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$850,000
3 Beds ⋅ 3 Baths ⋅ 73575705 MLS ⋅ NEW Status
Welcome to coastal living at its best — where ocean views meet sweeping golf course views, and the beach is just a five-minute walk from your front door.Fully rebuilt in 2025, this exceptional 3-bedroom, 3-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 and beautiful natural light flowing through the open living space. At the heart of the home is a chef’s kitchen with a large center island, quality finishes, and plenty of room to gather, cook, entertain, or simply enjoy your morning coffee while taking in the surroundings.The layout features TWO primary suites, each with its own beautifully designed, spa-like bathroom — private retreats with the feeling of a boutique hotel. Three full bathrooms throughout the home are finished with the same attention to quality and detail.And the beauty goes far beyond what you see. The home was 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.Two garage parking spaces complete the package — an incredible luxury so close to the ocean.But perhaps the best feature is the lifestyle.Wake up to ocean and golf course views. Walk five minutes to the beach. Spend your mornings by the water and your evenings watching the light change over the coast. Enjoy the peaceful feeling of a seaside community while remaining just minutes from Boston.3 bedrooms. 3 full baths. Two primary suites. Two garage spaces. Chef’s kitchen. Spa-like bathrooms. Ocean views. Golf course views. Fully rebuilt in 2025.A beautifully rebuilt home in an extraordinary location — sophisticated, comfortable, and surrounded by the sea. Water ferry to downtown is 3 min walk

194 Washington Ave Unit 3, Winthrop

Listing courtesy of Listing Agent: Ella Goren from Listing Office: Sunrise Realty & Investment LLC.
$775,000
2 Beds ⋅ 3 Baths ⋅ 73573609 MLS ⋅ ACTIVE Status ⋅ ['The Pearl'] BLDG.
Historic loft at The Pearl with soaring ceilings, oversized windows, and original wood details. kitchen with premium appliances and stone surfaces. Private deck off the primary suite with radiant heated bath. Two off-street parking spaces, private storage, secure entry. Come and enjoy what Winthrop has to offer, beaches, paths, cafes, a golf course, public pickleball & tennis courts with easy Boston access. Special developer pricing now offered at 775,000 Seller reserves the right to accept, reject, or counter any offer and may request highest and best. Pricing and terms subject to change without notice. Buyers are encouraged to submit their strongest offer promptly.

1001 Shirley St Unit 3, Winthrop

Listing courtesy of Listing Agent: Vincenzo Caraglia from Listing Office: Sciaraffa Real Estate, LLC.
$524,900
2 Beds ⋅ 3 Baths ⋅ 73572947 MLS ⋅ ACTIVE Status
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.
$865,000
2 Beds ⋅ 3 Baths ⋅ 73567772 MLS ⋅ ACTIVE Status ⋅ ['The Pearl'] BLDG.
Historic loft at The Pearl with soaring ceilings, oversized windows, and original wood details. kitchen with premium appliances and stone surfaces. Private deck off the primary suite with radiant heated bath. Two off-street parking spaces, private storage, secure entry. Come and enjoy what Winthrop has to offer, beaches, paths, cafes, a golf course, public pickleball & tennis courts with easy Boston access. Special developer pricing now offered at 865,000.00 Seller reserves the right to accept, reject, or counter any offer and may request highest and best. Pricing and terms subject to change without notice. Buyers are encouraged to submit their strongest offer promptly.

1001 Shirley St Unit 2, Winthrop

Listing courtesy of Listing Agent: Vincenzo Caraglia from Listing Office: Sciaraffa Real Estate, LLC.
$979,900
6 Beds ⋅ 3 Baths ⋅ 73567723 MLS ⋅ PRICE CHANGED Status
Stop by our OPEN HOUSE Sunday 9/13 1:00-2:30 for a viewing. A fantastic value for this home. It’s an opportunity to make it your own, and enjoy the quaint town of Winthrop by the sea. 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 furnace, cent A/C, on-demand HW, mini-split heat pump/AC units, plumbing lighting, all providing peace of mind for years to come. Generous space, new paint & plaster finishes, & a beautifully finished basement for extra-living space, or entertainment. Kitchen has S.S. appliances and convenient 1st fl stacked washer & dryer. Outside large welcoming porch, groomed backyard, newer asphalt driveway, & an updated 2-car garage w/new overhead doors. Energy conscious buyers can assume the term note solar panels.

217 Pleasant Street, Winthrop

Listing courtesy of Listing Agent: Louis Bonavita from Listing Office: Benton Real Estate Company.
$739,000
3 Beds ⋅ 3 Baths ⋅ 73566786 MLS ⋅ PRICE CHANGED Status
Welcome to coastal living at its finest in this truly unique and beautifully appointed townhome residence. Spanning three expansive levels, this exceptional three-bedroom, two-and-a-half-bath home seamlessly blends comfort, style, and privacy in the one and only seaside community of Winthrop 02152. Privately situated with its own separate entrance, this rare offering lives like a single-family home and features direct access to its own secluded backyard retreat — a perfect escape for relaxing, entertaining, or enjoying quiet moments outdoors. Inside, thoughtfully designed living spaces are filled with natural light and offer the ideal balance of elegance and functionality. Just one block from the beach, enjoy the very best of coastal living- and only minutes from downtown Boston, Logan Airport, and public transportation MBTA Orient Heights Blue Line for an effortless daily commute.

