Cheap Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA from $1,900 (24 Rentals)

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

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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property at 25 Pratt St

25 Pratt St, Unit 1

25 Pratt St
BostonMA02134

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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Showing Results 1-24, Page 1 of 1

Cottage Hill, Winthrop, MA Local Guide

Cheapest Available Cottage Hill Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
87-90 Win1BR/1.0BA1BR,1BA$2,200
AmayaM1Studio,1BA$2,390

Best Value Apartments for Rent in Cottage Hill, MA

As of July 29, 2025 the best value apartment in the Cottage Hill area is the $0.33 price per square foot 25 Pratt St Model at 25 Pratt St, Unit 2 in the in the Cottage Hill neighborhood starting from $3,300. The second greatest value Cottage Hill apartment is the 42 Ocean Ave Model at 42 Ocean Ave, Unit 2 starting at $2,950 with a $0.30 price per square foot in the Beachmont neighborhood. Here is today’s list of the best values for Cottage Hill apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
25 Pratt St, Unit 225 Pratt St3BR,1BA$0.33
42 Ocean Ave, Unit 242 Ocean Ave2BR,1BA$0.30
126 Barnes Ave, Unit 2126 Barnes Ave4BR,2BA$0.38
58 Lewis Ave, Unit #30258 Lewis Ave1BR,1BA$0.26
108 Quincy Ave, Unit #3108 Quincy Ave2BR,1BA$0.28
25 Pratt St, Unit 225 Pratt St4BR,2BA$2.39
82 Temple Ave, Unit #182 Temple Ave1BR,1BA$1.15
1018 Shirley St, Unit #11018 Shirley St2BR,1.5BA$2.09
37 Dolphin Ave, Unit #237 Dolphin Ave2BR,1BA$2.20
21 Gladstone St, Unit 321 Gladstone St1BR,1BA$2.29

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Frequently Asked Questions about Cottage Hill

What type of rentals are currently available in Cottage Hill?

There are currently 148 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $900 to $5,200. There are also 73 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $1,995 to $9,000.

What is the current price range for Rental Homes in Cottage Hill?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Cottage Hill ranges from $1,995 to $9,000 with an average monthly rent of $3,784.

How much are larger Three and Four Bedroom Rentals in Cottage Hill?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Cottage Hill range from $2,510 to $5,200, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,250 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,400 and Four Bedroom Apartments start at $3,400.

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.