15

Downtown Winthrop Homes for Sale

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  • 500 Governors Dr Unit 34, Winthrop, MA 02152
    500 Governors Dr Unit 34, Winthrop, MA 02152
    500 Governors Dr Unit 34, Winthrop, MA 02152
    /10

    $425,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 1 Bath
    • 782 Sq Ft

    500 Governors Dr Unit 34, Winthrop, MA 02152

    Experience modern coastal living in this completely renovated 2-bedroom, 1-bath condo located in the sought-after Governors Park community. This bright & open unit features brand-new flooring, kitchen, bathroom, appliances, lighting & finishes throughout—all thoughtfully designed for contemporary comfort & style. Enjoy an open-concept living & dining area that flows to a private balcony, perfect

    David White OwnerEntry.com

    500 Governors Dr Unit 34, Winthrop, MA 02152
  • 10 Somerset Ave Unit 406, Winthrop, MA 02152
    10 Somerset Ave Unit 406, Winthrop, MA 02152
    10 Somerset Ave Unit 406, Winthrop, MA 02152
    /14

    $655,000 Open Sat 3PM - 4:30PM

    • 2 Beds
    • 2 Baths
    • 985 Sq Ft

    10 Somerset Ave Unit 406, Winthrop, MA 02152

    Welcome to Unit 406 at The Somerset—Winthrop’s premier boutique condo community, where coastal charm meets modern design. This spacious 2-bed, 2-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing. A generous kitchen island anchors the space, complemented by quartz countertops, stainless steel appliances, central A/C, and stylish finishes

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 406, 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
    /23

    $555,000 Open Sat 3PM - 4:30PM

    • 1 Bed
    • 1 Bath
    • 684 Sq Ft

    10 Somerset Ave Unit 401, Winthrop, MA 02152

    Welcome to Unit 401 at The Somerset—Winthrop’s premier boutique condo community where coastal charm meets modern design. This spacious 1bed, 1-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing. This unit has exceptional views overlooking the center on a massive roof deck. Enjoy quartz countertops, stainless steel appliances, central

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 401, Winthrop, MA 02152
  • 54 Villa Ave Unit 2, Winthrop, MA 02152
    54 Villa Ave Unit 2, Winthrop, MA 02152
    54 Villa Ave Unit 2, Winthrop, MA 02152
    /26

    $879,000 Open Sat 11AM - 1:30PM

    • 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
  • 17 Buckthorn Terrace, Winthrop, MA 02152
    17 Buckthorn Terrace, Winthrop, MA 02152
    17 Buckthorn Terrace, Winthrop, MA 02152
    /25

    $849,900 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,764 Sq Ft

    17 Buckthorn Terrace, Winthrop, MA 02152

    Welcome to your dream home nestled on a quiet side street in the picturesque seaside town of Winthrop. This stunning 4 bedroom, 3.5 bathroom property blends timeless elegance with modern luxury, offering an abundance of space and upscale amenities just minutes from Boston. Step inside to discover a beautifully designed interior featuring elegant finishes all around, an exquisite almost seashell

    Richard Harkins EWK Realty

    17 Buckthorn Terrace, Winthrop, MA 02152
  • 10 Somerset Ave Unit 209, Winthrop, MA 02152
    10 Somerset Ave Unit 209, Winthrop, MA 02152
    10 Somerset Ave Unit 209, Winthrop, MA 02152
    /19

    $570,000 Open Sat 3PM - 4:30PM

    • 1 Bed
    • 1 Bath
    • 764 Sq Ft

    10 Somerset Ave Unit 209, Winthrop, MA 02152

    Welcome to Unit 209 at The Somerset—Winthrop’s premier boutique condo community where coastal charm meets modern design. This spacious 1bed, 1-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing. A generous kitchen island anchors the space and faces the front of the building, inviting natural light and a welcoming flow. Enjoy quartz

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 209, Winthrop, MA 02152
  • 10 Somerset Ave Unit 201, Winthrop, MA 02152
    10 Somerset Ave Unit 201, Winthrop, MA 02152
    10 Somerset Ave Unit 201, Winthrop, MA 02152
    /29

    $629,000 Open Sat 3PM - 4:30PM

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft

    10 Somerset Ave Unit 201, Winthrop, MA 02152

    Welcome to Unit 201 at The Somerset—Winthrop’s premier boutique condo community where coastal charm meets modern design. This spacious 2-bed, 2-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing. A generous kitchen island anchors the space and faces the front of the building, inviting natural light and a welcoming flow. Enjoy quartz

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 201, Winthrop, MA 02152
  • 37-39 Hutchinson St, Winthrop, MA 02152
    37-39 Hutchinson St, Winthrop, MA 02152
    37-39 Hutchinson St, Winthrop, MA 02152
    /41

