Cheap Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA from $900 (11 Rentals)

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

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

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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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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

Cottage Hill, Winthrop, MA Local Guide

Cheapest Available Cottage Hill Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
Broadway250A11BR,1BA$2,111

Best Value Apartments for Rent in Cottage Hill, MA

As of June 06, 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
720 Winthrop Ave, Unit #3720 Winthrop Ave2BR,1BA$0.26
25 Pratt St, Unit 225 Pratt St3BR,1BA$0.38
76 Fremont St, Unit #276 Fremont St2BR,1BA$0.28
271 Shirley St, Unit #2271 Shirley St2BR,1BA$0.42
65 Waldemar Ave, Unit #165 Waldemar Ave2BR,1BA$2.05
78 Temple Ave, Unit 178 Temple Ave2BR,1BA$2.10
1018 Shirley St, Unit #11018 Shirley St2BR,1.5BA$2.09
5 Hillside Ave, Unit #5A5 Hillside Ave2BR,2BA$2.09

Quick Rent Budget Calculator

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Pet Friendly Lifestyle
Cottage Hill, Winthrop, MA

Ranked #1

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 Cottage Hill Neighborhood in Winthrop, MA

Walk Score®

62 / 100

Somewhat Walkable

Some errands can be accomplished on foot

Bike Score®

35 / 100

Somewhat Bikeable

Minimal bike infrastructure

Frequently Asked Questions about Cheap Cottage Hill Apartments

What is a cheap apartment in Cottage Hill?

A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Cottage Hill is under $2,111.

What is the price of a cheap apartment in Cottage Hill?

The cheapest apartment in Cottage Hill is Broadway250 which is listed at $2,111, while the average apartment in Cottage Hill costs $3,800.

What types of apartments are the cheapest in Cottage Hill?

Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 9 regular apartments in Cottage Hill that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.

How do the prices of cheap apartments compare to the average apartment in Cottage Hill?

Cheap apartments in Cottage Hill have an average cost of $346 which is $3,454 cheaper than the average rent for all rentals in Cottage Hill.

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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