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16 Loring Rd., Winthrop
$569,000
2 Beds ⋅ 1 Baths ⋅ 73585619 MLS
Opportunity awaits at 16 Loring Road in Winthrop! This 6-room home offers 2 bedrooms and plenty of potential for buyers looking to renovate, customize, or invest. The property features oil heat, an unfinished basement with convenient walkout access, and a detached two-car garage offering additional parking and storage. Situated on an approximately 5,500 sq. ft. lot. Bring your ideas and vision to unlock the possibilities this property has to offer. Property is being sold strictly AS-IS. Seller makes no representations or warranties regarding the property or its condition. Buyer and buyer’s agent are responsible for conducting their own due diligence and verifying all information to their satisfaction.

16 Loring Rd., Winthrop

Listing courtesy of Listing Agent: Martin Tokos from Listing Office: Coldwell Banker First Quality Realty.
54 Trident Ave Unit 54, Winthrop
$574,995
2 Beds ⋅ 1 Baths ⋅ 73585000 MLS
Ocean views, salty breezes & beachside living just minutes from Boston! This bright 2-bedroom, two-level condo offers direct ocean views & a deeded patio exclusive to the unit. Across the street, enjoy the beach & a 2-mile walking trail, perfect for morning strolls. Abundant windows fill the open-concept living space with natural light, while a 3 sided gas fireplace adds warmth & charm to the center of the entertaining space. The updated and spacious eat-in kitchen features newer appliances, a coffee bar, and bar seating. Wake up to ocean views in the primary bedroom, complete with a walk-in closet! The updated bath offers a spacious shower & jetted tub with a unique ceiling-mounted water feature and a large steam shower. The lower level adds flexibility with a bonus room, separate office & ample storage. Deeded parking, in-unit laundry, central A/C, a new hot water heater & newer HVAC complete the package. Sip coffee on your deck, unwind to the sounds of waves & seagulls, & make every day feel like a vacation!

54 Trident Ave Unit 54, Winthrop

Listing courtesy of Listing Agent: Candice Pagliarulo Hodgson from Listing Office: Lyv Realty.
900 Governors Dr Unit 37, Winthrop
$349,900
2 Beds ⋅ 1 Baths ⋅ 73584904 MLS
Welcome to 900 Governors Dr, Unit 37, Winthrop, MA, where easy condo living meets the charm of one of Greater Boston’s most desirable seaside communities. Just minutes from the water, this inviting 2-bedroom, 1-bath condo offers a bright, comfortable interior, a functional layout, and the low-maintenance lifestyle today’s buyers are looking for. Whether you’re a first-time buyer ready to make the move from renting to owning, a downsizer looking for simplicity, or someone who wants to live close to Boston while enjoying a coastal setting, this home offers an excellent opportunity. Inside, you’ll find comfortable living space with plenty of flexibility for everyday life. The two bedrooms provide options for a primary bedroom, guest room, home office, or additional living space. The thoughtful layout makes the condo feel welcoming and functional while still offering the opportunity to add your own personal style. One of the biggest advantages is the convenience of condo living. Spend less time worrying about exterior maintenance and more time enjoying everything Winthrop has to offer. Outside you will experience the lifestyle that makes this location so appealing. Winthrop’s beaches and shoreline are just minutes away, along with local restaurants, shops, cafés, and everyday conveniences. And with Boston only a short commute away, you can enjoy the best of both worlds — the relaxed atmosphere of a coastal community with easy access to the city. Move-in ready, conveniently located, and full of potential, Unit 37 is ready for its next owner. Come experience Winthrop living and see what makes 900 Governors Dr a wonderful place to call home.

900 Governors Dr Unit 37, Winthrop

Listing courtesy of Listing Agent: Brandon Dervishian from Listing Office: Lyv Realty.
100 Governors Drive Unit 2, Winthrop
$260,000
1 Beds ⋅ 1 Baths ⋅ 73583670 MLS ⋅ ['Governors Park'] BLDG.
Rare one bedroom unit n desirable 100 building at Governors Park entrance. Recently vacated by tenant of over 10 years. Short walk to local restaurants and shops, bus line to T.