189 Shirley St Unit 1, Winthrop

Listing courtesy of Listing Agent: Tammy Merk from Listing Office: Real Broker MA, LLC.
$629,000
2 Beds ⋅ 3 Baths ⋅ 73563678 MLS ⋅ ACTIVE Status ⋅ ['Hutchinson Street Condominiums'] BLDG.
Completely renovated to the core with quality craftsmanship throughout, this exceptional property blends modern sophistication with the relaxed coastal lifestyle that makes Winthrop so special. This beautifully finished two-level unit offers a bright, open layout designed for comfortable everyday living and easy entertaining. The main level features a beautiful white kitchen with modern appliances, quartz countertops and backsplash, and crisp, timeless finishes that flows seamlessly into the living area. Also on this level, a generously sized bedroom offers a private ensuite bathroom with double vanity and bathtub, along with a spacious walk-in closet. A convenient guest half bath, high ceilings, hardwood flooring, and in-unit laundry add to the ease and functionality of the home. Upstairs, the impressive primary suite offers a generous retreat with an oversized private bathroom featuring a double vanity, beautifully tiled shower, and spacious walk-in closet. Outside, dedicated garage parking and an electric vehicle charging station make coming and going effortless. Located within walking distance of some of Winthrop’s favorite neighborhood spots for coffee, lunch, and dinner, this home also offers easy access to transportation and major routes into Boston and beyond. When it’s time to unwind, Winthrop Beach is just moments away, offering the perfect setting for a peaceful shoreline walk, a relaxing beach day, or simply enjoying the calming ocean breeze. Winthrop isn’t just a place to live—it’s a lifestyle. This is a rare opportunity to own a completely move-in-ready property that combines modern luxury, thoughtful design, and the relaxed coastal lifestyle so many dream of.

21 Hutchinson St Unit 2, Winthrop

Listing courtesy of Listing Agent: Atiyeh Cassidy from Listing Office: Blue Sky Realty.
$1,230,000
3 Beds ⋅ 3 Baths ⋅ 73560746 MLS ⋅ ACTIVE Status ⋅ ['Seal Harbor Condominiums'] BLDG.
Experience elevated waterfront living in this stunning 3 bedroom, 3 bath penthouse at the prestigious Seal Harbor III. This exceptional two-level residence features a spacious open-concept floor plan designed to maximize natural light and showcase its spectacular waterfront setting. Entertain effortlessly or simply relax on the massive private deck, offering the perfect space to enjoy ocean breezes and breathtaking views. The kitchen boasts SS appliances, granite counters, Poggenpohl cabinetry and a breakfast bar. Enjoy the beautiful views while cooking. This 2 level unit offers the flexibility of a first floor bedroom and/or office. Nice open staircase. Lovely primary bedroom with en suite. There is a separate jacuzzi room which could become a home office if one chooses to do so. Seal Harbor III offers an unmatched lifestyle with exceptional amenities, including 24/7 concierge, a beautiful fireplaced lobby, an indoor heated pool and hot tub, a recently renovated fitness center, sauna, rooftop deck with panoramic views, outdoor swimming pool, tennis courts and multiple private resident gathering spaces. Additional highlights include a rare heated two-car garage, G9 and G11. Ideally located in the seaside community of Winthrop, you'll enjoy the tranquility of waterfront living while being just minutes from Logan Airport and downtown Boston, providing the perfect balance of coastal charm and city convenience. LUXURY, LOCATION, AND LIFESTYLE come together in this extraordinary waterfront Penthouse.

3 Seal Harbor Rd Unit PH33, Winthrop

Listing courtesy of Listing Agent: Cathie Curran from Listing Office: Charlesgate Realty Group, llc.
$765,000
4 Beds ⋅ 3 Baths ⋅ 73560385 MLS ⋅ ACTIVE Status
This is your opportunity to own in beautiful Winthrop by the Sea at an incredible value! This spacious 4+ bedroom, 2.5-bath home offers the perfect blend of character, updates, and an unbeatable location. Relax on warm summer evenings from the inviting wraparound porch, or take a short stroll just one block to Winthrop Beach for sunrise walks and ocean breezes. Inside, you'll find oversized rooms, high ceilings, original hardwood floors, a renovated kitchen, spacious mudroom, and flexible living space, including two bonus rooms on the third floor and a partially finished basement with a bar, built-in shelving, and full bath. Major updates include the electrical system, gas furnace, water heater, most windows, allowing you to move in with confidence. A detached garage with electricity adds even more convenience. Just two blocks from a playground and basketball courts, walking distance to Winthrop's popular restaurants, coffee shops, breakfast spots, the Winthrop Yacht Club, and the seasonal Winthrop Ferry to Boston, this home offers the low-maintenance affordable coastal lifestyle you've been searching for. This is your chance to own a large single family in one of the most desirable seaside communities!

