Cheap Apartments for Rent in the Winthrop Highlands Neighborhood of Winthrop, MA from $1,100 (45 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winthrop Highlands area of Winthrop.

70 Beach Rd

87 Winthrop Shore Dr

85 Winthrop Shore Dr, Unit 8

76 Sunnyside Ave, Unit 3

12 Harvard St

265 Washington Ave, Unit #3A

312 Shirley St

267 Washington Ave, Unit #3A
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

Furnished Private Bedroom in East Boston

Furnished Private Bedroom in East Boston

Furnished Private Bedroom in East Boston

1061 Saratoga St

194 Shirley Ave

1047 Saratoga St

100 Shirley Ave

Ocean Point Apartments

136 Walnut Ave

1473 N Shore Rd

180 Shirley Ave

23 Endicott Ave, Unit #1F

720 Bennington St, Unit 207

728 Bennington St, Unit 207

720 Bennington St

55 Walnut Ave

1499 N Shore Rd

1543 N Shore Rd, Unit #405

501 Revere Beach Pky, Unit #408

Rumney Flats

1547 N Shore Rd, Unit #202

85 Bennington St, Unit #3

1540 N Shore Rd, Unit #202

207 Shirley Ave
Winthrop Highlands, Winthrop, MA Local Guide

How much does it cost to rent an apartment in Winthrop Highlands?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winthrop Highlands Studio Apartments | $2,483 | $1,500 | $4,532 |
Winthrop Highlands 1 Bedroom Apartments | $2,739 | $1,100 | $4,803 |
Winthrop Highlands 2 Bedroom Apartments | $3,353 | $2,000 | $8,439 |
Winthrop Highlands 3 Bedroom Apartments | $3,641 | $2,600 | $5,406 |
Winthrop Highlands 4 Bedroom Apartments | $4,215 | $3,700 | $5,595 |
Browse Apartments in this Neighborhood
There are currently 45 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 Neighborhoods for Apartments in Winthrop Highlands, MA
Pricing Updated: 03/21/2025Current apartment rentals in the Winthrop Highlands, MA area range in price from to with an overall median price of . Here is today’s list neighborhoods with the lowest median pricing for Winthrop Highlands Apartments for rent:
Neighborhood | Median Price | Min Price | Available Units |
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Cheapest Available Winthrop Highlands Apartments for Rent
 Apartment Listing | Model Name | Bed/Bath | Priced From |
---|---|---|---|
87-90 Win | 0BR/1.0BA | Studio,1BA | $1,650 |
Ocean Point Apartments | Studio | Studio,1BA | $1,800 |
Best Value Apartments for Rent in Winthrop Highlands, MA
As of March 21, 2025 the best value apartment in the Winthrop Highlands area is the $0.30 price per square foot 42 Ocean Ave Model at 42 Ocean Ave, Unit 2 in the in the Beachmont neighborhood starting from $2,950. The second greatest value Winthrop Highlands apartment is the 33 Franklin Ave Model at 33 Franklin Ave, Unit #8 starting at $2,500 with a $0.25 price per square foot in the West 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. |
---|---|---|---|
42 Ocean Ave, Unit 2 | 42 Ocean Ave | 2BR,1BA | $0.30 |
33 Franklin Ave, Unit #8 | 33 Franklin Ave | 2BR,1BA | $0.25 |
32 Franklin Pl, Unit #3 | 32 Franklin Pl | 2BR,1BA | $0.25 |
201 Ocean Ave, Unit #674-104 | 201 Ocean Ave | 1BR,1BA | $0.25 |
200 Ocean Ave, Unit #660-232 | 200 Ocean Ave | 1BR,1BA | $0.25 |
720 Winthrop Ave, Unit #3 | 720 Winthrop Ave | 2BR,1BA | $0.26 |
58 Lewis Ave, Unit #302 | 58 Lewis Ave | 1BR,1BA | $0.26 |
35 Franklin Ave, Unit #3 | 35 Franklin Ave | 2BR,1BA | $0.25 |
16 Franklin St, Unit A 16 Franklin St | 16 Franklin St | 2BR,1BA | $1.92 |
23 Endicott Ave, Unit #1F | 23 Endicott Ave | 1BR,1BA | $1.90 |
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Pet Friendly LifestyleWinthrop Highlands, Winthrop, MA
Ranked #3
Among neighborhoods in Winthrop, MA for Apartment listings with Pet Friendly Amenities
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Getting Around the Winthrop Highlands Neighborhood in Winthrop, MA
Walk Score®
56 / 100
Somewhat Walkable
Some errands can be accomplished on foot
Bike Score®
32 / 100
Somewhat Bikeable
Minimal bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
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 $1,650.
How much is rent for a Cheap One Bedroom Winthrop Highlands Apartment?
The lowest price for a Cheap One Bedroom Winthrop Highlands Apartment is $1,100 at .
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 $2,344 at Pratt Place Apartments.
What is the most affordable Winthrop Highlands Three Bedroom Apartment?
The best deal on a cheap Winthrop Highlands Three Bedroom Apartment rental is at and starts from $2,600.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

The 10 Best Affordable Neighborhoods in Boston, MA
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Understanding Amenity Fees: Know Where You Might Be Able to Save Money
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With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

What to Know About Fees and Fines When Renting
Written by: Trey Huguley
When it comes to renting a new apartment or home there can be a number of fees that you will want to keep in mind going into the process.

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.