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Downtown Winthrop Houses for Sale

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  • /25

    $879,000 Open Fri 5PM - 6:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,115 Sq Ft

    54 Villa Ave Unit 2, Winthrop, MA 02152

    Modern 2019 move-in ready townhouse with coastal charm! This meticulously crafted 3-bedroom, 2.5-bathroom home brimming with natural light and coastal charm with features such as soaring ceilings, walls of windows, and an open floor plan. Key Features: • Statement gas fireplace as living room focal point • Designer kitchen with premium appliances • Private backyard with dedicated driveway parking

    The Reference Group Reference Real Estate

    54 Villa Ave Unit 2, Winthrop, MA 02152
  • /42

    $870,000

    • 4 Beds
    • 3.5 Baths
    • 2,350 Sq Ft

    136 Pauline St, Winthrop, MA 02152

    Beautifully renovated 4-bedroom, 3.5-bath single-family home, fully gutted and updated in 2020. This turnkey property features an open floor plan with seamless flow between the spacious living room, dining area, and modern kitchen—perfect for today’s lifestyle and entertaining. The primary suite includes a walk-in closet and private en-suite bath. A finished basement (2021) provides flexible

    Anthony Carestia William Raveis R.E. & Home Services

    136 Pauline St, Winthrop, MA 02152
  • /30

    $699,900

    • 3 Beds
    • 1 Bath
    • 1,548 Sq Ft

    60 Waldemar Ave, Winthrop, MA 02152

    Located in one of Winthrop's most desirable Center locations, this well maintained 7 room, 3 bedroom single says welcome home! The kitchen has been updated with granite counters and stainless steel appliances and the bayed living and dining rooms with high ceilings are elegant and very inviting. The full bath has a jetted tub and separate shower! There are beautiful wood floors throughout. Love

    James Polino Compass

    60 Waldemar Ave, Winthrop, MA 02152

Why Live in Downtown Winthrop

Downtown Winthrop features a mix of peaceful beach cottages, Cape Cods, and colonial-inspired homes, with properties ranging from the early 1800s to the mid-20th century. Single-family houses, multi-family properties, condos, and commercial storefronts line the established streets, with lot sizes typically between 3,000 and 7,000 square feet. The neighborhood's coastal charm is enhanced by its proximity to beaches, marinas, and yacht clubs like Winthrop Yacht Club and Pleasant Park Yacht Club, which offer sailing programs and social activities. Residents enjoy walking along Donovan’s Beach and Winthrop Beach, with views of planes from nearby Logan International Airport, just 4 miles away. Community events such as the Independence Day Horrible’s Parade and the annual Strawberry Festival foster a strong sense of local culture. Ingleside Park hosts a farmers market, skate park, tennis courts, and a baseball field, while Winthrop Golf Club offers a public nine-hole course. Dining options include Belle Isle Seafood, the historic Winthrop Arms Hotel and Restaurant, Vuolo's Italian eatery, and Nick’s Place pizzeria. For groceries, Winthrop Market Place is centrally located, with additional shopping available 2 miles north at The Shops at Suffolk Downs. The neighborhood is served by Winthrop Public Schools, with the highly rated William P. Gorman Fort Banks Elementary School for young learners. Commuters benefit from easy access to downtown Boston, 6 miles away, via Massachusetts Route 1A, MBTA T subway lines at Orient Heights, and ferry service at Winthrop Landing. The area has a low crime risk compared to the national average, contributing to its appeal for residents.

Home Trends in Downtown Winthrop, MA

Housing Trends

Median Sale Price
$630,000
Median Single Family Sale Price
$685,000
Median Townhouse Sale Price
$879,000
Median 2 Bedroom Sale Price
$380,000
Median 1 Bedroom Sale Price
$550,766
Average Price Per Sq Ft
$464
Number of Homes for Sale
18
Last 12 months Home Sales
52
Months of Supply
4.20
Median List Price
$602,436
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
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