Welcome to 14 Irwin Street, a charming single-family home in one of Winthrop’s inviting residential neighborhoods. Offering approximately 1,413 square feet of living space, this classic two-story home features 3 bedrooms, 1.5 bathrooms, and 7 total rooms, providing a comfortable foundation for your next chapter. Enjoy the best of Winthrop’s coastal lifestyle with the beach just a short walk away at the end of the street. Plus, with a bus stop just steps away, public transportation is conveniently accessible for an easier daily commute. From morning walks by the water to summer afternoons at the beach, this location makes everyday living feel a little more special. Set on an approximately 4,792-square-foot lot, this home offers room to grow and plenty of opportunity to make it your own. Built circa 1900, the property retains the character of an earlier era while inviting buyers to bring their own vision and personal style. Whether you’re looking for a family home or a place to create lasting memories, 14 Irwin Street offers a wonderful opportunity in a desirable seaside setting. A wonderful combination of coastal charm, convenient public transportation, and neighborhood appeal—truly a must-see property!
NEW CONSTRUCTION WITH GARAGE PARKING — JUST ONE BLOCK FROM WINTHROP BEACH! Opportunities like this are increasingly difficult to find. 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.
Oceanfront living at One Seal Harbor! Welcome to this beautifully renovated 1-bedroom, 1-bath condominium offering breathtaking ocean views from the living room, dining room and bedroom. Tastefully updated throughout, this inviting home features a bright and open living space designed to take full advantage of its stunning coastal setting. Step out onto your private deck and enjoy sweeping views of the ocean. The spacious bedroom offers a generous walk-in closet, while the convenience of in-unit laundry adds to the ease of everyday living. Additional amenities include one deeded garage parking space, private storage, fitness center, sauna, game room and concierge service. Ideally located just moments from Winthrop Beach, local restaurants, shopping, and all that Winthrop has to offer. Enjoy easy access to Boston and Logan international Airport while coming home to the peaceful beauty of oceanfront living. A wonderful opportunity to enjoy a low-maintenance coastal lifestyle in a desirable Winthrop location!
Charming, move-in-ready Colonial offering ocean views in a desirable Winthrop location just moments from the newly renovated Winthrop Beach. The inviting main level features a sun-filled living room with a gas fireplace and classic arched doorways, a spacious kitchen overlooking the covered deck and fenced backyard, a formal dining room, a half bath, and a versatile room currently used as a home office. Upstairs, you'll find three spacious bedrooms, a cozy sitting area, and a full bath. A porch roof patio over looking the ocean is a favorite spot to appreciate the views while you sit back and reflect on your day. Perfect ADU potential or in-law space in the lovingly finished and conveniently laid out walk out lower level with an oversized family room featuring a gas fireplace and bamboo flooring, a three-quarter bath, full kitchen with stainless steel appliances and second refrigerator, a laundry area. Complete with a bedroom and a full sized cedar closet, this is the home for you! Walk out your lower level door to a covered area for a table or another sitting area. The outdoor shed has doors that open up to the pergola with a bar and tv so you can watch the games during your cookouts. Enjoy the convenience of three off-street parking spaces and easy access to Boston, Logan Airport, scenic waterfront trails, shopping, dining, and more. Don't miss it!
Welcome to The Somerset unit 205, an elevated boutique condominium in the heart of Winthrop, where refined modern living meets a relaxed coastal lifestyle. This beautifully designed 1+ bedroom, 1-bath residence features an open-concept layout with sophisticated finishes, including a sleek kitchen with quartz countertops and stainless steel appliances. Central A/C and elevator access add everyday comfort, while the building’s fitness room and inviting common area create an effortless sense of community. Ideally located near Winthrop’s beaches, waterfront, shops, restaurants, and cafés, The Somerset offers a stylish coastal retreat with convenient access to downtown Boston.
**$20k in seller credits available** Second-floor home in the heart of Winthrop, a short walk to the beach, parks, and the golf course. This three-bedroom condominium pairs 1920s character with modern updates. The living and dining rooms feature hardwood flooring, natural woodwork, and built-ins, with bay windows bringing in natural light throughout. The kitchen offers granite counters, stainless steel appliances, a breakfast bar, and a walk-through pantry. Three well-proportioned bedrooms and a tiled full bath complete the main level, with laundry located in the building. One assigned off-street spaces, gas heat, and a full basement add everyday convenience. The self-managed two-unit association carries a low monthly fee that covers master insurance and snow removal. Commuters gain quick access to the bus, the Blue Line, and the Winthrop ferry, putting downtown Boston within easy reach. Enjoy coastal living with the space and character of a classic New England home.
