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Winthrop Highlands Homes for Sale

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  • 89R Upland Rd, Winthrop, MA 02152
    89R Upland Rd, Winthrop, MA 02152
    89R Upland Rd, Winthrop, MA 02152
    /33

    $1,525,000

    • 4 Beds
    • 2.5 Baths
    • 2,475 Sq Ft

    89R Upland Rd, Winthrop, MA 02152

    Perched above the shoreline with sweeping, unobstructed water views toward Broad Sound and Revere Beach, this extensively reconstructed and reimagined coastal home has been recently completed. The home features 4 bedrooms, 2.5 baths, central air, natural gas heat, a new HVAC system, new water heater, new kitchen, new baths, new flooring, new windows, new siding, new roof, and extensive

    Agent Photo

    David Cody

    Orchard Park Realty

    (617) 925-6049

    89R Upland Rd, Winthrop, MA 02152
  • 1 Seal Harbor Rd Unit 413, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 413, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 413, Winthrop, MA 02152
    /18

    $579,000

    Open Sun 12PM - 1PM
    • 2 Beds
    • 2 Baths
    • 1,205 Sq Ft

    1 Seal Harbor Rd Unit 413, Winthrop, MA 02152

    Welcome to coastal living at its finest at the highly desirable Seal Harbor One. Perched on the fourth floor, this spacious and thoughtfully designed 2-bedroom, 2-bath residence offers an ideal layout with private bedroom suites, each featuring its own full bathroom and generous walk-in closet. Set on a stunning peninsula surrounded by the Atlantic Ocean, Seal Harbor offers a truly unique

    Tammy Merk Lantern Residential

    1 Seal Harbor Rd Unit 413, Winthrop, MA 02152
  • 47 Highland Ave, Winthrop, MA 02152
    47 Highland Ave, Winthrop, MA 02152
    47 Highland Ave, Winthrop, MA 02152
    /35

    $629,000

    $21K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,728 Sq Ft

    47 Highland Ave, Winthrop, MA 02152

    Wonderful opportunity to own a coastal Winthrop home with tremendous potential. A welcoming mudroom opens to a spacious foyer and a large living and dining area with great flow for everyday living. A bonus front room offers flexible space for a home office, playroom, or an expanded open-concept layout. The kitchen leads directly to the back deck for warm-weather entertaining. Upstairs features

    Elizabeth Ferrara Cottage Hill Real Estate

    47 Highland Ave, Winthrop, MA 02152
  • 3 Seal Harbor Rd Unit 632, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 632, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 632, Winthrop, MA 02152
    /34

    $654,000

    • 1 Bed
    • 2 Baths
    • 1,263 Sq Ft

    3 Seal Harbor Rd Unit 632, Winthrop, MA 02152

    Move-in ready! 1.5br 2ba renovated condo with spectacular views. Modern kitchen w/new appliances. New paint, flooring and hot water tank (2022). 1 underground, deeded parking space & multiple @ grade. The oceanfront Seal Harbor condominium community is just 15 min. from Boston's financial district. The building is amenity-rich offering 24/7 concierge, on-site management, secure underground garage

    Mark Carangelo Mark Carangelo

    3 Seal Harbor Rd Unit 632, Winthrop, MA 02152
  • 1 Seal Harbor Rd Unit PH16, Winthrop, MA 02152
    1 Seal Harbor Rd Unit PH16, Winthrop, MA 02152
    1 Seal Harbor Rd Unit PH16, Winthrop, MA 02152
    /32

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,417 Sq Ft

    1 Seal Harbor Rd Unit PH16, Winthrop, MA 02152

    Rare PENTHOUSE unit in Winthrop’s premier waterfront community, offering sweeping Atlantic Ocean views from a private top-flr balcony. 2023 renovated 2BR/2BA residence showcases oversized windows that flood the living area with natural light, built-in window seat, white oak HW floors throughout, and an elegant inlay foyer detail beneath skylight/ recessed lighting. Updated kitchen features

    Meg Grady The Persac Group, LLC

    1 Seal Harbor Rd Unit PH16, Winthrop, MA 02152
  • 1 Seal Harbor Rd Unit 815, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 815, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 815, Winthrop, MA 02152
    /22

