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Cottage Hill Homes for Rent

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  • /13

    $3,999 per month

    • 3 Beds
    • 1.5 Baths
    • 1,166 Sq Ft
    • House for Rent

    59 Park Ave, Winthrop, MA 02152

    If you haven't already found this hidden gem, it's time to discover Winthrop by the sea. This updated 3 Bedroom 1.5 Bathroom home is just what you're looking for as the Summer approaches. This 2 floor single family home is a commuters dream. Minutes from downtown Boston. Steps to the beach, bus stop and Ferry. Sit on the back deck and enjoy the view of the Boston skyline. Available May 1st.

    59 Park Ave, Winthrop, MA 02152
  • /13

    $2,675 per month

    • 2 Beds
    • 1 Bath
    • 1,055 Sq Ft
    • Apartment for Rent

    585 Shirley St Unit 2, Winthrop, MA 02152

    Welcome to 585 Shirley St unit 2 available May 1st, 2025, just in time for the amazing oceanside summer festivities!! Fully renovated two bedroom, one-bath waterfront in Winthrop. We are located within walking distance to restaurants, Winthrop Ferry and the MBTA Public transportation. A common area boasts even more fun with alluring views of the Winthrop Harbor, Marina and Boston skylines. HEAT

    Dawne Armitstead Reference Real Estate

    585 Shirley St Unit 2, Winthrop, MA 02152
  • /8

    $2,000 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    265 Washington Ave Unit 3A, Winthrop, MA 02152

    1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

    265 Washington Ave Unit 3A, Winthrop, MA 02152
  • /3

    $1,950 per month

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • Apartment for Rent

    26 Beacon St Unit 301, Winthrop, MA 02152

    HEAT INCLUDED!! Steps from Winthrop Beach and Winthrop Yacht Club this lovely studio has new hardwood floors, new appliances, updated bathroom and plenty of closet space. Just minutes to Downtown Boston and Logan Airport!

    Jessica Pumphret Blue Sky Realty

    26 Beacon St Unit 301, Winthrop, MA 02152
  • /10

    $2,200 per month

    • 1 Bed
    • 1 Bath
    • 1,076 Sq Ft
    • Condo for Rent

    95 Terrace Ave Unit 1, Winthrop, MA 02152

    1 bed and 1 bath located in Cottage Hill. Easy access to downtown and public transportation!

    95 Terrace Ave Unit 1, Winthrop, MA 02152
  • /8

    $1,950 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Apartment for Rent

    267 Washington Ave Unit 3A, Winthrop, MA 02152

    Conveniently located! Just a 10-minute drive or 20 minutes by public transport to the city center. The bus stop across the street connects directly to Orient Heights. Ideal for commuters, this one-bedroom apartment is situated on the first floor with a private back entrance from the parking lot behind the building. Enjoy the convenience of parking and entering through your own private access. The

    Elizabeth Ferrara Cottage Hill Real Estate

    267 Washington Ave Unit 3A, Winthrop, MA 02152
  • /18

    $2,700 per month

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    19 Underhill St Unit 2, Winthrop, MA 02152

    2 bed and 1 bath located in Winthrop Beach. Easy access to downtown and public transportation!

    19 Underhill St Unit 2, Winthrop, MA 02152
  • /15

    $3,000 per month

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Apartment for Rent

    56 Park Ave Unit 3, Winthrop, MA 02152

    HUGE 3 bedroom 2 bath DUPLEX unit located a block from the ocean, the landing, docks, restaurants and shops. Gleaming hardwood flooring throughout. Tons of light and space in this open layout floorpan. Living room, dining room, eat in kitchen, enclosed porch and 3 bedrooms and bonus room for office/exercise room, etc. 2 parking spaces and shared backyard. Don't miss out on this gem in the

    Josephine Marino DiMarzo Lyv Realty

    56 Park Ave Unit 3, Winthrop, MA 02152
  • /12

    $2,100 per month

    • 1 Bed
    • 1 Bath
    • 799 Sq Ft
    • Condo for Rent

    53 Park Ave Unit 1, Winthrop, MA 02152

    1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

    53 Park Ave Unit 1, Winthrop, MA 02152
  • /10

    $2,200 per month

    • 1 Bed
    • 1 Bath
    • 1,076 Sq Ft
    • Condo for Rent

    94 Terrace Ave Unit 1, Winthrop, MA 02152

    1 bed and 1 bath located in Cottage Hill. Easy access to downtown and public transportation!

    94 Terrace Ave Unit 1, Winthrop, MA 02152
  • /8

    $1,725 per month

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • Condo for Rent

    64 Moore St Unit 2, Winthrop, MA 02152

    1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

    64 Moore St Unit 2, Winthrop, MA 02152
  • /5

    $2,300 per month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    5 Hillside Ave Unit 5A, Winthrop, MA 02152

    2 bed and 2 bath located in Winthrop. Easy access to downtown and public transportation!

    5 Hillside Ave Unit 5A, Winthrop, MA 02152
  • /12

    $2,250 per month

    • 1 Bed
    • 1 Bath
    • 799 Sq Ft
    • Condo for Rent

    59 Park Ave Unit 1, Winthrop, MA 02152

    1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

    59 Park Ave Unit 1, Winthrop, MA 02152
  • /12

    $2,250 per month

    • 1 Bed
    • 1 Bath
    • 799 Sq Ft
    • Condo for Rent

    62 Park Ave Unit 1, Winthrop, MA 02152

    1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

    62 Park Ave Unit 1, Winthrop, MA 02152

About Cottage Hill

Cottage Hill in Winthrop, MA, is a serene New England beach town known for its ocean views and historic homes. Located just 7 miles from Boston, it offers a blend of city convenience and waterfront tranquility. The neighborhood is characterized by its close-knit community, with organizations like the Viking Pride Foundation enhancing local opportunities. Residents enjoy easy access to Winthrop Beach and Yirrell Beach, as well as Crystal Cove, which features the Winthrop Yacht Club and public boat ramps. Massa Playground provides a local spot for outdoor activities with a jungle gym and basketball courts. The homes, many with colonial-inspired architecture, have been modernized while retaining their historic charm. Condos are prevalent, with a mix of multifamily and duplex options. Streets are walkable, though some are curved and steep. Annual events such as the Winthrop Town Wide Yard Sale and Winthrop Family Beach Day foster community spirit. Dining options include Ferrante’s for steaks and seafood, and Selva Coffee House for breakfast. Winthrop Marketplace is a local grocery staple, while larger stores like Target are about 4 miles away in Revere. The neighborhood is served by Winthrop Public Schools, which have good ratings. Commuting to Boston is convenient via Massachusetts Route 1A or the MBTA bus and Blue Line subway. Boston Logan International Airport is just 5 to 6 miles away, making travel easy.

Frequently Asked Questions

What are the most popular neighborhoods for renters near Cottage Hill?
The most popular neighborhoods for renters near Cottage Hill are Winthrop Beach, Point Shirley, Downtown Winthrop, Winthrop Highlands and Court Park.
What are the most popular zip codes for renters near Cottage Hill?
The most popular zip codes for renters near Cottage Hill are 02135, 02125, 02127, 02134 and 02215.
How to Rent a Home