435 Shirley St, Unit 15
435 Shirley St
WinthropMA02152
Cheap Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA from $1,200 (50 Rentals)
Search the lowest-cost Apartments available for rent right now in the Cottage Hill area of Winthrop.
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$1,595Studio Apartments Available Now
435 Shirley St, Unit 15
435 Shirley StWinthrop, MA 02152
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$1,750Studio Apartments Available Now
312 Shirley St, Unit 208
312 Shirley StWinthrop, MA 02152
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$1,795 - $3,000
Total Monthly Price12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$1,795 - $3,000
Total Monthly Price
$1,795 - $3,000
The Abby
91 Veterans RdWinthrop, MA 02152
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$1,895Studio Apartments Available Jun 15
90 Winthrop Shore Dr, Unit 8A
90 Winthrop Shore DrWinthrop, MA 02152
435 Shirley St, Unit 36
435 Shirley St
WinthropMA02152
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$2,0001 Bedroom Apartments Available Now
312 Shirley St, Unit 203
312 Shirley StWinthrop, MA 02152
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$2,0951 Bedroom Apartments Available Jul 1
435 Shirley St, Unit 36
435 Shirley StWinthrop, MA 02152
150 Locust St
WinthropMA02152
45 Sturgis St
WinthropMA02152
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
100 Quincy Ave
WinthropMA02152
12 Forrest St
WinthropMA02152
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$2,300
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Jul 1Total Monthly Price
Base Rent
$2,300
Total Monthly Price
$2,300
304 Main St, Unit 2
304 Main StWinthrop, MA 02152
600 Shirley St, Unit 9
600 Shirley St
WinthropMA02152
789 Shirley St
WinthropMA02152
97 Winthrop Shore Dr
WinthropMA02152
31-33-33 Pleasant Park Rd
WinthropMA02152
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$2,4952 Bedroom Apartments Available Now
90 Winthrop Shore Dr, Unit B
90 Winthrop Shore DrWinthrop, MA 02152
5 Fremont St
WinthropMA02152
31-33 Pleasant St
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.
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1 to 2 Bedroom Apartments
Fort Heath Apartments
1 Pond StWinthrop, MA 02152
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Studio to 2 Bedroom Apartments
Oceanside Apartments
87-90 Winthrop Shore DrWinthrop, MA 02152
900 Governors Dr
WinthropMA02152
267 Washington Ave
WinthropMA02152
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$1,2001 Bedroom Apartments Available Sep 1
Furnished Private Bedroom in East Boston
1059 Saratoga StBoston, MA 02128
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$1,2051 Bedroom Apartments Available Jun 22
Furnished Private Bedroom in East Boston
1059 Saratoga StBoston, MA 02128
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$1,2251 Bedroom Apartments Available Sep 1
Furnished Private Bedroom in East Boston
1057 Saratoga StBoston, MA 02128
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$1,2251 Bedroom Apartments Available Sep 1
Furnished Private Bedroom in East Boston
1057 Saratoga StBoston, MA 02128
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$1,3501 Bedroom Apartments Available Sep 1
Furnished Private Bedroom in East Boston
1061 Saratoga StBoston, MA 02128
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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
Cash 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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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1061 Saratoga StBoston, MA 02128
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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1061 Saratoga StBoston, MA 02128
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$1,5501 Bedroom Apartments Available Jul 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,6001 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1061 Saratoga StBoston, MA 02128
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$1,6001 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,6001 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,6001 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1061 Saratoga StBoston, MA 02128
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$2,000Studio Apartments Available Sep 1
11 Boardman St, Unit B
11 Boardman StBoston, MA 02128
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$2,100
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,100
Total Monthly Price
$2,100
25 Pratt St, Unit 1
25 Pratt StBoston, MA 02134
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.
