
Apartments for Rent in Winthrop, MA Under $5,500 (439 Rentals)


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181 Winthrop Shore Dr, Unit #2, Unit #2

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76 Fremont St, Unit 763, Unit 763

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92 Winthrop Shore Dr, Unit 2, Unit 2

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37 Bellevue Ave, Unit Sunny spacious apt, Unit Sunny spacious apt

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288 Pleasant St, Unit 1, Unit 1

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220 Winthrop St

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The Abby

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94 Winthrop Shore Dr

40 Ocean Ave, Unit Apt 1
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180 Shirley St

370 Main St, Unit 2

585 Shirley St

90 Winthrop Shore Dr, Unit 2

29R Cutler St

117 Winthrop Shore Dr

800 Governors Dr

31-33 Pleasant St

90 Winthrop Shore Dr, Unit B

97 Winthrop Shore Dr
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31-33-33 Pleasant Park Rd

220 Winthrop St

33 Central St

90 Winthrop Shore Dr, Unit 10

45 Sturgis St

23 B Siren St

312 Shirley St, Unit 210

312 Shirley St, Unit 208

90 Winthrop Shore Dr, Unit 9

90 Winthrop Shore Dr, Unit 1A
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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.

90 Winthrop Shore Dr, Unit 8A

Fort Heath Apartments

87-90 Win

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100 Brooks St, Unit 1, Unit 1

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158 Everett St, Unit 203, Unit 203

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47 Orleans St, Unit 1, Unit 1

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159 Everett St, Unit 204, Unit 204

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174 Princeton St

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179 Putnam St, Unit 1, Unit 1

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303 Maverick St
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74 Brooks St, Unit 2, Unit 2

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131 Cottage St, Unit 2, Unit 2

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117 Cottage St, Unit 2, Unit 2

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303 Maverick St

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179 Putnam St, Unit 1, Unit 1

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25 Pratt St, Unit 2, Unit 2

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159 Everett St, Unit 203, Unit 203

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66 Lubec St

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344 Saratoga St, Unit 2, Unit 2

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312 Sumner St, Unit 1, Unit 1
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Winthrop, MA Local Guide

How much does it cost to rent an apartment in Winthrop?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winthrop Studio Apartments Under $5500 | $2,499 | $1,595 | $5,269 |
| Winthrop 1 Bedroom Apartments Under $5500 | $2,717 | $1,175 | $7,515 |
| Winthrop 2 Bedroom Apartments Under $5500 | $3,415 | $920 | $10,000+ |
| Winthrop 3 Bedroom Apartments Under $5500 | $3,702 | $1,120 | $10,000+ |
| Winthrop 4 Bedroom Apartments Under $5500 | $3,917 | $870 | $5,600 |
| Winthrop 5 Bedroom Apartments | $5,399 | $3,600 | $7,995 |
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Winthrop, MA Local Guide
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Read ArticleTop Neighborhoods Near Boston Colleges and Universities
Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com
Read ArticleQuick 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.
Best Local Schools in Winthrop, MA
Arthur T. Cummings Elementary School
School data provided by Great Schools
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winthrop, MA Rentals by Map
See the most popular apartments and homes in Winthrop, MA
Frequently Asked Questions about Winthrop
How much are Studio apartments in Winthrop?
There are currently 158 Studio Apartments in Winthrop with rent ranges from $1,595 to $5,269 with an average price of $2,499.
What is the current price range for One Bedroom Winthrop Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winthrop ranges from $1,175 to $7,515 with an average monthly rent of $2,717.
What does renting a Two Bedroom Apartment in Winthrop cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winthrop range from $920 to $10,372. Today's average rental price for Two Bedrooms here is $3,415.
How expensive are Winthrop Three Bedroom Apartments?
There are currently 130 Three Bedroom Apartments listings available in Winthrop on ApartmentHomeLiving.com. The pricing ranges from $1,120 to $12,098 - averaging $3,702 for the location.
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

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.

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!

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.

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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This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

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This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

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Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.