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Downtown Winthrop Homes for Sale

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  • 193 Winthrop St, Winthrop, MA 02152
    193 Winthrop St, Winthrop, MA 02152
    193 Winthrop St, Winthrop, MA 02152
    /42

    $1,199,900

    $100K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,799 Sq Ft

    193 Winthrop St, Winthrop, MA 02152

    $2,500 bonus to buyer or buyer broker* Exceptional opportunity to live where you work. Corner lot with off-street parking, this unique property offers endless possibilities for investors, developers, or owner-occupants.The ground level features professional office space complete with a reception area, conference room, workspace, and 1/2 bath. Also included is a vacant 2-level, 2-bedroom, 1.5-bath

    Agent Photo

    Lisa Licata-Schepici

    L.L.S. Realty LLC

    193 Winthrop St, Winthrop, MA 02152
  • 50 Main St, Winthrop, MA 02152
    50 Main St, Winthrop, MA 02152
    50 Main St, Winthrop, MA 02152
    /41

    $799,986

    $30K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 2,560 Sq Ft

    50 Main St, Winthrop, MA 02152

    Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience

    Matt Tasgin United Brokers

    50 Main St, 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
    /35

    $649,000

    Open Wed 11AM - 1PM
    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft

    10 Somerset Ave Unit 402, Winthrop, MA 02152

    Start your homeownership journey at Unit 402 at The Somerset, a bright and spacious top-floor 2-bedroom, 2-bath condo in the heart of Winthrop. Designed for modern living, this move-in-ready home features an open-concept layout, two private balconies, quartz countertops, stainless steel appliances, central A/C, and generous closet space. Garage parking is included, along with access to an

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 402, Winthrop, MA 02152
  • 516 Pleasant St, Winthrop, MA 02152
    516 Pleasant St, Winthrop, MA 02152
    516 Pleasant St, Winthrop, MA 02152
    /42

    $1,499,000

    $101K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,889 Sq Ft

    516 Pleasant St, Winthrop, MA 02152

    Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, (all outside the flood-zone by the way!!) this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain

    Amanda George Lamacchia Realty, Inc.

    516 Pleasant St, Winthrop, MA 02152
  • 55 Banks St Unit 2, Winthrop, MA 02152
    55 Banks St Unit 2, Winthrop, MA 02152
    55 Banks St Unit 2, Winthrop, MA 02152
    /33

    $779,000

    $46K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,996 Sq Ft

    55 Banks St Unit 2, Winthrop, MA 02152

    Stunning 2022 rebuild—taken down to the original foundation and rebuilt with a fresh, nearly-new feel throughout! This townhome-style condo feels like a single-family, nearly 2,000 sq ft, featuring 3 beds, 3 full baths, private outdoor space, and 2-car parking. NO monthly condo or HOA fees; annual master insurance just $1,670. A standout alternative to East/South Boston with quick Downtown Boston

    Cheng Liang CWQ Realty Group LLC

    55 Banks St Unit 2, Winthrop, MA 02152
  • 43 Sagamore Ave Unit 1, Winthrop, MA 02152
    43 Sagamore Ave Unit 1, Winthrop, MA 02152
    43 Sagamore Ave Unit 1, Winthrop, MA 02152
    /21

    $485,000

    $14K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 913 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. The

    Philip Lundberg Lantern Residential

    43 Sagamore Ave Unit 1, Winthrop, MA 02152
  • 70 Edgehill Rd, Winthrop, MA 02152
    70 Edgehill Rd, Winthrop, MA 02152
    70 Edgehill Rd, Winthrop, MA 02152
    /40

    $1,199,999

    $799K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 1,904 Sq Ft

    70 Edgehill Rd, Winthrop, MA 02152

    Nestled on a peaceful street between the shoreline of Donovan's Beach and the green space of Ingleside Park, this beautifully renovated single-family home offers exceptional flexibility and comfort across multiple levels. Thoughtfully updated from the rooftop to the lower level, the home is truly move-in ready with modern finishes and inviting spaces throughout. Sun-filled interiors create the

    Kelvin Peters Redfin Corp.