100 Governors Drive Unit 2, Winthrop

Listing courtesy of Listing Agent: Pat Sullivan from Listing Office: Century 21 Seaport.
10 Somerset Unit 210, Winthrop
$555,900
1 Beds ⋅ 1 Baths ⋅ 73582183 MLS
Welcome to The Somerset, Winthrop’s newest boutique condominium community. Unit 210 is a beautifully designed 1-bedroom, 1-bath residence offers modern living with a relaxed coastal feel. The open-concept floor plan features quality finishes throughout, including stainless steel appliances, quartz countertops, central A/C, and stylish contemporary details. The elevator building offers a fitness room and inviting common area for residents to enjoy. Most residences include garage parking, and select homes feature private decks. Ideally located in the heart of Winthrop, The Somerset is close to sandy beaches, local shops, restaurants, and everyday amenities, with convenient access to downtown Boston. Enjoy the ease of low-maintenance condo living in a vibrant coastal community just outside the city.

10 Somerset Unit 210, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
43 Sagamore Ave Unit 1, Winthrop
$459,900
2 Beds ⋅ 1 Baths ⋅ 73582000 MLS
Whether you’re buying your first home or looking to simplify your life with easy one-level living, this beautifully renovated and meticulously maintained 2-bedroom condo checks all the boxes! Located entirely on the first floor with no stairs required, the home offers a bright, open-concept layout filled with natural light and an easy, move-in-ready lifestyle, just minutes from Winthrop Beach. The updated kitchen features white shaker cabinetry, granite countertops, stainless steel appliances, peninsula seating and plenty of storage, opening seamlessly into the spacious living area. The living area boasts space for a large sofa and television plus an extra storage closet. The generous primary bedroom is bright and inviting, with a double closet. It’s complemented by a versatile second bedroom, ideal for remote work, guests, or a roommate to help offset the mortgage, or simply a nice, bonus flex space. An updated full bath, in-unit laundry and dedicated parking add the everyday convenience of this home! Outside, enjoy your own exclusive patio space, perfect for morning coffee, summer grilling or relaxing after a day at the beach. An excellent option for a first-time buyer, empty nester or downsizer seeking low-maintenance, single-level living without sacrificing a second bedroom or private outdoor space. Convenient to Boston, Logan Airport and all that Winthrop has to offer, this seaside gem is ready for its next owner!

43 Sagamore Ave Unit 1, Winthrop

Listing courtesy of Listing Agent: Katelyn E. Sullivan from Listing Office: Coldwell Banker Realty - Boston.
483 Shirley St. Unit 6A, Winthrop
$309,900
1 Beds ⋅ 1 Baths ⋅ 73579862 MLS
HERE IS A GREAT INVESTMENT OPPORTUNITY OR OWNER OCCUPY.....Why rent when this updated seaside condo can give you a start to have a place of your own? Conveniently located on the Bus Line to the Blue Line and just steps to the beach. This unit has been freshly painted, new grey vinyl flooring throughout, new updated fully applianced kitchen with white cabinets, quartz counters and good size rooms. A large main bedroom, generous living room and a bonus room/office all waiting for your personal touches. This area has some of the many great eateries that can be enjoyed around this amazing seaside town. SMALL TOWN LIVING JUST MINUTES TO BOSTON and LOGAN AIRPORT, DON'T MISS OUT !!

483 Shirley St. Unit 6A, Winthrop

Listing courtesy of Listing Agent: Sharon Tallent from Listing Office: Compass.
130 Shirley Street Unit 220, Winthrop
$549,900
2 Beds ⋅ 1 Baths ⋅ 73579484 MLS
Discover the perfect blend of modern design and seaside charm at 140 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 heating and cooling, elevator access from the elegant lobby, and garage parking (with the option to purchase a second space). Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston’s best-kept secrets.

130 Shirley Street Unit 220, Winthrop

Listing courtesy of Listing Agent: The Kovacs Team from Listing Office: Compass.
34 Underhill Street Unit #4, Winthrop
$475,000
2 Beds ⋅ 2 Baths ⋅ 73579212 MLS ⋅ ['34 Underhill Street Condominium'] BLDG.
Gut renovated and converted in 2020, this upper-level 2-bedroom, 2-bath condo at 34 Underhill Street brings new construction finishes to one of Winthrop's most sought-after pockets. The white shaker kitchen is fitted with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including electric cooking. Wide plank hardwood floors & high ceilings run throughout, and recessed lighting and energy efficient mini-split systems keep the space comfortable year-round. The primary bedroom includes a custom walk-in closet with built-in shelving and drawers and direct access to a full bath. Upstairs positioning means added privacy and elevated sight lines in a building where no detail was overlooked. The Boston ferry, Rt. 1A, and Logan Airport are all minutes away, and the Winthrop coastline is right at your doorstep. Turnkey condition, standout finishes, and a location buyers keep coming back to.

