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Cottage Hill Homes for Sale

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  • 24 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    24 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    24 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    /25

    $450,000 Open Sun 12PM - 1:30PM

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    24 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

    WELCOME TO OCEAN FRONT LIVING ON WINTHROP BEACH. OCEAN VIEWS , OCEAN VIEWS, OCEAN VIEWS ! Wake up every morning and sit and enjoy the beautiful views of Winthrop Beach and the sun rising. Large Massport Windows that let in a ton of sunlight , step out of your door and put your feet in the sand ! This WELL MAINTAINED TOP CORNER UNIT condo boasts scenic views, hardwood thru out, newer tiled bath,

    Kevin Ferrara Cottage Hill Real Estate

    24 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
  • 100 Cottage Ave, Winthrop, MA 02152
    100 Cottage Ave, Winthrop, MA 02152
    100 Cottage Ave, Winthrop, MA 02152
    /37

    $879,900

    • 3 Beds
    • 2.5 Baths
    • 2,293 Sq Ft

    100 Cottage Ave, Winthrop, MA 02152

    Ideally located just steps from the Winthrop Yacht Club, The Landing, local restaurants, and both Winthrop and Yirrell Beach, this spacious single-family home offers stunning water views and a clear line to Boston’s skyline. The first level features a unique and expansive layout with a formal living and dining room anchored by a double-sided fireplace wrapped in lava-rock, plus two additional

    The Reference Group Reference Real Estate

    100 Cottage Ave, Winthrop, MA 02152
  • 500 Shirley St, Winthrop, MA 02152
    500 Shirley St, Winthrop, MA 02152
    500 Shirley St, Winthrop, MA 02152
    /36

    $829,900

    • 4 Beds
    • 2 Baths
    • 2,088 Sq Ft

    500 Shirley St, Winthrop, MA 02152

    Located just 3.5 miles from the game-changing Suffolk Downs redevelopment, this fantastic two-family home offers incredible long-term upside in one of the fastest-growing areas north of Boston. The project promises millions of square feet of new housing, retail, parks, and life science space—adding immense value & convenience to the surrounding neighborhoods. Just steps from the beach, this

    Jose Zambrano RE/MAX 360

    500 Shirley St, Winthrop, MA 02152
  • 247 Washington Ave Unit 9, Winthrop, MA 02152
    247 Washington Ave Unit 9, Winthrop, MA 02152
    247 Washington Ave Unit 9, Winthrop, MA 02152
    /24

    $520,000

    • 2 Beds
    • 2 Baths
    • 1,116 Sq Ft

    247 Washington Ave Unit 9, Winthrop, MA 02152

    Beautiful corner end-unit condominium in the desirable Nautilus Building offering panoramic views of Boston, the marina, Winthrop Yacht Club, and Elks from every room. This spacious 2-bedroom, 2-bathroom condominium features a private balcony that spans the entire length of the unit, perfect for relaxing and watching the boats go by. Inside this bright and airy unit, is a white kitchen, hardwood

    Erica Gore Century 21 Seaport

    247 Washington Ave Unit 9, Winthrop, MA 02152
  • 600 Shirley St Unit 3, Winthrop, MA 02152
    600 Shirley St Unit 3, Winthrop, MA 02152
    600 Shirley St Unit 3, Winthrop, MA 02152
    /32

    $549,900

    • 2 Beds
    • 2 Baths
    • 773 Sq Ft

    600 Shirley St Unit 3, Winthrop, MA 02152

    “The Cove at 600” was converted in 2022 and is located on the site of the historic Crystal Cove Hotel with breathtaking views of the Boston Skyline and the Atlantic Ocean. Unit 3, located on the side of the building with a private entrance, exclusive use patio and exclusive use deck at the front of the building offers many ways to take in the view and the sea air. The open concept living room and

    Erika Leigh Pereira Keller Williams Realty Boston Northwest

    600 Shirley St Unit 3, Winthrop, MA 02152
  • 600 Shirley St Unit 16, Winthrop, MA 02152
    600 Shirley St Unit 16, Winthrop, MA 02152
    600 Shirley St Unit 16, Winthrop, MA 02152
    /26

    $510,000 Open Sun 11AM - 12:30PM

    • 2 Beds
    • 2 Baths
    • 865 Sq Ft

    600 Shirley St Unit 16, Winthrop, MA 02152

    Always wanted to live across from the beach? This might be the place for you! Enjoy breathtaking water and Boston skyline views from this beautifully renovated 2-bed, 2-bath condo at the former Historic Crystal Cove Hotel. Offering first-floor convenience with a private entrance and two deeded parking spaces right outside your door, this home lives like a private residence. The open layout

    Elizabeth Crowley William Raveis R.E. & Home Services

    600 Shirley St Unit 16, Winthrop, MA 02152
  • 600 Shirley St Unit 1, Winthrop, MA 02152
    600 Shirley St Unit 1, Winthrop, MA 02152
    600 Shirley St Unit 1, Winthrop, MA 02152
    /31

    $415,000 Open Sun 11AM - 12PM

    • 1 Bed
    • 2 Baths
    • 604 Sq Ft

    600 Shirley St Unit 1, Winthrop, MA 02152

    WATER VIEWS & PRIVATE DECK! Welcome to The Cove at 600, a premier condominium development in Winthrop, situated on the historic site of the Crystal Cove Hotel. This meticulously renovated first-floor unit features 1 bedroom and 2 baths, epitomizing perfect beach town living. Every detail has been updated finishes, including newer kitchen & bathrooms. Your living room offers stunning water views,

    The Movement Group Compass

    600 Shirley St Unit 1, Winthrop, MA 02152
Massachusetts Suffolk County Winthrop Cottage Hill

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

Frequently Asked Questions

Is Cottage Hill a good place to live?
Cottage Hill is a good place to live. Cottage Hill is considered somewhat walkable and somewhat bikeable. Cottage Hill has 6 parks for recreational activities. It is fairly dense in population with 14.4 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 majority of residents in Cottage Hill are renters, with 50.3% of residents renting and 49.7% of residents owning their home. 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 3 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 $360,000. If you put a 20% down payment of $72,000 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $1,860 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $80K a year to afford the median home price in Cottage Hill. 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, 02151, 02128, 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, Downtown Winthrop, Cottage Park and Court Park.
Are home prices dropping in Cottage Hill?
Yes, home prices in Cottage Hill are down 58% in the last 12 months.

Home Trends in Cottage Hill, MA

On average, homes in Cottage Hill, Winthrop sell after 13 days on the market compared to the national average of 70 days. The median sale price for homes in Cottage Hill, Winthrop over the last 12 months is $348,000, down 61% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$348,000
Median Single Family Sale Price
$348,000
Median 1 Bedroom Sale Price
$214,000
Average Price Per Sq Ft
$217
Number of Homes for Sale
2
Last 12 months Home Sales
38
Months of Supply
0.60
Median List Price
$360,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-61%
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