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Downtown Winthrop Multifamily Homes & Duplexes for Sale

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  • 19 Jefferson St, Winthrop, MA 02152
    19 Jefferson St, Winthrop, MA 02152
    19 Jefferson St, Winthrop, MA 02152
    /42

    $1,249,000

    • 9 Beds
    • 3 Baths
    • 2,775 Sq Ft

    19 Jefferson St, Winthrop, MA 02152

    Rare find 3family with separate utilities, off street parking, beautiful fence enclosed yard, porches w/views and many updates. Unit 1 was a 3 bed but now has laundry in unit, a huge livingroom/diningroom, bath with jacuzzi tub, central air and large eat in kitchen with oak cabinets and ample counter space perfect for owner occupied. Unit 2 is beautifully renovated with 5rms/3beds and private

    Lisa Licata-Schepici L.L.S. Realty LLC

    19 Jefferson St, Winthrop, MA 02152
  • 308 Bowdoin St, Winthrop, MA 02152
    308 Bowdoin St, Winthrop, MA 02152
    308 Bowdoin St, Winthrop, MA 02152
    /42

    $995,000

    • 7 Beds
    • 3 Baths
    • 3,628 Sq Ft

    308 Bowdoin St, Winthrop, MA 02152

    Pride filled neighborhood for this substantial and very well maintained 2 family home 5/8. Both units are move in ready with beautiful, gleaming hardwood floors and high plaster ceilings. The windows are new and the roof is just 8 years old. The newer gas utilities are separate and there have been electric updates. The baths are newer and the kitchens, while not recently remodeled, are in clean,

    James Polino Compass

    308 Bowdoin St, Winthrop, MA 02152
  • 80 Shirley St, Winthrop, MA 02152
    80 Shirley St, Winthrop, MA 02152
    80 Shirley St, Winthrop, MA 02152
    /29

    $1,100,000

    • 4 Beds
    • 2 Baths
    • 2,366 Sq Ft

    80 Shirley St, Winthrop, MA 02152

    Gorgeous farmhouse revival!!! Coastal vibes flow through this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. Both units boast modern open floor plans. Actual high end finishes throughout for an obvious upscale vibe. Huge

    Nick Burnes Red Tree Real Estate

    80 Shirley St, Winthrop, MA 02152
  • 50-52 Wilshire St, Winthrop, MA 02152
    50-52 Wilshire St, Winthrop, MA 02152
    /2

    $1,300,000

    • 5 Beds
    • 2 Baths
    • 2,212 Sq Ft

    50-52 Wilshire St, Winthrop, MA 02152

    Just Renovated – Perfect for Owner-Occupants or Investors!Welcome to 50-52 Wilshire Street, a fully updated two-family home located in the picturesque seaside community of Winthrop, Massachusetts. This property has 5 bedrooms and 2 bathrooms. Fresh from a complete renovation, this property blends modern finishes with timeless New England charm, offering unmatched flexibility for both comfortable

    Bin Yan Ark Real Estate Inc.

    50-52 Wilshire St, Winthrop, MA 02152
Massachusetts Suffolk County Winthrop Downtown Winthrop

Multi-Family Homes & Duplexes for Sale in Downtown Winthrop, Winthrop

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.
Learn more about living in Downtown Winthrop

Home Trends in Downtown Winthrop, MA

On average, homes in Downtown Winthrop, Winthrop sell after 20 days on the market compared to the national average of 52 days. The median sale price for homes in Downtown Winthrop, Winthrop over the last 12 months is $635,000, up 15% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$635,000
Median Single Family Sale Price
$686,500
Median Townhouse Sale Price
$879,000
Median 2 Bedroom Sale Price
$378,000
Median 1 Bedroom Sale Price
$548,316
Average Price Per Sq Ft
$461
Number of Homes for Sale
15
Last 12 months Home Sales
51
Months of Supply
3.50
Median List Price
$629,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
15%
How to Buy a Home How to Finance a Home How to Sell a Home

In Downtown Winthrop, there are currently 4 multi-family homes for sale, providing an appealing investment opportunity for buyers. With multi-family homes ranging from $995,000 to $1,300,000, there's something for every budget. As of August, 2025 the median home price in Downtown Winthrop, Winthrop is $629,000, while the average sale price is $616,800, providing insight into local market trends. On average, multi-family homes spend 20 days on the market before being sold. Multi-family homes encompass various property types, including duplexes, triplexes, fourplexes, and apartment complexes, all within a single building divided to accommodate multiple families living separately. These multi-family properties for sale offer investors the chance to generate rental income. Whether you're interested in a duplex for a starter investment or an apartment complex for a larger-scale venture, there are investment properties available to suit your needs. Explore the range of multi-family homes for sale in Downtown Winthrop, Winthrop.

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