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Downtown Winthrop Homes for Sale

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  • 43 Sagamore Ave Unit 1, Winthrop, MA 02152
    43 Sagamore Ave Unit 1, Winthrop, MA 02152
    43 Sagamore Ave Unit 1, Winthrop, MA 02152
    /25

    $519,000 Open Sun 1PM - 2PM

    • 2 Beds
    • 1 Bath
    • 769 Sq Ft

    43 Sagamore Ave Unit 1, Winthrop, MA 02152

    Welcome home to this pristine and exceptionally well-kept two-bedroom, one-bath condominium in the heart of Winthrop’s vibrant 02152 community. This inviting home offers comfortable living along with private outdoor space—perfect for relaxing, entertaining, or enjoying coastal breezes. Conveniently located with easy access to Orient Heights, major highways, Logan Airport, and downtown Boston,

    Agent Photo

    Nicole Bettano

    Lantern Residential

    (857) 420-5091

    43 Sagamore Ave Unit 1, Winthrop, MA 02152
  • 1000 Governors Dr Unit 4, Winthrop, MA 02152
    1000 Governors Dr Unit 4, Winthrop, MA 02152
    1000 Governors Dr Unit 4, Winthrop, MA 02152
    /25

    $379,000 Open Sun 11AM - 1PM

    • 2 Beds
    • 1 Bath
    • 977 Sq Ft

    1000 Governors Dr Unit 4, Winthrop, MA 02152

    Get ready to discover your next dream home! A fantastic condo for sale in the vibrant town of Winthrop, MA. This inviting residence features two generously sized bedrooms and a modern bathroom, complemented by an open concept living room and kitchen area.Situated in a large, welcoming complex, you'll enjoy excellent amenities including a tennis court and convenient laundry facilities in the

    Agent Photo

    Jose Rojas

    William Raveis R.E. & Home Services

    (617) 612-4270

    1000 Governors Dr Unit 4, Winthrop, MA 02152
  • 10 Somerset Ave Unit 309, Winthrop, MA 02152
    10 Somerset Ave Unit 309, Winthrop, MA 02152
    10 Somerset Ave Unit 309, Winthrop, MA 02152
    /23

    $519,900 Open Sun 1PM - 3PM

    • 1 Bed
    • 1 Bath
    • 729 Sq Ft

    10 Somerset Ave Unit 309, Winthrop, MA 02152

    Welcome to Unit 309—a bright corner 1-bedroom, 1-bath home featuring an open-concept layout, high-quality finishes, and a relaxed coastal style. The kitchen features stainless steel appliances, quartz countertops, central A/C, and modern design touches throughout. Residents enjoy elevator access, a fitness room, and a stylish common area—perfect for relaxing or savoring a morning coffee. Ideally

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 309, Winthrop, MA 02152
  • 35 Somerset Ave Unit 3, Winthrop, MA 02152
    35 Somerset Ave Unit 3, Winthrop, MA 02152
    35 Somerset Ave Unit 3, Winthrop, MA 02152
    /29

    $559,900 Open Sun 11:30AM - 1PM

    • 2 Beds
    • 2 Baths
    • 969 Sq Ft

    35 Somerset Ave Unit 3, Winthrop, MA 02152

    MAJOR NEW RENOVATION IN 2023.......EXCITING 2 BEDROOM, 2BATH UPSCALE CONDOMINIUM AT WINTHROP CENTER. Stunning oak floors and state of the art quartz and stainless kitchen, fully applianced with subway tile accents and an over sized island with pendant lighting. All open to a generous living area and access to an exclusive deck for personal outdoor space. A beautiful main suite with an amazing

    Sharon Tallent Compass

    35 Somerset Ave Unit 3, Winthrop, MA 02152
  • 10 Somerset Ave Unit 207, Winthrop, MA 02152
    10 Somerset Ave Unit 207, Winthrop, MA 02152
    10 Somerset Ave Unit 207, Winthrop, MA 02152
    /9

    $569,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 1 Bath
    • 898 Sq Ft

