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$1,500
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1 Bedroom Apartments Available Jan 16, 2026Furnished Bedroom with Private Bath in East Boston
1061 Saratoga StBoston, MA 02128
Cheap Homes for Rent in Winthrop, MA from $1,500 (43 Rentals)
Search the lowest-cost Homes available for rent right now in Winthrop.
40 Cottage Park Rd
WinthropMA02152
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$1,500
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1 Bedroom Apartments Available Jan 1, 2026Furnished Private Bedroom with Private Bath in East Boston!
695 Bennington StBoston, MA 02128
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$1,550
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1 Bedroom Apartments Available Feb 11, 2026Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
85 Winthrop Shore Dr
WinthropMA02152
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$1,695
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Studio Apartments Available Jan 1, 202690 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
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$1,850
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Studio Apartments Available Now90 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
90 Winthrop Shore Dr, Unit 1-b 1-b U10
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.
34 Trident Ave
WinthropMA02152
170 Beach St
RevereMA02151
435 Shirley St
WinthropMA02152
6 Drake Pl
BostonMA02128
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1030 Bennington St, Unit 15
1030 Bennington St
BostonMA02128
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.
1030 Bennington St
BostonMA02128
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149 Meridian St
BostonMA02128
932 Broadway
ChelseaMA02150
12 Sewall Ave
WinthropMA02152
151 Princeton St, Unit 2
151 Princeton St
BostonMA02128
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251 Bennington St, Unit 1
251 Bennington St
BostonMA02128
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.
35 Ford St
RevereMA02151
249 Bennington St
BostonMA02128
960 Broadway
ChelseaMA02150
960 Broadway
ChelseaMA02150
48 Brooks St, Unit 1
48 Brooks St
BostonMA02128
221 Trenton St, Unit #2
221 Trenton St
BostonMA02128
42 Jeffries St
BostonMA02128
179 Putnam St, Unit 1
179 Putnam St
BostonMA02128
Explore Like a Local: The Insider's Guide to Boston
Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.
149 Meridian St, Unit 4
149 Meridian St
BostonMA02128
22 Sherman Ave
NahantMA01908
194 Marion St, Unit 182-1
194 Marion St
BostonMA02128
182 Marion St
BostonMA02128
10 Franklin Ave
RevereMA02151
329 Paris St, Unit 2
329 Paris St
BostonMA02128
230 Havre St
BostonMA02128
83 Lubec St, Unit 4
83 Lubec St
BostonMA02128
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.
10 Cheever Ct, Unit 2
10 Cheever Ct
BostonMA02128
12 Cheever Ct, Unit 2
12 Cheever Ct
BostonMA02128
900 Governors Dr
WinthropMA02152
Showing Results 1-43, Page 1 of 1
Winthrop, MA Local Guide
View of Winthrop, Massachusetts from the northeast by Sean 2015 is licensed under Internal
How much does it cost to rent a home in Winthrop?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winthrop 2 Bedroom Homes for Rent | $3,037 | $2,200 | $4,500 |
| Winthrop 3 Bedroom Homes for Rent | $3,590 | $2,450 | $5,500 |
| Winthrop 4 Bedroom Homes for Rent | $3,983 | $3,200 | $4,800 |
| Winthrop 5 Bedroom Homes for Rent | $5,339 | $3,900 | $7,995 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Winthrop
Explore Winthrop
Winthrop, MA Local Guide
- Winthrop Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Winthrop Apartments for Rent
The cheapest available apartment rental in Winthrop, MA is a 1 Bed unit found at 14 Horace St in the Waterfront neighborhood priced from $1,100. 87-90 Win in the Beachmont neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,695. Here is today’s list of the most affordable Winthrop apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 14 Horace St | 3 | 1BR,1BA | $1,100 |
| 87-90 Win | 0BR/1.0BA | Studio,1BA | $1,695 |
| Pratt Place Apartments | 1 Bedroom, 1st Floor | 1BR,1BA | $1,869 |
Best Value Apartments for Rent in Winthrop, MA
As of December 14, 2025 the best value apartment in the Winthrop area is the $0.22 price per square foot 44 Princeton St Model at 44 Princeton St, Unit 1 in the in the Waterfront neighborhood starting from $2,200. The second greatest value Winthrop apartment is the 25 Pratt St Model at 25 Pratt St, Unit 2 starting at $3,800 with a $0.38 price per square foot in the Cottage Hill neighborhood. Here is today’s list of the best values for Winthrop apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 44 Princeton St, Unit 1 | 44 Princeton St | 1BR,1BA | $0.22 |
| 25 Pratt St, Unit 2 | 25 Pratt St | 3BR,1BA | $0.38 |
| 8 Curtis St, Unit 6 | 8 Curtis St | 1BR,1BA | $0.20 |
| 187 Webster St, Unit 1 | 187 Webster St | 1BR,1BA | $0.29 |
| 95 Cottage St, Unit 1 | 95 Cottage St | 1BR,1BA | $0.22 |
| 288 Pleasant St, Unit 1 | 288 Pleasant St | 2BR,1BA | $0.27 |
| 160 Everett St, Unit 303 | 160 Everett St | 4BR,2.5BA | $0.40 |
| 12 Sewall Ave, Unit 3 | 12 Sewall Ave | 1BR,1BA | $0.23 |
| 12 Chelsea St, Unit 2 | 12 Chelsea St | 2BR,1BA | $0.29 |
| 110 Grovers Ave, Unit 2F | 110 Grovers Ave | 1BR,1BA | $0.18 |
Boston Neighborhood Guide: Living Near UMass, MGH, and State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.
Read Article
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.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
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
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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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Best Local Schools in Winthrop, MA
Arthur T. Cummings Elementary School
Winthrop School District
Public School - Grades 3-5 (431)
6 out of 10
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
What type of rentals are currently available in Winthrop?
There are currently 613 Apartments for Rent in Winthrop, MA with pricing that ranges from $1,100 to $9,014. There are also 299 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winthrop ranging from $1,500 to $7,995.
What is the current price range for Rental Homes in Winthrop?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winthrop ranges from $1,500 to $7,995 with an average monthly rent of $3,443.
How much are larger Three and Four Bedroom Rentals in Winthrop?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winthrop range from $2,450 to $5,406, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,450 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,200 and Four Bedroom Apartments start at $3,000.
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
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.