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Cottage Hill Homes for Sale

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  • 546 Shirley St, Winthrop, MA 02152
    546 Shirley St, Winthrop, MA 02152
    546 Shirley St, Winthrop, MA 02152
    /42

    $765,000

    Open Sat 11:30AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 1,933 Sq Ft

    546 Shirley St, Winthrop, MA 02152

    This is your opportunity to own in beautiful Winthrop by the Sea at an incredible value! This spacious 4+ bedroom, 2.5-bath home offers the perfect blend of character, updates, and an unbeatable location. Relax on warm summer evenings from the inviting wraparound porch, or take a short stroll just one block to Winthrop Beach for sunrise walks and ocean breezes. Inside, you'll find oversized

    Christine D'Ambrosio Bowdoin Real Estate Partners

    546 Shirley St, Winthrop, MA 02152
  • 566 Shirley St, Winthrop, MA 02152
    566 Shirley St, Winthrop, MA 02152
    566 Shirley St, Winthrop, MA 02152
    /20

    $2,250,000

    • 16 Beds
    • 6 Baths
    • 5,553 Sq Ft

    566 Shirley St, Winthrop, MA 02152

    566 Shirley St contains six (6) units, consisting of two (2), 2-Bedroom/1-Bathroom units and four (4), 3-Bedroom/1-Bathroom units with 5,553 square feet of living area in 7,968 square feet of total gross area on a 0.09-acre corner parcel. The Property is across the street from the Crystal Cove Marina and is 1,000 feet from Winthrop Beach and the shores of the Atlantic Ocean. The Property has been

    Steve Girolamo Horvath & Tremblay

    566 Shirley St, Winthrop, MA 02152
  • 600 Shirley St Unit 7, Winthrop, MA 02152
    600 Shirley St Unit 7, Winthrop, MA 02152
    600 Shirley St Unit 7, Winthrop, MA 02152
    /20

    $485,000

    • 1 Bed
    • 1.5 Baths
    • 591 Sq Ft

    600 Shirley St Unit 7, Winthrop, MA 02152

    Stunning water views from every angle make this exceptional condo truly one of a kind. Enjoy breathtaking sunsets over the Boston skyline and harbor from the comfort of your own home. Nestled in the charming seaside community of Winthrop, you'll experience the perfect balance of coastal living and city convenience. The ferry is just one block away, offering a scenic and stress free commute to

    Elizabeth Ferrara Cottage Hill Real Estate

    600 Shirley St Unit 7, Winthrop, MA 02152
  • 229 Washington Ave Unit 3A, Winthrop, MA 02152
    229 Washington Ave Unit 3A, Winthrop, MA 02152
    229 Washington Ave Unit 3A, Winthrop, MA 02152
    /7

    $219,999

    • 1 Bed
    • 1 Bath
    • 350 Sq Ft

    229 Washington Ave Unit 3A, Winthrop, MA 02152

    Enjoy coastal living in this charming waterfront condominium in Winthrop, offering the perfect balance of convenience and seaside lifestyle. Located just minutes from Boston Logan Airport and with easy access to public transportation including nearby bus routes, the Orient Heights MBTA station, and the East Boston ferry, this home is ideal for commuters seeking quick access to Boston while

    Marcia De Paula REMAX Executive Realty

    229 Washington Ave Unit 3A, Winthrop, MA 02152
  • 600 Shirley St Unit 11, Winthrop, MA 02152
    600 Shirley St Unit 11, Winthrop, MA 02152
    600 Shirley St Unit 11, Winthrop, MA 02152
    /17

    $299,999

    Open Sat 1:30PM - 2:30PM $20K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 351 Sq Ft

    600 Shirley St Unit 11, Winthrop, MA 02152

    Welcome to The Cove, a distinguished condominium community in coastal Winthrop, offering a spectacular seaside setting with the Boston skyline as the backdrop for unforgettable sunsets. This renovated second-floor studio features wood flooring throughout, an updated kitchen with dining space, and a private balcony off the living area. The unit includes a modern bathroom with a walk-in shower,

    Alla Rossi Coldwell Banker Realty - Boston

    600 Shirley St Unit 11, Winthrop, MA 02152
  • 600 Shirley St Unit 4, Winthrop, MA 02152
    600 Shirley St Unit 4, Winthrop, MA 02152
    600 Shirley St Unit 4, Winthrop, MA 02152
    /29