    10 Somerset Ave Unit 207, Winthrop, MA 02152

    Welcome to Unit 207 at The Somerset—Winthrop’s boutique condo community, where coastal living meets modern design. This spacious 2-bedroom, 1-bath home features an open-concept living and dining area, a well-appointed kitchen with quartz countertops and stainless steel appliances, central A/C, and modern finishes throughout, plus access to a fitness room, elevator, and resident lounge for added

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 207, Winthrop, MA 02152
  • 10 Somerset Ave Unit 405, Winthrop, MA 02152
    10 Somerset Ave Unit 405, Winthrop, MA 02152
    10 Somerset Ave Unit 405, Winthrop, MA 02152
    /11

    $512,250 Open Sun 1PM - 3PM

    • 1 Bed
    • 1 Bath
    • 683 Sq Ft

    10 Somerset Ave Unit 405, Winthrop, MA 02152

    Welcome to Unit 405 at The Somerset, Winthrop’s premier boutique condo community, where coastal charm meets modern design. This bright, open 1-bedroom, 1-bath home features a spacious living and dining area perfect for relaxing or entertaining. The kitchen blends style and functionality with quartz countertops and stainless steel appliances. Enjoy a pet-friendly building, a fitness studio,

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 405, Winthrop, MA 02152
  • 10 Somerset Ave Unit 308, Winthrop, MA 02152
    10 Somerset Ave Unit 308, Winthrop, MA 02152
    10 Somerset Ave Unit 308, Winthrop, MA 02152
    /31

    $559,000 Open Sun 1PM - 3PM

    • 1 Bed
    • 1 Bath
    • 774 Sq Ft

    10 Somerset Ave Unit 308, Winthrop, MA 02152

    Welcome to Unit 308 at The Somerset—a premier boutique condo community in the heart of Winthrop. This thoughtfully designed 1 + bedroom 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

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 308, Winthrop, MA 02152
  • 95 Shirley St Unit 3, Winthrop, MA 02152
    95 Shirley St Unit 3, Winthrop, MA 02152
    95 Shirley St Unit 3, Winthrop, MA 02152
    /25

    $469,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft

    95 Shirley St Unit 3, Winthrop, MA 02152

    Top floor unit with exposed brick and a private garage, offering the perfect blend of character and modern updates! This sun filled home features a spacious open floor plan with white kitchen cabinetry, quartz countertops, and wood floors throughout. Generous bedrooms include a primary with a large closet and a second bedroom with a brand new custom closet system and washer and dryer for

    Elizabeth Ferrara Cottage Hill Real Estate

    95 Shirley St Unit 3, Winthrop, MA 02152
  • 5 Oceanview St, Winthrop, MA 02152
    5 Oceanview St, Winthrop, MA 02152
    5 Oceanview St, Winthrop, MA 02152
    /21

    $829,000 Open Sat 12PM - 1:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    5 Oceanview St, Winthrop, MA 02152

    Welcome to your fully renovated and updated home on a quiet corner in Winthrop. This home features a brand new kitchen with wide spanning island, open to the living room. Perfect for entertaining. All new electrical, water heater, furnace, plumbing, insulation and hard wired fire alarms. Approximately 250 sqft was added on and 2 bathrooms were also added making this a 3 bedroom 3 bathroom home.

    Nezihe Hewson Mariano Smith & Co.

    5 Oceanview St, 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 Open Sun 1PM - 3PM

    • 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
  • 24 Fairview St, Winthrop, MA 02152
    24 Fairview St, Winthrop, MA 02152
    24 Fairview St, Winthrop, MA 02152
    /32

    $1,300,000 Open Sat 11:30AM - 1PM

    • 4 Beds
    • 1.5 Baths
    • 2,916 Sq Ft

    24 Fairview St, Winthrop, MA 02152

    Introducing 24 FAIRVIEW STREET - a charming 4-bedroom, 1.5 bath Victorian in a prime, central location offering inside and outside enjoyment . This beautiful home has been enjoyed and maintained by the same family for many years and offers timeless appeal throughout. First floor has a family room, living room with a fireplace, modern kitchen with s/s appliances, separate dining area and a

