
Apartments for Rent in the Winthrop Highlands Neighborhood of Winthrop, MA Under $2,000 (37 Rentals)


312 Shirley St, Unit 203

90 Winthrop Shore Dr, Unit 8A

312 Shirley St, Unit 208

435 Shirley St, Unit 36

435 Shirley St, Unit 15

87-90 Win

Fort Heath Apartments

3739 Walnut
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.

1510 N Shore Rd

Total Monthly Price
88 Eustis St, Unit 1st fl

Total Monthly Price
720 Bennington St, Unit 207

Furnished Private Bedroom in East Boston

Furnished Bedroom with Private Bath in East Boston

Furnished Bedroom with Private Bath in East Boston

Furnished Bedroom with Private Bath in East Boston

Furnished Bedroom with Private Bath in East Boston

Furnished Private Bedroom in East Boston
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.

Furnished Private Bedroom in East Boston

11 Boardman St, Unit B

Furnished Private Bedroom in East Boston

Furnished Bedroom with Private Bath in East Boston

Furnished Private Bedroom in East Boston

Furnished Bedroom with Private Bath in East Boston

Furnished Bedroom with Private Bath in East Boston

Furnished Private Bedroom in East Boston

720 Bennington St
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.

133 Kimball Ave

Furnished Bedroom with Private Bath in East Boston

Furnished Private Bedroom in East Boston

The Willet

Waldemar Ave

Revere Bell Apartments

566 Beach

565 Beach St

Pratt Place Apartments
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

Bennington Arms
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 | $2,725 | $1,750 | $9,492 |
| Winthrop Highlands 1 Bedroom Apartments | $2,901 | $1,200 | $9,979 |
| Winthrop Highlands 2 Bedroom Apartments | $3,704 | $2,195 | $10,000+ |
| Winthrop Highlands 3 Bedroom Apartments | $3,580 | $2,250 | $5,719 |
| Winthrop Highlands 4 Bedroom Apartments | $3,943 | $3,400 | $4,650 |
Browse Apartments in this Neighborhood
There are currently 37 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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Real 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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How much rent can you afford?
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.
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
How much are Studio apartments in Winthrop Highlands?
There are currently 69 Studio Apartments in Winthrop Highlands with rent ranges from $1,750 to $9,492 with an average price of $2,725.
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 $1,200 to $9,979 with an average monthly rent of $2,901.
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 $16,292. Today's average rental price for Two Bedrooms here is $3,704.
How expensive are Winthrop Highlands Three Bedroom Apartments?
There are currently 43 Three Bedroom Apartments listings available in Winthrop Highlands on ApartmentHomeLiving.com. The pricing ranges from $2,250 to $5,719 - averaging $3,580 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.
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
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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
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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

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
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Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
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Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.