34 Underhill Street Unit #4, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
194 Washington Ave Unit 4, Winthrop
$540,000
2 Beds ⋅ 2 Baths ⋅ 73575716 MLS
Welcome to coastal living at its best — where ocean views meet beautiful golf course views, and the beach is just a five-minute walk from your front door.Fully rebuilt in 2025, this exceptional first-floor 2-bedroom, 2-bath residence offers the rare combination of brand-new luxury, thoughtful design, and an incredible Winthrop-by-the-Sea location. Every detail was carefully considered, creating a home that feels elegant, comfortable, and effortless.Step inside to gleaming hardwood floors, beautiful natural light, and an inviting open living space. The chef’s kitchen is beautifully designed with quality finishes, generous workspace and storage, creating a perfect setting for cooking, entertaining, or simply enjoying a quiet morning at home.The spacious primary suite is its own private retreat, complete with a beautifully designed spa-like bathroom. A second bedroom and full bath offer flexibility for family, guests, or a home office. Both bathrooms have been finished with the same attention to quality, comfort, and detail found throughout the home.And the beauty goes far beyond what you see. The home was completely rebuilt with modern comfort in mind, including hypoallergenic hydro-air heating and cooling, tankless hot water, high-quality systems and finishes, and thoughtful details throughout. This is not a quick renovation — it is a home where everything was considered and done with care.First-floor living makes the home especially convenient, and one dedicated parking space completes the package.But perhaps the best feature is the lifestyle.Wake up by the sea. Walk five minutes to the beach. Enjoy beautiful ocean and golf course views and the peaceful atmosphere of a coastal community, all while remaining incredibly close to Boston.2 bedrooms. 2 full baths. Primary suite. Spa-like bathrooms. Chef’s kitchen. Gleaming hardwood floors. One parking space. First-floor living. Ocean and golf course views. Fully rebuilt in 2025.A beautifully rebuilt coastal home in an extraordinary location — sophisticated, comfortable, and surrounded by the magic of Winthrop by the sea. Ferry to downtown is 3 min walk.

194 Washington Ave Unit 4, Winthrop

Listing courtesy of Listing Agent: Ella Goren from Listing Office: Sunrise Realty & Investment LLC.
194 Washington Ave Unit 2, Winthrop
$575,000
2 Beds ⋅ 2 Baths ⋅ 73575711 MLS
Welcome to coastal living at its best — where ocean views meet beautiful golf course views, and the beach is just a five-minute walk from your front door.Fully rebuilt in 2025, this exceptional first-floor 2-bedroom, 2-bath residence offers the rare combination of brand-new luxury, thoughtful design, and an incredible Winthrop-by-the-Sea location. Every detail was carefully considered, creating a home that feels elegant, comfortable, and effortless.Step inside to gleaming hardwood floors, beautiful natural light, and an inviting open living space. The chef’s kitchen is beautifully designed with quality finishes, generous workspace and storage, creating a perfect setting for cooking, entertaining, or simply enjoying a quiet morning at home.The spacious primary suite is its own private retreat, complete with a beautifully designed spa-like bathroom. A second bedroom and full bath offer flexibility for family, guests, or a home office. Both bathrooms have been finished with the same attention to quality, comfort, and detail found throughout the home.And the beauty goes far beyond what you see. The home was completely rebuilt with modern comfort in mind, including hypoallergenic hydro-air heating and cooling, tankless hot water, high-quality systems and finishes, and thoughtful details throughout. This is not a quick renovation — it is a home where everything was considered and done with care.First-floor living makes the home especially convenient, and one dedicated parking space completes the package.But perhaps the best feature is the lifestyle.Wake up by the sea. Walk five minutes to the beach. Enjoy beautiful ocean and golf course views and the peaceful atmosphere of a coastal community, all while remaining incredibly close to Boston.2 bedrooms. 2 full baths. Primary suite. Spa-like bathrooms. Chef’s kitchen. Gleaming hardwood floors. One parking space. First-floor living. Ocean and golf course views. Fully rebuilt in 2025.A beautifully rebuilt coastal home in an extraordinary location — sophisticated, comfortable, and surrounded by the magic of Winthrop by the sea. Ferry to downtown is 3 min walk.

