Winthrop, MA Homes for Sale

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Discover the charm of Winthrop, Massachusetts, a coastal gem offering a unique blend of seaside tranquility and convenient access to Boston. Explore a diverse real estate market featuring everything from historic homes with character to modern condos boasting ocean views. Life in Winthrop means waking up to the sounds of the waves and enjoying breathtaking sunsets over the Atlantic.

Beyond its beautiful homes, Winthrop provides a vibrant community atmosphere. Stroll along the picturesque beaches, indulge in fresh seafood at local restaurants, and explore charming shops. Enjoy outdoor activities like boating, fishing, and swimming, or take a relaxing walk through scenic parks and nature reserves. Winthrop's friendly neighborhoods and welcoming spirit make it a truly special place to call home.

Winthrop's prime location offers the best of both worlds. Enjoy the peace and quiet of a seaside town while remaining close to the cultural and professional opportunities of Boston. With convenient transportation options, commuting is a breeze. Experience the unique lifestyle that Winthrop offers – a perfect blend of coastal living, community spirit, and easy access to urban amenities.

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Winthrop, MA Homes for Sale

$619,000

3 Beds ⋅ 2 Baths ⋅ 73568805 MLS ⋅ ACTIVE Status

Opportunity knocks to own a beachside property!!! This highly desirable "tight knit" community have many homes that are passed down through the generations! This 3 bdrm, 1 3/4 bath Beach Bungalow is the perfect condo alternative with room to grow! The Main BDRM & FR have been fully renovated offering a Classic timeless design! New doors, recessed lighting, smooth ceilings, custom trim & crown molding, walk in closet, built in seating/cabinet, custom made covers for radiators, electric fireplace w/natural wood mantel & shiplap on the walls! Spacious bright and cheery Kitchen offers water views, New HDWD, New Paint throughout, Natural Gas range, New SS Refrigerator, DW and dining area! There's 2 additional rooms off of kitchen with water views, crown molding, new paint and HDWD. Large unfinished walkout (separate entry) basement has full bath w/shower stall, laundry, 3 door cedar closet offering endless possibilities to add an add'l 1200 sq.ft of living space! Updates also include Roof (2016), Washer & Dryer (2023), Hot water tank (12/2023). Conveniently hooked up to Town water & Town sewer. Front porch sunroom highlights beadboard ceiling, recessed lighting, HDWD flooring, surrounded by windows and adds an additional 144 sq ft of unheated space! Entertain friends, grill out, relax on your newly built expansive rear deck with steps to the beach! Start your day by catching the natural beauty of the "sunrise", swim, surf, sunbathe, kayak, paddleboard or head down the street in the evening for the amazing "sunset" views of the Boston skyline! Perfect year round or vacation home! Imagine living in a coastal neighborhood on a peninsula! Point Shirley residents enjoy all the amenities and Boston Harbor views at Coughlin Park & the "Deer Island" walking path! Bus service to Orient Heights train station, seasonal Ferry Service from Winthrop Landing to Seaport /Aquarium and only 5.6 miles to Logan Airport!

84 Tafts Ave., Winthrop

Listing courtesy of Listing Agent: Patricia Nemes from Listing Office: Century 21 Tassinari & Assoc..

$419,900

1 Beds ⋅ 1 Baths ⋅ 73568595 MLS ⋅ ACTIVE Status ⋅ ['Pauline Place'] BLDG.

Visit our open house on Sunday, Nov 1 from 11:30 AM to 1:00 P.M at 22 Pauline St. Winthrop and enter to win a FREE RAFFLE for gift cards to 4 local Winthrop Restaurants. There will be four winners with each winner receiving one gift card. Disappointed about high mortgage rates? No need to be disappointed! Pauline Place is offering 4.125% 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.

$399,900

1 Beds ⋅ 1 Baths ⋅ 73568569 MLS ⋅ ACTIVE Status ⋅ ['Pauline Place'] BLDG.

Visit our open house on Sunday, Nov 1 from 11:30 AM to 1:00 P.M at 22 Pauline St. Winthrop and enter to win a FREE RAFFLE for gift cards to one of 4 local Winthrop Restaurants. There will be four winners with each winner receiving one gift card.Disappointed about high mortgage rates? No need to be disappointed! Pauline Place is offering 4.125% 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.