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$2,200
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
190 Crescent Ave, Unit 190 Crescent Ave #2
190 Crescent AveRevere, MA 02151
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Rent Specials
$2,293 - $5,378
Total Monthly Price
Studio to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,293 - $5,378
Total Monthly Price
Varies
Amaya
50 Salt StRevere, MA 02151
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$2,3001 Bedroom Apartments Available Sep 1
100 St Andrew Rd, Unit B
100 St Andrew RdBoston, MA 02128
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Rent Specials
$2,300 - $3,900
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Contact Us For AvailabilitySora
93 Bennington StRevere, MA 02151
164 Leyden St
BostonMA02128
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$2,400
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$2,400
Total Monthly Price
$2,400
25 Pratt St, Unit 1
25 Pratt StBoston, MA 02134
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$2,4952 Bedroom Apartments Available Sep 1
972-974 Saratoga Street, Unit 4
972-974-974 Saratoga StBoston, MA 02128
37 Gladstone St
BostonMA02128
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1 to 2 Bedroom Apartments
Waldemar Ave
75 Waldemar AveEast Boston, MA 02128
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Studio to 2 Bedroom Apartments
Revere Bell Apartments
45-55 Belle Isle AveRevere, MA 02151
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.
Showing Results 1-50, Page 1 of 1
Cottage Hill, Winthrop, MA Local Guide
How much does it cost to rent an apartment in Cottage Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Cottage Hill Studio Apartments | $2,566 | $1,595 | $2,910 |
| Cottage Hill 1 Bedroom Apartments | $2,662 | $1,200 | $4,269 |
| Cottage Hill 2 Bedroom Apartments | $3,150 | $2,195 | $4,256 |
| Cottage Hill 3 Bedroom Apartments | $3,281 | $2,250 | $4,775 |
| Cottage Hill 4 Bedroom Apartments | $4,090 | $3,600 | $4,650 |
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 50 rentals with your search options within a 2 mile radius of the Cottage Hill Neighborhood of Winthrop, MA.
See all Apartments in WinthropExplore Winthrop
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 |
|---|---|---|---|
| The Abby | Studio | Studio,1BA | $1,795 |
| Amaya | M1.2 | Studio,1BA | $2,293 |
Best Value Apartments for Rent in Cottage Hill, MA
As of June 10, 2026 the best value apartment in the Cottage Hill area is the $2.65 price per square foot 411 Shirley St Model at 411 Shirley St, Unit 2 in the in the Beachmont neighborhood starting from $3,450. The second greatest value Cottage Hill apartment is the 44 Ashley St Model at 44 Ashley St, Unit #2 starting at $3,800 with a $3.17 price per square foot in the Beachmont 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. |
|---|---|---|---|
| 411 Shirley St, Unit 2 | 411 Shirley St | 3BR,1BA | $2.65 |
| 44 Ashley St, Unit #2 | 44 Ashley St | 4BR,2BA | $3.17 |
| 953 Shirley St, Unit 2 | 953 Shirley St | 3BR,1BA | $3.08 |
| 25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $2.10 |
| 82 Gladstone St, Unit 2 | 82 Gladstone St | 2BR,1BA | $3.15 |
| 92 Winthrop Shore Dr, Unit 2 | 92 Winthrop Shore Dr | 2BR,1BA | $3.24 |
| 172 Endicott Ave, Unit 2 | 172 Endicott Ave | 1BR,1BA | $3.60 |
| 85 Gladstone St, Unit 85 Gladstone Street | 85 Gladstone St | 3BR,1BA | $4.00 |
| 190 Crescent Ave, Unit 190 Crescent Ave #2 | 190 Crescent Ave | 1BR,1BA | $3.14 |
| The Abby | Studio | Studio ,1BA | $3.99 |
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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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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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.
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Pet Friendly LifestyleCottage Hill, Winthrop, MA
Ranked #3
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 K-5 (466)
5 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 The Abby listed at $1,795.
How much is rent for a Cheap One Bedroom Cottage Hill Apartment?
The lowest price for a Cheap One Bedroom Cottage Hill Apartment is $2,295 at The Abby.
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 $2,895 at The Abby.
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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The 10 Best Affordable Neighborhoods in Boston, MA
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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.