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Winthrop Highlands Homes for Sale

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  • 144 Quincy Ave, Winthrop, MA 02152
    144 Quincy Ave, Winthrop, MA 02152
    144 Quincy Ave, Winthrop, MA 02152
    /39

    $1,699,900 Open Thu 4PM - 5:30PM

    • 5 Beds
    • 4 Baths
    • 3,866 Sq Ft

    144 Quincy Ave, Winthrop, MA 02152

    Welcome to the Highlands, Winthrop’s most coveted neighborhood where modern design meets sweeping Boston views. This renovated home rises high on the hill with sunlit interiors, wide white oak floors, and timeless details throughout. The main level offers an open layout with a living room and fireplace, Thermador-Pro kitchen with island, beverage bar, and pantry, plus a dining area that opens to

    Leighann Eruzione Lantern Residential

    144 Quincy Ave, Winthrop, MA 02152
  • 1 Seal Harbor Rd Unit 415, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 415, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 415, Winthrop, MA 02152
    /42

    $550,000

    • 2 Beds
    • 2 Baths
    • 1,203 Sq Ft

    1 Seal Harbor Rd Unit 415, Winthrop, MA 02152

    SELLER MOTIVATED! NEW PRICE! AMAZING VALUE! Enjoy the ease of COASTAL LIVING in this beautiful 2-bed, 2-bath unit designed for comfort and convenience. Filled with natural light, it offers an open layout and a private balcony with OCEAN VIEWS—perfect for morning coffee or sunset unwinding. The spacious primary suite includes an EN-SUITE BATH and a generous walk-in closet. FRESHLY PAINTED

    Camilo & Co. Group Realty One Group Nest

    1 Seal Harbor Rd Unit 415, Winthrop, MA 02152
  • 5 Quincy Ave, Winthrop, MA 02152
    5 Quincy Ave, Winthrop, MA 02152
    5 Quincy Ave, Winthrop, MA 02152
    /41

    $950,000

    • 3 Beds
    • 2 Baths
    • 2,820 Sq Ft

    5 Quincy Ave, Winthrop, MA 02152

    Welcome to 5 Quincy Avenue, an architecturally stunning Bungalow located in Winthrop's highly sought-after Highlands neighborhood . This sun-filled 3-bedroom, 2-bath Craftsman home has an open-concept living and dining area featuring original rich oak woodwork, built-in cabinets, hardwood floors, decorative molding, wainscoting, fireplace and a New Furnace! The renovated eat-in kitchen, equipped

    William Raye William Raveis R.E. & Home Services

    5 Quincy Ave, Winthrop, MA 02152
  • 3 Seal Harbor Rd Unit 137, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 137, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 137, Winthrop, MA 02152
    /29

    $685,995

    • 2 Beds
    • 2 Baths
    • 1,327 Sq Ft

    3 Seal Harbor Rd Unit 137, Winthrop, MA 02152

    RARELY AVAILABLE "37 stack" spacious 2 bed/2bath corner unit in The Seal Harbor Condominiums. The open dining/living area is the true heart of the home with a working fireplace, gleaming hardwood floors and direct ocean views. The kitchen showcases stone countertops, updated stainless steel appliances, open island concept and plenty of cabinets for storage, blending style with functionality.

    Christine Goldstein Lyv Realty

    3 Seal Harbor Rd Unit 137, Winthrop, MA 02152
  • 3 Seal Harbor Rd Unit 634, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 634, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 634, Winthrop, MA 02152
    /30

    $525,000

    • 1 Bed
    • 1 Bath
    • 840 Sq Ft

    3 Seal Harbor Rd Unit 634, Winthrop, MA 02152

    Situated at the ocean's edge in Winthrop, Seal Harbor is located just fifteen minutes from Boston's financial district. Building is amenity-rich- 24/7 concierge, on-site management, secure underground deeded garage parking, heated outdoor pool with shower, bathrooms, full poolhouse kitchen, outdoor Jacuzzi & 2 gas grills, year-round access to an indoor pool on the 9th floor, complete with

    Mark Carangelo Mark Carangelo

    3 Seal Harbor Rd Unit 634, Winthrop, MA 02152
Massachusetts Suffolk County Winthrop Winthrop Highlands

Real Estate & Homes for Sale in Winthrop Highlands, Winthrop

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.
Learn more about living in Winthrop Highlands

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 is a suburban neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. 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 1 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 $671,500. If you put a 20% down payment of $134,300 and had a 30-year fixed mortgage with an interest rate of 6.19%, your estimated principal and interest payment would be $3,290 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $141K a year to afford the median home price in Winthrop Highlands. Learn how much home you can afford with our Home Affordability Calculator. 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 02149.
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 Park and Cottage Hill.
Are home prices dropping in Winthrop Highlands?
Yes, home prices in Winthrop Highlands are down 3% in the last 12 months.

Home Trends in Winthrop Highlands, MA

On average, homes in Winthrop Highlands, Winthrop sell after 46 days on the market compared to the national average of 53 days. The median sale price for homes in Winthrop Highlands, Winthrop over the last 12 months is $660,000, down 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$660,000
Median Single Family Sale Price
$857,500
Median Townhouse Sale Price
$1,437,450
Median 2 Bedroom Sale Price
$650,000
Median 1 Bedroom Sale Price
$537,500
Average Price Per Sq Ft
$504
Number of Homes for Sale
5
Last 12 months Home Sales
21
Months of Supply
2.90
Median List Price
$671,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-8%
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