194 Washington Ave Unit 2, Winthrop

Listing courtesy of Listing Agent: Ella Goren from Listing Office: Sunrise Realty & Investment LLC.
111 Locust St Unit 2, Winthrop
$525,000
3 Beds ⋅ 1 Baths ⋅ 73574430 MLS
Just moments from Winthrop Beach, this charming three-bedroom condo offers a bright and inviting place to call home in a wonderful coastal setting. Inside, a thoughtfully designed layout features spacious living and dining rooms that flow together, filled with natural light. Charming details, including dentil molding, add character throughout. The kitchen features updated countertops and stainless steel appliances, while three comfortable bedrooms, generous closet space and in-unit laundry add to the home’s functional layout. Newly rebuilt front and rear porches offer space to enjoy a morning coffee or unwind after a day at the beach. One off-street parking space and additional basement storage add everyday convenience. Close to the shoreline, local restaurants, schools and playgrounds, this home offers a wonderful opportunity to enjoy the relaxed coastal lifestyle of Winthrop, all within easy reach of Boston.

111 Locust St Unit 2, Winthrop

Listing courtesy of Listing Agent: Max Dublin Team from Listing Office: Gibson Sotheby's International Realty.
130 Shirley Street Unit 330, Winthrop
$499,900
1 Beds ⋅ 1 Baths ⋅ 73573838 MLS
5.5% interest rate available along with 1 year of pre paid HOA fees. NEW CONSTRUCTION UNDER $500K WITH GARAGE PARKING — JUST ONE BLOCK FROM WINTHROP BEACH! Opportunities like this are increasingly difficult to find. Unit 330 is the final remaining one-bedroom residence at 140 Shirley Street and one of the rare opportunities to purchase a brand-new construction condominium under $500,000 in Greater Boston. Even better, this home includes a private garage parking space and is located just one block from Winthrop Beach. This is not a dated condo or a quick cosmetic renovation. 140 Shirley Street is true ground-up construction, designed and built by a reputable local builder with quality, durability, and long-term value in mind. Enjoy modern finishes, low-maintenance living, and the peace of mind that comes with new construction—all without the typical new-construction price tag. Enjoy easy access to Winthrop Beach, local restaurants, shops, and waterfront amenities, while downtown Boston is just a short commute away. It’s the perfect combination of coastal living and city convenience. New construction. One bedroom. Garage parking. One block to the beach. Under $500,000. The last one available. Don’t miss it.

130 Shirley Street Unit 330, Winthrop

Listing courtesy of Listing Agent: The Kovacs Team from Listing Office: Compass.
10 Somerset Unit 309U, Winthrop
$508,900
1 Beds ⋅ 1 Baths ⋅ 73574045 MLS
Unit 309 at The Somerset is a bright and airy one-bedroom, one-bath condominium offering an open-concept layout, high-quality finishes, and a relaxed coastal style. The kitchen features stainless steel appliances, quartz countertops, and modern design touches, while central A/C adds everyday comfort. Residents at The Somerset enjoy elevator access, a fitness room, garage parking, pet-friendly living, and stylish common areas. Ideally located in the heart of Winthrop, The Somerset is just minutes from sandy beaches, local shops, and an easy commute to downtown Boston.

10 Somerset Unit 309U, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
15 Ocean Ave Unit 203, Winthrop
$524,900
2 Beds ⋅ 3 Baths ⋅ 73572947 MLS
A True Pride of Home Ownership!!! LOW CONDO FEE comes w/This Meticulously Maintained 2 Bed 2.5 Bath Penthouse Condo w/ 2 OFF STREET PARKING SPACES is Nestled in a Quiet Residential Neighborhood Just Steps from 4 Beaches, EZ ACCESS TO Public Transportation, Fine Shops and Dining and is Only a 10 Minute Drive to Downtown Boston/Logan Airport. Natural Light Spills Into This Unit Through the Over Sized Windows and 3 Sky Lights on the 2nd Level. Other Notable Features Include Newly Installed Waterproof Vinyl Plank Flooring , Fresh Paint Throughout, Central Heat /AC, Custom Blinds, Galley Kitchen, In Unit Washer and Dryer, Recessed Lighting, Newer Oversized Windows on 2nd Level, Private Balcony Off Both Bedrooms w/ Ocean Views, Common Roof Deck w/ Ocean Views, Extra DEEDED Storage in Basement and Much Much More!!!

