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$1,275
Total Monthly Price12 Month Lease Term
5 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,275
Total Monthly Price
$1,275
42 Irwin St, Unit 1
42 Irwin StWinthrop, MA 02152
Cheap Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA from $1,100 (13 Rentals)
Search the lowest-cost Apartments available for rent right now in the Cottage Hill area of Winthrop.
68 Beach Rd
WinthropMA02152
220 Winthrop St
WinthropMA02152
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$1,800
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$1,800
Total Monthly Price
$1,800
312 Shirley St
312 Shirley StWinthrop, MA 02152
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$1,875
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Nov 15Total Monthly Price
Base Rent
$1,875
Total Monthly Price
$1,875
36 Trident Ave, Unit 1
36 Trident AveWinthrop, MA 02152
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34 Trident Ave
WinthropMA02152
Furnished Private Bedroom in East Boston
1057 Saratoga St
BostonMA02128
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$1,325
Plus Fees
1 Bedroom Apartments Available Dec 1Furnished Private Bedroom in East Boston
1061 Saratoga StBoston, MA 02128
Furnished Bedroom with Private Bath in Eas
1047 Saratoga St
BostonMA02128
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$1,800
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Dec 1Total Monthly Price
Base Rent
$1,800
Total Monthly Price
$1,800
129 Bradstreet Ave, Unit 3
129 Bradstreet AveRevere, MA 02151
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Showing Results 1-13, 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 | $2,530 | $1,750 | $2,850 |
| Cottage Hill 1 Bedroom Apartments | $2,910 | $1,175 | $3,700 |
| Cottage Hill 2 Bedroom Apartments | $3,185 | $2,500 | $4,075 |
| Cottage Hill 3 Bedroom Apartments | $3,348 | $2,450 | $4,995 |
| Cottage Hill 4 Bedroom Apartments | $3,645 | $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 13 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 |
|---|---|---|---|
| Amaya | M1 | Studio,1BA | $2,285 |
Best Value Apartments for Rent in Cottage Hill, MA
As of November 10, 2025 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 71 Wilshire St Model at 71 Wilshire St, Unit 2 starting at $3,350 with a $0.37 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 |
| 71 Wilshire St, Unit 2 | 71 Wilshire St | 3BR,1BA | $0.37 |
| 97 Bradstreet Ave, Unit 97 | 97 Bradstreet Ave | 5BR,2BA | $1.79 |
| 1148 Bennington St, Unit 1 | 1148 Bennington St | 4BR,2BA | $1.93 |
| 21 Seafoam Ave, Unit 3 | 21 Seafoam Ave | 4BR,2BA | $2.13 |
| 42 Irwin St, Unit 1 | 42 Irwin St | 5BR,2BA | $0.91 |
| 354 Shirley St, Unit 3 | 354 Shirley St | 3BR,1BA | $2.04 |
| 25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $2.40 |
| 312 Shirley St, Unit 309 | 312 Shirley St | 1BR,1BA | $2.10 |
| 312 Shirley St | 312 Shirley St | Studio ,1BA | $1.80 |
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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 3-5 (431)
6 out of 10
School data provided by Great Schools
Getting Around the Cottage Hill Neighborhood in Winthrop, MA
Walk Score®
62 / 100
Somewhat Walkable
Some errands can be accomplished on foot
Bike Score®
35 / 100
Somewhat Bikeable
Minimal bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
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 $2,285.
How much is rent for a Cheap One Bedroom Cottage Hill Apartment?
The lowest price for a Cheap One Bedroom Cottage Hill Apartment is $2,615 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 $3,935 at Amaya.
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.
Apartment Common Area Rules: What Renters Need to Know
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!
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.