Waterfront homes for sale & real estate in Downtown Winthrop, MA

20 homes

Sort:

Recommended

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Waterfront Home for sale in Downtown Winthrop, MA:
Penthouse Waterfront Luxury at Atlantis Marina – Oversized Boat Slip Included!Experience sophisticate 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 2-bedroom, 2-bath home features an open-concept layout perfect for entertaining, complete with private deck overlooking the marina and city. Gourmet kitchen with stainless steel appliances, gas cooking, stone counters, and an oversized refrigerator. Gas fireplace, recessed lighting, and abundant natura

$1,087,000

2 beds2 baths1,975 sq ft

550 Pleasant St #506, Winthrop, MA 02152

Private deck • Oversized boat slip • Gourmet kitchen

REDFIN OPEN SAT, 12PM TO 2PM3D WALKTHROUGH

ABOUT THIS HOME
Waterfront Home for sale in Downtown Winthrop, MA:
Experience the best of coastal living just minutes from Boston—close to the city without the high prices! This bright and spacious home features soaring ceilings, abundant natural light, large rooms, and hardwood floors. The traditional dining room with a built-in cabinet adds classic charm, while the fully applianced kitchen offers warm wood cabinetry and an oversized pantry. Enjoy morning coffee or evening breezes on either of two private porches. Each unit includes its own washer and dryer in the basement, and the pet-friendly building is well-maintained with a low condo fee. Perfectly located near Winthrop’s beautiful beaches, scenic trails, and popular local restaurants. Pr

$425,000

2 beds1 bath1,092 sq ft

9 Atlantic St #2, Winthrop, MA 02152

Built-in cabinet • Private porches • Oversized pantry

ABOUT THIS HOME
Waterfront Home for sale in Downtown Winthrop, MA:
Traditional two-family home featuring two spacious 3-bedroom apartments. Recently upgraded with a new roof and windows, as well as newer vinyl siding, gas FHA heating units, and updated electrical service. While the interior of both units requires a complete makeover, this property holds immense potential. A similar home just a few doors down recently sold for $885,000. Conveniently located approximately 100 yards from the bus stop offering access to the T for a quick commute to Boston. Situated in Winthrop by the Sea, residents enjoy proximity to Boston via the T, car, or water shuttle. The area boasts a variety of quality restaurants, bistros, coffee shops, a golf course, three yacht club

$799,900

6 beds2 baths2,454 sq ft

441 Winthrop St, Winthrop, MA 02152

Public beaches • Newer vinyl siding • Proximity to boston

ABOUT THIS HOME
Waterfront Home for sale in Downtown Winthrop, MA:
Welcome to 19 Pleasant Park Road - a beautifully updated coastal retreat that blends timeless character with modern comfort. Step inside to discover warm hardwood floors, sun-filled rooms, and a layout designed for easy everyday living. The inviting dining room flows seamlessly into the living space, while the updated kitchen features stainless steel appliances and classic white cabinetry. Both bathrooms have been thoughtfully remodeled, one with a sleek walk-in shower and oversized vanity, the other with designer wallpaper and stylish brass fixtures. Upstairs, three bedrooms offer comfortable space to unwind, with an added bonus in the potential to finish the unfinished attic into a spacio

$722,000

3 beds1.5 baths1,325 sq ft

19 Pleasant Park Rd, Winthrop, MA 02152

Oversized vanity • Firepit • Updated kitchen

ABOUT THIS HOME
Waterfront Home for sale in Downtown Winthrop, MA:
Welcome to Governor’s Park Condominiums in Winthrop! This well-maintained third-level, two-bedroom, one-bath unit offers the perfect balance of city convenience and coastal charm. Featuring an open-concept layout with a spacious living room and kitchen/dining area, this home also includes hardwood floors, granite countertops, SS appliances, a private balcony, and two deeded off-street parking spaces. The professionally landscaped grounds and common areas enhance the appeal of this desirable community. Ideally located just 10 minutes from downtown Boston and Logan Airport, a short distance to Orient Heights T Station, and only a 3-minute walk to the scenic Belle Isle Marsh Reservation,