15 Ocean Ave Unit 203, Winthrop

Listing courtesy of Listing Agent: Kenneth Celano from Listing Office: Turn Key Realty.
35 Somerset Ave Unit 3A, Winthrop
$549,900
2 Beds ⋅ 2 Baths ⋅ 73571733 MLS
Welcome to 35 Somerset Avenue, Unit 3, a sophisticated two-bedroom, two-bath residence offering modern design and effortless coastal living in the heart of Winthrop. Thoughtfully renovated in 2023, the home features beautiful oak flooring and a bright, open-concept layout ideal for both everyday living and entertaining. The stylish kitchen is anchored by an oversized island and finished with quartz countertops, stainless steel appliances, subway tile accents, and contemporary pendant lighting. The spacious primary suite offers a private retreat with a beautifully appointed marble bath, while the second bedroom provides flexibility for guests, a home office, or additional living space. Step outside to your exclusive private deck, perfect for morning coffee or summer evenings. In-unit laundry, basement storage, and off-street parking complete the offering. Ideally situated near Winthrop Center's restaurants, cafés, shops, parks, and the waterfront, this turnkey home delivers the perfect blend of style, convenience, and coastal charm.

35 Somerset Ave Unit 3A, Winthrop

Listing courtesy of Listing Agent: Mark Savage from Listing Office: Byrnes Real Estate Group LLC.
10 Somerset Unit U.305, Winthrop
$473,900
1 Beds ⋅ 1 Baths ⋅ 73570684 MLS ⋅ ['Somerset'] BLDG.
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 throughout. Located in the heart of Winthrop, The Somerset has become a sought-after address, transforming a landmark property into a vibrant 29-home condominium community that celebrates the town's rich seaside character while offering today's conveniences. Residents enjoy an elevator, fitness center, coffee station, resident lounge, and secure mailroom. Just moments from beaches, local restaurants, cafés, the ferry, and downtown Boston, this move-in-ready home offers the perfect blend of coastal tranquility and city accessibility.

10 Somerset Unit U.305, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
33 Bay View Ave, Winthrop
$600,000
3 Beds ⋅ 1 Baths ⋅ 73569960 MLS
Welcome to 33 Bay View Ave, a charming coastal bungalow offering the perfect blend of comfort, convenience, and seaside living in Winthrop. This 3-bedroom, 1-bath home features hardwood floors, a bright and inviting living space, dedicated dining area, and a functional kitchen with new appliances. Enjoy water views and take advantage of the spacious fenced in yard, ideal for entertaining, gardening, or relaxing outdoors. Additional highlights include an enclosed porch, wood deck, patio, first-floor laundry, and off street parking. Located just moments from the beach, parks, walking and biking trails, public transportation, and all that Winthrop has to offer. A great opportunity to enjoy the coastal lifestyle while remaining just minutes from Boston and Logan Airport.

33 Bay View Ave, Winthrop

Listing courtesy of Listing Agent: Michael Cimmino from Listing Office: Real Broker MA, LLC.
60 Hermon St Unit 3, Winthrop
$519,900
1 Beds ⋅ 1 Baths ⋅ 73569128 MLS
Oversized one bedroom condo in Winthrop's historic Playmakers building, just minutes from Winthrop Center. This bright, modern unit features an open concept living space with cathedral ceilings and hardwood floors throughout. The kitchen offers a large island, stone countertops, stainless steel appliances, a gas stove, and a wine chiller. A spacious bedroom and office sit on the primary floor, with ladders leading up to two additional multi-use loft spaces. Stacked washer and dryer in unit. One off-street parking spot. Steps to public transportation, parks, tennis courts, and less than a half mile to the beach.

60 Hermon St Unit 3, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
22 Pauline St. Unit 5, Winthrop
$419,900
1 Beds ⋅ 1 Baths ⋅ 73568595 MLS ⋅ ['Pauline Place'] BLDG.
Disappointed about high mortgage rates? No need to be disappointed! Pauline Place is offering 4.25% mortgage rates that will save buyers thousands of dollars in mortgage payments. Call for details.WINTHROP BY THE SEA IS CALLING! Welcome to Pauline Place at Winthrop Center, a brand-new boutique community perfectly positioned right on the bus line for a quick connection to the T and into Boston. Imagine being the very first person to live in one of these high-end, one-bedroom condos. With five distinct units to choose from, you’ll find gorgeous, color-coordinated kitchens and baths that truly wow. The kitchens are a chef’s dream, featuring sleek LG stainless steel appliances, crisp quartz countertops, stylish shaker cabinets with modern black hardware, and luxury vinyl flooring that ties the whole aesthetic together. The upscale baths, finished with striking tile and glass, feel like a private spa retreat.Every room feels bright and airy thanks to Pella windows that invite the sunlight to pour in. You’ll stay perfectly comfortable year-round with high-efficiency Mitsubishi heating and cooling, and the convenience of in-unit laundry and off-street parking makes daily life a breeze.Step outside and you’re just moments away from local restaurants and shopping. Living here means embracing the best of Winthrop—beaches, boating, marinas, yacht clubs, a golf course, and miles of scenic seaside paths for biking and exploring. ITS A STUNNING PALCE TO CALL HOME AND BEST OF ALL YOU CAN OWN THIS LIFESTYLE FOR LESS THAN THE COST OF RENTING!

