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Cottage Hill Homes for Sale

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  • 483 Shirley St Unit 6A, Winthrop, MA 02152
    483 Shirley St Unit 6A, Winthrop, MA 02152
    483 Shirley St Unit 6A, Winthrop, MA 02152
    /10

    $309,900

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft

    483 Shirley St Unit 6A, Winthrop, MA 02152

    HERE IS A GREAT INVESTMENT OPPORTUNITY OR OWNER OCCUPY.....Why rent when this updated seaside condo can give you a start to have a place of your own? Conveniently located on the Bus Line to the Blue Line and just steps to the beach. This unit has been freshly painted, new grey vinyl flooring throughout, new updated fully applianced kitchen with white cabinets, quartz counters and good size rooms.

    Sharon Tallent Compass

    483 Shirley St Unit 6A, Winthrop, MA 02152
  • 546 Shirley St, Winthrop, MA 02152
    546 Shirley St, Winthrop, MA 02152
    546 Shirley St, Winthrop, MA 02152
    /42

    $765,000

    • 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
  • 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
  • 34 Underhill St Unit 4, Winthrop, MA 02152
    34 Underhill St Unit 4, Winthrop, MA 02152
    34 Underhill St Unit 4, Winthrop, MA 02152
    /17

    $475,000

    • 2 Beds
    • 2 Baths
    • 903 Sq Ft

    34 Underhill St Unit 4, Winthrop, MA 02152

    Gut renovated and converted in 2020, this upper-level 2-bedroom, 2-bath condo at 34 Underhill Street brings new construction finishes to one of Winthrop's most sought-after pockets. The white shaker kitchen is fitted with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including electric cooking. Wide plank hardwood floors & high ceilings run

    Reserve Team Reference Real Estate

    34 Underhill St Unit 4, 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
  • 542 Shirley St, Winthrop, MA 02152
    542 Shirley St, Winthrop, MA 02152
    542 Shirley St, Winthrop, MA 02152
    /27

    $710,000

    • 4 Beds
    • 2 Baths
    • 1,193 Sq Ft

    542 Shirley St, Winthrop, MA 02152

    The perfect blend of comfort, convenience, and affordability! Whether you’re a first-time homebuyer, looking to downsize, or searching for an alternative to condo living, this charming 4-bedroom home offers the space you need with the low-maintenance lifestyle you want all just one block from the beach. The main level features a comfortable bedroom and full bathroom with a convenient walk-in

    Christine D'Ambrosio Bowdoin Real Estate Partners

    542 Shirley St, Winthrop, MA 02152
  • 807 Shirley St, Winthrop, MA 02152
    807 Shirley St, Winthrop, MA 02152
    807 Shirley St, Winthrop, MA 02152
    /30

    $865,000

    • 3 Beds
    • 2.5 Baths
    • 1,564 Sq Ft

    807 Shirley St, Winthrop, MA 02152

    A rare opportunity to own a lovingly cared for home in a truly special location! For over 50 years, the same owners have cherished this home, and it shows. Offering a flexible layout with first floor living, the main level features a spacious living room, dining room, and large eat-in kitchen, all with beautiful hardwood floors. A first floor bedroom and full bath provide the convenience of

    Elizabeth Ferrara Cottage Hill Real Estate

    807 Shirley St, 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

    $384,888

    $15K 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
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, Winthrop, MA Home Prices vs. Nearby Neighborhoods

Cottage Hill Downtown Winthrop Winthrop Beach Winthrop Highlands
Median Home Price
$499,000
$599,950
$529,000
$644,000
Median Sale Price
$490,000
-6% YoY
$602,450
-4% YoY
$490,000
-1% YoY
$632,000
-6% YoY
Avg. Price per Square Foot
$531
$492
$493
$496
Median Single Family Price
$765,000
$723,500
$764,450
$965,000
Median Condo Price
$460,000
$506,950
$490,000
$575,000
Total Active Listings
8 listings
20 listings
12 listings
11 listings
Market Conditions
5 Months of Supply
Balanced Market
5 Months of Supply
Balanced Market
7 Months of Supply
Buyer's Market
5 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 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.
How much do you need to make to afford a house in Cottage Hill?
The median home price in Cottage Hill is $499,000. If you put a 20% down payment of $99,800 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $2,470 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $106K 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, Downtown Winthrop, Winthrop Beach, Cottage Park and Winthrop Highlands.
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