Cheap Apartments for Rent in the Winthrop Highlands Neighborhood of Winthrop, MA from $1,100 (44 Rentals)

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

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87-90 Win
Studio to 2 Bedroom Apartments

87-90 Win

87-90 Winthrop Shore DrWinthrop, MA 02152

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 951 Saratoga St

951 Saratoga St

BostonMA02128
property at 55 Walnut Ave

55 Walnut Ave

RevereMA02151
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Bennington Arms
Studio to 1 Bedroom Apartments

Bennington Arms

720 Bennington StEast Boston, MA 02128
  • Utilities Included
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Waldemar Ave
2 Bedroom Apartments

Waldemar Ave

75 Waldemar AveEast Boston, MA 02128
  • Utilities Included
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Revere Bell Apartments
Studio to 2 Bedroom Apartments

Revere Bell Apartments

45-55 Belle Isle AveRevere, MA 02151
  • Utilities Included
  • Smoke Free
Showing Results 1-44, Page 1 of 1

Winthrop Highlands, Winthrop, MA Local Guide

Cheapest Available Winthrop Highlands Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
87-90 Win0BR/1.0BAStudio,1BA$1,650
Ocean Point ApartmentsStudioStudio,1BA$1,800

Best Value Apartments for Rent in Winthrop Highlands, MA

As of March 23, 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
201 Ocean Ave, Unit #674-104201 Ocean Ave1BR,1BA$0.25
200 Ocean Ave, Unit #660-232200 Ocean Ave1BR,1BA$0.25
720 Winthrop Ave, Unit #3720 Winthrop Ave2BR,1BA$0.26
58 Lewis Ave, Unit #30258 Lewis Ave1BR,1BA$0.26
35 Franklin Ave, Unit #335 Franklin Ave2BR,1BA$0.25
16 Franklin St, Unit A 16 Franklin St16 Franklin St2BR,1BA$1.92
23 Endicott Ave, Unit #1F23 Endicott Ave1BR,1BA$1.90

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Pet Friendly Lifestyle
Winthrop Highlands, Winthrop, MA

Ranked #3

Among neighborhoods in Winthrop, MA for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Getting Around the Winthrop Highlands Neighborhood in Winthrop, MA

Walk Score®

56 / 100

Somewhat Walkable

Some errands can be accomplished on foot

Bike Score®

32 / 100

Somewhat Bikeable

Minimal bike infrastructure

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 Cheap Winthrop Highlands Apartments

What is the Cheapest Studio apartment in Winthrop Highlands?

Currently the most affordable Cheap Studio Apartment in Winthrop Highlands is at 87-90 Win listed at $1,650.

How much is rent for a Cheap One Bedroom Winthrop Highlands Apartment?

The lowest price for a Cheap One Bedroom Winthrop Highlands Apartment is $1,175 at .

What is the lowest price for a Cheap Two Bedroom Winthrop Highlands Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Winthrop Highlands is starting from $2,344 at Pratt Place Apartments.

What is the most affordable Winthrop Highlands Three Bedroom Apartment?

The best deal on a cheap Winthrop Highlands Three Bedroom Apartment rental is at and starts from $2,600.

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.

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

The 10 Best Affordable Neighborhoods in Boston, MA

Written by: Amelia Ramstead

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

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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

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What to Know About Fees and Fines When Renting

Written by: Trey Huguley

When it comes to renting a new apartment or home there can be a number of fees that you will want to keep in mind going into the process.

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Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.