5 Bedroom Homes for Rent in Highland Park Neighborhood of Roxbury, MA (40 Rentals)

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property at 739 Parker St

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

5 Bedroom, 2 Bath Condo for Rent

Available Jan 1, 2026

739 Parker St

BostonMA02120
property at 739 Parker St

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

5 Bedroom, 2 Bath Condo for Rent

Available Jan 1, 2026

739 Parker St, Unit 3

739 Parker St
BostonMA02120
property at 34 Cherokee St

$4,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,600

Total Monthly Price
$4,600

5 Bedroom, 2 Bath Condo for Rent

Available Jan 1, 2026

34 Cherokee St, Unit 2

34 Cherokee St
BostonMA02120
property at 124 Calumet St

$4,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,750

Total Monthly Price
$4,750

5 Bedroom, 1 Bath Condo for Rent

Available Now

124 Calumet St, Unit 2

124 Calumet St
BostonMA02120
property at 23 Highland Park Ave

$5,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,100

Total Monthly Price
$5,100

5 Bedroom, 2 Bath Condo for Rent

Available Now

23 Highland Park Ave, Unit 2

23 Highland Park Ave
BostonMA02119
property at 127 Cedar St

$5,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,100

Total Monthly Price
$5,100

5 Bedroom, 2 Bath Condo for Rent

Available Now

127 Cedar St, Unit 3

127 Cedar St
BostonMA02119
property at 127 Cedar St

$5,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,100

Total Monthly Price
$5,100

5 Bedroom, 2 Bath Condo for Rent

Available Now

127 Cedar St, Unit 3

127 Cedar St
BostonMA02119
property at 23 Highland Park Ave

$5,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,900

Total Monthly Price
$5,900

5 Bedroom, 2 Bath Condo for Rent

Available Now

23 Highland Park Ave, Unit 2

23 Highland Park Ave
BostonMA02119
property at 172 Saint Alphonsus St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

5 Bedroom, 1 Bath Condo for Rent

Available Now

property at 172 Saint Alphonsus St

$6,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

5 Bedroom, 1 Bath Condo for Rent

Available Now

172 Saint Alphonsus St, Unit 2

172 Saint Alphonsus St
BostonMA02120

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.

property at 156 Calumet St

$6,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,600

Total Monthly Price
$6,600

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

156 Calumet St, Unit 1

156 Calumet St
BostonMA02120
property at 12 Wensley St

$7,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,250

Total Monthly Price
$7,250

5 Bedroom, 2 Bath Condo for Rent

Available Now

12 Wensley St, Unit 1

12 Wensley St
BostonMA02120
property at 67 Beech Glen St

$7,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,250

Total Monthly Price
$7,250

5 Bedroom, 2.5 Bath Condo for Rent

Available Sep 1, 2026

67 Beech Glen St

BostonMA02119
property at 72 Hillside St

$7,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,300

Total Monthly Price
$7,300

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

72 Hillside St, Unit 3

72 Hillside St
BostonMA02120
property at 124 Calumet St

$7,695

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,695

Total Monthly Price
$7,695

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

124 Calumet St, Unit 1

124 Calumet St
BostonMA02120
property at 9 Carmel St

$7,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,750

Total Monthly Price
$7,750

5 Bedroom, 2 Bath Condo for Rent

Available Now

9 Carmel St, Unit 3

9 Carmel St
BostonMA02120
property at 224 Calumet St

$7,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,750

Total Monthly Price
$7,750

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

224 Calumet St, Unit 1

224 Calumet St
BostonMA02120
property at 226 Calumet St

$7,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,750

Total Monthly Price
$7,750

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

226 Calumet St, Unit 1

226 Calumet St
BostonMA02120
property at 14 Wensley St

$7,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,750

Total Monthly Price
$7,750

5 Bedroom, 2 Bath Condo for Rent

Available Now

14 Wensley St

BostonMA02120
property at 11 Alleghany St

$7,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,950

Total Monthly Price
$7,950

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

11 Alleghany St, Unit 1

11 Alleghany St
BostonMA02120

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

property at 9 Carmel St

$8,095

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,095

Total Monthly Price
$8,095

5 Bedroom, 2 Bath Townhome for Rent

Available Sep 1, 2026

9 Carmel St

BostonMA02120
property at 47 Hillside St

$8,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,500

Total Monthly Price
$8,500

5 Bedroom, 2 Bath Condo for Rent

Available Now

47 Hillside St, Unit 1

47 Hillside St
BostonMA02120
property at 44 Hillside St

$8,625

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,625

Total Monthly Price
$8,625

5 Bedroom, 2 Bath Condo for Rent

Available Sep 1, 2026

44 Hillside St, Unit 3

44 Hillside St
BostonMA02120
property at 8 Sewall St

$9,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,000

Total Monthly Price
$9,000

5 Bedroom, 2.5 Bath Condo for Rent

Available Now

8 Sewall St, Unit 8

8 Sewall St
Roxbury CrossingMA02120
property at 8 Sewall St

$9,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,000

Total Monthly Price
$9,000

5 Bedroom, 2.5 Bath Condo for Rent

Available Now

8 Sewall St, Unit 1

8 Sewall St
Roxbury CrossingMA02120
property at 8 Sewall St

$9,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,000

Total Monthly Price
$9,000

5 Bedroom, 2.5 Bath Townhome for Rent

Available Sep 1, 2026

8 Sewall St

BostonMA02120

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

property at 2601 Washington St

$5,750

Total Monthly Price

Total Monthly Price

Base Rent
$5,750

Total Monthly Price
$5,750

5 Bedroom, 2 Bath Townhome for Rent

Available Now

2601 Washington St

BostonMA02119
property at 2595 Washington St

$5,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,750

Total Monthly Price
$5,750

5 Bedroom, 3 Bath Townhome for Rent

Available Now

2595 Washington St

BostonMA02119
property at 2593 Washington St

$5,750

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,750

Total Monthly Price
$5,750

5 Bedroom, 2 Bath Townhome for Rent

Available Now

2593 Washington St

BostonMA02119
property at 2597 Washington St

$5,750

Total Monthly Price

Total Monthly Price

Base Rent
$5,750

Total Monthly Price
$5,750

5 Bedroom, 2 Bath Townhome for Rent

Available Now

2597 Washington St

BostonMA02119

Frequently Asked Questions about Highland Park

What type of rentals are currently available in Highland Park?

There are currently 736 Apartments for Rent in Highland Park, MA with pricing that ranges from $1,093 to $17,900. There are also 279 Single Family Homes for rent, Condos, and Townhome rentals currently available in Highland Park ranging from $750 to $14,000.

What is the current price range for Rental Homes in Highland Park?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Highland Park ranges from $750 to $14,000 with an average monthly rent of $6,002.

How much are larger Three and Four Bedroom Rentals in Highland Park?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Highland Park range from $1,300 to $6,013, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,075 to $6,195. Four Bedroom Single-Family rentals are also available starting from $750 and Four Bedroom Apartments start at $3,150.

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.

Articles, How-To's, and Tips

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.

decorative image for How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips article

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.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

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.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate!