
Luxury Apartments for Rent in Chestnut Hill, MA with Swimming Pool (68 Rentals)
The most luxurious Apartments in Chestnut Hill with high-end amenities, features, and finishes.


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Avalon at Chestnut Hill

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120 Gerry Rd

The Franklin at Hancock Village

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The Aven at Newton Highlands

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Overlook at St. Gabriel's

The Charley

1443 Beacon

Reservoir Towers

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Elan Union Market
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

Barclay on Beacon

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Gables Arsenal Street

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Lantera at Boston Landing

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204 Sherman Rd, Unit 829, Unit 829

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142 North Beacon St, Unit A1, Unit A1

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144 North Beacon St, Unit A1, Unit A1

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40 Puddingstone Ln, Unit 1, Unit 1

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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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66 Bryon Rd, Unit 4, Unit 4
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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1471 Beacon St, Unit 6, Unit 6

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1441 Beacon St

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

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50-56 Broadlawn Park, Unit 3, Unit 3

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33 Pond Ave, Unit 502, Unit 502

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124 Sutherland Rd, Unit 1, Unit 1

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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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94 Babcock St
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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1089 Commonwealth Ave

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1441 Beacon St, Unit 616, Unit 616

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7 Sutherland Rd, Unit 31, Unit 31

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144 North Beacon St, Unit A1d, Unit A1d

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144 North Beacon St, Unit B16, Unit B16

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295 Tremont St, Unit #322, Unit #322

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273 Tremont St, Unit #322, Unit #322

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1965 Commonwealth Ave

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86 Babcock St, Unit #P1, Unit #P1

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90 Babcock St, Unit #P1, Unit #P1
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, Unit #P1, Unit #P1

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40 Gardner Rd, Unit #1E, Unit #1E

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2 Sutherland Rd, Unit #31, Unit #31

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158 Kelton St, Unit 507, Unit 507

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67-69 Ashford St

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245 Kelton St, Unit 24, Unit 24

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239 Kelton St, Unit 24, Unit 24

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181 Washington St, Unit 710, Unit 710

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99 Pond Ave

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66 Bryon Rd, Unit #4, Unit #4
The Art of the Rental Viewing: What to look for during a property tour
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 | $2,332 | $1,550 | $6,552 |
| Chestnut Hill 1 Bedroom Apartments | $2,780 | $1,000 | $10,000+ |
| Chestnut Hill 2 Bedroom Apartments | $3,495 | $2,000 | $10,000+ |
| Chestnut Hill 3 Bedroom Apartments | $4,049 | $1,295 | $10,000+ |
| Chestnut Hill 4 Bedroom Apartments | $4,909 | $1,295 | $10,000+ |
| Chestnut Hill 5 Bedroom Apartments | $6,002 | $3,600 | $10,000+ |
| Chestnut Hill 6 Bedroom Apartments | $8,326 | $4,000 | $10,000+ |
Explore Chestnut Hill
Chestnut Hill, MA Local Guide
- Nearby Cities
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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 $3,817.
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 2,144 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

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.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.