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Downtown Winthrop Homes for Sale

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  • 50-52 Wilshire St, Winthrop, MA 02152
    50-52 Wilshire St, Winthrop, MA 02152
    50-52 Wilshire St, Winthrop, MA 02152
    /14

    $1,075,000

    • 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
  • 10 Somerset Ave Unit 401, Winthrop, MA 02152
    10 Somerset Ave Unit 401, Winthrop, MA 02152
    10 Somerset Ave Unit 401, Winthrop, MA 02152
    /19

    $545,701

    • 1 Bed
    • 1 Bath
    • 684 Sq Ft

    10 Somerset Ave Unit 401, Winthrop, MA 02152

    Welcome to Unit 401 at The Somerset, a spacious 1-bedroom, 1-bath home with an open-concept layout and a large living and dining area perfect for both everyday living and entertaining. With warmer days ahead, the expansive private deck is set to become a natural extension of the living space for dining, relaxing, and entertaining, all with views overlooking the town center. Inside, enjoy quartz

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 401, Winthrop, MA 02152
  • 10 Somerset Ave Unit 304, Winthrop, MA 02152
    10 Somerset Ave Unit 304, Winthrop, MA 02152
    10 Somerset Ave Unit 304, Winthrop, MA 02152
    /10

    $399,000

    • 1 Bed
    • 1 Bath
    • 546 Sq Ft

    10 Somerset Ave Unit 304, Winthrop, MA 02152

    LAST STUDIO! Unit 304 at The Somerset—a premier boutique condo community in the heart of Winthrop. This thoughtfully designed studio features an open-concept kitchen and living area, perfect for entertaining or relaxing, along with a versatile bonus room with a sliding barn door for flexible use. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout.

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 304, Winthrop, MA 02152
  • 800 Governors Dr Unit 6, Winthrop, MA 02152
    800 Governors Dr Unit 6, Winthrop, MA 02152
    800 Governors Dr Unit 6, Winthrop, MA 02152
    /11

    $340,000

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft

    800 Governors Dr Unit 6, Winthrop, MA 02152

    Located at 800 Governors Dr U:6 in the charming coastal community of Winthrop, Massachusetts, this condominium presents an inviting home, ready to move in and enjoy. This residence offers a delightful opportunity to experience comfortable living in a convenient setting. The kitchen stands as a testament to thoughtful design, featuring elegant stone countertops complemented by stylish shaker

    Fiorella Marte StartPoint Realty

    800 Governors Dr Unit 6, Winthrop, MA 02152
  • 56 Main St, Winthrop, MA 02152
    56 Main St, Winthrop, MA 02152
    56 Main St, Winthrop, MA 02152
    /27

    $799,900

    • 4 Beds
    • 2 Baths
    • 2,103 Sq Ft

    56 Main St, Winthrop, MA 02152

    OPPORTUNITY KNOCKS.......Two family with large yard is located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! Some renovations as of 2001. The owner's unit is on the second and third floors with an open floor plan and lots of natural lighting. It contains a living room, dining area, kitchen, bath and one bedroom. The top floor consists of a

    Sharon Tallent Compass

    56 Main St, Winthrop, MA 02152
  • 550 Pleasant St Unit 506, Winthrop, MA 02152
    550 Pleasant St Unit 506, Winthrop, MA 02152
    550 Pleasant St Unit 506, Winthrop, MA 02152
    /21

    $1,030,000

    • 2 Beds
    • 2 Baths
    • 1,975 Sq Ft

    550 Pleasant St Unit 506, Winthrop, MA 02152

    Penthouse Waterfront Luxury at Atlantis Marina – Oversized Boat Slip Included!Experience sophisticated coastal living in this stunning top-floor corner penthouse at Atlantis Marina, offering sweeping water views and panoramic Boston skyline vistas. This rare fifth-floor residence combines luxury, space, and an unbeatable location in the charming seaside town of Winthrop.This exceptional

