24

Downtown Winthrop Homes for Sale

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

    $1,300,000

    • 5 Beds
    • 4 Baths
    • 2,799 Sq Ft

    193 Winthrop St, Winthrop, MA 02152

    Exceptional opportunity to live where you work. Situated on a 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 unit that has been

    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
    /40

    $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 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
  • 516 Pleasant St, Winthrop, MA 02152
    516 Pleasant St, Winthrop, MA 02152
    516 Pleasant St, Winthrop, MA 02152
    /42

    $1,600,000

    • 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, this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where

    Amanda George Lamacchia Realty, Inc.

    516 Pleasant St, Winthrop, MA 02152
  • 10 Somerset Ave Unit 203, Winthrop, MA 02152
    10 Somerset Ave Unit 203, Winthrop, MA 02152
    10 Somerset Ave Unit 203, Winthrop, MA 02152
    /11

    $549,000

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

    10 Somerset Ave Unit 203, Winthrop, MA 02152

    Welcome to The Somerset, this thoughtfully designed 2-bedroom, 1-bath residence blends modern comfort with coastal charm. The open-concept layout offers an inviting living and dining area, complemented by a stylish kitchen featuring quartz countertops, stainless steel appliances, and contemporary finishes. Central A/C, abundant natural light, and quality craftsmanship create a comfortable and

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 203, 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

    $499,000

    • 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

    Jennifer Boncore Lantern Residential

    43 Sagamore Ave Unit 1, Winthrop, MA 02152
  • 496 Winthrop St, Winthrop, MA 02152
    496 Winthrop St, Winthrop, MA 02152
    496 Winthrop St, Winthrop, MA 02152
    /29

    $650,000

    • 3 Beds
    • 2 Baths
    • 800 Sq Ft

    496 Winthrop St, Winthrop, MA 02152

    Beautifully maintained 3-bedroom single-family ranch in desirable Winthrop offering comfortable one-level living plus the bonus of a spacious finished lower level, providing versatile additional rooms for a variety of needs. The main floor features a welcoming living room with fireplace, updated eat-in kitchen, recessed lighting, modern full bath with tile flooring, and three bedrooms with

    Angela Dello Russo United Brokers

    496 Winthrop St, 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

    $509,000

    $11K PRICE DROP
    • 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
  • 70 Edgehill Rd, Winthrop, MA 02152
    70 Edgehill Rd, Winthrop, MA 02152
    70 Edgehill Rd, Winthrop, MA 02152
    /40

    $1,899,000

    $100K 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
  • 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

    $549,900

    Open Sun 11AM - 12:30PM $10K PRICE DROP
    • 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
  • 217 Pleasant St, Winthrop, MA 02152
    217 Pleasant St, Winthrop, MA 02152
    217 Pleasant St, Winthrop, MA 02152
    /41

    $1,199,000

    • 6 Beds
    • 2.5 Baths
    • 3,263 Sq Ft

    217 Pleasant St, Winthrop, MA 02152

    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. Extensive updates include all new mechanical systems including elec. wiring, FWA

    Louis Bonavita Benton Real Estate Company

    217 Pleasant St, Winthrop, MA 02152
  • 95 Marshall St, Winthrop, MA 02152
    95 Marshall St, Winthrop, MA 02152
    95 Marshall St, Winthrop, MA 02152
    /16

    $539,900

    Open Sun 12PM - 1:30PM
    • 3 Beds
    • 2 Baths
    • 1,351 Sq Ft

    95 Marshall St, Winthrop, MA 02152

    Attention builders, developers, investors & rehabbers! Situated on 4,869 sq ft lot in desirable Winthrop neighborhood, this legal two-family home has been loved for generations & now ready for its next chapter. Originally a single-family, this unique property now offers many options for future use. For ambitious owner-occupants, this could be a great home for multi-generational living or having a

    Ryan Wilson Keller Williams Realty

    95 Marshall St, Winthrop, MA 02152
  • 5 Oceanview St, Winthrop, MA 02152
    5 Oceanview St, Winthrop, MA 02152
    5 Oceanview St, Winthrop, MA 02152
    /17

    $699,900

    $129K 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
    /32

    $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
  • 10 Somerset Ave Unit 405, Winthrop, MA 02152
    10 Somerset Ave Unit 405, Winthrop, MA 02152
    10 Somerset Ave Unit 405, Winthrop, MA 02152
    /23

    $499,000

    • 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 plus a flex area for those who work from home. The kitchen blends style and functionality with quartz countertops and stainless steel appliances. Enjoy a

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 405, 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
    /16

    $749,000

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    21 Hutchinson St Unit 1, Winthrop, MA 02152

    Welcome to 21 A Hutchison Street Condominium. This new construction 1800 sf unit has two levels of living space. Main level features open floor plan for kitchen, living area, dining and office. Kitchen is equipped with stainless steal appliances, island with built in drawer microwave, granite countertops and backsplash. Main bedroom has on-suite bathroom and walk-in closet. Convenient in unit

