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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

    $1,480,000

    Open Sat 11AM - 12PM $45K PRICE DROP
    • 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 thoughtfully expanded coastal home offers an exceptional combination of natural light, modern design, and quality craftsmanship. Recently completed following an extensive reconstruction and thoughtful expansion, the home features 4 bedrooms, 2.5 baths,

    Agent Photo

    David Cody

    Orchard Park Realty

    89R Upland Rd, 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

    $639,000

    $40K 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
  • 3 Seal Harbor Rd Unit 336, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 336, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 336, Winthrop, MA 02152
    /42

    $859,900

    • 2 Beds
    • 1.5 Baths
    • 1,674 Sq Ft

    3 Seal Harbor Rd Unit 336, Winthrop, MA 02152

    A rare offering at the prestigious Seal Harbor III, this exceptional corner residence captures breathtaking panoramic water views from an expansive, light filled interior and a private balcony - perfect for enjoying morning coffee, evening sunsets, or simply taking in the every changing waterfront scenery. Completely reimagined with a full gut reno in 2010, the home showcases timeless design, an

    Cathie Curran Charlesgate Realty Group, llc

    3 Seal Harbor Rd Unit 336, 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

    $578,000

    $1K PRICE DROP
    • 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
  • 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

    $775,000

    Open Sun 11AM - 12:30PM $24K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,417 Sq Ft

    1 Seal Harbor Rd Unit PH16, Winthrop, MA 02152

    Turnkey corner PENTHOUSE unit in Seal Harbor with $5k credit if UAG by 7/20! Offering sweeping Atlantic Ocean views from a private top-flr balcony this 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

    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
    /25

    $615,000

    $34K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,203 Sq Ft

    1 Seal Harbor Rd Unit 815, Winthrop, MA 02152

    Seal Harbor I Gorgeous ocean 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 area, and a

    Peggie Gilbert Coldwell Banker Peggy Carter Team

    1 Seal Harbor Rd Unit 815, Winthrop, MA 02152
  • 211 Grovers Ave, Winthrop, MA 02152
    211 Grovers Ave, Winthrop, MA 02152
    211 Grovers Ave, Winthrop, MA 02152
    /3

    $977,700

    • 3 Beds
    • 2.5 Baths
    • 2,451 Sq Ft

    211 Grovers Ave, Winthrop, MA 02152

    Location, location, location! Welcome to 211 Grovers Avenue, perfectly situated in the highly sought-after ocean community of Winthrop Highlands. This iconic brick-front Cape Cod sits on a 5,227 sq. ft. lot and radiates timeless character. Inside, you'll find an inviting living room featuring elegant tray ceilings and a warm fireplace. The home offers 3 bedrooms and 2.5 bathrooms, with incredible

    Concetta Cicolini Lamacchia Realty, Inc.

    211 Grovers Ave, 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
    /40

    $499,900

    • 1 Bed
    • 1 Bath
    • 947 Sq Ft

    1 Seal Harbor Rd Unit 210, Winthrop, MA 02152

    Wake up to SPECTACULAR SUNRISES over the Atlantic and fall asleep to the soothing sound of OCEAN WAVES in this affordable OCEANFRONT UNIT at Seal Harbor Condominiums! Offering UNOBSTRUCTED OCEAN VIEWS from EVERY ROOM, this beautifully maintained home delivers the ultimate coastal lifestyle while being a short drive to Boston & Logan Airport! Gleaming HW FLOORS flow throughout the OPEN CONCEPT

    Rita Angelesco LAER Realty Partners

    1 Seal Harbor Rd Unit 210, Winthrop, MA 02152
  • 1 Seal Harbor Rd Unit 700, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 700, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 700, Winthrop, MA 02152
    /32

    $749,995

    • 2 Beds
    • 2 Baths
    • 1,414 Sq Ft

    1 Seal Harbor Rd Unit 700, Winthrop, MA 02152

    Step inside and you'll immediately understand why this residence is unlike any other at Seal Harbor. Thoughtfully redesigned with timeless finishes and meticulously maintained, every detail has been curated to create an exceptional coastal retreat. Wake up to panoramic ocean views and unwind each evening with spectacular sunsets from your private covered balcony, where the fresh salt air and

    Candice Hodgson Lyv Realty

    1 Seal Harbor Rd Unit 700, Winthrop, MA 02152
Massachusetts Suffolk County Winthrop

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

Winthrop Highlands Home Prices vs. Nearby Winthrop, MA Neighborhoods

Winthrop Highlands Downtown Winthrop Winthrop Beach Cottage Hill
Median Home Price
$679,000
$599,900
$519,500
$489,900
Median Sale Price
$650,000
-2% YoY
$594,900
-6% YoY
$499,999
+6% YoY
$490,000
-6% YoY
Median Single Family Price
$976,350
$721,000
$670,000
$720,000
Median Townhouse Price
$1,175,000
$887,450
$499,999
--
Median Condo Price
$630,000
$499,000
$494,500
$433,500
Total Active Listings
9
14
9
8
Market Conditions
5 Months of Supply
Balanced Market
3 Months of Supply
Seller's Market
5 Months of Supply
Balanced Market
5 Months of Supply
Balanced Market

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 $679,000. If you put a 20% down payment of $135,800 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $3,460 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $148K 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.
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