90 Winthrop Shore Dr
WinthropMA02152
Cheap Apartments for Rent in the Winthrop Highlands Neighborhood of Winthrop, MA from $1,100 (81 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winthrop Highlands area of Winthrop.
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$1,595Studio Apartments Available May 1
90 Winthrop Shore Dr, Unit 8A
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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Rent Specials
$1,795 - $3,000
Total Monthly Price12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$1,795 - $3,000
Total Monthly Price
$1,795 - $3,000
The Abby
91 Veterans RdWinthrop, MA 02152
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$1,795Studio Apartments Available May 1
90 Winthrop Shore Dr, Unit 9
90 Winthrop Shore DrWinthrop, MA 02152
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$1,800Studio Apartments Available Now
312 Shirley St, Unit 208
312 Shirley StWinthrop, MA 02152
312 Shirley St
WinthropMA02152
23 B Siren St
WinthropMA02152
45 Sturgis St
WinthropMA02152
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$2,1501 Bedroom Apartments Available Jun 1
90 Winthrop Shore Dr, Unit 10
90 Winthrop Shore DrWinthrop, MA 02152
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
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$2,300 - $2,400
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,300 - $2,400
Total Monthly Price
$2,300 - $2,400
220 Winthrop St
220 Winthrop StWinthrop, MA 02152
220 Winthrop St
WinthropMA02152
97 Winthrop Shore Dr
WinthropMA02152
31-33-33 Pleasant Park Rd
WinthropMA02152
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$2,4952 Bedroom Apartments Available May 1
90 Winthrop Shore Dr, Unit B
90 Winthrop Shore DrWinthrop, MA 02152
800 Governors Dr
WinthropMA02152
5 Fremont St
WinthropMA02152
31-33 Pleasant 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
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.
90 Winthrop Shore Dr, Unit B, Unit B
90 Winthrop Shore Dr
WinthropMA02152
53 Trident Ave, Unit 101, Unit 101
53 Trident Ave
WinthropMA02152
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$1,1751 Bedroom Apartments Available Jun 1
Furnished Private Bedroom in East Boston
1059 Saratoga StBoston, MA 02128
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$1,2051 Bedroom Apartments Available Sep 1
Furnished Private Bedroom in East Boston
951 Saratoga StBoston, MA 02128
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$1,2251 Bedroom Apartments Available Jul 1
Furnished Private Bedroom in East Boston
1057 Saratoga StBoston, MA 02128
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$1,2251 Bedroom Apartments Available Sep 1
Furnished Private Bedroom in East Boston
1059 Saratoga StBoston, MA 02128
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$1,3251 Bedroom Apartments Available Sep 1
Furnished Private Bedroom in East Boston
1061 Saratoga StBoston, MA 02128
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$1,3501 Bedroom Apartments Available Sep 1
Furnished Private Bedroom in East Boston
1061 Saratoga StBoston, MA 02128
Furnished Private Bedroom in East Boston
1061 Saratoga St
BostonMA02128
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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1061 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
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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,6001 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,6001 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1061 Saratoga StBoston, MA 02128
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$1,700
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available May 1Total Monthly Price
Base Rent
$1,700
Total Monthly Price
$1,700
43 Bryant St, Unit 1, Unit 1
43 Bryant StRevere, MA 02151
43 Bryant St
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, Unit 207
720 Bennington StBoston, MA 02128
136-138 Walnut Ave
RevereMA02151
136 Walnut Ave
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.
133 Kimball 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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Rent Specials
$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
Varies
Amaya
50 Salt StRevere, MA 02151
394 Ocean Ave, Unit 412
394 Ocean Ave
RevereMA02151
720 Bennington St
BostonMA02128
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$2,095 - $2,820
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Available May 23Blu Revere
388-394 Ocean AveRevere, MA 02151
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Rent Specials
$2,200 - $2,950
Plus Fees12 Month Lease Term
1 to 2 Bedroom Apartments Available May 15Ocean Point Apartments
2 Ocean AveRevere, MA 02151
2 Second St
RevereMA02151
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$2,280 - $3,860
Total Monthly Price12 Month Lease Term
1 to 3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,280 - $3,860
Total Monthly Price
$2,280 - $3,860
112 Lynnway
112 LynnwayRevere, MA 02151
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Rent Specials
$2,292 - $3,983
Plus Fees
Studio to 2 Bedroom Apartments Available NowRyder Revere Beach
21 Revere Beach BlvdRevere, 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.
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 | $2,530 | $1,595 | $5,599 |
| Winthrop Highlands 1 Bedroom Apartments | $2,825 | $1,175 | $7,628 |
| Winthrop Highlands 2 Bedroom Apartments | $3,666 | $2,400 | $6,402 |
| Winthrop Highlands 3 Bedroom Apartments | $3,928 | $2,600 | $9,188 |
| Winthrop Highlands 4 Bedroom Apartments | $3,895 | $3,200 | $5,000 |
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 81 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
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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 The Abby priced from $1,795. 3739 Walnut has the second lowest priced unit, which is a Studio apartment currently listed from $1,800. Here are the most affordable Winthrop Highlands apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Abby | Studio | Studio,1BA | $1,795 |
| 3739 Walnut | 0BR/1.0BA | Studio,1BA | $1,800 |
| The Willet | Studio - 501 | Studio,1BA | $1,815 |
| Pratt Place Apartments | 1 Bedroom, 1st Floor | 1BR,1BA | $1,869 |
| 1510 N Shore Rd | Studio | Studio,1BA | $2,000 |
| Amaya | M1 | Studio,1BA | $2,175 |
Best Value Apartments for Rent in Winthrop Highlands, MA
As of April 29, 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 238 Everett St Model at 238 Everett St, Unit #1 starting at $2,450 with a $0.25 price per square foot in the East Revere 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 |
| 238 Everett St, Unit #1 | 238 Everett St | 2BR,1BA | $0.25 |
| 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 |
| 411 Shirley St | 411 Shirley St | 3BR,1BA | $2.42 |
| 105 Leyden St, Unit 1 | 105 Leyden St | 3BR,1BA | $2.55 |
| 299 Crescent Ave, Unit 1 | 299 Crescent Ave | 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 |
| Pratt Place Apartments | 1 Bedroom, 2nd Floor | 1BR,1BA | $2.75 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
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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 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 The Abby listed at $1,795.
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 $2,429 at Pratt Place Apartments.
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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