    70 Edgehill Rd, Winthrop, MA 02152
  • 10 Somerset Ave Unit 305, Winthrop, MA 02152
    10 Somerset Ave Unit 305, Winthrop, MA 02152
    10 Somerset Ave Unit 305, Winthrop, MA 02152
    /31

    $505,000

    • 1 Bed
    • 1 Bath
    • 693 Sq Ft

    10 Somerset Ave Unit 305, Winthrop, MA 02152

    Welcome to The Somerset, Winthrop's premier boutique condominium community, where coastal charm meets effortless modern living. This thoughtfully designed 693± sq. ft. one-bedroom, one-bath residence offers an open-concept layout with a spacious living area, oversized bedroom with walk-in closet, quartz countertops, stainless steel appliances, in-unit laundry, and contemporary finishes

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 305, Winthrop, MA 02152
  • 217 Pleasant St, Winthrop, MA 02152
    217 Pleasant St, Winthrop, MA 02152
    217 Pleasant St, Winthrop, MA 02152
    /39

    $999,000

    $200K PRICE DROP
    • 6 Beds
    • 2.5 Baths
    • 3,263 Sq Ft

    217 Pleasant St, Winthrop, MA 02152

    PRICE IMPROVEMENT, not another reduction, but an opportunity to make this your own. Spacious and beautifully updated, 6-bedroom, 2.5-bath home with the perfect blend of classic character & modern efficiency, all located in the wonderful seaside community of Winthrop by the Sea. Featuring gleaming hardwood floors throughout, newer windows 2 fireplaces giving warmth & charm to the living spaces.

    Louis Bonavita Benton Real Estate Company

    217 Pleasant St, Winthrop, MA 02152
  • 5 Oceanview St, Winthrop, MA 02152
    5 Oceanview St, Winthrop, MA 02152
    5 Oceanview St, Winthrop, MA 02152
    /17

    $690,000

    $139K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    5 Oceanview St, Winthrop, MA 02152

    ***Seller is VERY motivated***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

    Nezihe Hewson Mariano Smith & Co.

    5 Oceanview St, Winthrop, MA 02152
  • 24 Fairview St, Winthrop, MA 02152
    24 Fairview St, Winthrop, MA 02152
    24 Fairview St, Winthrop, MA 02152
    /36

    $975,000

    $325K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,916 Sq Ft

    24 Fairview St, Winthrop, MA 02152

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

    Mary Ann Cash Charlesgate Realty Group, llc

    24 Fairview St, Winthrop, MA 02152
  • 69 Summit Ave Unit 1, Winthrop, MA 02152
    69 Summit Ave Unit 1, Winthrop, MA 02152
    69 Summit Ave Unit 1, Winthrop, MA 02152
    /13

    $369,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    69 Summit Ave Unit 1, Winthrop, MA 02152

    Welcome to Summit View Condominiums. This sunfilled 1 bedroom unit , with private deck with magnificent views overlooking the town of Winthrop. Great neighborhood, steps to the beach, 1 min to bus stop, minutes to Orient heights t-station and just minutes to downtown Boston and easy access to the North Shore. OVERSIZED 1 bedroom, plenty of storage and closet space, walk in cedar closet, separate

    Kevin Ferrara Cottage Hill Real Estate

    69 Summit Ave Unit 1, Winthrop, MA 02152
  • 1000 Governors Dr Unit 15, Winthrop, MA 02152
    1000 Governors Dr Unit 15, Winthrop, MA 02152
    1000 Governors Dr Unit 15, Winthrop, MA 02152
    /18