546 Shirley St, Winthrop

Listing courtesy of Listing Agent: Christine D'Ambrosio from Listing Office: Bowdoin Real Estate Partners.
$975,000
3 Beds ⋅ 3 Baths ⋅ 73557515 MLS ⋅ ACTIVE Status
Brand-new construction in the heart of Winthrop, offering a rare opportunity to own a thoughtfully designed new-build townhome in a coastal setting just outside of the city. As construction progresses, buyers may have the opportunity to personalize select interior finishes, making this home uniquely their own. Spanning approximately 2,100 square feet across two levels, the home features an open-concept kitchen, living, and dining area, along with a first-floor bedroom, full bath, and welcoming entry foyer. Upstairs, two spacious bedrooms each offer a private en-suite bath, with conveniently located second-floor laundry. Enjoy a private yard, city views, and one dedicated parking space. Located just minutes from Boston, Logan Airport, Winthrop Center, beaches, local shops, and restaurants, this is one of only two newly constructed townhomes at this address... a truly uncommon opportunity in Winthrop.

200 Main St Unit 1, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
$625,000
3 Beds ⋅ 3 Baths ⋅ 73556640 MLS ⋅ ACTIVE Status
Luxury living with downtown Boston just a few Train stops away! Escape the hustle and bustle of the city and enjoy the best of coastal living, with the beach right down the street. Step inside to a spacious mudroom that opens to a stunning open-concept kitchen—perfect for entertaining. Gleaming hardwood floors, granite countertops, and sun-drenched windows create a warm and inviting atmosphere throughout. With three beautifully finished levels of living space, there is plenty of room to spread out and make yourself at home. At the very top of the home, the charming widow’s peak offers the perfect opportunity to create your own private reading nook—one that would make any book club jealous! The private, fully fenced yard is ideal for relaxing, entertaining, or gathering around a fire after a day at the beach. Completely renovated in 2019, this beautiful home is ready for its new owner.

189 Shirley Unit 2, Winthrop

Listing courtesy of Listing Agent: Doyle & Waldron Team from Listing Office: Coldwell Banker Realty - Easton.
$829,900
5 Beds ⋅ 3 Baths ⋅ 73556586 MLS ⋅ ACTIVE Status
Welcome to 43 Dolphin Ave, a 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. A perfect ADU or in-law space in the finished lower level with a oversized family room featuring a gas fireplace and bamboo flooring, a three-quarter bath, full kitchen with stainless steel appliances and second refrigerator, with a laundry area, along with a bedroom with a full sized cedar closet. Right out your lower door is an area to have a table or another sitting area under cover. 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!

43 Dolphin Ave, Winthrop

Listing courtesy of Listing Agent: Patricia Nunez from Listing Office: Redfin Corp..
$840,000
3 Beds ⋅ 3 Baths ⋅ 73526371 MLS ⋅ ACTIVE Status
This gut-renovated home delivers three levels of flexible living that is hard to replicate. The sun-filled entryway with built-in bench seating & ceiling fan sets a relaxed tone from the moment you walk in. The open main level flows seamlessly from the living room with hardwood floors, beamed ceilings, and built-in electric fireplace through the dining area with its own wine cooler and into a renovated kitchen with white beadboard cabinetry, quartz countertops, subway tile backsplash, and stainless appliances. The entire 2nd floor is dedicated to a private primary retreat, complete with two closets and a private en suite with glass shower. The sun-filled sitting room connects the suite to the 2nd-floor deck where ocean views make for the perfect spot for morning coffee or evening entertaining. A wood spiral staircase leads to the third-floor bedrooms tucked under vaulted ceilings. Corner lot with 2 driveways & the opportunity to expand the yard practically on the water in Pt. Shirley!

27 Billows St, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
$1,324,900
4 Beds ⋅ 3 Baths ⋅ 73452093 MLS ⋅ ACTIVE Status
Discover true beachfront living at 129 Strandway, where every day feels like vacation. Step from your back door directly into the sand and enjoy panoramic ocean views from the heated sunroom. The main level offers an updated kitchen with marble counters, a cozy fireplaced living room, two bedrooms, and a convenient beach-entry bath. The spacious second-floor primary suite provides its own private bath and sweeping coastal vistas. The fully finished lower level is one of only ten legal Airbnbs in Winthrop, offering exceptional income potential, or use it as an ideal in-law or au pair suite with its family room, bonus room, full bath, and laundry. Parking is effortless with two off-street spots and additional front potential. Low, transferable flood insurance at $1,138.00. Embrace waterfront living at its best.

129 Strandway, Winthrop

Listing courtesy of Listing Agent: Mark Savage from Listing Office: Byrnes Real Estate Group LLC.

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