
Cheap Homes for Rent in Winthrop Highlands Neighborhood of Winthrop, MA from $1,700 (65 Rentals)
Search the lowest-cost Homes available for rent right now in the Winthrop Highlands area of Winthrop.


23 Endicott Ave, Unit 1

180 Shirley Ave

180 Shirley Ave

180 Shirley Ave

180 Shirley Ave

180 Shirley Ave

180 Shirley Ave

55 Walnut Ave

1499 N Shore Rd
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

1499 N Shore Rd

1499 N Shore Rd

55 Walnut Ave

55 Walnut Ave

55 Walnut Ave

55 Walnut Ave

55 Walnut Ave

55 Walnut Ave

1499 N Shore Rd

55 Walnut Ave
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

55 Walnut Ave

55 Walnut Ave

55 Walnut Ave

55 Walnut Ave

55 Walnut Ave

87 Winthrop Shore Dr, Unit 3

312 Shirley St

312 Shirley St

1499 N Shore Rd

312 Shirley St

1540 N Shore Rd, Unit 202

100 Shirley Ave

95 Centennial Ave

900 Governors Dr

1499 N Shore Rd

1499 N Shore Rd

200 Harris St, Unit 2

207 Shirley Ave

1473 N Shore Rd

400 Governors Dr

60 Shirley Ave

60 Shirley Ave

1499 N Shore Rd

1499 N Shore Rd

1499 N Shore Rd

1499 N Shore Rd

1499 N Shore Rd

1499 N Shore Rd

1499 N Shore Rd

1499 N Shore Rd
Winthrop Highlands, Winthrop, MA Local Guide

How much does it cost to rent a home in Winthrop Highlands?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winthrop Highlands 2 Bedroom Homes for Rent | $2,863 | $2,100 | $4,000 |
Winthrop Highlands 3 Bedroom Homes for Rent | $3,440 | $2,600 | $4,200 |
Winthrop Highlands 4 Bedroom Homes for Rent | $4,033 | $3,700 | $4,200 |
Winthrop Highlands 5 Bedroom Homes for Rent | $5,400 | $5,000 | $5,800 |
Browse Homes for Rent in this Neighborhood
There are currently 65 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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Best Value Apartments for Rent in Winthrop Highlands, MA
As of April 17, 2025 the best value apartment in the Winthrop Highlands area is the $0.22 price per square foot 200 Harris St Model at 200 Harris St, Unit 2 in the in the East Revere neighborhood starting from $2,200. The second greatest value Winthrop Highlands apartment is the 136 Walnut Ave Model at 136 Walnut Ave, Unit #1 starting at $2,400 with a $0.24 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. |
---|---|---|---|
200 Harris St, Unit 2 | 200 Harris St | 1BR,1BA | $0.22 |
136 Walnut Ave, Unit #1 | 136 Walnut Ave | 2BR,1BA | $0.24 |
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 |
33 Franklin Ave, Unit #8 | 33 Franklin Ave | 2BR,1BA | $0.25 |
41 Broadsound Ave, Unit #3 | 41 Broadsound Ave | 2BR,1BA | $0.25 |
58 Lewis Ave, Unit #302 | 58 Lewis Ave | 1BR,1BA | $0.26 |
355 Revere Beach Pky, Unit #9Furn | 355 Revere Beach Pky | 1BR,1BA | $0.27 |
42 Ocean Ave, Unit 2 | 42 Ocean Ave | 2BR,1BA | $0.30 |
271 Shirley St, Unit #2 | 271 Shirley St | 2BR,1BA | $0.42 |
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Frequently Asked Questions about Winthrop Highlands
What type of rentals are currently available in Winthrop Highlands?
There are currently 360 Apartments for Rent in Winthrop Highlands, MA with pricing that ranges from $1,175 to $7,859. There are also 138 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winthrop Highlands ranging from $1,795 to $5,800.
What is the current price range for Rental Homes in Winthrop Highlands?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winthrop Highlands ranges from $1,795 to $5,800 with an average monthly rent of $3,354.
How much are larger Three and Four Bedroom Rentals in Winthrop Highlands?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winthrop Highlands range from $2,600 to $5,406, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $4,200. Four Bedroom Single-Family rentals are also available starting from $3,700 and Four Bedroom Apartments start at $3,200.
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
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
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.

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Written by: Christine Leonard, Esq.
Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.

Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.