Cheap Homes for Rent in Winthrop, MA from $1,200 (51 Rentals)

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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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.

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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.

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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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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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Showing Results 1-50, Page 1 of 2

Winthrop, MA Local Guide

Cheapest Available Winthrop Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
The Box DistrictTwo Bedroom2BR,1BA$1,994

Best Value Apartments for Rent in Winthrop, MA

As of June 25, 2025 the best value apartment in the Winthrop area is the $0.21 price per square foot 247 Bennington St Model at 247 Bennington St, Unit 1 in the in the Airport neighborhood starting from $2,120. The second greatest value Winthrop apartment is the 247 Bennington St Model at 247 Bennington St, Unit 1 starting at $2,120 with a $0.21 price per square foot in the Airport neighborhood. Here is today’s list of the best values for Winthrop apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
247 Bennington St, Unit 1247 Bennington St1BR,1BA$0.21
247 Bennington St, Unit 1247 Bennington St1BR,1BA$0.21
765 Broadway, Unit 5765 Broadway1BR,1BA$0.22
75 Putnam St, Unit 375 Putnam St2BR,1BA$0.24
95 Cottage St, Unit 195 Cottage St1BR,1BA$0.23
97 Cottage St, Unit #297 Cottage St1BR,1BA$0.23
200 London St, Unit 2200 London St2BR,1BA$0.24
102 Cottage St, Unit #2102 Cottage St1BR,1BA$0.22
96 Cottage St, Unit #296 Cottage St1BR,1BA$0.22
235 Lexington St, Unit #3235 Lexington St2BR,1BA$0.22

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Frequently Asked Questions about Winthrop

What type of rentals are currently available in Winthrop?

There are currently 1047 Apartments for Rent in Winthrop, MA with pricing that ranges from $900 to $9,413. There are also 526 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winthrop ranging from $1,750 to $7,995.

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

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winthrop ranges from $1,750 to $7,995 with an average monthly rent of $3,800.

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

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winthrop range from $1,275 to $5,600, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,550 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,100 and Four Bedroom Apartments start at $3,100.

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

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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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.