    Jason Saphire www.HomeZu.com

    21 Hutchinson St Unit 1, Winthrop, MA 02152
  • 550 Pleasant St Unit 411, Winthrop, MA 02152
    550 Pleasant St Unit 411, Winthrop, MA 02152
    550 Pleasant St Unit 411, Winthrop, MA 02152
    /27

    $689,000

    Open Sun 12:30PM - 2PM
    • 2 Beds
    • 2 Baths
    • 1,183 Sq Ft

    550 Pleasant St Unit 411, Winthrop, MA 02152

    Wake up to the sights of the marina and unwind each evening with spectacular sunset views at Atlantis Marina. This beautifully positioned 2-bedroom corner unit offers an effortless waterfront lifestyle and a sense of calm that's hard to find so close to the city. An extension of the living space, the balcony is perfect for morning coffee or capturing sunsets over the water. Inside, the

    Ricardo Rodriguez Coldwell Banker Realty - Boston

    550 Pleasant St Unit 411, Winthrop, MA 02152
  • 105 Oceanview St, Winthrop, MA 02152
    105 Oceanview St, Winthrop, MA 02152
    105 Oceanview St, Winthrop, MA 02152
    /41

    $989,000

    Open Sun 12PM - 1:30PM
    • 3 Beds
    • 2 Baths
    • 1,924 Sq Ft

    105 Oceanview St, Winthrop, MA 02152

    Exceptional 2-family in desirable Winthrop. Same owner for 20 years! Fresh updates + meticulous maintenance equal a turnkey opportunity for Investors or Owner-Occupants seeking strong rental income. Great for Multi-Gen living! Both units offer hardwood floors, closets, and spacious Kitchens w/ Pantrys. Windows galore! Gorgeous natural light! Beautifully proportioned rooms, easy floorplans, great

    Claudia Perkins William Raveis R.E. & Home Services

    105 Oceanview 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

    $799,000

    $26K 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

    55 Banks 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 StartPoint Realty

    800 Governors Dr Unit 6, Winthrop, MA 02152
  • 23 Sagamore Ave, Winthrop, MA 02152
    23 Sagamore Ave, Winthrop, MA 02152
    23 Sagamore Ave, Winthrop, MA 02152
    /42

    $895,000

    $85K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,204 Sq Ft

    23 Sagamore Ave, Winthrop, MA 02152

    SPACIOUS, STYLISH AND PRICED TO MOVE! Welcome to the Winthrop Highlands! This beautifully updated home offers three levels of versatile living space, starting with a freshly updated kitchen featuring granite countertops, slate appliances, and gas cooking—perfect for whipping up meals and memories. The living room flows seamlessly into the dining room, both boasting refinished hardwood floors.

    Sharon Tallent Compass

    23 Sagamore Ave, Winthrop, MA 02152
  • 21 Hutchinson St Unit B, Winthrop, MA 02152
    21 Hutchinson St Unit B, Winthrop, MA 02152
    21 Hutchinson St Unit B, Winthrop, MA 02152
    /32

    $675,000

    Open Sun 12:30PM - 2PM
    • 2 Beds
    • 2.5 Baths
    • 1,540 Sq Ft

    21 Hutchinson St Unit B, Winthrop, MA 02152

    21 B Hutchinson Street Condo offers 1360 SF of living space. The first floor of this unit includes open floor kitchen/living room. First floor main bedroom includes on suite bathroom and walk in closet. A quaint half bathroom, pantry closet and in unit laundry is a nice convenience for this unit. The second level offers another main bedroom with on suite bathroom, walk in closet and storage.

    Matthew Gallego Gallego Realty

    21 Hutchinson St Unit B, 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

    $629,000

    • 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
  • 63-69 Putnam St, Winthrop, MA 02152
    63-69 Putnam St, Winthrop, MA 02152
    /2

    $2,460,000

    New Construction
    • 16 Beds
    • 14 Baths
    • 10,000 Sq Ft

    63-69 Putnam St, Winthrop, MA 02152

    DEVELOPMENT OPPORTUNITY with existing income property++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

    The Bill Butler Group Leading Edge Real Estate

    63-69 Putnam 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

Downtown Winthrop Home Prices vs. Nearby Winthrop, MA Neighborhoods

Downtown Winthrop Winthrop Beach Weymouth Landing Winthrop Highlands
Median Home Price
$637,000
$519,500
$629,950
$649,997
Median Sale Price
$594,900
-5% YoY
$494,999
+4% YoY
$639,500
+8% YoY
$660,000
-2% YoY
Median Single Family Price
$731,000
$699,000
$639,000
$929,500
Median Townhouse Price
$887,450
$499,999
--
$1,175,000
Median Condo Price
$502,000
$484,500
$737,500
$625,000
Total Active Listings
19
10
6
11
Market Conditions
4 Months of Supply
Balanced Market
5 Months of Supply
Balanced Market
1 Months of Supply
Seller's Market
6 Months of Supply
Balanced 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 $637,000. If you put a 20% down payment of $127,400 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $3,220 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 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.
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group