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Winthrop Highlands Homes for Sale

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  • /35

    $538,999 Open Sat 10:30AM - 12PM

    • 2 Beds
    • 2 Baths
    • 874 Sq Ft

    12 Sewall Ave Unit 2, Winthrop, MA 02152

    Welcome to coastal living at its finest. This completely renovated 2-bedroom, 2-bathroom condominium offers a rare opportunity to own a turnkey home in one of Winthrop’s most sought-after locations—just moments from the water, with partial views to enjoy from the comfort of your own home. The brand-new kitchen features quartz countertops, custom cabinetry, and stainless steel appliances, while

    Alex Walsh Access

    12 Sewall Ave Unit 2, Winthrop, MA 02152
  • /41

    $1,265,000

    • 4 Beds
    • 3.5 Baths
    • 2,214 Sq Ft

    72 Sewall Ave, Winthrop, MA 02152

    Highly desirable location this home is only 16 years old built over its original foundation. this 4-bed, 3.5-bath home spans three levels in Winthrop’s Highlands. The first floor offers an open layout ideal for entertaining, with a spacious kitchen featuring white cabinets and updated countertops flowing into the living and dining rooms. French doors lead to a deck and patio overlooking a large,

    Elizabeth Ferrara Cottage Hill Real Estate

    72 Sewall Ave, Winthrop, MA 02152
  • /33

    $679,000

    • 3 Beds
    • 2 Baths
    • 1,849 Sq Ft

    44 Cliff Ave Unit 3, Winthrop, MA 02152

    Welcome to this expansive 1,850 sq ft condo that lives like a single-family home, perfectly perched in the highly desirable Winthrop Highlands. Enjoy breathtaking panoramic ocean views from not one, but two private decks. Inside, you're greeted by sun-drenched spaces, soaring ceilings, and a wide open floor plan that makes entertaining effortless. The modern eat-in kitchen features direct access

    Jenny Golic Lantern Residential

    44 Cliff Ave Unit 3, Winthrop, MA 02152
  • /42

    $1,400,000

    • 10 Beds
    • 4 Baths
    • 4,671 Sq Ft

    45 Highland Ave, Winthrop, MA 02152

    Incredible investment opportunity in the heart of the Highlands! This oversized 3-family property is has been generating strong income with potential for more. One unit is available for an owner occupant or savvy investor looking to maximize cashflow. Walk-out ground level 2-bedroom apartment. First-floor 2-bedroom unit with an additional office, living room, and dining room. Owner’s unit,

    Jonathan Mathews Legacy Realty Advisors LLC

    45 Highland Ave, Winthrop, MA 02152
  • /42

    $1,170,000

    • 5 Beds
    • 2 Baths
    • 2,151 Sq Ft

    328-330 Revere St, Winthrop, MA 02152

    This property is what the competition see as a "Triple Threat" *TURN KEY *LOCATION & *BIG LOT OF LAND! The first floor's Craftsman style details have had restoration, preserving the stain glass windows, hardwood floors, working wood fireplace, beamed ceilings & built-ins to really embody the character of days gone by. A gas stove with hood vent, & sliders to a deck off the kitchen, makes this

    Debra Messana LAER Realty Partners

    328-330 Revere St, Winthrop, MA 02152
  • /32

    $999,900

    • 4 Beds
    • 3.5 Baths
    • 3,432 Sq Ft

    68-70 Floyd St, Winthrop, MA 02152

    VERY IMPORTANT! BOM and VERY MUCH AVAILABLE......AMAZING PICTURE POST CARD SETTING FOR THIS BEAUTIFUL HOME IN WINTHROP'S HIGHLANDS LOCATION. This legal 2 family will appeal to single family Buyers as well. A " younger" home compared to most, this multi-level Contemporary has an open floor plan, eat in kitchen open to a great room with skylights and a slider to the large private yard. The

    Sharon Tallent Compass

    68-70 Floyd St, Winthrop, MA 02152
  • /30

    $825,000

    • 3 Beds
    • 2.5 Baths
    • 2,112 Sq Ft

    75 Sewall Ave, Winthrop, MA 02152

    Discover this vintage 1970s-style gem just a block from the ocean, perfectly situated in one of Winthrop's most sought-after neighborhoods. This inviting single-family home features three spacious bedrooms and two and a half baths, ideal for comfortable living. Step inside to find a blend of retro charm and modern convenience. The spacious mezzanine living room has soaring ceilings and is open to