    $380,000

    • 2 Beds
    • 1 Bath
    • 782 Sq Ft

    1000 Governors Dr Unit 15, Winthrop, MA 02152

    This bright 2 bedroom 1 bathroom unit is the perfect space for a new owner to put their stamp on! The main bedroom has laminate flooring which is in excellent condition and the rest of the unit is carpeted. Heating and cooking for the condo is gas and there are 2 in-wall air conditioners...one in the living room and one in the main bedroom. The kitchen appliances are all in great shape. You can

    Kenny Kelleher Compass

    1000 Governors Dr Unit 15, Winthrop, MA 02152
  • 92 Lincoln St Unit 2, Winthrop, MA 02152
    92 Lincoln St Unit 2, Winthrop, MA 02152
    92 Lincoln St Unit 2, Winthrop, MA 02152
    /21

    $459,900

    • 2 Beds
    • 1 Bath
    • 1,153 Sq Ft

    92 Lincoln St Unit 2, Winthrop, MA 02152

    Welcome to this inviting 2-bed, 1-bath second floor garden-style condo at Lincoln Place Condominium, a stunning brownstone in the heart of Winthrop. Blending historic character with modern updates, this sun-filled unit features upgraded vinyl flooring, plantation shutters in the kitchen, and a recently reglazed bath tub. The spacious living room showcases a beautiful bay window with views of

    The Dovetail Group eXp Realty LLC - Corporate Office

    92 Lincoln St Unit 2, Winthrop, MA 02152
  • 21 Hutchinson St Unit 2, Winthrop, MA 02152
    21 Hutchinson St Unit 2, Winthrop, MA 02152
    21 Hutchinson St Unit 2, Winthrop, MA 02152
    /24

    $629,000

    • 2 Beds
    • 2.5 Baths
    • 1,463 Sq Ft

    21 Hutchinson St Unit 2, Winthrop, MA 02152

    Completely renovated to the core with quality craftsmanship throughout, this exceptional property blends modern sophistication with the relaxed coastal lifestyle that makes Winthrop so special. This beautifully finished two-level unit offers a bright, open layout designed for comfortable everyday living and easy entertaining. The main level features a beautiful white kitchen with modern

    Atiyeh Cassidy Blue Sky Realty

    21 Hutchinson St Unit 2, 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
    /3

    $340,000

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft

    800 Governors Dr Unit 6, Winthrop, MA 02152

    Bright and updated 2-bedroom condo at Governors Park featuring an open floor plan, renovated kitchen with granite countertops and stainless steel appliances, and spacious bedrooms with ample closet space. Professionally managed complex offers on-site laundry, swimming pool, tennis courts, and off-street parking. Conveniently located near public transportation, Winthrop Beach, shopping, dining,

    Fiorella Marte Coldwell Banker Realty - Beverly

    800 Governors Dr Unit 6, 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 AVAILABLE! Discover effortless coastal living at Unit 304 at The Somerset, a boutique condominium community ideally located in the heart of Winthrop. This well-appointed studio offers a bright and airy open layout designed for both comfort and functionality, featuring a flexible bonus room with a sliding barn door ideal for a home office, guest room, or additional living space. The

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 304, Winthrop, MA 02152
  • 21 Hutchinson St, Winthrop, MA 02152
    21 Hutchinson St, Winthrop, MA 02152
    21 Hutchinson St, Winthrop, MA 02152
    /38

    $1,260,000

    • 4 Beds
    • 6 Baths
    • 3,705 Sq Ft

    21 Hutchinson St, Winthrop, MA 02152

    Completely renovated from its core with quality craftsmanship throughout, this exceptional two-family home blends modern luxury with the relaxed coastal lifestyle that makes Winthrop so special. Thoughtfully designed for comfortable everyday living, each residence spans two levels and offers its own distinctive layout, allowing for privacy and versatility whether you’re looking for a

    Atiyeh Cassidy Blue Sky Realty

    21 Hutchinson 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
    /5

    $2,250,000

    New Construction $210K PRICE DROP
    • 16 Beds
    • 14 Baths
    • 10,000 Sq Ft

