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$1,5001 Bedroom Apartments Available May 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
Cheap Homes for Rent in Winthrop Highlands Neighborhood of Winthrop, MA from $1,700 (23 Rentals)
Search the lowest-cost Homes available for rent right now in the Winthrop Highlands area of Winthrop.
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$1,650Studio Apartments Available Now
90 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
90 Winthrop Shore Dr
WinthropMA02152
90 Winthrop Shore Dr, Unit 3
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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$1,800Studio Apartments Available Now
312 Shirley St
312 Shirley StWinthrop, MA 02152
312 Shirley St
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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$2,000Studio Apartments Available Now
312 Shirley St
312 Shirley StWinthrop, MA 02152
394 Ocean Ave
RevereMA02151
93 Kimball Ave, Unit 1
93 Kimball Ave
RevereMA02151
10 Franklin Ave
RevereMA02151
214 Bradstreet Ave, Unit 2
214 Bradstreet Ave
RevereMA02151
900 Governors Dr
WinthropMA02152
394 Ocean Ave
RevereMA02151
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.
394 Ocean Ave
RevereMA02151
394 Ocean Ave
RevereMA02151
10 Ocean 4004
RevereMA02151
394 Ocean Ave, Unit 515
394 Ocean Ave
RevereMA02151
5 Fremont St
WinthropMA02152
238 Everett St, Unit 1
238 Everett St
BostonMA02128
23 Tafts Ave
WinthropMA02152
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.
41 Winthrop Pkwy
RevereMA02151
67 Curtis Rd
RevereMA02151
Showing Results 1-23, 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 a home in Winthrop Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winthrop Highlands 2 Bedroom Homes for Rent | $2,840 | $2,400 | $3,800 |
| Winthrop Highlands 3 Bedroom Homes for Rent | $3,345 | $2,600 | $4,200 |
| Winthrop Highlands 4 Bedroom Homes for Rent | $4,407 | $3,650 | $5,500 |
| Winthrop Highlands 5 Bedroom Homes for Rent | $4,000 | $4,000 | $4,000 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 23 rentals with your search options within a 2 mile radius of the Winthrop Highlands Neighborhood of Winthrop, MA.
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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 $1,650. 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.
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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 Winthrop Highlands
What type of rentals are currently available in Winthrop Highlands?
There are currently 228 Apartments for Rent in Winthrop Highlands, MA with pricing that ranges from $1,175 to $6,999. There are also 81 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winthrop Highlands ranging from $1,700 to $5,500.
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 $1,700 to $5,500 with an average monthly rent of $3,189.
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 $2,500 to $6,889, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $4,200. Four Bedroom Single-Family rentals are also available starting from $3,650 and Four Bedroom Apartments start at $3,200.
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
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.