Stunning home in the heart of Winthrop. This exceptional American Foursquare combines timeless architectural character with extensive renovations and modern finishes throughout. Spacious and sun-filled, the home offers beautifully remodeled interiors, off-street parking, and exceptional indoor/outdoor living while preserving its classic craftsmanship. A newly remodeled mudroom with custom storage, new windows, and recessed lighting opens to a gracious living room with hardwood floors and a gas fireplace with a newly constructed surround. The spacious dining room features traditional wainscoting and an elegant setting for entertaining.The fully remodeled kitchen is the centerpiece of the home, featuring a large center island, custom cabinetry, designer tilework, new flooring, and generous workspace. An expansive Trex deck overlooks the fully fenced, professionally landscaped 6,000 sq. ft. lot, creating an exceptional setting for outdoor dining and entertaining. A full bath completes the main level.The second floor offers three generously sized bedrooms, and fourth bedroom currently being used as a home office. A fully remodeled bath with new finishes and fixtures caps off the second floor. The finished third floor provides flexible bonus space ideal for an office, guest retreat, media room, playroom, or library.The newly finished lower level offers a separate in-law suite with a brand-new kitchenette, second gas fireplace featuring hand-built stonework, half bath, dedicated gym, and laundry area—ideal for extended family, guests, or additional work-from-home space. Short distance to schools, Town Center restaurants and cafés, shops, the library, parks, and beaches, with convenient access to Boston, the Seaport, Financial District, and Logan Airport.
Welcome to this immaculate top-floor corner condo in Chase Condominiums, where privacy, natural light, and effortless one-level living come together beautifully. Abundant corner windows fill the spacious home with light while offering a peaceful sense of privacy. The generously sized primary suite features an updated en-suite bath with a tiled shower, Jacuzzi tub, and walk-in closet. The second bedroom offers its own private bathroom and tall, bright windows. An open-concept layout seamlessly connects the living and dining areas, creating endless possibilities for entertaining, relaxing, and everyday living.The updated kitchen features granite countertops, tall cabinetry, stainless steel appliances, and a brand-new washer and dryer. Step outside to your large private deck—perfect for morning coffee, outdoor dining, or simply enjoying your own private outdoor retreat. Extra Storage unit is deeded with the unit(#5), along with 1 deeded parking spot (#14)The well-maintained complex offers an inviting shared roof deck with ocean views, tables, comfortable seating, and seasonal décor. It’s an exceptional spot to take in the Fourth of July fireworks over Boston or from Winthrop High School. Enjoy beautifully landscaped grounds and a convenient location just moments from marsh trails, playgrounds, dog parks, and access to Winthrop Beach. With its spacious floor plan, abundant natural light, private outdoor spaces, and fantastic coastal lifestyle, this condo offers the perfect blend of comfort, convenience, and privacy.
Welcome to your ultimate beachfront oasis in Winthrop, where every day feels like a permanent getaway with direct access from your back door straight into the sand. This stunning home features an inviting, fireplaced living room, a kitchen boasting sleek marble countertops and tile flooring, a convenient main-floor full bath and an outdoor shower for rinsing off after the beach, and two flexible bedrooms ideal for guests, children, or a home office. Take in breathtaking ocean sunrises over morning coffee from the year-round heated sunroom, and retreat upstairs to a spacious primary suite complete with its own private bath. The finished lower level functions as a fully separate suite—an incredible asset as one of only 10 legal Airbnbs in all of Winthrop, complete with its own family room, bonus space, full bathroom, and laundry. Positioned in an unbeatable location with two off-street parking spots and an EV charger, this property sits less than 1 mile from the Winthrop Landing MBTA ferry for easy transit to Logan, Central Wharf, and the Seaport, perfectly balancing everyday coastal luxury with elite short-term rental potential.
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.
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!
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.
Introducing Unit 307 at Somerset Winthrop, where refined design, modern convenience, and effortless comfort come together in a beautifully appointed residence. Ideally situated in the heart of Winthrop, this spacious 2-bedroom, 2-bath home offers an inviting retreat just moments from local shops, restaurants, and neighborhood amenities.The thoughtfully designed interior features an open-concept living space and a modern kitchen appointed with quartz countertops, stainless steel appliances, and a convenient breakfast bar. The private primary suite offers a generous walk-in closet, while the additional bedroom and full bath provide exceptional flexibility for guests, a home office, or everyday living. In-unit laundry adds to the ease and convenience. Residents also enjoy access to a well-equipped exercise room and meeting room, with carport parking. With its sophisticated finishes, generous living spaces, and prime Winthrop location, Unit 307 offers an exceptional opportunity to enjoy a polished, low-maintenance lifestyle.