    Mary Ann Cash Charlesgate Realty Group, llc

    24 Fairview St, Winthrop, MA 02152
  • 54 Wilshire St, Winthrop, MA 02152
    54 Wilshire St, Winthrop, MA 02152
    54 Wilshire St, Winthrop, MA 02152
    /8

    $549,000

    • Land
    • 8,276 Sq Ft
    • $2,889,474 per Acre

    54 Wilshire St, Winthrop, MA 02152

    Rare Winthrop duplex development opportunity offering the chance to build ground-up new construction in a highly desirable coastal community. The project allows for two spacious 2,500+ sqft units, ideal for resale as luxury condos or as long-term income-producing properties. Each unit includes two off-street parking spaces, a valuable amenity in this sought-after location. With strong buyer

    Lou Markakis Lynnway Associates

    54 Wilshire St, Winthrop, MA 02152
  • 63-69 Putnam St, Winthrop, MA 02152
    63-69 Putnam St, Winthrop, MA 02152
    63-69 Putnam St, Winthrop, MA 02152
    /6

    $2,460,000

    • Land
    • 11,325 Sq Ft
    • $9,461,538 per Acre

    63-69 Putnam St, Winthrop, MA 02152

    ++The Breakwater++A rare coastal investment and development opportunity in the heart of Winthrop, Massachusetts. The mixed use property currently consists of a cash-flowing four-unit mixed-use building with stable in-place NOI of 71,300, combined with a Board of Appeals–approved plan to construct a new 12-unit building with podium parking beneath — all on one site steps from the harbor and in the

    The Bill Butler Group Leading Edge Real Estate

    63-69 Putnam St, Winthrop, MA 02152
  • 7 Willis Ave, Winthrop, MA 02152
    7 Willis Ave, Winthrop, MA 02152
    7 Willis Ave, Winthrop, MA 02152
    /37

    $949,900 Open Sat 12PM - 1:30PM

    • 5 Beds
    • 3 Baths
    • 2,843 Sq Ft

    7 Willis Ave, Winthrop, MA 02152

    Corner Lot Modern 2 family close to the bay next to Mary Kelly Pavilion.1st floor has 4 large rooms & 2 bed.Kitchen has Induction Stove Top Granite Island & Counter Tops.Stanless Steel Induction Wall Microwave & Wall Oven.Top of the line Stanless Steel Refrigerator & Dishwasher.Granite tile floor. Plenty of Cabenit Space. Beautiful Tiger Hardwood Floors & Natural Wood.Work Throughout. Crown

    Philip Consolo Century 21 North East

    7 Willis Ave, Winthrop, MA 02152
  • 300 Governors Dr Unit 21, Winthrop, MA 02152
    300 Governors Dr Unit 21, Winthrop, MA 02152
    300 Governors Dr Unit 21, Winthrop, MA 02152
    /13

    $365,000

    • 2 Beds
    • 1 Bath
    • 723 Sq Ft

    300 Governors Dr Unit 21, Winthrop, MA 02152

    Open House Sunday 04/26 1-2pm. Rarely available corner-unit condo offering exceptional privacy and abundant natural light. (Situated at the corner of the building, this home benefits from a side entrance that feels like private access). Freshly painted, the unit features a well-designed layout with comfortable living spaces and a seamless flow ideal for everyday living or entertaining.Located in

    Alla Rossi Coldwell Banker Realty - Boston

    300 Governors Dr Unit 21, Winthrop, MA 02152
  • 10 Somerset Ave Unit 402, Winthrop, MA 02152
    10 Somerset Ave Unit 402, Winthrop, MA 02152
    10 Somerset Ave Unit 402, Winthrop, MA 02152
    /32

