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$1,250
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$1,250
Total Monthly Price
$1,250
42 Irwin St, Unit 2
42 Irwin StWinthrop, MA 02152
Cheap Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA from $1,200 (23 Rentals)
Search the lowest-cost Apartments available for rent right now in the Cottage Hill area of Winthrop.
40 Cottage Park Rd
WinthropMA02152
85 Winthrop Shore Dr
WinthropMA02152
68 Beach Rd
WinthropMA02152
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$1,695
Plus Fees
Studio Apartments Available Jan 1, 202690 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
220 Winthrop St
WinthropMA02152
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$1,800
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
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$1,800
Total Monthly Price
$1,800
98 Winthrop Shore Dr
98 Winthrop Shore DrWinthrop, MA 02152
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.
312 Shirley St
WinthropMA02152
312 Shirley St
WinthropMA02152
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$1,850
Plus Fees
Studio Apartments Available Now90 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
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$1,850
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Studio Apartment Available NowTotal Monthly Price
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$1,850
Total Monthly Price
$1,850
95 Bowdoin St, Unit 3
95 Bowdoin StWinthrop, MA 02152
90 Winthrop Shore Dr, Unit 1-b 1-b U10
90 Winthrop Shore Dr
WinthropMA02152
435 Shirley St
WinthropMA02152
40 Cottage Park Rd
WinthropMA02152
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.
5 Irwin St
WinthropMA02152
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34 Trident Ave
WinthropMA02152
Furnished Private Bedroom in East Boston
1061 Saratoga St
BostonMA02128
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$1,550
Plus Fees
1 Bedroom Apartments Available Feb 11, 2026Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,800
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
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$1,800
Total Monthly Price
$1,800
129 Bradstreet Ave, Unit 3
129 Bradstreet AveRevere, MA 02151
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.
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Showing Results 1-23, Page 1 of 1
Cottage Hill, 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 an apartment in Cottage Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Cottage Hill Studio Apartments | $2,614 | $1,695 | $2,930 |
| Cottage Hill 1 Bedroom Apartments | $2,974 | $1,250 | $3,775 |
| Cottage Hill 2 Bedroom Apartments | $2,985 | $2,200 | $4,075 |
| Cottage Hill 3 Bedroom Apartments | $3,237 | $2,600 | $4,995 |
| Cottage Hill 4 Bedroom Apartments | $3,827 | $3,300 | $4,250 |
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 23 rentals with your search options within a 2 mile radius of the Cottage Hill Neighborhood of Winthrop, MA.
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Cottage Hill, Winthrop, MA Local Guide
- Nearby Winthrop neighborhoods
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Cheapest Available Cottage Hill Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 87-90 Win | 0BR/1.0BA | Studio,1BA | $1,695 |
| Amaya | M1 | Studio,1BA | $2,410 |
Best Value Apartments for Rent in Cottage Hill, MA
As of December 25, 2025 the best value apartment in the Cottage Hill area is the $0.38 price per square foot 25 Pratt St Model at 25 Pratt St, Unit 2 in the in the Cottage Hill neighborhood starting from $3,800. The second greatest value Cottage Hill apartment is the 25 Pratt St Model at 25 Pratt St, Unit 2 starting at $4,250 with a $0.43 price per square foot in the Cottage Hill neighborhood. Here is today’s list of the best values for Cottage Hill apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 25 Pratt St, Unit 2 | 25 Pratt St | 3BR,1BA | $0.38 |
| 25 Pratt St, Unit 2 | 25 Pratt St | 4BR,2BA | $0.43 |
| 183 Cottage Park Rd, Unit 3 | 183 Cottage Park Rd | 4BR,2BA | $1.55 |
| 31 Faywood Ave, Unit 3 | 31 Faywood Ave | 4BR,2BA | $2.25 |
| 42 Irwin St, Unit 2 | 42 Irwin St | 1BR,2BA | $0.89 |
| 44 Ashley St | 44 Ashley St | 4BR,2BA | $3.17 |
| 25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $2.40 |
| 40 Dolphin Ave, Unit #2 | 40 Dolphin Ave | 2BR,1BA | $2.20 |
| 233 Pleasant St, Unit Apt 2 | 233 Pleasant St | 2BR,1BA | $2.63 |
| 129 Bradstreet Ave, Unit 3 | 129 Bradstreet Ave | 1BR,1BA | $2.00 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
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Pet Friendly LifestyleCottage Hill, Winthrop, MA
Ranked #2
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Best Local Schools in Cottage Hill, Winthrop, MA
Arthur T. Cummings Elementary School
Winthrop School District
Public School - Grades 3-5 (431)
6 out of 10
School data provided by Great Schools
Frequently Asked Questions about Cheap Cottage Hill Apartments
What is the Cheapest Studio apartment in Cottage Hill?
Currently the most affordable Cheap Studio Apartment in Cottage Hill is at 87-90 Win listed at $1,695.
How much is rent for a Cheap One Bedroom Cottage Hill Apartment?
The lowest price for a Cheap One Bedroom Cottage Hill Apartment is $2,665 at Amaya.
What is the lowest price for a Cheap Two Bedroom Cottage Hill Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Cottage Hill is starting from $3,800 at Amaya.
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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Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!