Luxury Apartments for Rent in the Chestnut Hill Middlesex Neighborhood of Chestnut Hill, MA (348 Rentals) Page 5 of 7

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

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249 Chestnut Hill Ave
$2,850
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850
2 Bedroom Apartment Available Now

249 Chestnut Hill Ave

249 Chestnut Hill AveBoston, MA 02135
Affordability
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25 Greycliff Rd, Unit #1
$4,650
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,650

Total Monthly Price
$4,650
3 Bedroom Apartment Available Now

25 Greycliff Rd, Unit #1

25 Greycliff RdBoston, MA 02135
Affordability
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16 Chestnut Hill Ave, Unit 28-6
$2,750
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750
1 Bedroom Apartment Available Now

16 Chestnut Hill Ave, Unit 28-6

16 Chestnut Hill AveBoston, MA 02135
Affordability
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83 Brayton Rd
$3,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200
3 Bedroom Apartment Available Now

83 Brayton Rd

83 Brayton RdBoston, MA 02135
Affordability
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73 Nonantum St
$3,250
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,250

Total Monthly Price
$3,250
3 Bedroom Apartment Available Now

73 Nonantum St

73 Nonantum StBoston, MA 02135
Affordability
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72 Nonantum St
$4,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000
4 Bedroom Apartment Available Now

72 Nonantum St

72 Nonantum StBoston, MA 02135
Affordability
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120 Kenrick St
$4,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000
3 Bedroom Apartment Available Now

120 Kenrick St

120 Kenrick StBoston, MA 02135
Affordability
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45 Radnor Rd, Unit 1A
$9,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,800

Total Monthly Price
$9,800
6 Bedroom Apartment Available Aug 23, 2026

45 Radnor Rd, Unit 1A

45 Radnor RdBoston, MA 02135
Cost Per Sq.Ft.
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22 Radnor Rd, Unit 1
$9,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,800

Total Monthly Price
$9,800
6 Bedroom Apartment Available Aug 23, 2026

22 Radnor Rd, Unit 1

22 Radnor RdBoston, MA 02135
Cost Per Sq.Ft.
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6 Lothian Rd
$3,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600
3 Bedroom Apartment Available Now

6 Lothian Rd

6 Lothian RdBoston, MA 02135
Affordability
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2 Lothian Rd, Unit 6-2
$5,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500
5 Bedroom Apartment Available Sep 1, 2026

2 Lothian Rd, Unit 6-2

2 Lothian RdBoston, MA 02135
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148 Strathmore Rd, Unit 1
$4,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,100

Total Monthly Price
$4,100
4 Bedroom Apartment Available Now

148 Strathmore Rd, Unit 1

148 Strathmore RdBoston, MA 02135
Affordability
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9 Radnor Rd, Unit 1
$6,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500
4 Bedroom Apartment Available Sep 1, 2026

9 Radnor Rd, Unit 1

9 Radnor RdBoston, MA 02135
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37 Radnor Rd, Unit 2
$9,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,800

Total Monthly Price
$9,800
6 Bedroom Apartment Available Aug 23, 2026

37 Radnor Rd, Unit 2

37 Radnor RdBoston, MA 02135
Cost Per Sq.Ft.
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36 Dighton St, Unit 15
$2,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600
2 Bedroom Apartment Available Dec 1

36 Dighton St, Unit 15

36 Dighton StBoston, MA 02135
Cost Per Sq.Ft.
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22 Radnor Rd, Unit 2
$6,000
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000
4 Bedroom Apartment Available Now

22 Radnor Rd, Unit 2

22 Radnor RdBoston, MA 02135
Cost Per Sq.Ft.

Getting Around the Chestnut Hill Middlesex Neighborhood in Chestnut Hill, MA

Walk Score®

59 / 100

Somewhat Walkable

Some errands can be accomplished on foot

Bike Score®

47 / 100

Somewhat Bikeable

Minimal bike infrastructure

Transit Score®

53 / 100

Good Transit

Many nearby public transportation options

Frequently Asked Questions about Chestnut Hill Middlesex

How much are Studio apartments in Chestnut Hill Middlesex?

There are currently 49 Studio Apartments in Chestnut Hill Middlesex with rent ranges from $1,950 to $3,730 with an average price of $2,515.

What is the current price range for One Bedroom Chestnut Hill Middlesex Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Chestnut Hill Middlesex ranges from $1,050 to $4,500 with an average monthly rent of $2,526.

What does renting a Two Bedroom Apartment in Chestnut Hill Middlesex cost?

The monthly rent prices of Two Bedroom Apartments currently available in Chestnut Hill Middlesex range from $2,000 to $5,200. Today's average rental price for Two Bedrooms here is $3,411.

How expensive are Chestnut Hill Middlesex Three Bedroom Apartments?

There are currently 112 Three Bedroom Apartments listings available in Chestnut Hill Middlesex on ApartmentHomeLiving.com. The pricing ranges from $2,550 to $5,955 - averaging $3,881 for the location.

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.

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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.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.