Luxury Apartments for Rent in Chestnut Hill, MA with Swimming Pool (65 Rentals)

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The most luxurious Apartments in Chestnut Hill with high-end amenities, features, and finishes.

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Overlook at St. Gabriels
Rent Specials
$2,633 - $6,682
Total Monthly Price

Total Monthly Price

Base Rent
$2,633 - $6,682
Total Monthly Price
$2,633 - $6,682
Studio to 3 Bedroom Apartments Available Now

Overlook at St. Gabriels

175 Washington StBrighton, MA 02135
Furnished
  • Verified
  • Customer Reviewed
  • 3D Tour
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Gables Arsenal Street
$2,638 - $9,282
Total Monthly Price

Total Monthly Price

Base Rent
$2,638 - $9,282
Total Monthly Price
$2,638 - $9,282
1 to 3 Bedroom Apartments Available Now

Gables Arsenal Street

204 Arsenal StWatertown, MA 02472
Family Friendly
  • Verified
  • Customer Reviewed
  • Utilities Included

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.

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Elan Union Market
$2,588 - $8,008
Total Monthly Price

Total Monthly Price

Base Rent
$2,588 - $8,008
Total Monthly Price
$2,588 - $8,008
Studio to 2 Bedroom Apartments Available Now

Elan Union Market

130 Arsenal StWatertown, MA 02472
Transit Friendly
  • Verified
  • Customer Reviewed
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Lantera at Boston Landing
Rent Specials
$2,666 - $7,350
Total Monthly Price

Total Monthly Price

Base Rent
$2,666 - $7,350
Total Monthly Price
$2,666 - $7,350
Studio to 3 Bedroom Apartments Available Now

Lantera at Boston Landing

125 Guest StBoston, MA 02135
Outdoors
  • Verified
  • Customer Reviewed
  • Utilities Included
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55 Colborne Rd, Unit #1
$2,700
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700
Total Monthly Price
$2,700
2 Bedroom Apartment Available Now

55 Colborne Rd, Unit #1

55 Colborne RdBoston, MA 02135
Affordability
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15 North Beacon St, Unit 420
$2,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900
Total Monthly Price
$2,900
2 Bedroom Apartment Available Now

15 North Beacon St, Unit 420

15 North Beacon StBoston, MA 02134
Affordability

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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33 Pond Ave, Unit 502
$3,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,000
Total Monthly Price
$3,000
1 Bedroom Apartment Available Now

33 Pond Ave, Unit 502

33 Pond AveBrookline, MA 02445
Affordability
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190 Kelton St, Unit 706
$2,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900
Total Monthly Price
$2,900
2 Bedroom Apartment Available Dec 12

190 Kelton St, Unit 706

190 Kelton StBoston, MA 02134
Furnished
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58 Winship St, Unit NA
$2,950
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,950
Total Monthly Price
$2,950
3 Bedroom Apartment Available Now

58 Winship St, Unit NA

58 Winship StBoston, MA 02135
Affordability
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6 Sutherland Rd, Unit NA
$3,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500
Total Monthly Price
$3,500
3 Bedroom Apartment Available Now

6 Sutherland Rd, Unit NA

6 Sutherland RdBoston, MA 02135
Affordability
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12 Everett St, Unit 15-803
$3,610
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,610
Total Monthly Price
$3,610
2 Bedroom Apartment Available Dec 15

12 Everett St, Unit 15-803

12 Everett StBoston, MA 02134
Affordability

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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170 Lake Shore Rd, Unit 2
$3,750
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,750
Total Monthly Price
$3,750
3 Bedroom Apartment Available Now

170 Lake Shore Rd, Unit 2

170 Lake Shore RdBoston, MA 02135
Affordability
  • Smoke Free

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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142 North Beacon St, Unit A1
$2,875
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,875
Total Monthly Price
$2,875
2 Bedroom Apartment Available Now

142 North Beacon St, Unit A1

142 North Beacon StBoston, MA 02135
Cost Per Sq.Ft.
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67-69 Ashford St, Unit 2
$6,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,300
Total Monthly Price
$6,300
5 Bedroom Apartment Available Now

67-69 Ashford St, Unit 2

67-69 Ashford StBoston, MA 02134
  • Smoke Free
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99 Pond Ave
$3,450
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,450
Total Monthly Price
$3,450
1 Bedroom Apartment Available Now

99 Pond Ave

99 Pond AveBrookline, MA 02445
Affordability
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85 Brainerd Rd, Unit 404
$3,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900
Total Monthly Price
$3,900
2 Bedroom Apartment Available Now

85 Brainerd Rd, Unit 404

85 Brainerd RdBoston, MA 02134
Cost Per Sq.Ft.

Cash 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.

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Showing Results 1-50, Page 1 of 2

Chestnut Hill, MA Local Guide

Boston 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.

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Don'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.

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The 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.

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Top 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

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chestnut Hill, MA Rentals by Map

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See the most popular apartments and homes in Chestnut Hill, MA

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Getting Around Chestnut Hill, MA

Walk Score®

54 / 100

Somewhat Walkable

Some errands can be accomplished on foot

Bike Score®

47 / 100

Somewhat Bikeable

Minimal bike infrastructure

Transit Score®

46 / 100

Some Transit

A few nearby public transportation options

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

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 $3,585.

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 142 North Beacon St, Unit A11.

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 1,855 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

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The 10 Best Affordable Neighborhoods in Boston, MA

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Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

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A Local Experts Guide to the Top Boston Neighborhoods for College Renters

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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!

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Explore Like a Local: The Insider's Guide to Boston

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Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street

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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.

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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.

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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.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.