Cheap Homes for Rent in Winthrop Highlands Neighborhood of Winthrop, MA from $1,500 (29 Rentals)

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Search the lowest-cost Homes available for rent right now in the Winthrop Highlands 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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property at 90 Winthrop Shore Dr

$1,595 - $1,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,595 - $1,700
Total Monthly Price
$1,595 - $1,700

Studio To 1 Bedroom Condos for Rent

Available Now

90 Winthrop Shore Dr

WinthropMA02152

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

$2,200 - $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

$2,350

Total Monthly Price

Total Monthly Price

Base Rent
$2,350
Total Monthly Price
$2,350

2 Bedroom, 1 Bath Condo for Rent

Available Jul 1

267 Washington Ave

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 238 Everett St

$2,350

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,350
Total Monthly Price
$2,350

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

238 Everett St, Unit 1

238 Everett St
BostonMA02128
Showing Results 1-29, Page 1 of 1

Winthrop Highlands, Winthrop, MA Local Guide

Cheapest Available Winthrop Highlands Apartments for Rent

 

The cheapest available apartment rental in the Winthrop Highlands area of Boston, MA is a Studio unit found at The Abby priced from $1,795. The Willet has the second lowest priced unit, which is a Studio apartment currently listed from $1,815. Here are the most affordable Winthrop Highlands apartments for rent in Boston, MA:

Apartment ListingModel NameBed/BathPriced From
The AbbyStudioStudio,1BA$1,795
The WilletStudio - 501Studio,1BA$1,815
87-90 Win0BR/1.0BAStudio,1BA$1,895
1510 N Shore RdStudioStudio,1BA$2,000
Ocean 650Studio (535 SF)Studio,1BA$2,276
SORASAStudio,1BA$2,350

Best Value Apartments for Rent in Winthrop Highlands, MA

As of June 20, 2026 the best value apartment in the Winthrop Highlands area is the $0.19 price per square foot 720 Bennington St Model at 720 Bennington St, Unit 207 in the in the Waterfront neighborhood starting from $1,900. The second greatest value Winthrop Highlands apartment is the 411 Shirley St Model at 411 Shirley St, Unit 2 starting at $3,250 with a $2.50 price per square foot in the Beachmont neighborhood. Here is today’s list of the best values for Winthrop Highlands apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
720 Bennington St, Unit 207720 Bennington StStudio ,1BA$0.19
411 Shirley St, Unit 2411 Shirley St3BR,1BA$2.50
42 Irwin St42 Irwin St5BR,2BA$0.87
901 Saratoga St, Unit 3901 Saratoga St3BR,1BA$2.63
953 Shirley St, Unit 2953 Shirley St3BR,1BA$3.08
23 Endicott Ave23 Endicott Ave1BR,1BA$2.56
78 Haddon St, Unit 178 Haddon St2BR,1BA$2.47
82 Gladstone St, Unit 282 Gladstone St2BR,1BA$3.15
47 Roosevelt St, Unit #147 Roosevelt St2BR,1BA$3.11
190 Crescent Ave, Unit 190 Crescent Ave #2190 Crescent Ave1BR,1BA$3.14

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
Winthrop Highlands, Winthrop, MA

Ranked #1

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

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Frequently Asked Questions about Winthrop Highlands

What type of rentals are currently available in Winthrop Highlands?

There are currently 221 Apartments for Rent in Winthrop Highlands, MA with pricing that ranges from $1,100 to $16,360. There are also 109 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winthrop Highlands ranging from $1,595 to $6,000.

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

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winthrop Highlands ranges from $1,595 to $6,000 with an average monthly rent of $3,251.

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

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winthrop Highlands range from $2,250 to $5,719, 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 $3,400.

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.

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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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