22 Pauline St. Unit 5, Winthrop

Listing courtesy of Listing Agent: Highland Group from Listing Office: Compass.
22 Pauline St. Unit 3, Winthrop
$399,900
1 Beds ⋅ 1 Baths ⋅ 73568569 MLS ⋅ ['Pauline Place'] BLDG.
Disappointed about high mortgage rates? No need to be disappointed! Pauline Place is offering 4.25% mortgage rates that will save buyers thousands of dollars in mortgage payments. Call for details.WINTHROP BY THE SEA IS CALLING! Welcome to Pauline Place at Winthrop Center, a brand-new boutique community perfectly positioned right on the bus line for a quick connection to the T and into Boston. Imagine being the very first person to live in one of these high-end, one-bedroom condos. With five distinct units to choose from, you’ll find gorgeous, color-coordinated kitchens and baths that truly wow. The kitchens are a chef’s dream, featuring sleek LG stainless steel appliances, crisp quartz countertops, stylish shaker cabinets with modern black hardware, and luxury vinyl flooring that ties the whole aesthetic together. The upscale baths, finished with striking tile and glass, feel like a private spa retreat.Every room feels bright and airy thanks to Pella windows that invite the sunlight to pour in. You’ll stay perfectly comfortable year-round with high-efficiency Mitsubishi heating and cooling, and the convenience of in-unit laundry and off-street parking makes daily life a breeze.Step outside and you’re just moments away from local restaurants and shopping. Living here means embracing the best of Winthrop—beaches, boating, marinas, yacht clubs, a golf course, and miles of scenic seaside paths for biking and exploring. ITS A STUNNING PALCE TO CALL HOME AND BEST OF ALL YOU CAN OWN THIS LIFESTYLE FOR LESS THAN THE COST OF RENTING!

22 Pauline St. Unit 3, Winthrop

Listing courtesy of Listing Agent: Highland Group from Listing Office: Compass.
1 Seal Harbor Rd Unit 413, Winthrop
$549,999
2 Beds ⋅ 2 Baths ⋅ 73564816 MLS ⋅ ['Seal Harbor'] BLDG.
Welcome to coastal living at its finest at the highly desirable Seal Harbor One. Perched on the fourth floor, this spacious and thoughtfully designed 2-bedroom, 2-bath residence offers an ideal layout with private bedroom suites, each featuring its own full bathroom and generous walk-in closet. Set on a stunning peninsula surrounded by the Atlantic Ocean, Seal Harbor offers a truly unique lifestyle where beautiful grounds, ocean breezes, and even visiting seals create a peaceful everyday retreat. Enjoy resort-style amenities including an outdoor pool complete with kitchen and bbqs, on-site concierge, basement gym & exercise room with sauna, a lobby card room, a Penthouse Clubroom and meeting space complete with kitchen, extra cage storage, jogging trails, gazebo, beach, extra surface parking for guests, and the convenience of underground garage parking so you can stay protected from the elements year-round. Your monthly fee includes water, sewer, master insurance, maintenance of exterior, road, and landscaping; snow removal, refuse removal, and a professional management company. Cose to shops, restaurants, public transportation, Winthrop beach, Deer Island walking and bike paths. Take MBTA transit from Orient Heights or drive to Logan Airport and downtown Boston. This is a rare combination of ocean views, garage parking, and full-service amenities. Whether you are relaxing at home or enjoying the breathtaking waterfront surroundings, this is seaside condominium living at its best.