    $625,000

    Open Sun 12PM - 2PM $24K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,203 Sq Ft

    1 Seal Harbor Rd Unit 815, Winthrop, MA 02152

    Seal Harbor I — Gorgeous ocean and harbor views from this sunny corner 8th-floor unit. Spacious living room with slider to a private balcony-This home features two comfortable bedrooms with large closets and beautiful views, a well-appointed kitchen with ample cabinetry and updated appliances, plus a newer washer/dryer. Enjoy resort-style amenities including an in-ground heated pool, fitness

    Peggie Gilbert Coldwell Banker Peggy Carter Team

    1 Seal Harbor Rd Unit 815, Winthrop, MA 02152
  • 1 Seal Harbor Rd Unit 300, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 300, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 300, Winthrop, MA 02152
    /39

    $550,000

    Open Sun 12:30PM - 1:30PM $20K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 994 Sq Ft

    1 Seal Harbor Rd Unit 300, Winthrop, MA 02152

    Experience refined waterfront living in this fully renovated, ocean-facing residence. The chef’s kitchen is a true centerpiece, featuring a brand-new center island, quartz countertops, and premium appliances—perfect for effortless entertaining. Modern upgrades shine throughout, including new electrical, recessed lighting, and sleek ceiling fans. Relax in the spa-inspired bathroom with a walk-in

    Alla Rossi Coldwell Banker Realty - Boston

    1 Seal Harbor Rd Unit 300, Winthrop, MA 02152
  • 1 Seal Harbor Rd Unit 210, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 210, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 210, Winthrop, MA 02152
    /27

    $499,900

    • 1 Bed
    • 1 Bath
    • 947 Sq Ft

    1 Seal Harbor Rd Unit 210, Winthrop, MA 02152

    This Oceanside unit is waiting for you! Unit 210 has an unobstructed view of the ocean and the town of Nahant. as well as a long expanse of lawn and the gazebo. Enjoy your beautiful fully applianced custom kitchen with granite counters and stainless steel appliances , in unit laundry and full bath The hardwood floors throughout add to the value of this condo and the open floor living room/dining

    James Lonergan Lonergan Real Estate

    1 Seal Harbor Rd Unit 210, Winthrop, MA 02152
  • 3 Seal Harbor Rd Unit 342, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 342, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 342, Winthrop, MA 02152
    /42

    $649,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,302 Sq Ft

    3 Seal Harbor Rd Unit 342, Winthrop, MA 02152

    Seal Harbor in Winthrop offers an elevated coastal living experience that is unparalleled. Timeless detail inside & out of this building is complemented by white-glove concierge service. Unit 342 is a luxury residence with ocean & pool views from every window. It is conveniently located a few steps from the new elevators & welcomes you into an open floor plan with striking natural sunlight;

    Nancy McLaughlin Redfin Corp.

    3 Seal Harbor Rd Unit 342, 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 somewhat walkable and bikeable with some transit options. 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 very dense in population with 15.0 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% of residents renting and 53% 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 $654,000. If you put a 20% down payment of $130,800 and had a 30-year fixed mortgage with an interest rate of 6.52%, your estimated principal and interest payment would be $3,310 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $142K 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 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.

Winthrop Highlands Home Prices vs. Nearby Winthrop, MA Neighborhoods

Winthrop Highlands Downtown Winthrop Wollaston Winthrop Beach
Median Home Price
$654,000
$614,450
$749,900
$499,900
Median Sale Price
$665,000
-1% YoY
$584,950
-6% YoY
$760,000
+3% YoY
$480,000
+1% YoY
Median Single Family Price
$929,500
$740,000
$786,500
$699,000
Median Townhouse Price
$1,175,000
$887,450
$1,149,500
$499,999
Median Condo Price
$631,000
$492,500
$570,500
$462,000
Total Active Listings
9
16
7
8
Market Conditions
5 Months
Balanced Market
4 Months
Seller's Market
2 Months
Seller's Market
5 Months
Balanced Market
How to Buy a Home How to Finance a Home How to Sell a Home

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