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$1,250
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,250
Total Monthly Price
$1,250
42 Irwin St, Unit 2
42 Irwin StWinthrop, MA 02152
Cheap Apartments for Rent in the Winthrop Highlands Neighborhood of Winthrop, MA from $1,200 (27 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winthrop Highlands area of Winthrop.
40 Cottage Park Rd
WinthropMA02152
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$1,695
Plus Fees
Studio Apartments Available Jan 1, 202690 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
68 Beach Rd
WinthropMA02152
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$1,750
Total Monthly Price
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,750
Total Monthly Price
$1,750
110 Grovers Ave, Unit 2F
110 Grovers AveWinthrop, MA 02152
110 Grovers Ave
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.
220 Winthrop St
WinthropMA02152
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$1,800
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
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$1,800
Total Monthly Price
$1,800
98 Winthrop Shore Dr
98 Winthrop Shore DrWinthrop, MA 02152
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$1,850
Plus Fees
Studio Apartments Available Now90 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
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$1,985
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$1,985
Total Monthly Price
$1,985
95 Bowdoin St, Unit 3
95 Bowdoin StWinthrop, MA 02152
45 Sturgis St
WinthropMA02152
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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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$1,500
Plus Fees
1 Bedroom Apartments Available Jan 16, 2026Furnished Bedroom with Private Bath in East Boston
1061 Saratoga StBoston, MA 02128
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$1,550
Plus Fees
1 Bedroom Apartments Available Feb 9, 2026Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
55 Walnut Ave
RevereMA02151
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$1,800
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,800
Total Monthly Price
$1,800
129 Bradstreet Ave, Unit 3
129 Bradstreet AveRevere, MA 02151
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$1,900
Total Monthly Price12 Month Lease Term
Studio Apartment Available Dec 15Total Monthly Price
Base Rent
$1,900
Total Monthly Price
$1,900
720 Bennington St, Unit 207
720 Bennington StBoston, MA 02128
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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$2,000 - $2,500
Plus Fees
Studio to 1 Bedroom Apartments Available Now1510 N Shore Rd
1510 N Shore RdRevere, MA 02151
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$2,025
Total Monthly Price
Studio Apartments Available NowTotal Monthly Price
Base Rent
$1,570
Required Monthly Fees
$455
Total Monthly Price
$2,025
50 Salt St
50 Salt StRevere, MA 02151
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The Art of the Rental Viewing: What to look for during a property tour
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.
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Showing Results 1-27, Page 1 of 1
Winthrop Highlands, 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 an apartment in Winthrop Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winthrop Highlands Studio Apartments | $2,622 | $1,695 | $3,849 |
| Winthrop Highlands 1 Bedroom Apartments | $2,907 | $1,250 | $3,932 |
| Winthrop Highlands 2 Bedroom Apartments | $3,679 | $2,200 | $9,014 |
| Winthrop Highlands 3 Bedroom Apartments | $3,593 | $2,600 | $5,406 |
| Winthrop Highlands 4 Bedroom Apartments | $3,794 | $3,375 | $4,250 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments in this Neighborhood
There are currently 27 rentals with your search options within a 2 mile radius of the Winthrop Highlands Neighborhood of Winthrop, MA.
See all Apartments in WinthropExplore Winthrop
Winthrop Highlands, Winthrop, MA Local Guide
- Nearby Winthrop neighborhoods
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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 87-90 Win priced from $1,695. Pratt Place Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,869. Here are the most affordable Winthrop Highlands apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 87-90 Win | 0BR/1.0BA | Studio,1BA | $1,695 |
| Pratt Place Apartments | 1 Bedroom, 1st Floor | 1BR,1BA | $1,869 |
| 1510 N Shore Rd | Studio | Studio,1BA | $2,000 |
| One Beachmont | SA | Studio,1BA | $2,142 |
Best Value Apartments for Rent in Winthrop Highlands, MA
As of December 12, 2025 the best value apartment in the Winthrop Highlands area is the $0.27 price per square foot 288 Pleasant St Model at 288 Pleasant St, Unit 1 in the in the Beachmont neighborhood starting from $2,650. The second greatest value Winthrop Highlands apartment is the 12 Sewall Ave Model at 12 Sewall Ave, Unit 3 starting at $2,250 with a $0.23 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 288 Pleasant St, Unit 1 | 288 Pleasant St | 2BR,1BA | $0.27 |
| 12 Sewall Ave, Unit 3 | 12 Sewall Ave | 1BR,1BA | $0.23 |
| 97 Bradstreet Ave, Unit 97 | 97 Bradstreet Ave | 5BR,2BA | $1.79 |
| 183 Cottage Park Rd, Unit 3 | 183 Cottage Park Rd | 4BR,2BA | $1.55 |
| 1148 Bennington St, Unit 1 | 1148 Bennington St | 4BR,2BA | $1.93 |
| 31 Faywood Ave, Unit 3 | 31 Faywood Ave | 4BR,2BA | $2.25 |
| 42 Irwin St, Unit 2 | 42 Irwin St | 1BR,2BA | $0.89 |
| 40 Dolphin Ave, Unit #2 | 40 Dolphin Ave | 2BR,1BA | $2.20 |
| 23 Endicott Ave | 23 Endicott Ave | 1BR,1BA | $2.56 |
| 129 Bradstreet Ave, Unit 3 | 129 Bradstreet Ave | 1BR,1BA | $2.00 |
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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The 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.
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Pet Friendly LifestyleWinthrop Highlands, Winthrop, MA
Ranked #1
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Getting Around the Winthrop Highlands Neighborhood in Winthrop, MA
Walk Score®
56 / 100
Somewhat Walkable
Some errands can be accomplished on foot
Bike Score®
32 / 100
Somewhat Bikeable
Minimal bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Winthrop Highlands Apartments
What is the Cheapest Studio apartment in Winthrop Highlands?
Currently the most affordable Cheap Studio Apartment in Winthrop Highlands is at 87-90 Win listed at $1,695.
How much is rent for a Cheap One Bedroom Winthrop Highlands Apartment?
The lowest price for a Cheap One Bedroom Winthrop Highlands Apartment is $1,869 at Pratt Place Apartments.
What is the lowest price for a Cheap Two Bedroom Winthrop Highlands Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winthrop Highlands is starting from $3,098 at One Beachmont.
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.