Stunning single family home located in the desirable Town of Winthrop. This completely updated and spacious single family home offers four bedrooms with one and a half baths and plenty of space for everyone. Additional bonus rooms on the attic level and a large unfinished basement provide even more opportunities for expanded living. An open floor plan and a beautiful kitchen, complete with stainless steel appliances and upgraded countertops make this a perfect home for entertaining. Hardwood flooring throughout, central forced air, and ductless mini-splits round out some of the great features this home has to offer. An ample and airy backyard and off-street parking are a huge plus. Incredible location - just steps to the ocean and minutes to Downtown Boston, Logan Airport and the North Shore. See all that Winthrop has to offer - close to beaches, parks, restaurants and much more!
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.
Welcome to 7 Enfield Road, a captivating single-family residence in Winthrop, MA. Built in 1930, this inviting home spans 1144 square feet and is ready for you to move in. It offers a unique blend of classic charm and comfortable living, set on a generous 6969 square foot lot. The living room provides a warm and inviting atmosphere, centered around a charming fireplace, and features elegant hardwood flooring that extends throughout the space. The bedrooms, designed for comfort and tranquility, also boast classic hardwood flooring, creating a cohesive and timeless feel throughout the private areas of the home. This property also includes a convenient one-car garage, a full basement offering ample storage or potential for future customization, and a welcoming porch perfect for enjoying the outdoors. Discover the effortless lifestyle awaiting you at this charming Winthrop address. Convenient location to Winthrop Center and shopping, Cummings Elementary School or walk to Ingleside Park, tennis and basketball courts, pickle ball courts and Donovan's beach.
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.
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!
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, two-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 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. Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston’s best-kept secrets.
The largest residence in the Pearl, loft-style living, high ceilings, oversized windows, and original wood details. The layout offers flexibility, including space that works well for a home office. Premium kitchen, radiant-heated primary bath,2 off-street parking spaces, private storage, and secure entry. Close to beaches, trails, cafes, and an easy ride into Boston. Also being offered for SALE & LEASE!
Ready for more space? Unit4 at The Pearl offers 1,665 square feet of loft style living, ideal for buyers who have outgrown a starter condo. Soaring ceilings, oversized windows, original wood details and premium finishes give it character and room to spread out. Premium kitchen, radiant-heated primary bath, 2 off-street parking spaces, private storage and secure entry. All that plus Winthrop’s beaches, trails, cafés and quick access to Boston. Also available for lease see 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 !!
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.
THIS ONE FEELS LIKE A SINGLE FAMILY HOME!!! Off in the distance you will enjoy spectacular sunsets over the water in this beautifully renovated and spacious two-level condominium offering 3 bedrooms, 2 full baths and an open layout ideal for ease of living and outside enjoy exclusive to this unit yard space with deck, paver patio and fire pit. Highlights include new paint, lighting, an updated kitchen, updated baths, central air, in-unit laundry, a striking staircase and more of those ocean views from various windows. Commuting is easy with the Boston bus line nearby, providing access to the T in approximately 15 minutes and Boston in about 30. The Winthrop Ferry offers another convenient option. Enjoy Winthrop’s beaches, waterfront trails, golf course, yacht clubs, and popular restaurants—all just minutes from Boston. No monthly association fee; owners share the insurance expenses, pets allowed, private outdoor spaces, and 2 car parking round up the benefits of this beautiful townhome! Each unit owner responsible for 1/2 the insurance costs - no condo fee otherwise!
**$20k in seller credits available** Rare land offering directly across from Winthrop Beach. This 13,920 square foot (0.32 acre) residential parcel is offered together with the existing structure on it, a two-story gambrel home built in 1880 with 5 rooms, 3 bedrooms, 1.5 baths, forced hot water heat, and vinyl siding. Ocean views across from the beach reservation. Renovate the existing house, build new, or explore other options for the site; buyer and buyer agent to complete their own due diligence with the Town of Winthrop regarding zoning, permitted uses, and redevelopment potential. Public water and sewer serve the site. Quick access to Boston, Logan Airport, and MBTA connections.
Winthrop is located in Massachusetts.
