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Cheap Homes for Rent in Winthrop Highlands Neighborhood of Winthrop, MA from $1,900 (13 Rentals)
Search the lowest-cost Homes available for rent right now in the Winthrop Highlands area of Winthrop.
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435 Shirley St
WinthropMA02152
34 Trident Ave
WinthropMA02152
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.
900 Governors Dr
WinthropMA02152
90 Winthrop Shore Dr, Unit 1-b 1-b U10
90 Winthrop Shore Dr
WinthropMA02152
714 Winthrop Ave, Unit 101
714 Winthrop Ave
RevereMA02151
238 Everett St, Unit 1
238 Everett St
BostonMA02128
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.
352 Shirley St
WinthropMA02152
15 Walley St, Unit 206
15 Walley St
BostonMA02128
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200 Governors Dr
WinthropMA02152
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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 a home in Winthrop Highlands?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winthrop Highlands 2 Bedroom Homes for Rent | $2,828 | $2,050 | $3,450 |
| Winthrop Highlands 3 Bedroom Homes for Rent | $4,008 | $2,550 | $6,500 |
| Winthrop Highlands 4 Bedroom Homes for Rent | $3,737 | $3,500 | $4,200 |
| Winthrop Highlands 5 Bedroom Homes for Rent | $4,075 | $3,900 | $4,500 |
| Winthrop Highlands 6 Bedroom Homes for Rent | $8,000 | $8,000 | $8,000 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 13 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 Available Winthrop Highlands Apartments for Rent
The cheapest available apartment rental in the Winthrop Highlands area of Boston, MA is a 1 Bed unit found at 565 Beach priced from $1,800. Pratt Place Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,869. Here are the most affordable Winthrop Highlands apartments for rent in Boston, MA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 565 Beach | 1BR/1.0BA | 1BR,1BA | $1,800 |
| Pratt Place Apartments | 1 Bedroom, 1st Floor | 1BR,1BA | $1,869 |
| Ocean 650 | Studio (535 SF) | Studio,1BA | $2,178 |
| Ryder | A4 | 1BR,1BA | $2,203 |
| Amaya | M1 | Studio,1BA | $2,225 |
Best Value Apartments for Rent in Winthrop Highlands, MA
As of September 10, 2025 the best value apartment in the Winthrop Highlands area is the $0.17 price per square foot 23 Endicott Ave Model at 23 Endicott Ave in the in the Belle Circle neighborhood starting from $1,745. The second greatest value Winthrop Highlands apartment is the 288 Pleasant St Model at 288 Pleasant St, Unit 1 starting at $2,650 with a $0.27 price per square foot in the Beachmont 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. |
|---|---|---|---|
| 23 Endicott Ave | 23 Endicott Ave | 1BR,1BA | $0.17 |
| 288 Pleasant St, Unit 1 | 288 Pleasant St | 2BR,1BA | $0.27 |
| 42 Ocean Ave, Unit 2 | 42 Ocean Ave | 2BR,1BA | $0.30 |
| 85 Gladstone St, Unit 3 | 85 Gladstone St | 4BR,1BA | $0.40 |
| 1148 Bennington St, Unit 1 | 1148 Bennington St | 4BR,2BA | $2.09 |
| 500 Shirley St, Unit 1 | 500 Shirley St | 2BR,1BA | $2.42 |
| 238 Everett St, Unit 1 | 238 Everett St | 2BR,1BA | $2.45 |
| 23 Endicott Ave | 23 Endicott Ave | 1BR,1BA | $2.56 |
| 51 Somerset Ave, Unit 51 Somerset Ave | 51 Somerset Ave | 1BR,1BA | $2.10 |
| 312 Shirley St | 312 Shirley St | Studio ,1BA | $1.80 |
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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 type of rentals are currently available in Winthrop Highlands?
There are currently 225 Apartments for Rent in Winthrop Highlands, MA with pricing that ranges from $1,745 to $6,945. There are also 73 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winthrop Highlands ranging from $1,995 to $8,000.
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 $1,995 to $8,000 with an average monthly rent of $4,151.
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 $2,595 to $5,406, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,550 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,500 and Four Bedroom Apartments start at $3,600.
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
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.