    Jessica Pumphret Blue Sky Realty

    550 Pleasant St Unit 506, Winthrop, MA 02152
  • 10 Somerset Ave Unit 204, Winthrop, MA 02152
    10 Somerset Ave Unit 204, Winthrop, MA 02152
    10 Somerset Ave Unit 204, Winthrop, MA 02152
    /11

    $598,395

    • 2 Beds
    • 2 Baths
    • 832 Sq Ft

    10 Somerset Ave Unit 204, Winthrop, MA 02152

    Welcome to Unit 204 at The Somerset—Winthrop’s premier boutique condo community where coastal charm meets modern design. This spacious 1+-bed, 1-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing and an exterior private balcony. A generous kitchen island anchors the space and faces the front of the building, inviting natural light and a

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 204, Winthrop, MA 02152
  • 35 Somerset Ave Unit 6, Winthrop, MA 02152
    35 Somerset Ave Unit 6, Winthrop, MA 02152
    35 Somerset Ave Unit 6, Winthrop, MA 02152
    /31

    $509,900

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft

    35 Somerset Ave Unit 6, Winthrop, MA 02152

    UPSCALE 2 BEDROOM, 2 BATH TOP FLOOR UNIT WITH ROOFTOP EXCLUSIVE OUTDOOR DECK......A two year old renovation and a must see! Bright sun-filled condo with a spacious kitchen/living room combo with plenty of cabinets and huge center island with pretty pendant lighting......perfect for entertaining and personal enjoyment. Two large bedrooms, one a main suite with it's own full bath and the other bath

    Sharon Tallent Compass

    35 Somerset Ave Unit 6, Winthrop, MA 02152
Massachusetts Suffolk County Winthrop Downtown Winthrop

Real Estate & Homes 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

Frequently Asked Questions

Is Downtown Winthrop a good place to live?
Downtown Winthrop is a good place to live. Downtown Winthrop is considered fairly walkable and somewhat bikeable. Downtown Winthrop is a neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. Downtown Winthrop has 1 park for recreational activities. It has a median age of 45. The average household income is $118,624 which is above the national average. College graduates make up 38.6% of residents. A majority of residents in Downtown Winthrop are home owners, with 48.2% of residents renting and 51.8% of residents owning their home. A local real estate agent serving Downtown Winthrop can help you decide if this neighborhood is the right one for you. Learn more on our Downtown Winthrop neighborhood guide.
Is Downtown Winthrop, MA a safe neighborhood?
Downtown Winthrop, MA is safer than the average neighborhood in the United States. It received a crime score of 2 out of 10.
How much do you need to make to afford a house in Downtown Winthrop?
The median home price in Downtown Winthrop is $615,000. If you put a 20% down payment of $123,000 and had a 30-year fixed mortgage with an interest rate of 6.11%, your estimated principal and interest payment would be $2,980 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $128K a year to afford the median home price in Downtown Winthrop. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Downtown Winthrop is $119K.
What are the best public schools in Downtown Winthrop?
The best public schools that serve Downtown Winthrop are:
What are the best private schools in Downtown Winthrop?
The best private schools that serve Downtown Winthrop are:
What are the most popular zip codes in Downtown Winthrop, Winthrop, MA?
The most popular zip codes in Downtown Winthrop, Winthrop, MA include 02152, 02128, 02151, 02150 and 02149.
What are the most popular neighborhoods near Downtown Winthrop, Winthrop, MA?
The most popular neighborhoods near Downtown Winthrop, Winthrop, MA are Winthrop Beach, Cottage Park, Winthrop Highlands, Harbor View-Orient Heights and Cottage Hill.

Home Trends in Downtown Winthrop, MA

On average, homes in Downtown Winthrop, Winthrop sell after 28 days on the market compared to the national average of 53 days. The median sale price for homes in Downtown Winthrop, Winthrop over the last 12 months is $661,250, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$661,250
Median Single Family Sale Price
$701,500
Median Townhouse Sale Price
$849,000
Median 2 Bedroom Sale Price
$385,000
Median 1 Bedroom Sale Price
$545,000
Average Price Per Sq Ft
$447
Number of Homes for Sale
7
Last 12 months Home Sales
52
Months of Supply
1.60
Median List Price
$615,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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