Westgate Rd

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245 Kelton St, Unit 24B, Unit 24B

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290 Corey Rd, Unit 42, Unit 42

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40 Puddingstone Ln, Unit 1, Unit 1

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66 Bryon Rd, Unit 4, Unit 4

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14 Bryon Rd, Unit 6, Unit 6

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1471 Beacon St, Unit 6, Unit 6

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50-56 Broadlawn Park, Unit 1, Unit 1

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35 Westgate Rd, Unit 3, Unit 3

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14 Bryon Rd, Unit 3, Unit 3
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.

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1441 Beacon St

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50-56 Broadlawn Park, Unit 3, Unit 3

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1065 Commonwealth Ave, Unit 4-47, Unit 4-47

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33 Pond Ave, Unit 502, Unit 502

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1959 Commonwealth Ave, Unit 2, Unit 2

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124 Sutherland Rd

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6 Sutherland Rd, Unit 3, Unit 3

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19 Winchester St, Unit 604, Unit 604

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12 Everett St

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110 Lanark Rd, Unit 12, Unit 12
Explore Like a Local: The Insider's Guide to Boston
Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.

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94 Babcock St

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1441 Beacon St, Unit 616, Unit 616

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1089 Commonwealth Ave

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144 North Beacon St, Unit A1d, Unit A1d

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7 Sutherland Rd, Unit 31, Unit 31

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1411 Commonwealth Ave, Unit 504, Unit 504

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144 North Beacon St, Unit B16, Unit B16

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39 South St, Unit 62, Unit 62

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1965 Commonwealth Ave

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295 Tremont St, Unit #322, Unit #322
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Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
Chestnut Hill, MA Local Guide

How much does it cost to rent an apartment in Chestnut Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Chestnut Hill Studio Apartments with Swimming Pool | $2,337 | $1,550 | $6,552 |
| Chestnut Hill 1 Bedroom Apartments with Swimming Pool | $2,782 | $1,000 | $8,272 |
| Chestnut Hill 2 Bedroom Apartments with Swimming Pool | $3,509 | $2,000 | $10,000+ |
| Chestnut Hill 3 Bedroom Apartments with Swimming Pool | $4,056 | $1,295 | $10,000+ |
| Chestnut Hill 4 Bedroom Apartments with Swimming Pool | $4,926 | $1,295 | $10,000+ |
| Chestnut Hill 5 Bedroom Apartments | $6,042 | $3,900 | $10,000+ |
| Chestnut Hill 6 Bedroom Apartments | $8,247 | $4,000 | $10,000+ |
Browse Top Apartments in Chestnut Hill
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Chestnut Hill, MA Local Guide
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10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read ArticleBoston Neighborhood Guide: Living Near UMass, MGH, and State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.
Read ArticleDon't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleTop Neighborhoods Near Boston Colleges and Universities
Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Chestnut Hill, MA Rentals by Map
See the most popular apartments and homes in Chestnut Hill, MA
Frequently Asked Questions about Chestnut Hill Apartments with Swimming Pool
What is the Cheapest Swimming Pool apartment in Chestnut Hill?
Currently the most affordable Apartment in Chestnut Hill with Swimming Pool is at 1411 Commonwealth Ave, Unit 504 listed at $1,950.
How much is the average rent for Chestnut Hill Apartments with Swimming Pool?
The average rent for a Apartment in Chestnut Hill with Swimming Pool is $3,799.
What is the largest Chestnut Hill Apartment for rent with Swimming Pool?
Today's Apartment with Swimming Pool and the most square footage in Chestnut Hill is a 9,999 square feet unit starting from $2,825 at 144 North Beacon St, Unit A1d.
What is the average size for Chestnut Hill Apartments for rent with Swimming Pool?
The average size for a rental with Swimming Pool in Chestnut Hill is currently at 2,285 sq ft.
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

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.