1 Seal Harbor Rd Unit 413, Winthrop

Listing courtesy of Listing Agent: Tammy Merk from Listing Office: Real Broker MA, LLC.
175 Shirley Street Unit 5, Winthrop
$350,000
2 Beds ⋅ 1 Baths ⋅ 73563869 MLS ⋅ ['Shirley Place Condominium'] BLDG.
If you are a beach person or enjoy a short commute to the city you've come to the right place. Take this opportunity to live in the perfect location at a price that is ideal. Your two bedroom one bath is the perfect size at just under 700 square feet with an additional 300 square feet in the attic that is deeded exclusively to you to use as you like. Enjoy fresh air on your roof deck or a view of the ocean down Neptune Ave. Hardwood floors, stainless appliances, recessed lights, newer kitchen and bath are just the beginning. Close to shopping, restaurants, library, book / coffee shops, golf, tennis, beach, conservation areas. Nearby bus to blue line / Orient Heights provides convenient access to Logan International Airport and surrounding communities, with Boston's downtown in 30 minutes.

175 Shirley Street Unit 5, Winthrop

Listing courtesy of Listing Agent: Tammy Merk from Listing Office: Real Broker MA, LLC.
12 Sewall Ave Unit 2B, Winthrop
$549,000
2 Beds ⋅ 2 Baths ⋅ 73563560 MLS ⋅ ['12 Sewall Ave Condominium'] BLDG.
Imagine coming home to the relaxed rhythm of coastal living, where the water is just moments away and the best of Winthrop is right outside your door. This beautifully renovated 2-bedroom, 2-bath condominium has been thoughtfully transformed into a stylish and welcoming retreat, offering partial water views and a fresh, move-in-ready interior. Enter to warm hardwood floors that flow throughout the home and a bright, inviting layout designed for both everyday living and entertaining. At the heart of the home, the updated kitchen pairs timeless style with modern convenience, featuring quartz countertops, custom cabinetry, and stainless steel appliances. Whether you’re enjoying a quiet morning, preparing dinner, or gathering with friends, the space feels both polished and comfortable. Two beautifully renovated bathrooms continue the home’s clean, contemporary aesthetic, while the two bedrooms offer flexibility for overnight guests, a home office, or additional living space. Private basement storage with direct access provides plenty of room for beach gear, bikes, and seasonal items, and a deeded parking space adds everyday ease. Beyond the front door, enjoy the charm and character that make Winthrop such a special place to live- from waterfront walks and days at the beach to neighborhood restaurants, local shops, and easy access to Boston. Beautifully updated and perfectly positioned to enjoy life by the coast, this is a home where you can settle in, slow down, and make the most of every season.

12 Sewall Ave Unit 2B, Winthrop

Listing courtesy of Listing Agent: Leighann Eruzione from Listing Office: Bowdoin Real Estate Partners.
229 Washington Ave Unit 3A, Winthrop
$219,999
1 Beds ⋅ 1 Baths ⋅ 73560224 MLS
Enjoy coastal living in this charming waterfront condominium in Winthrop, offering the perfect balance of convenience and seaside lifestyle. Located just minutes from Boston Logan Airport and with easy access to public transportation including nearby bus routes, the Orient Heights MBTA station, and the East Boston ferry, this home is ideal for commuters seeking quick access to Boston while enjoying a quieter coastal setting.

229 Washington Ave Unit 3A, Winthrop

Listing courtesy of Listing Agent: Marcia De Paula from Listing Office: REMAX Executive Realty.
10 Somerset Unit U304, Winthrop
$397,900
1 Beds ⋅ 1 Baths ⋅ 73559020 MLS
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 modern kitchen and living area are complemented by quartz countertops, stainless steel appliances, central A/C, and stylish contemporary finishes throughout. Residents enjoy convenient amenities including a fitness center, elevator access, and a welcoming resident lounge perfect for working remotely or gathering with friends. Just minutes from beaches, waterfront parks, local dining, and cafés, with quick access to downtown Boston via the Blue Line or seasonal ferry. Whether you're looking for a primary residence, investment property, or weekend escape, Unit 304 is home.

10 Somerset Unit U304, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
16 Billows Street Unit B, Winthrop
$499,000
2 Beds ⋅ 1 Baths ⋅ 73557185 MLS ⋅ ['Finlayson House On The Point Condominium'] BLDG.
This renovated 2-bedroom, 1-bath condo sits in the heart of Winthrop's Point Shirley, offering single-floor living with vaulted ceilings and skylights that give the space a brightness and openness rarely found at this price point. Natural light pours through every room throughout the day, flowing over hardwood floors that run wall to wall and tie the entire living space together seamlessly. Two private entrances add a level of independence and privacy that sets this home apart from typical condo living. The updated kitchen is well-equipped with gas cooking and stainless steel appliances, and the layout makes everyday living feel easy. In-unit washer/dryer and two off-street parking spots check the boxes that matter most to buyers in this market. Bonus: Private outdoor space add a layer or privacy most condos don't offer. Enjoy the best of coastal living, where the beach is just steps away & commuting to Boston is easy with quick access to the ferry, T stations, Rt. 1A, Logan Airport.

