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$1,650Studio Apartments Available Now
90 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
Cheap Apartments for Rent in the Winthrop Highlands Neighborhood of Winthrop, MA from $1,100 (35 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winthrop Highlands area of Winthrop.
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$1,650
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$1,650
Total Monthly Price
$1,650
92 Winthrop Shore Dr, Unit 3
92 Winthrop Shore DrWinthrop, MA 02152
90 Winthrop Shore Dr
WinthropMA02152
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$1,750Studio Apartments Available Apr 1
90 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
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$1,750
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$1,750
Total Monthly Price
$1,750
94 Winthrop Shore Dr
94 Winthrop Shore DrWinthrop, MA 02152
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$1,800Studio Apartments Available Now
312 Shirley St
312 Shirley StWinthrop, MA 02152
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$2,000Studio Apartments Available Now
312 Shirley St
312 Shirley StWinthrop, MA 02152
20 Coral 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.
23 B Siren St
WinthropMA02152
45 Sturgis St
WinthropMA02152
5 Fremont St
WinthropMA02152
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Studio to 2 Bedroom Apartments
87-90 Win
87-90 Winthrop Shore DrWinthrop, MA 02152
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1 to 2 Bedroom Apartments
Fort Heath Apartments
1 Pond StWinthrop, MA 02152
1057 Saratoga St
BostonMA02128
Furnished Private Bedroom in East Boston
1061 Saratoga St
BostonMA02128
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$1,5001 Bedroom Apartments Available May 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
34 Franklin Ave
RevereMA02151
21 McClure St
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
43 Bryant St, Unit 2
43 Bryant StRevere, MA 02151
26 Centennial Ave
RevereMA02151
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$1,900
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$1,900
Total Monthly Price
$1,900
720 Bennington St, Unit 207
720 Bennington StBoston, MA 02128
720 Bennington St
BostonMA02128
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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
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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$2,065 - $4,075
Total Monthly Price
Studio to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,065 - $4,075
Total Monthly Price
Varies
Amaya
50 Salt StRevere, MA 02151
198 Harris St
RevereMA02151
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Studio to 1 Bedroom Apartments
Bennington Arms
720 Bennington StEast Boston, MA 02128
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Studio to 2 Bedroom Apartments
Pratt Place Apartments
16-30 Pratt PlRevere, MA 02151
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1 to 2 Bedroom Apartments
Waldemar Ave
75 Waldemar AveEast Boston, MA 02128
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1 to 2 Bedroom Apartments
565 Beach
565 Beach StRevere, MA 02151
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Studio to 2 Bedroom Apartments
The Willet
13 Nahant AveRevere, MA 02151
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1 to 2 Bedroom Apartments
388 Ocean Revere
388-394 Ocean AveRevere, MA 02151
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
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Studio to 2 Bedroom Apartments
Revere Bell Apartments
45-55 Belle Isle AveRevere, MA 02151
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1 to 2 Bedroom Apartments
566 Beach
566 Beach StRevere, MA 02151
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Studio to 2 Bedroom Apartments
The Bennington
917 Bennington StEast Boston, MA 02128
Showing Results 1-35, 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 | $2,470 | $1,650 | $4,671 |
| Winthrop Highlands 1 Bedroom Apartments | $2,842 | $1,175 | $6,999 |
| Winthrop Highlands 2 Bedroom Apartments | $3,649 | $2,250 | $6,553 |
| Winthrop Highlands 3 Bedroom Apartments | $3,878 | $2,500 | $6,889 |
| Winthrop Highlands 4 Bedroom Apartments | $3,624 | $3,200 | $3,800 |
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 35 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
- Nearby Cities
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- School Districts
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 $1,650. 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 | $1,650 |
| Pratt Place Apartments | 1 Bedroom, 1st Floor | 1BR,1BA | $1,869 |
| 1510 N Shore Rd | Studio | Studio,1BA | $2,000 |
| Amaya | M1 | Studio,1BA | $2,085 |
| Ocean 650 | Studio (535 SF) | Studio,1BA | $2,122 |
Best Value Apartments for Rent in Winthrop Highlands, MA
As of March 15, 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 183 Cottage Park Rd Model at 183 Cottage Park Rd, Unit 3 starting at $3,400 with a $1.55 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. |
|---|---|---|---|
| 720 Bennington St, Unit 207 | 720 Bennington St | Studio ,1BA | $0.19 |
| 183 Cottage Park Rd, Unit 3 | 183 Cottage Park Rd | 4BR,2BA | $1.55 |
| 31 Faywood Ave, Unit 3 | 31 Faywood Ave | 4BR,2BA | $2.25 |
| 1656 N Shore Rd, Unit 1 | 1656 N Shore Rd | 4BR,1BA | $2.77 |
| 135 Bellingham Ave, Unit 1 | 135 Bellingham Ave | 3BR,1BA | $2.08 |
| 21 Prescott St, Unit 1 | 21 Prescott St | 2BR,1BA | $2.18 |
| 23 Endicott Ave | 23 Endicott Ave | 1BR,1BA | $2.56 |
| 81 Gladstone St, Unit 2 | 81 Gladstone St | 2BR,1BA | $3.04 |
| 82 Gladstone St, Unit 2 | 82 Gladstone St | 2BR,1BA | $3.04 |
| Pratt Place Apartments | 1 Bedroom, 3rd Floor | 1BR,1BA | $2.82 |
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.
Read ArticleCash 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.
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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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
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 $1,650.
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 $3,318 at Ryder Revere Beach.
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
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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
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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
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
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.