Cheap Homes for Rent in Winthrop Highlands Neighborhood of Winthrop, MA from $1,700 (60 Rentals)

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Cheap Homes in the Winthrop Highlands area of Winthrop.

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.

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property at 312 Shirley St

312 Shirley St

WinthropMA02152

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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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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 87-90 Win priced from $1,650. 1510 N Shore Rd has the second lowest priced unit, which is a 1 Bed apartment currently listed from $2,000. Here are the most affordable Winthrop Highlands apartments for rent in Boston, MA:

Apartment ListingModel NameBed/BathPriced From
87-90 Win0BR/1.0BAStudio,1BA$1,650
1510 N Shore Rd1 Bed 1 Bath1BR,1BA$2,000
Rumney FlatsSAStudio,1BA$2,200

Best Value Apartments for Rent in Winthrop Highlands, MA

As of May 06, 2025 the best value apartment in the Winthrop Highlands area is the $0.30 price per square foot 42 Ocean Ave Model at 42 Ocean Ave, Unit 2 in the in the Beachmont neighborhood starting from $2,950. The second greatest value Winthrop Highlands apartment is the 33 Franklin Ave Model at 33 Franklin Ave, Unit #8 starting at $2,500 with a $0.25 price per square foot in the West Revere 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.
42 Ocean Ave, Unit 242 Ocean Ave2BR,1BA$0.30
33 Franklin Ave, Unit #833 Franklin Ave2BR,1BA$0.25
32 Franklin Pl, Unit #332 Franklin Pl2BR,1BA$0.25
740 Winthrop Ave, Unit 11740 Winthrop Ave2BR,1BA$0.27
35 Franklin Ave, Unit #335 Franklin Ave2BR,1BA$0.25
355 Revere Beach Pky, Unit #9Furn355 Revere Beach Pky1BR,1BA$0.27
82 Gladstone St, Unit 182 Gladstone St2BR,1BA$0.28
22 Adams St, Unit #222 Adams St3BR,1BA$1.90
42 Irwin St, Unit 342 Irwin St1BR,2BA$1.26
17 Waldemar Ave, Unit #30117 Waldemar Ave2BR,1BA$2.00

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Frequently Asked Questions about Winthrop Highlands

What type of rentals are currently available in Winthrop Highlands?

There are currently 296 Apartments for Rent in Winthrop Highlands, MA with pricing that ranges from $1,175 to $11,684. There are also 115 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winthrop Highlands ranging from $1,795 to $5,800.

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 $1,795 to $5,800 with an average monthly rent of $3,359.

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 $5,406, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,995 to $3,700. Four Bedroom Single-Family rentals are also available starting from $3,700 and Four Bedroom Apartments start at $3,500.

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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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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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

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Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.

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Rise of Digital Nomads: Remote Work Tips for Apartment Renters

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