    $388,888

    $11K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 585 Sq Ft

    600 Shirley St Unit 4, Winthrop, MA 02152

    8**Back on market due to out of state sale contingency falling through*** WELCOME TO WINTHROP BY THE SEA! THE COVE AT 600 SHIRLEY WAS CONVERTED IN 2022 AND IS LOCATED ON THE SITE OF THE HISTORIC CRYSTAL COVE HOTEL AND HAS AMAZING VIEWS OF BOSTON AND THE ATLANTIC OCEAN! WALK TO THE BEACH, THE YACHT CLUB, VARIOUS RESTAURANTS AND PARKS. THIS 1 BEDROOM UNIT FEATURES NOT ONE BUT TWO BATHROOMS AND 2

    Peggy Pratt Century 21 North East

    600 Shirley St Unit 4, Winthrop, MA 02152
  • 16 Underhill St Unit 3, Winthrop, MA 02152
    16 Underhill St Unit 3, Winthrop, MA 02152
    16 Underhill St Unit 3, Winthrop, MA 02152
    /31

    $474,899

    Open Sat 11AM - 1PM $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,036 Sq Ft

    16 Underhill St Unit 3, Winthrop, MA 02152

    Welcome to 16 Underhill Rd. #3, a beautifully updated 3-bedroom, 1-bath condo offering 1,036 sq. ft. of move-in ready living space. This bright and inviting home features modern updates, a functional layout, and private laundry in the basement for added convenience. Enjoy your own private deck, perfect for relaxing or entertaining. The property also includes a private garage plus ample additional

    Goldpath Real Estate Group United Brokers

    16 Underhill St Unit 3, Winthrop, MA 02152
  • 34 Underhill St Unit 3, Winthrop, MA 02152
    34 Underhill St Unit 3, Winthrop, MA 02152
    34 Underhill St Unit 3, Winthrop, MA 02152
    /17

    $474,900

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 879 Sq Ft

    34 Underhill St Unit 3, Winthrop, MA 02152

    This like-new 2-bedroom, 2 bath condo at 34 Underhill Street delivers the finish level of new construction at a fraction of the cost. Gut renovated and converted in 2020, every detail was approached with care, from the white shaker kitchen with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including gas cooking, to the wide plank hardwood floors

    Reserve Team Reference Real Estate

    34 Underhill St Unit 3, Winthrop, MA 02152
Massachusetts Suffolk County Winthrop

Real Estate & Homes for Sale in Cottage Hill, Winthrop

Why Live in 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.
Learn more about living in Cottage Hill

Cottage Hill Home Prices vs. Nearby Winthrop, MA Neighborhoods

Cottage Hill Downtown Winthrop Winthrop Beach
Median Home Price
$487,450
$619,000
$537,000
Median Sale Price
$489,500
-7% YoY
$602,450
-5% YoY
$499,999
+6% YoY
Median Single Family Price
$724,000
$723,500
$684,500
Median Townhouse Price
--
$839,900
$599,999
Median Condo Price
$433,500
$495,750
$494,500
Total Active Listings
8 listings
15 listings
11 listings
Market Conditions
5 Months of Supply
Balanced Market
3 Months of Supply
Seller's Market
6 Months of Supply
Balanced Market

Frequently Asked Questions

Is Cottage Hill a good place to live?
Cottage Hill is a good place to live. Cottage Hill is considered car-dependent and bikeable with some transit options. Cottage Hill is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Cottage Hill has 6 parks for recreational activities. It is very dense in population with 15.0 people per acre and a median age of 44. The average household income is $121,508 which is above the national average. College graduates make up 45.8% of residents. A local real estate agent serving Cottage Hill can help you decide if this neighborhood is the right one for you. Learn more on our Cottage Hill neighborhood guide.
Is Cottage Hill, MA a safe neighborhood?
Cottage Hill, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Cottage Hill?
The median home price in Cottage Hill is $487,450. If you put a 20% down payment of $97,500 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $2,510 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $108K a year to afford the median home price in Cottage Hill. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Cottage Hill is $122K.
What are the best public schools in Cottage Hill?
The best public schools that serve Cottage Hill are:
What are the most popular zip codes in Cottage Hill, Winthrop, MA?
The most popular zip codes in Cottage Hill, Winthrop, MA include 02152, 02128, 02151, 02150 and 02127.
What are the most popular neighborhoods near Cottage Hill, Winthrop, MA?
The most popular neighborhoods near Cottage Hill, Winthrop, MA are Point Shirley, Winthrop Beach, Cottage Park, Downtown Winthrop and Winthrop Highlands.
Are home prices dropping in Cottage Hill?
Yes, home prices in Cottage Hill are down 6% in the last 12 months.
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