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Rent Specials
$1,795 - $2,995
Total Monthly Price
Base Rent$1,795 - $2,995
Total Monthly Price$1,795 - $2,995
The Abby
91 Veterans RdWinthrop, MA 02152
Apartments for Rent in the Winthrop Highlands Neighborhood of Winthrop, MA (305 Rentals)
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$3,200
Total Monthly Price
Base Rent$3,200
Total Monthly Price$3,200
55 Brewster Ave, Unit 55A
55 Brewster AveWinthrop, MA 02152
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$1,000
Total Monthly Price
Base Rent$1,000
Total Monthly Price$1,000
42 Irwin St, Unit 3-4
42 Irwin StWinthrop, MA 02152
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$3,200
Total Monthly Price
Base Rent$3,200
Total Monthly Price$3,200
28 Beach Rd, Unit Beach Rd
28 Beach RdWinthrop, MA 02152
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$2,875
Total Monthly Price
Base Rent$2,875
Total Monthly Price$2,875
68 Park Ave
68 Park AveWinthrop, MA 02152
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$3,500
Total Monthly Price
Base Rent$3,500
Total Monthly Price$3,500
11 Pearl Ave, Unit Apt 2
11 Pearl AveWinthrop, MA 02152
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$1,950
Total Monthly Price
Base Rent$1,950
Total Monthly Price$1,950
50 Moore St, Unit 1R
50 Moore StWinthrop, MA 02152
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$3,000
Total Monthly Price
Base Rent$3,000
Total Monthly Price$3,000
87 Washington Ave, Unit 1BR Waterfront Oasis
87 Washington AveWinthrop, MA 02152
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$3,700
Total Monthly Price
Base Rent$3,700
Total Monthly Price$3,700
953 Shirley St, Unit 2
953 Shirley StWinthrop, MA 02152
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$2,550
Total Monthly Price
Base Rent$2,550
Total Monthly Price$2,550
12 Sewall Ave, Unit 3
12 Sewall AveWinthrop, MA 02152
Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead
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$1,700
Total Monthly Price
Base Rent$1,700
Total Monthly Price$1,700
63C Brewster Ave, Unit C
63C Brewster AveWinthrop, MA 02152
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$2,800
Total Monthly Price
Base Rent$2,800
Total Monthly Price$2,800
81 Sunnyside Ave, Unit 1
81 Sunnyside AveWinthrop, MA 02152
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$3,300
Total Monthly Price
Base Rent$3,300
Total Monthly Price$3,300
55 Cliff Ave, Unit 1
55 Cliff AveWinthrop, MA 02152
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$2,000
Total Monthly Price
Base Rent$2,000
Total Monthly Price$2,000
12 Harvard St, Unit 1
12 Harvard StWinthrop, MA 02152
600 Shirley St, Unit 9
600 Shirley St
WinthropMA02152
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$2,6952 Bedroom Apartments Available Now
87 Winthrop Shore Dr, Unit 2
87 Winthrop Shore DrWinthrop, MA 02152
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$2,9502 Bedroom Apartments Available Now
70 Cottage Park Rd, Unit 1
70 Cottage Park RdWinthrop, MA 02152
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$2,1001 Bedroom Apartments Available Now
87 Winthrop Shore Dr, Unit 1
87 Winthrop Shore DrWinthrop, MA 02152
170 Cliff Ave
WinthropMA02152
98 Woodside Ave
WinthropMA02152
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
400 Governors Dr, Unit 5
400 Governors Dr
WinthropMA02152
81 Sunnyside Ave
WinthropMA02152
32 Irwin St
WinthropMA02152
11 Pearl Ave
WinthropMA02152
21 Siren St
WinthropMA02152
31-33 Pleasant St
WinthropMA02152
68 Fremont St
WinthropMA02152
78 Read St
WinthropMA02152
16-18 Wave Way
WinthropMA02152
117 Revere St
WinthropMA02152
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
6 Elmwood Ct
WinthropMA02152
87 Undine Ave
WinthropMA02152
40 Seafoam Ave
WinthropMA02152
49 Seafoam Ave
WinthropMA02152
26 Forrest St
WinthropMA02152
46 Washington Ave
WinthropMA02152
900 Governors Dr
WinthropMA02152
31-33-33 Pleasant Park Rd
WinthropMA02152
1 Seal Harbor Rd
WinthropMA02152
249 Winthrop Shore Dr
WinthropMA02152
Neighborhood & Market Insights: How to Choose the Right Area to Rent
Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.
400 Governors Dr
WinthropMA02152
200 Governors Dr
WinthropMA02152
427 Winthrop St
WinthropMA02152
63 Coral Ave
WinthropMA02152
61 Coral Ave
WinthropMA02152
50 Trident Ave
WinthropMA02152
393 Main St
WinthropMA02152
60 Hermon St
WinthropMA02152
17 Irwin St
WinthropMA02152
235 Washington 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.
Showing Results 1-50, Page 1 of 7
Winthrop Highlands, Winthrop, MA Local Guide
How much does it cost to rent an apartment in Winthrop Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winthrop Highlands Studio Apartments | $2,907 | $1,795 | $9,755 |
| Winthrop Highlands 1 Bedroom Apartments | $2,858 | $1,000 | $8,641 |
| Winthrop Highlands 2 Bedroom Apartments | $3,660 | $2,195 | $10,000+ |
| Winthrop Highlands 3 Bedroom Apartments | $3,585 | $2,600 | $5,719 |
| Winthrop Highlands 4 Bedroom Apartments | $3,500 | $3,500 | $3,500 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
How much does it cost to rent a home in Winthrop Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| 2 Bedroom Homes | $3,050 | $2,500 | $3,995 |
| 3 Bedroom Homes | $3,386 | $2,500 | $4,900 |
| 4 Bedroom Homes | $4,550 | $3,550 | $6,500 |
| 5 Bedroom Homes | $4,425 | $4,350 | $4,500 |
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 305 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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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.
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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.
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Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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Pet Friendly LifestyleWinthrop Highlands, Winthrop, MA
Ranked #2
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 is the current pricing and availability for apartments for rent in the Winthrop Highlands area of Winthrop, MA?
As of today, September 19, 2026, there are currently 305 available Winthrop Highlands apartments priced from $1,000 to $18,964, with an average monthly rent of $3,229.
How much are Studio apartments in Winthrop Highlands?
There are currently 66 Studio Apartments in Winthrop Highlands with rent ranges from $1,795 to $9,755 with an average price of $2,907.
What is the current price range for One Bedroom Winthrop Highlands Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winthrop Highlands ranges from $1,000 to $8,641 with an average monthly rent of $2,858.
What does renting a Two Bedroom Apartment in Winthrop Highlands cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winthrop Highlands range from $2,195 to $18,964. Today's average rental price for Two Bedrooms here is $3,660.
How expensive are Winthrop Highlands Three Bedroom Apartments?
There are currently 45 Three Bedroom Apartments listings available in Winthrop Highlands on ApartmentHomeLiving.com. The pricing ranges from $2,600 to $5,719 - averaging $3,585 for the location.
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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Many housing markets throughout America share a common complaint: a lack of affordable rental properties.
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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
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Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
First Apartment Regrets: Real Renters Share What They'd Do Differently
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Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.