    $899,000

    • 5 Beds
    • 2 Baths
    • 2,958 Sq Ft

    37-39 Hutchinson St, Winthrop, MA 02152

    Endless Potential in Prime Seaside Location – 02152 Welcome to this oversized two-family home located in the highly desirable seaside community of Winthrop, 02152. Perfectly situated on a generous lot, this property offers a rare opportunity for investors, multi-generational living, or owner-occupants looking to customize and create value.Each unit features spacious layouts with room to grow, and

    Nicole Bettano Lantern Residential

    37-39 Hutchinson St, Winthrop, MA 02152
  • 136 Pauline St, Winthrop, MA 02152
    136 Pauline St, Winthrop, MA 02152
    136 Pauline St, 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
  • 123 Buchanan St, Winthrop, MA 02152
    123 Buchanan St, Winthrop, MA 02152
    123 Buchanan St, Winthrop, MA 02152
    /31

    $588,888

    • 4 Beds
    • 1.5 Baths
    • 1,785 Sq Ft

    123 Buchanan St, Winthrop, MA 02152

    Step back in time, a stately home ready to be restored and reimagined. This 4-bedroom, 1.5-bath is rich with character—featuring original beamed ceilings, ornamental exterior wood trim, and timeless architectural details that set the stage for a stunning transformation. Located near Winthrop Golf Club, High School, and the coastal beauty of Boston’s shoreline, this home offers a rare opportunity

    Ronda Cogliano Century 21 North East

    123 Buchanan St, Winthrop, MA 02152
  • 60 Waldemar Ave, Winthrop, MA 02152
    60 Waldemar Ave, Winthrop, MA 02152
    60 Waldemar Ave, 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
  • 35 Somerset Ave Unit 6, Winthrop, MA 02152
    35 Somerset Ave Unit 6, Winthrop, MA 02152
    35 Somerset Ave Unit 6, Winthrop, MA 02152
    /27

    $540,000 Open Sat 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 823 Sq Ft

    35 Somerset Ave Unit 6, Winthrop, MA 02152

    Welcome to 35 Somerset Ave, Unit #6 (Pent House), nestled in the heart of Winthrop! This stunning newly renovated 2-bedroom, 2 full bathroom condo, offers a perfect fusion of modern comfort and seaside charm. Located just moments from the beach, this inviting unit offers breathtaking views from its massive private roof deck and seamless access to downtown and the beach. Every aspect of this unit

    John Maggio EVO Real Estate Group, LLC

    35 Somerset Ave Unit 6, 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
  • 80 Shirley St Unit 2, Winthrop, MA 02152
    80 Shirley St Unit 2, Winthrop, MA 02152
    80 Shirley St Unit 2, Winthrop, MA 02152
    /39

    $649,900

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft

    80 Shirley St Unit 2, Winthrop, MA 02152

    Gorgeous farmhouse revival!!! Coastal vibes flow throughout 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. The unit boasts a modern open floor plan. Actual high end finishes throughout for an obvious upscale vibe. Huge

    Nick Burnes Red Tree Real Estate

    80 Shirley St Unit 2, Winthrop, MA 02152
  • 80 Shirley St Unit 1, Winthrop, MA 02152
    80 Shirley St Unit 1, Winthrop, MA 02152
    80 Shirley St Unit 1, Winthrop, MA 02152
    /29

    $449,900

    • 1 Bed
    • 1 Bath
    • 836 Sq Ft

    80 Shirley St Unit 1, Winthrop, MA 02152

    Gorgeous farmhouse revival! Coastal vibes flow throughout 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. The unit boasts a modern open floor plan. Actual high end finishes throughout for an obvious upscale vibe. Huge

    Nick Burnes Red Tree Real Estate

    80 Shirley St Unit 1, 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 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.
How much do you need to make to afford a house in Downtown Winthrop?
The median home price in Downtown Winthrop is $519,780. If you put a 20% down payment of $104,000 and had a 30-year fixed mortgage with an interest rate of 6.63%, your estimated principal and interest payment would be $2,660 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $114K a year to afford the median home price in Downtown Winthrop. 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 02135.
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, Court Park and Cottage Hill.

Home Trends in Downtown Winthrop, MA

On average, homes in Downtown Winthrop, Winthrop sell after 36 days on the market compared to the national average of 70 days. The median sale price for homes in Downtown Winthrop, Winthrop over the last 12 months is $520,000, up 31% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$520,000
Median Single Family Sale Price
$520,000
Median 2 Bedroom Sale Price
$294,450
Median 1 Bedroom Sale Price
$195,000
Average Price Per Sq Ft
$276
Number of Homes for Sale
7
Last 12 months Home Sales
28
Months of Supply
3.00
Median List Price
$519,780
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
31%
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