90 Winthrop Shore Dr
WinthropMA02152
Cheap Apartments for Rent in the Winthrop Highlands Neighborhood of Winthrop, MA from $1,100 (31 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winthrop Highlands area of Winthrop.
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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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$1,750
Plus Fees
Studio Apartments Available Jun 190 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
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$1,750
Plus Fees
Studio Apartments Available Now90 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
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$1,800
Plus Fees
Studio Apartments Available Now312 Shirley St
312 Shirley StWinthrop, MA 02152
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$1,800
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$1,800
Total Monthly Price
$1,800
312 Shirley St
312 Shirley StWinthrop, MA 02152
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$1,800
Plus Fees
Studio Apartments Available Now312 Shirley St
312 Shirley StWinthrop, MA 02152
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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$2,000
Plus Fees
Studio Apartments Available Now312 Shirley St
312 Shirley StWinthrop, MA 02152
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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
1 Pond St
1 Pond StWinthrop, MA 02152
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$1,175
Plus Fees
1 Bedroom Apartments Available Mar 1Furnished Private Bedroom in East Boston
951 Saratoga StBoston, MA 02128
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$1,550
Plus Fees
1 Bedroom Apartments Available Feb 11Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
34 Franklin 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
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.
124 Atlantic 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
4 Crest Ave
RevereMA02151
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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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$2,010 - $4,075
Total Monthly Price
Studio to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,010 - $4,075
Total Monthly Price
$2,010 - $4,075
Amaya
50 Salt StRevere, MA 02151
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$2,050
Plus Fees
2 Bedroom Apartments Available Now165 Hichborn St
165 Hichborn StRevere, MA 02151
93 Bennington St
RevereMA02151
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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Rent Specials
$2,100 - $2,500
Plus Fees12 Month Lease Term
1 Bedroom Apartments Available NowOcean Point Apartments
2 Ocean AveRevere, MA 02151
133 Kimball Ave
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 1 Bedroom Apartments
The Willet
13 Nahant 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 1-31, 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 | $2,533 | $1,650 | $4,438 |
| Winthrop Highlands 1 Bedroom Apartments | $2,898 | $1,175 | $6,706 |
| Winthrop Highlands 2 Bedroom Apartments | $3,723 | $2,200 | $8,568 |
| Winthrop Highlands 3 Bedroom Apartments | $4,071 | $2,600 | $5,719 |
| Winthrop Highlands 4 Bedroom Apartments | $3,664 | $3,200 | $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 31 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
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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 $1,750. 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 | $1,750 |
| Pratt Place Apartments | 1 Bedroom, 1st Floor | 1BR,1BA | $1,869 |
| 566 Beach | 1BR/1.0BA | 1BR,1BA | $1,900 |
| 1510 N Shore Rd | Studio | Studio,1BA | $2,000 |
| Amaya | M1 | Studio,1BA | $2,010 |
| Ocean Point Apartments | 1 Bedroom | 1BR,1BA | $2,100 |
Best Value Apartments for Rent in Winthrop Highlands, MA
As of January 27, 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 85 Gladstone St Model at 85 Gladstone St, Unit 3 starting at $2,800 with a $0.28 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 |
| 85 Gladstone St, Unit 3 | 85 Gladstone St | 3BR,1BA | $0.28 |
| 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 |
| 31 Faywood Ave, Unit 2 | 31 Faywood Ave | 4BR,2BA | $2.40 |
| 21 Prescott St, Unit 1 | 21 Prescott St | 2BR,1BA | $2.27 |
| 23 Endicott Ave | 23 Endicott Ave | 1BR,1BA | $2.56 |
| 312 Shirley St | 312 Shirley St | Studio ,1BA | $1.80 |
| 129 Bradstreet Ave, Unit 3 | 129 Bradstreet Ave | 1BR,1BA | $2.00 |
| Ocean Point Apartments | 1 Bedroom | 1BR,1BA | $2.52 |
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 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 $1,750.
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 $3,149 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.
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