$395,000

2 beds1 bath782 sq ft

1000 Governors Dr #25, Winthrop, MA 02152

Private balcony • Open-concept layout • $470 HOA

Property at 550 Pleasant St Unit 11D, Winthrop, MA 02152, 2 beds, 2 baths

$89,000

2 beds2 baths600 sq ft

550 Pleasant St Unit 11D, Winthrop, MA 02152

Property at 70 Edgehill Rd, Winthrop, MA 02152, 4 beds, 3 baths

$1,100,000

4 beds3 baths2,654 sq ft

70 Edgehill Rd, Winthrop, MA 02152

Property at 10 Somerset #204, Winthrop, MA 02152, 2 beds, 2 baths

$598,395

2 beds2 baths832 sq ft

10 Somerset #204, Winthrop, MA 02152

Property at 308 Bowdoin St, Winthrop, MA 02152, 7 beds, 3 baths

$1,067,000

7 beds3 baths3,628 sq ft

308 Bowdoin St, Winthrop, MA 02152

Property at 14 Pleasant Park Rd, Winthrop, MA 02152, 4 beds, 1 bath

$729,900

4 beds1 bath1,964 sq ft

14 Pleasant Park Rd, Winthrop, MA 02152

Property at 10 Somerset #304, Winthrop, MA 02152, 1 bed, 1 bath

$399,000

1 bed1 bath546 sq ft

10 Somerset #304, Winthrop, MA 02152

Property at 136 Pauline St, Winthrop, MA 02152, 4 beds, 3.5 baths

$867,000

4 beds3.5 baths2,350 sq ft

136 Pauline St, Winthrop, MA 02152

Property at 10 Somerset #201, Winthrop, MA 02152, 2 beds, 2 baths

$629,000

2 beds2 baths1,036 sq ft

10 Somerset #201, Winthrop, MA 02152

Property at 35 Somerset Ave #6, Winthrop, MA 02152, 2 beds, 2 baths

$515,000

2 beds2 baths800 sq ft

35 Somerset Ave #6, Winthrop, MA 02152

Property at 80 Shirley St, Winthrop, MA 02152, 4 beds, 2 baths

$899,900

4 beds2 baths2,366 sq ft

80 Shirley St, Winthrop, MA 02152

Property at 174 Winthrop St #2, Winthrop, MA 02152, 3 beds, 2.5 baths

$729,900

3 beds2.5 baths1,973 sq ft

174 Winthrop St #2, Winthrop, MA 02152

Property at 80 Shirley St #2, Winthrop, MA 02152, 3 beds, 2 baths

$499,000

3 beds2 baths1,252 sq ft

80 Shirley St #2, Winthrop, MA 02152

Property at 50-52 Wilshire St, Winthrop, MA 02152, 5 beds, 2 baths

$1,150,000

5 beds2 baths2,212 sq ft

50-52 Wilshire St, Winthrop, MA 02152

Property at 80 Shirley St #1, Winthrop, MA 02152, 2 beds, 1 bath

$449,900

2 beds1 bath836 sq ft

80 Shirley St #1, Winthrop, MA 02152

Property at 800 Governors Dr #6, Winthrop, MA 02152, 2 beds, 1 bath

$340,000

2 beds1 bath772 sq ft

800 Governors Dr #6, Winthrop, MA 02152

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

OPEN TODAY, 3:30PM TO 5PM

ABOUT THIS HOME
Waterfront Home for sale in Downtown Winthrop, MA:
Don’t miss this luxury oceanfront penthouse style condo with unbeatable views in one of Winthrop’s most sought after neighborhoods. Enjoy sunset views from BOTH your ocean private decks, perfect for relaxing or entertaining overlooking the Atlantic. Gutted & converted in 2022 from top to bottom, 191 Court has modern smart-home features including smart thermostats, WiFi-connected blinds, and Ring security system for comfort & energy efficiency. Take in the expansive floor plan beaming with sunlight & original restored hardwood floors throughout. The kitchen features top of the line smart appliances, a wine fridge & oversized island opening to the living ro

$1,075,000

4 beds3.5 baths2,575 sq ft

191 Court Rd #3, Winthrop, MA 02152

$237 HOA • Car-dependent

OPEN SAT, 11AM TO 12:30PM

ABOUT THIS HOME
Waterfront Home for sale in Downtown Winthrop, MA:
Ideally located just steps from Winthrop Beach, this spacious top-floor condo has been meticulously maintained over the years. Filled with natural light and water views, the unit feels bright and welcoming from the moment you walk in. Hardwood floors throughout, with high ceilings & large windows create an open, bright living space. The living room features charming bay windows and opens to a generous formal dining room, perfect for entertaining. The kitchen, set toward the back of the unit, features stainless steel appliances, a pantry, and a convenient laundry room with a washer & dryer included, plus access to your private back deck. Three comfortable bedrooms all with ceilin

$549,900

3 beds1 bath1,280 sq ft

28 Pearl Ave #3, Winthrop, MA 02152

$497 HOA • Very walkable

ABOUT THIS HOME
Waterfront Home for sale in Downtown Winthrop, MA:
Discover the perfect blend of modern design and seaside charm at 130 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This two-bedroom, one-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you’ll find engineered hardwood flooring, recessed lighting, and a bright, open-concept layout ideal for everyday living or entertaining. The contemporary kitchen features double-stacked soft-close shaker cabinets, quartz countertops, and stainless-steel appliances, creating a clean and timeless look. Enjoy the comfort of central he

$569,900

2 beds1 bath782 sq ft

130 Shirley St #202, Winthrop, MA 02152

$250 HOA • Garage • Very walkable

ABOUT THIS HOME
Waterfront Home for sale in Downtown Winthrop, MA:
Discover the perfect blend of modern design and seaside charm at 130 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This one-bedroom, one-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you’ll find engineered hardwood flooring, recessed lighting, and a bright, open-concept layout ideal for everyday living or entertaining. The contemporary kitchen features double-stacked soft-close shaker cabinets, quartz countertops, and stainless-steel appliances, creating a clean and timeless look. Enjoy the comfort of central he

