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$1,595Studio Apartments Available Now
90 Winthrop Shore Dr, Unit 1A
90 Winthrop Shore DrWinthrop, MA 02152
Cheap Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA from $1,100 (48 Rentals)
Search the lowest-cost Apartments available for rent right now in the Cottage Hill area of Winthrop.
90 Winthrop Shore Dr
WinthropMA02152
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$1,595Studio Apartments Available May 1
90 Winthrop Shore Dr, Unit 8A
90 Winthrop Shore DrWinthrop, MA 02152
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$1,750
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$1,750
Total Monthly Price
$1,750
94 Winthrop Shore Dr
94 Winthrop Shore DrWinthrop, MA 02152
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$1,750Studio Apartments Available Jun 1
90 Winthrop Shore Dr, Unit 3A
90 Winthrop Shore DrWinthrop, MA 02152
90 Winthrop Shore Dr, Unit 3, Unit 3
90 Winthrop Shore Dr
WinthropMA02152
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$1,795Studio Apartments Available May 1
87 Winthrop Shore Dr, Unit 9
87 Winthrop Shore DrWinthrop, MA 02152
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$1,800Studio Apartments Available Now
312 Shirley St, Unit 208
312 Shirley StWinthrop, MA 02152
2 Deane Ave
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.
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$2,000
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Jun 1Total Monthly Price
Base Rent
$2,000
Total Monthly Price
$2,000
41 Somerset Ave, Unit B, Unit B
41 Somerset AveWinthrop, MA 02152
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$2,000Studio Apartments Available Now
312 Shirley St, Unit 210
312 Shirley StWinthrop, MA 02152
20 Coral Ave
WinthropMA02152
23 B Siren St
WinthropMA02152
45 Sturgis St
WinthropMA02152
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$2,1501 Bedroom Apartments Available Jun 1
90 Winthrop Shore Dr, Unit 10
90 Winthrop Shore DrWinthrop, MA 02152
33 Central St
WinthropMA02152
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$2,300 - $2,400
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,300 - $2,400
Total Monthly Price
$2,300 - $2,400
220 Winthrop St
220 Winthrop StWinthrop, MA 02152
31-33-33 Pleasant Park Rd
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.
1 Pond St
WinthropMA02152
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$2,4952 Bedroom Apartments Available May 1
90 Winthrop Shore Dr, Unit B
90 Winthrop Shore DrWinthrop, MA 02152
800 Governors Dr
WinthropMA02152
5 Fremont St
WinthropMA02152
220 Winthrop St
WinthropMA02152
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Studio to 2 Bedroom Apartments
87-90 Win
87-90 Winthrop Shore DrWinthrop, MA 02152
90 Winthrop Shore Dr, Unit 3A, Unit 3A
90 Winthrop Shore Dr
WinthropMA02152
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1 to 2 Bedroom Apartments
Fort Heath Apartments
1 Pond StWinthrop, MA 02152
53 Trident Ave, Unit 101, Unit 101
53 Trident Ave
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.
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$1,1751 Bedroom Apartments Available Sep 1
Furnished Private Bedroom in East Boston
1057 Saratoga StBoston, MA 02128
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$1,1751 Bedroom Apartments Available Jun 1
Furnished Private Bedroom in East Boston
1059 Saratoga StBoston, MA 02128
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$1,2251 Bedroom Apartments Available Jul 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
1059 Saratoga StBoston, MA 02128
Furnished Private Bedroom in East Boston
1057 Saratoga St
BostonMA02128
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$1,3251 Bedroom Apartments Available Sep 1
Furnished Private Bedroom in East Boston
1061 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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$1,4251 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
1061 Saratoga StBoston, MA 02128
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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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,5501 Bedroom Apartments Available May 2
Furnished Bedroom with Private Bath in East Boston
1061 Saratoga StBoston, MA 02128
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Rent Specials
$2,125 - $4,075
Total Monthly Price
Studio to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,125 - $4,075
Total Monthly Price
Varies
Amaya
50 Salt StRevere, MA 02151
25 Pratt St
BostonMA02134
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$2,400
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,400
Total Monthly Price
$2,400
25 Pratt St, Unit 1, Unit 1
25 Pratt StBoston, MA 02134
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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, Unit #1
25 Pratt StBoston, MA 02134
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$2,400
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,400
Total Monthly Price
$2,400
25 Pratt St, Unit 1, Unit 1
25 Pratt StBoston, MA 02134
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$2,400
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available May 1Total Monthly Price
Base Rent
$2,400
Total Monthly Price
$2,400
83 Bradstreet Ave, Unit #202, Unit #202
83 Bradstreet AveRevere, MA 02151
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
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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
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Studio to 2 Bedroom Apartments
Sora
93 Bennington StRevere, MA 02151
Showing Results 1-48, 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 | $2,373 | $1,595 | $2,705 |
| Cottage Hill 1 Bedroom Apartments | $2,551 | $1,175 | $3,480 |
| Cottage Hill 2 Bedroom Apartments | $3,302 | $2,400 | $7,106 |
| Cottage Hill 3 Bedroom Apartments | $3,779 | $2,700 | $9,199 |
| Cottage Hill 4 Bedroom Apartments | $3,664 | $3,200 | $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 48 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
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Cottage Hill Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Amaya | M1 | Studio,1BA | $2,125 |
Best Value Apartments for Rent in Cottage Hill, MA
As of April 11, 2026 the best value apartment in the Cottage Hill area is the $0.27 price per square foot 288 Pleasant St Model at 288 Pleasant St, Unit 1 in the in the Beachmont neighborhood starting from $2,650. The second greatest value Cottage Hill apartment is the 49R Siren St Model at 49R Siren St, Unit 1 starting at $3,000 with a $1.00 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. |
|---|---|---|---|
| 288 Pleasant St, Unit 1 | 288 Pleasant St | 2BR,1BA | $0.27 |
| 49R Siren St, Unit 1 | 49R Siren St | 3BR,1BA | $1.00 |
| 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 |
| 37 Bellevue Ave, Unit Sunny spacious apt | 37 Bellevue Ave | 3BR,1BA | $2.08 |
| 44 Ashley St | 44 Ashley St | 4BR,2BA | $3.17 |
| 105 Leyden St, Unit 1 | 105 Leyden St | 3BR,1BA | $2.64 |
| 25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $2.40 |
| 82 Gladstone St, Unit 2 | 82 Gladstone St | 2BR,1BA | $3.15 |
| 81 Gladstone St, Unit 2 | 81 Gladstone St | 2BR,1BA | $3.04 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read Article
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.
Read ArticleThe 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.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
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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If you’re an expert on all things Cottage Hill, tell us what you love (and don't) by rating it and writing a review.
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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 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 Amaya listed at $2,125.
How much is rent for a Cheap One Bedroom Cottage Hill Apartment?
The lowest price for a Cheap One Bedroom Cottage Hill Apartment is $2,490 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 $3,875 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.
Helpful Local Expert Guides
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.
A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.