    Harry Silverstein Keller Williams Realty Boston Northwest

    75 Sewall Ave, Winthrop, MA 02152

Why Live in Winthrop Highlands

Winthrop Highlands, a picturesque neighborhood surrounded by water on three sides, is known for its stunning natural beauty and close-knit community. Residents enjoy breathtaking sunrises and sunsets over the Atlantic Ocean, with opportunities to see the full moon rise over the horizon. The area is ideal for outdoor enthusiasts, offering activities such as boating, fishing, surfing, and jogging. Halford Beach and Highlands Beach provide convenient water access, while Fort Heath Park on Grovers Cliff is a popular spot for dog walking and occasional concerts. The neighborhood also features the Pond Street Playground and the John Joseph Kilmartin Pathway for recreational activities. Winthrop Highlands is characterized by its historic single-family homes, including Cape Cods, colonials, and the occasional Victorian, most of which were built around the turn of the 20th century. The neighborhood's streets are peaceful and well-established, with slightly larger lots compared to other parts of town. The local restaurant scene is vibrant, with notable spots like the Winthrop Arms Hotel and Restaurant, Jac’s Café, Antique Table Restaurant, and Bridges Nepali Cuisine. Families in the area benefit from highly rated schools, including William P. Gorman Fort Banks Elementary School, Winthrop Middle School, and Winthrop High School, all recognized for their strong academic performance. The neighborhood's proximity to Downtown Boston, just 10 miles away via U.S. Route 145, and the ferry service less than 2 miles away, make commuting convenient. Additionally, Boston Logan International Airport is just over 5 miles from the neighborhood. With its low crime risk compared to the national average, Winthrop Highlands offers a serene and engaging environment for its residents.

Frequently Asked Questions

Is Winthrop Highlands a good place to live?
Winthrop Highlands is a good place to live. Winthrop Highlands is considered fairly walkable and somewhat bikeable. Winthrop Highlands has 6 parks for recreational activities. It is fairly dense in population with 14.3 people per acre and a median age of 59. The average household income is $125,618 which is above the national average. College graduates make up 55.1% of residents. A majority of residents in Winthrop Highlands are home owners, with 47.5% of residents renting and 52.5% of residents owning their home. A local real estate agent serving Winthrop Highlands can help you decide if this neighborhood is the right one for you. Learn more on our Winthrop Highlands neighborhood guide.
Is Winthrop Highlands, MA a safe neighborhood?
Winthrop Highlands, 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 Winthrop Highlands?
The median home price in Winthrop Highlands is $600,000. If you put a 20% down payment of $120,000 and had a 30-year fixed mortgage with an interest rate of 6.74%, your estimated principal and interest payment would be $3,110 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $133K a year to afford the median home price in Winthrop Highlands. The average household income in Winthrop Highlands is $126K.
What are the best public schools in Winthrop Highlands?
The best public schools that serve Winthrop Highlands are:
What are the best private schools in Winthrop Highlands?
The best private schools that serve Winthrop Highlands are:
What are the most popular zip codes in Winthrop Highlands, Winthrop, MA?
The most popular zip codes in Winthrop Highlands, Winthrop, MA include 02152, 02151, 02128, 02150 and 01908.
What are the most popular neighborhoods near Winthrop Highlands, Winthrop, MA?
The most popular neighborhoods near Winthrop Highlands, Winthrop, MA are Downtown Winthrop, Winthrop Beach, Beachmont, Cottage Hill and Harbor View-Orient Heights.
Are home prices dropping in Winthrop Highlands?
Yes, home prices in Winthrop Highlands are down 30% in the last 12 months.

Home Trends in Winthrop Highlands, MA

Housing Trends

Median Sale Price
$600,000
Median Single Family Sale Price
$600,000
Average Price Per Sq Ft
$212
Number of Homes for Sale
0
Last 12 months Home Sales
18
Months of Supply
0.00
Median List Price
$600,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-25%
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