    $699,000 Open Sun 1PM - 3PM

    • 1 Bed
    • 1 Bath
    • 1,024 Sq Ft

    10 Somerset Ave Unit 402, Winthrop, MA 02152

    Bright and spacious top-floor 2-bedroom, 2-bath condo with two private balconies and open-concept living in the heart of Winthrop. Located in The Somerset, this home features modern finishes throughout, including stainless steel appliances, quartz countertops, central A/C, and ample closet space. Move-in ready, it includes garage parking and access to an elevator, fitness room, and a welcoming

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 402, Winthrop, MA 02152
  • 308 Bowdoin St, Winthrop, MA 02152
    308 Bowdoin St, Winthrop, MA 02152
    308 Bowdoin St, Winthrop, MA 02152
    /41

    $999,900 Open Sat 11AM - 1PM

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

    308 Bowdoin St, Winthrop, MA 02152

    This spacious multi-family offers 7 bedrooms and 3 full baths across 3,628 sq ft, with high ceilings on a 6,429 sq ft lot. Rarely available in Winthrop, it delivers exceptional size, flexibility, and strong rental potential. A cabin-style garage plus a driveway for 4 cars adds convenience, while the lot provides inviting outdoor space. Interiors are well maintained and move-in ready.The

    Jefri Liriano Liriano Realty

    308 Bowdoin St, Winthrop, MA 02152
  • 26 Shirley St Unit B, Winthrop, MA 02152
    26 Shirley St Unit B, Winthrop, MA 02152
    26 Shirley St Unit B, Winthrop, MA 02152
    /40

    $774,995 Open Sat 12PM - 1:30PM

    • 4 Beds
    • 2 Baths
    • 1,833 Sq Ft

    26 Shirley St Unit B, Winthrop, MA 02152

    Welcome to where coastal living meets effortless style in the heart of Winthrop. This is more than a home. It’s a lifestyle. Wake up just moments from the ocean, where morning walks along the shoreline become part of your daily routine. Inside, the residence welcomes you with a bright, open flow designed for both comfort and connection—sunlight pouring in, tranquility at its finest, and a layout

    The Boston ONE Team Serhant

    26 Shirley St Unit B, Winthrop, MA 02152
  • 22 Adams St, Winthrop, MA 02152
    22 Adams St, Winthrop, MA 02152
    22 Adams St, Winthrop, MA 02152
    /40

    $1,299,000

    • 7 Beds
    • 3 Baths
    • 3,989 Sq Ft

    22 Adams St, Winthrop, MA 02152

    Stunning turn of the century three family home in a prime commuter location! Unit 1 &3 offers a spacious layout with large living room, formal dining room, kitchen, 2 bedrooms. Unit 2 offers smilar layout with 3 bedrooms and private deck. Tucked away on a quiet side street just above the town center, yet only a half-block to the bus line, restaurants, and everyday amenities. Enjoy easy access to

    Elizabeth Ferrara Cottage Hill Real Estate

    22 Adams St, 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 somewhat walkable and bikeable with some transit options. 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 6.23%, your estimated principal and interest payment would be $3,020 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $129K 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 02129.
What are the most popular neighborhoods near Downtown Winthrop, Winthrop, MA?
The most popular neighborhoods near Downtown Winthrop, Winthrop, MA are Winthrop Beach, Winthrop Highlands, Cottage Hill, Harbor View-Orient Heights and Beachmont.

Home Trends in Downtown Winthrop, MA

On average, homes in Downtown Winthrop, Winthrop sell after 41 days on the market compared to the national average of 56 days. The median sale price for homes in Downtown Winthrop, Winthrop over the last 12 months is $657,500, up 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$657,500
Median Single Family Sale Price
$715,450
Median Townhouse Sale Price
$849,000
Median 2 Bedroom Sale Price
$423,500
Median 1 Bedroom Sale Price
$532,450
Average Price Per Sq Ft
$459
Number of Homes for Sale
12
Last 12 months Home Sales
53
Months of Supply
2.70
Median List Price
$615,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
8%
How to Buy a Home How to Finance a Home How to Sell a Home

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