Cheap Homes for Rent in the Winthrop Highlands Neighborhood of Winthrop, MA from $2,000 (35 Rentals)

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Search the lowest-cost Homes available for rent right now in the Winthrop Highlands area of Winthrop.

property at 2 Malden St

$2,099

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,099
Total Monthly Price
$2,099

1 Bedroom, 1 Bath Condo for Rent

Available Now

2 Malden St, Unit #3

2 Malden St
RevereMA02151
property at 595 Revere Beach Pkwy

$2,100

Total Monthly Price

Total Monthly Price

Base Rent
$2,100
Total Monthly Price
$2,100

1 Bedroom, 1 Bath Condo for Rent

Available Now

595 Revere Beach Pkwy

RevereMA02151
property at 900 Governors Dr

$2,100 - $2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,100
Total Monthly Price
$2,100

1 To 2 Bedroom Rentals

Available Now

900 Governors Dr

WinthropMA02152
property at 600 Shirley St

$2,350

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,350
Total Monthly Price
$2,350

Studio, 1 Bath Condo for Rent

Available Oct 1

600 Shirley St, Unit 9

600 Shirley St
WinthropMA02152
property at 10 Franklin Ave

$2,400 - $3,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,400
Total Monthly Price
$2,400

1 To 2 Bedroom Rentals

Available Now

10 Franklin Ave

RevereMA02151

Boston's Best Affordable Neighborhoods

Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

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property at 4 Foam St

$2,450

Total Monthly Price

Total Monthly Price

Base Rent
$2,450
Total Monthly Price
$2,450

1 Bedroom, 1 Bath Condo for Rent

Available Sep 1

4 Foam St

WinthropMA02152
property at 394 Ocean Ave

$2,490 - $2,960

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,490 - $2,960
Total Monthly Price
$2,490 - $2,960

1 To 2 Bedroom Condos for Rent

Available Now

394 Ocean Ave

RevereMA02151

Rent According to Income: A Look at Income-Restricted Rentals

Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.

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property at 11 Boardman St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500
Total Monthly Price
$2,500

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

11 Boardman St, Unit #2

11 Boardman St
BostonMA02128
property at 67 Curtis Rd

$2,500 - $3,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500
Total Monthly Price
$2,500

1 To 2 Bedroom Rentals

Available Now

67 Curtis Rd

RevereMA02151

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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property at 400 Governors Dr

$2,600

Total Monthly Price

Total Monthly Price

Base Rent
$2,600
Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Now

400 Governors Dr

WinthropMA02152
property at 1 Avalon St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600
Total Monthly Price
$2,600

2 Bedroom, 1 Bath Condo for Rent

Available Now

1 Avalon St, Unit 1

1 Avalon St
RevereMA02151
property at 56 Winthrop Shore Dr

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650
Total Monthly Price
$2,650

1 Bedroom, 1.5 Bath Condo for Rent

Available Sep 11

56 Winthrop Shore Dr, Unit 1F

56 Winthrop Shore Dr
WinthropMA02152

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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property at 585 Revere Beach Pkwy

$2,650

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650
Total Monthly Price
$2,650

2 Bedroom, 2 Bath Home for Rent

Available Aug 31

585 Revere Beach Pkwy

RevereMA02151
Showing Results 1-35, Page 1 of 1

Winthrop Highlands, Winthrop, MA Local Guide

Cheapest Available Winthrop Highlands Apartments for Rent

 

The cheapest available apartment rental in the Winthrop Highlands area of Boston, MA is a Studio unit found at The Abby priced from $1,795. The Willet has the second lowest priced unit, which is a Studio apartment currently listed from $1,815. Here are the most affordable Winthrop Highlands apartments for rent in Boston, MA:

Apartment ListingModel NameBed/BathPriced From
The AbbyStudioStudio,1BA$1,795
The WilletStudio - 501Studio,1BA$1,815
Pratt Place Apartments1 Bedroom, 1st Floor1BR,1BA$1,869
87-90 Win1BR/1.0BA1BR,1BA$2,100
Ryder Revere BeachS4 GROUP 2AStudio,1BA$2,147
Ocean 650Studio (535 SF)Studio,1BA$2,158
SORASBStudio,1BA$2,350
Revio Revere BeachStudio-S5Studio,1BA$2,510

Best Value Apartments for Rent in Winthrop Highlands, MA

As of August 05, 2026 the best value apartment in the Winthrop Highlands area is the $0.26 price per square foot 12 Sewall Ave Model at 12 Sewall Ave, Unit 3 in the in the Beachmont neighborhood starting from $2,550. The second greatest value Winthrop Highlands apartment is the 26 Curtis Rd Model at 26 Curtis Rd starting at $4,000 with a $2.76 price per square foot in the Belle Circle neighborhood. Here is today’s list of the best values for Winthrop Highlands apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
12 Sewall Ave, Unit 312 Sewall Ave1BR,1BA$0.26
26 Curtis Rd26 Curtis Rd4BR,1.5BA$2.76
411 Shirley St, Unit 2411 Shirley St3BR,1BA$2.62
3 WalleyEBA14002BR,1.5BA$2.54
901 Saratoga St901 Saratoga St3BR,1BA$2.88
40 Breed St, Unit #140 Breed St3BR,1BA$2.75
19 Charles St, Unit Two19 Charles St2BR,1BA$2.54
126 Leyden St2BR/1.0BA2BR,1BA$2.85
72 Orient Ave, Unit 272 Orient Ave2BR,1BA$2.89
87-90 Win1BR/1.0BA1BR,1BA$2.90

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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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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Quick 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.

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Pet Friendly Lifestyle
Winthrop Highlands, Winthrop, MA

Ranked #2

Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Frequently Asked Questions about Winthrop Highlands

What type of rentals are currently available in Winthrop Highlands?

There are currently 216 Apartments for Rent in Winthrop Highlands, MA with pricing that ranges from $1,000 to $18,529. There are also 89 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winthrop Highlands ranging from $2,075 to $9,200.

What is the current price range for Rental Homes in Winthrop Highlands?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winthrop Highlands ranges from $2,075 to $9,200 with an average monthly rent of $3,097.

How much are larger Three and Four Bedroom Rentals in Winthrop Highlands?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winthrop Highlands range from $2,600 to $5,719, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $6,000. Four Bedroom Single-Family rentals are also available starting from $3,500 and Four Bedroom Apartments start at $3,400.

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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