    63-69 Putnam St, Winthrop, MA 02152

    DEVELOPMENT OPPORTUNITY WITH EXISTING MIXED USE PROPERTY GENERATING $71K NET ANNUAL INCOME.++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

    The Bill Butler Group Leading Edge Real Estate

    63-69 Putnam St, Winthrop, MA 02152
  • 69 Summit Ave Unit 2, Winthrop, MA 02152
    69 Summit Ave Unit 2, Winthrop, MA 02152
    69 Summit Ave Unit 2, Winthrop, MA 02152
    /21

    $469,000

    • 2 Beds
    • 1 Bath
    • 1,029 Sq Ft

    69 Summit Ave Unit 2, Winthrop, MA 02152

    WELCOME TO SUMMIT VIEW CONDOMINIUMS. This sun filled 2 bedroom unit boasts amazing views of the town of Winthrop and Boston skyline. Private deck with magnificent views and a huge back yard space. Great time to get in to be a part of a condo association. Great neighborhood, plenty of off street parking, just steps to Winthrop beach, 1 min to bus stop, just minutes to Orient Height T-Station, and

    Kevin Ferrara Cottage Hill Real Estate

    69 Summit Ave Unit 2, Winthrop, MA 02152
  • 120 Hermon St, Winthrop, MA 02152
    120 Hermon St, Winthrop, MA 02152
    120 Hermon St, Winthrop, MA 02152
    /9

    $780,000

    $20K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 2,000 Sq Ft

    120 Hermon St, Winthrop, MA 02152

    Ingleside Park 2-unit with oversized 10,000sqft lot and parking for 2 cars that offers plenty of potential in a central Winthrop location. Property is in need of interior updating and the back yard is ready to become either expanded parking, a beautiful yard space, or more. First floor unit has two bedrooms, one full bath, and a large rear deck. Second floor unit has two levels with four total

    Steve Binder Binder Residential

    120 Hermon St, Winthrop, MA 02152
  • 21 Hutchinson St Unit 1, Winthrop, MA 02152
    21 Hutchinson St Unit 1, Winthrop, MA 02152
    21 Hutchinson St Unit 1, Winthrop, MA 02152
    /22

    $659,000

    • 2 Beds
    • 2.5 Baths
    • 1,790 Sq Ft

    21 Hutchinson St Unit 1, Winthrop, MA 02152

    Completely renovated to the core with quality craftsmanship throughout, this exceptional property blends modern luxury with the relaxed coastal lifestyle that makes Winthrop so special. This beautifully finished two-level unit offers a bright, open layout designed for easy everyday living and makes entertaining a breeze. The main level features a stunning white kitchen designed with upgraded

    Atiyeh Cassidy Blue Sky Realty

    21 Hutchinson St Unit 1, Winthrop, MA 02152
Massachusetts Suffolk County 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

Downtown Winthrop Home Prices vs. Nearby Winthrop, MA Neighborhoods

Downtown Winthrop Winthrop Beach Winthrop Highlands Cottage Park
Median Home Price
$624,000
$529,000
$649,497
$662,450
Median Sale Price
$610,000
-3% YoY
$499,999
+6% YoY
$632,000
-6% YoY
$660,000
+5% YoY
Median Single Family Price
$725,000
$684,500
$976,350
$747,000
Median Townhouse Price
$839,900
$499,999
$1,175,000
$595,000
Median Condo Price
$482,500
$494,500
$599,999
$552,500
Total Active Listings
17 listings
10 listings
11 listings
3 listings
Market Conditions
4 Months of Supply
Seller's Market
5 Months of Supply
Balanced Market
7 Months of Supply
Buyer's Market
3 Months of Supply
Seller's Market

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% of residents renting and 52% 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 $624,000. If you put a 20% down payment of $124,800 and had a 30-year fixed mortgage with an interest rate of 6.67%, your estimated principal and interest payment would be $3,210 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $138K 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, Cottage Hill and Harbor View-Orient Heights.
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