16 Billows Street Unit B, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
1 Seal Harbor Rd Unit 812, Winthrop
$499,000
1 Beds ⋅ 1 Baths ⋅ 73556652 MLS
Waterfront Living at Its Best! Enjoy breathtaking ocean views from this spacious 8th floor condominium offering 974 sq ft of comfortable living space. Relax on your private balcony overlooking the water, or good size bedroom including a large walk-in closet and a separate tub/shower room. This full service building offers outstanding amenities, including concierge service, an oceanside heated pool with BBQ areas, tennis courts, an exercise room, and a scenic walking path along the shoreline. One garage parking space is included. Ideally located walking distance to restaurants. Minutes to Boston and Logan. This is coastal living with unmatched convenience. A wonderful place to enjoy waterfront living. Open Saturday and Sunday 11–12:30 Oct 3rd and Oct 4th.

1 Seal Harbor Rd Unit 812, Winthrop

Listing courtesy of Listing Agent: Peggie Gilbert from Listing Office: Coldwell Banker Peggy Carter Team.
1 Seal Harbor Unit 210, Winthrop
$479,900
1 Beds ⋅ 1 Baths ⋅ 73551484 MLS ⋅ ['Seal Harbor'] BLDG.
IMPROVED PRICE = A GREAT OPPORTUNITY for Winthrop's LARGEST AND MOST REASONABLY PRICED 1 bedroom ocean front unit with OCEAN VIEWS from EVERY ROOM! Wake up to SPECTACULAR SUNRISES over the Atlantic and fall asleep to the soothing sound of OCEAN WAVES in this affordable OCEANFRONT UNIT at Seal Harbor Condominiums! Offering UNOBSTRUCTED OCEAN VIEWS from EVERY ROOM, this beautifully maintained home delivers the ultimate coastal lifestyle while being a short drive to Boston & Logan Airport! Gleaming HW FLOORS flow throughout the OPEN CONCEPT LIVING & DINING AREAS, where a PRIVATE BALCONY provides the perfect setting to relax with the ocean as your backdrop. The updated kitchen features SS APPLIANCES, GRANITE counters, with a FULL HEIGHT BACKSPLASH complementing the stylish cabinetry. A SPACIOUS BEDROOM and UPDATED FULL BATH, a private shower area with a wall of closets and a NEW WASHER AND DRYER complete the space. Experience RESORT STYLE LIVING w/exceptional amenities including an inground pool, fitness center, sauna, steam room, tennis courts, clubhouse, beautifully manicured gardens with a gazebo, scenic oceanfront walking paths, recreational facilities and the convenience of a 24/7 concierge! If you’ve been waiting for an opportunity to own oceanfront property in Winthrop, now is the time! This is COASTAL LIVING at its best!

1 Seal Harbor Unit 210, Winthrop

Listing courtesy of Listing Agent: Rita Angelesco from Listing Office: LAER Realty Partners.
600 Shirley St Unit 7, Winthrop
$485,000
1 Beds ⋅ 2 Baths ⋅ 73535636 MLS ⋅ ['Crystal Cove'] BLDG.
Stunning water views from every angle make this exceptional condo truly one of a kind. Enjoy breathtaking sunsets over the Boston skyline and harbor from the comfort of your own home. Nestled in the charming seaside community of Winthrop, you'll experience the perfect balance of coastal living and city convenience. The ferry is just one block away, offering a scenic and stress free commute to Boston. Unit features tasteful upgrades, including a custom kitchen marble backsplash, quartz countertop and boasts not one, but two private decks featuring Trex decking. Unit 7 is widely considered the premier residence in the building, featuring the largest private waterfront-facing deck an ideal setting for morning coffee, outdoor dining, or simply taking in the spectacular views. Vinyle double hung windows with thermopane glass. Just in time for summer, this rare offering presents an incredible opportunity to enjoy, waterfront living at its finest.

600 Shirley St Unit 7, Winthrop

Listing courtesy of Listing Agent: Elizabeth Ferrara from Listing Office: Cottage Hill Real Estate.

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