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Cottage Hill Homes for Sale

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  • 19 Moore St, Winthrop, MA 02152
    19 Moore St, Winthrop, MA 02152
    19 Moore St, Winthrop, MA 02152
    /42

    $829,974

    • 5 Beds
    • 2.5 Baths
    • 2,212 Sq Ft

    19 Moore St, Winthrop, MA 02152

    Rare opportunity just one street from the beach, offering strong rental income potential ideal for investors and owner-occupants alike. This well-maintained two-family offers a flexible layout with a 2-bedroom 1st floor unit and a spacious second unit with 3 bedrooms & 1.5 baths across two levels. The second unit is currently rented for $3,650/month, providing immediate income, while the 1st

    Mission Impossible Team United Brokers

    19 Moore 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
    /17

    $499,000

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

    247 Washington Ave Unit 9, Winthrop, MA 02152

    Corner-positioned harborfront residence at Nautilus Condominiums with unobstructed Boston skyline and water views from every room. This 2-bedroom, 2-bath home spans 1,100+ sq ft and benefits from a south-to-west exposure, delivering consistent natural light throughout the day. A private balcony is set directly over the harbor, extending the living space outward. The layout balances openness and

    Federico Creatini eXp Realty

    247 Washington Ave Unit 9, Winthrop, MA 02152
  • 51 Harbor View Ave Unit 2, Winthrop, MA 02152
    51 Harbor View Ave Unit 2, Winthrop, MA 02152
    51 Harbor View Ave Unit 2, Winthrop, MA 02152
    /30

    $659,000

    • 2 Beds
    • 1 Bath
    • 1,220 Sq Ft

    51 Harbor View Ave Unit 2, Winthrop, MA 02152

    Street-Level Coastal Condo with Sweeping Views! Welcome to The Condos at 51 Harborview. This street-level condo offers easy access with sweeping harbor and city skyline views. The home features two bedrooms, one bath, and a modern kitchen and bath with quartz countertops, tile backsplash, stainless steel appliances, and luxury vinyl flooring.Relax or entertain on the front porch, deck off the

    Susan Doig Donnelly + Co.

    51 Harbor View Ave Unit 2, 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
    /14

    $410,000

    • 1 Bed
    • 2 Baths
    • 604 Sq Ft

    600 Shirley St Unit 1, Winthrop, MA 02152

    $6,000 closing cost credit to buyer!!! 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

    The Movement Group Compass

    600 Shirley St Unit 1, Winthrop, MA 02152
  • 51 Harbor View Ave Unit 1, Winthrop, MA 02152
    51 Harbor View Ave Unit 1, Winthrop, MA 02152
    51 Harbor View Ave Unit 1, Winthrop, MA 02152
    /30

    $639,000

    • 2 Beds
    • 1 Bath
    • 1,213 Sq Ft

    51 Harbor View Ave Unit 1, Winthrop, MA 02152

    Harborview Condo with Sweeping ViewsWelcome to The Condos at 51 Harborview. This beautifully renovated condo is perched high on the hill with stunning harbor and city skyline views. Unit 1 features two bedrooms and one bath, including a spacious primary with walk-in closet, and a brand-new kitchen and bath with quartz countertops, tile backsplash, stainless steel appliances, and luxury vinyl

    Susan Doig Donnelly + Co.

    51 Harbor View Ave Unit 1, Winthrop, MA 02152
  • 51 Harbor View Ave Unit 3, Winthrop, MA 02152
    51 Harbor View Ave Unit 3, Winthrop, MA 02152
    51 Harbor View Ave Unit 3, Winthrop, MA 02152
    /36

    $689,000

    • 2 Beds
    • 1 Bath
    • 1,304 Sq Ft

    51 Harbor View Ave Unit 3, Winthrop, MA 02152

    Penthouse Condo with Harbor Views!Welcome to The Condos at 51 Harborview. This penthouse residence offers sweeping harbor and city skyline views from atop the hill. Unit 3 features two bedrooms, one bath, and a modern kitchen and bath with quartz countertops, tile backsplash, stainless steel appliances, and luxury vinyl flooring.Enjoy a harbor-facing deck, private yard, and one deeded off-street

    Susan Doig Donnelly + Co.

    51 Harbor View Ave Unit 3, 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

    $389,900

    • 1 Bed
    • 2 Baths
    • 585 Sq Ft

    600 Shirley St Unit 4, Winthrop, MA 02152

    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 DEEDED PARKING SPOTS. ENJOY YOUR IN UNIT LAUNDRY AND EXCLUSIVE REAR PATIO ON

    Peggy Pratt Century 21 North East

    600 Shirley St Unit 4, Winthrop, MA 02152
  • 600 Shirley St Unit 15, Winthrop, MA 02152
    600 Shirley St Unit 15, Winthrop, MA 02152
    600 Shirley St Unit 15, Winthrop, MA 02152
    /20

    $299,995

    • 1 Bed
    • 1 Bath
    • 330 Sq Ft

    600 Shirley St Unit 15, Winthrop, MA 02152

    Stop renting, start owning your slice of the coast! Welcome to The Cove at 600 Shirley Street in Winthrop! This charming studio offers stunning, unobstructed ocean views from your own private deck, perfect for enjoying morning coffee or evening sunsets. Inside, you’ll find warm wood flooring throughout and an updated kitchen with space for a dining table, creating both functionality and comfort.

    Christine Goldstein Lyv Realty

    600 Shirley St Unit 15, Winthrop, MA 02152
  • 247 Washington Ave Unit 10, Winthrop, MA 02152
    247 Washington Ave Unit 10, Winthrop, MA 02152
    247 Washington Ave Unit 10, Winthrop, MA 02152
    /15

    $399,000

    • 1 Bed
    • 1 Bath
    • 702 Sq Ft

    247 Washington Ave Unit 10, Winthrop, MA 02152

    Rare opportunity to own a harbor front condo with beautiful marina and water views in desirable Winthrop. This bright second-floor unit features an open layout and updated kitchen with granite countertops, stainless steel appliances, recessed lighting, and a peninsula that opens to the living area. Sliding glass doors lead to a private balcony overlooking the water, perfect for relaxing and

    Reserve Team Reference Real Estate

    247 Washington Ave Unit 10, 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 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 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 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 $536,950. If you put a 20% down payment of $107,400 and had a 30-year fixed mortgage with an interest rate of 6.22%, your estimated principal and interest payment would be $2,640 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $113K 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, Downtown Winthrop, Harbor View-Orient Heights and Crescent Beach.

Home Trends in Cottage Hill, MA

On average, homes in Cottage Hill, Winthrop sell after 33 days on the market compared to the national average of 55 days. The median sale price for homes in Cottage Hill, Winthrop over the last 12 months is $552,500, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$552,500
Median Single Family Sale Price
$724,000
Median 2 Bedroom Sale Price
$494,500
Median 1 Bedroom Sale Price
$389,900
Average Price Per Sq Ft
$518
Number of Homes for Sale
8
Last 12 months Home Sales
16
Months of Supply
6.00
Median List Price
$536,950
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
3%
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