Cheap Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA from $1,900 (23 Rentals)

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

property at 312 Shirley St

312 Shirley St

WinthropMA02152
property at 57 White St

57 White St, Unit G

57 White St
BostonMA02128
property at 25 Pratt St

25 Pratt St, Unit 1

25 Pratt St
BostonMA02134
property at 25 Pratt St

25 Pratt St, Unit 1

25 Pratt St
BostonMA02134
property at 11 Walley St

11 Walley St

BostonMA02128

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 1-23, Page 1 of 1

Cottage Hill, Winthrop, MA Local Guide

Cheapest Available Cottage Hill 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 Cottage Hill, MA

As of March 27, 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 125 Pratt St1BR,1BA$0.24
25 Pratt St, Unit 125 Pratt St1BR,1BA$0.24
25 Pratt St, Unit 225 Pratt St3BR,1BA$0.38
58 Lewis Ave, Unit #30258 Lewis Ave1BR,1BA$0.26
16 Franklin St, Unit A 16 Franklin St16 Franklin St2BR,1BA$1.92
17 Waldemar Ave, Unit #30117 Waldemar Ave2BR,1BA$2.00
94 Terrace Ave, Unit #194 Terrace Ave1BR,1BA$2.04

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Frequently Asked Questions about Cottage Hill

What type of rentals are currently available in Cottage Hill?

There are currently 185 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $1,155 to $5,595. There are also 67 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $1,900 to $5,200.

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 $1,900 to $5,200 with an average monthly rent of $3,324.

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 $3,000 to $5,000, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,100 to $3,700. Four Bedroom Single-Family rentals are also available starting from $3,900 and Four Bedroom Apartments start at $3,950.

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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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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Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

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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.