$499,900

1 bed1 bath611 sq ft

130 Shirley St #204, Winthrop, MA 02152

$225 HOA • Garage • Very walkable

$435,000

2 beds1 bath779 sq ft

220 Woodside Ave #1, Winthrop, MA 02152

5,968 sq ft lot • $230 HOA • Very walkable

OPEN SUN, 12PM TO 3PM

ABOUT THIS HOME
Waterfront Home for sale in Downtown Winthrop, MA:
Welcome to 5 Quincy Avenue, an architecturally stunning Bungalow located in Winthrop's highly sought-after Highlands neighborhood . This sun-filled 3-bedroom, 2-bath Craftsman home has an open-concept living and dining area featuring original rich oak woodwork, built-in cabinets, hardwood floors, decorative molding, wainscoting, and a fireplace. The renovated eat-in kitchen, equipped with stainless steel appliances and marble countertops, overlooks a private backyard with an inground heated swimming pool, ideal for summer entertaining. The home's classic details are beautifully complemented by contemporary elements. Both renovated baths feature marble and subway tile. Ample stora

$950,000

3 beds2 baths2,820 sq ft

5 Quincy Ave, Winthrop, MA 02152

8,393 sq ft lot • Garage • Pool

Property at 51 Cutler St #3, Winthrop, MA 02152, 2 beds, 2 baths

$670,000

2 beds2 baths1,283 sq ft

51 Cutler St #3, Winthrop, MA 02152

Property at 10 Beach Rd #1, Winthrop, MA 02152, 3 beds, 1 bath

$559,000

3 beds1 bath1,377 sq ft

10 Beach Rd #1, Winthrop, MA 02152

Property at 144 Quincy Ave, Winthrop, MA 02152, 5 beds, 4 baths

$1,800,000

5 beds4 baths3,866 sq ft

144 Quincy Ave, Winthrop, MA 02152

Property at 2 Deane Ave, Winthrop, MA 02152, 5 beds, 2.5 baths

$865,000

5 beds2.5 baths2,397 sq ft

2 Deane Ave, Winthrop, MA 02152

Property at 23 Trident Ave #2, Winthrop, MA 02152, 3 beds, 1 bath

$499,900

3 beds1 bath1,369 sq ft

23 Trident Ave #2, Winthrop, MA 02152

Property at 279 Shirley St #2, Winthrop, MA 02152, 3 beds, 1 bath

$529,000

3 beds1 bath1,105 sq ft

279 Shirley St #2, Winthrop, MA 02152

Property at 66 Lowell Rd, Winthrop, MA 02152, 6 beds, 2.5 baths

$1,150,000

6 beds2.5 baths3,458 sq ft

66 Lowell Rd, Winthrop, MA 02152

Property at 191 Cottage Park Rd, Winthrop, MA 02152, 6 beds, 3.5 baths

$1,799,000

6 beds3.5 baths4,455 sq ft

191 Cottage Park Rd, Winthrop, MA 02152

Property at 600 Shirley St #15, Winthrop, MA 02152, 1 bath

$340,000

0 beds1 bath338 sq ft

600 Shirley St #15, Winthrop, MA 02152

Property at 148 Winthrop Shore Dr #5, Winthrop, MA 02152, 2 beds, 2 baths

$669,009

2 beds2 baths971 sq ft

148 Winthrop Shore Dr #5, Winthrop, MA 02152

Property at 328-330 Revere St, Winthrop, MA 02152, 5 beds, 2 baths

$1,170,000

5 beds2 baths2,151 sq ft

328-330 Revere St, Winthrop, MA 02152

Waterfront Homes for Sale in Downtown Winthrop

There are currently 20 waterfront homes for sale in Downtown Winthrop at a median listing price of $726K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Downtown Winthrop stay on the market for 38 days and receive 6 offers. Popular neighborhoods include East Boston, Beachmont, West Revere, Jeffries Point, and South Boston Waterfront. This map is refreshed with the newest listings in Downtown Winthrop every 15 minutes.

In the past month, 2 homes have been sold in Downtown Winthrop. In addition to houses in Downtown Winthrop, there were also 18 condos, 2 townhouses, and 9 multi-family units for sale in Downtown Winthrop last month. Find your dream home in Downtown Winthrop using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Downtown Winthrop are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Downtown Winthrop. If you're looking to sell your home in the Downtown Winthrop area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Downtown Winthrop with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Downtown Winthrop, MA

Cities

Nearby Neighborhoods

Nearby Neighborhoods with Waterfront Homes

Nearby Cities with Waterfront Homes

More to explore in Downtown Winthrop, MA

How to buy a house in Downtown Winthrop, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Massachusetts

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.