Cheap Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA from $1,500 (30 Rentals)

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

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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property at 600 Shirley St

$2,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,300
Total Monthly Price
$2,300

Studio, 1 Bath Condo for Rent

Available Sep 1

600 Shirley St, Unit 9

600 Shirley St
WinthropMA02152
property at 900 Governors Dr

$2,300 - $2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,300
Total Monthly Price
$2,300

1 To 2 Bedroom Rentals

Available Now

900 Governors Dr

WinthropMA02152
property at 267 Washington Ave

$2,450

Total Monthly Price

Total Monthly Price

Base Rent
$2,450
Total Monthly Price
$2,450

2 Bedroom, 1 Bath Condo for Rent

Available Now

267 Washington Ave

WinthropMA02152
property at 5 Fremont St

$2,500 - $3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500 - $3,200
Total Monthly Price
$2,500 - $3,200

1 To 2 Bedroom Condos for Rent

Available Now

5 Fremont St

WinthropMA02152

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 15 Walley St

$2,550

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,550
Total Monthly Price
$2,550

1 Bedroom, 1 Bath Condo for Rent

Available Now

15 Walley St, Unit 206

15 Walley St
BostonMA02128
Showing Results 1-30, Page 1 of 1

Cottage Hill, Winthrop, MA Local Guide

Cheapest Available Cottage Hill Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
The AbbyStudioStudio,1BA$1,795
AmayaM1.2Studio,1BA$2,293

Best Value Apartments for Rent in Cottage Hill, MA

As of June 11, 2026 the best value apartment in the Cottage Hill area is the $2.65 price per square foot 411 Shirley St Model at 411 Shirley St, Unit 2 in the in the Beachmont neighborhood starting from $3,450. The second greatest value Cottage Hill apartment is the 44 Ashley St Model at 44 Ashley St, Unit #2 starting at $3,800 with a $3.17 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.
411 Shirley St, Unit 2411 Shirley St3BR,1BA$2.65
44 Ashley St, Unit #244 Ashley St4BR,2BA$3.17
953 Shirley St, Unit 2953 Shirley St3BR,1BA$3.08
25 Pratt St, Unit 125 Pratt St1BR,1BA$2.10
82 Gladstone St, Unit 282 Gladstone St2BR,1BA$3.15
92 Winthrop Shore Dr, Unit 292 Winthrop Shore Dr2BR,1BA$3.24
172 Endicott Ave, Unit 2172 Endicott Ave1BR,1BA$3.60
85 Gladstone St, Unit 85 Gladstone Street85 Gladstone St3BR,1BA$4.00
190 Crescent Ave, Unit 190 Crescent Ave #2190 Crescent Ave1BR,1BA$3.14
The AbbyStudioStudio ,1BA$3.99

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Pet Friendly Lifestyle
Cottage Hill, Winthrop, MA

Ranked #3

Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Best Local Schools in
Cottage Hill, Winthrop, MA

School data provided by Great Schools

Frequently Asked Questions about Cottage Hill

What type of rentals are currently available in Cottage Hill?

There are currently 100 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $1,200 to $4,680. There are also 74 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $1,595 to $6,000.

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 $1,595 to $6,000 with an average monthly rent of $3,372.

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 $2,250 to $4,680, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $6,000. Four Bedroom Single-Family rentals are also available starting from $3,700 and Four Bedroom Apartments start at $3,700.

Expert Rental Resources

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.

Helpful Local Expert Guides

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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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A Local Experts Guide to the Top Boston Neighborhoods for College Renters

Written by: Amelia Ramstead

Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!

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Explore Like a Local: The Insider's Guide to Boston

Written by: Amelia Ramstead

Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.

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Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street

Written by: Amelia Ramstead

Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.

Articles, How-To's, and Tips

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

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Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.