$939,000

6 Beds ⋅ 3 Baths ⋅ 73567723 MLS ⋅ PRICE CHANGED Status

UNBELIEVABLE VALUE MEETS UNMATCHED OPPORTUNITY. The best value proposition in Winthrop. Sellers are highly motivated and have re-priced the property aggressively to prompt a sale. Buyers can secure instant equity for the newly optimized price point. Featuring over 2,600 square feet of living space (plus additional 600+ sq ft in finished basement) gleaming hardwood floors, fireplaces, a partially finished lower level, and a very welcoming front porch, every space invites you to relax, gather, and create lasting memories. Extensive upgrades, including updated electrical, plumbing, heating, central A/C and very efficient mini spit system. Outside, enjoy a good sized, fenced backyard, large 2-car detached garage, and plenty of off-street parking. At this price, opportunities like this are hard to find in this section of Winthrop! Come experience the charm, space, and value for yourself! Very easy to view! Book your appointment now before it is too late!

217 Pleasant Street, Winthrop

Listing courtesy of Listing Agent: Louis Bonavita from Listing Office: Benton Real Estate Company.

$723,999

3 Beds ⋅ 3 Baths ⋅ 73566786 MLS ⋅ ACTIVE Status

**To directly address high mortgage rates, SELLER WILL PAY CONCESSIONS of up to two discounted points to buy down the buyer's interest rate!** 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. CLOSING COST CREDITS available with purchase.

189 Shirley St Unit 1, Winthrop

Listing courtesy of Listing Agent: Living Coastal Group-Greater Boston & Northshore from Listing Office: Real Broker MA, LLC.

$529,999

2 Beds ⋅ 2 Baths ⋅ 73564816 MLS ⋅ ACTIVE Status ⋅ ['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: Living Coastal Group-Greater Boston & Northshore from Listing Office: Real Broker MA, LLC.

$335,000

2 Beds ⋅ 1 Baths ⋅ 73563869 MLS ⋅ ACTIVE Status ⋅ ['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: Living Coastal Group-Greater Boston & Northshore 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 gorgeous 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.

$549,000

2 Beds ⋅ 2 Baths ⋅ 73563560 MLS ⋅ ACTIVE Status ⋅ ['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.

$549,999

2 Beds ⋅ 2 Baths ⋅ 73561782 MLS ⋅ ACTIVE Status ⋅ ['Seal Harbor'] BLDG.

PRICE IMPROVED + $5,000 SELLER CONCESSION! Now offered at $549,999 this waterfront condo at One Seal Harbor comes with $5,000 back to the buyer, to use however works best for you. Put it toward closing costs, buy down your interest rate to lower your monthly payment, take it as a $5,000 credit to repaint in your own colors, or use any combination of the three.Enjoy direct ocean views from this sixth-floor, 2-bedroom, 2-bath home with 1,203 square feet of single-level living. The open living and dining layout flows out to a private balcony overlooking the water. It's the perfect spot for morning coffee or watching the sunset. Brand-new hardwood floors run throughout, and you also get in-unit laundry and central heat and air.The unit comes with one garage parking space plus on-site storage. One Seal Harbor offers a resort-style lifestyle with a concierge, pool, tennis courts, fitness center, sauna and steam room, clubroom, and beach access. The condo fee of $879/month covers water, sewer, building insurance, landscaping, snow removal, and professional management.You're just minutes from Winthrop Beach and the Deer Island walking trails, with a quick drive to Logan Airport and downtown Boston. At the new price, with $5,000 in buyer flexibility, this is one of the best values on the Winthrop waterfront. Schedule your private showing today!Seller concession subject to lender approval and guidelines. Select photos have been digitally enhanced or virtually staged for illustrative purposes. Buyer to verify square footage and all information.Select photos have been digitally enhanced or virtually staged for illustrative purposes.

1 Seal Harbor Rd. Unit 615, Winthrop

Listing courtesy of Listing Agent: Kevin Chiles from Listing Office: Charlesgate Realty Group LLC.

$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.

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Winthrop, MA Homes for Sale

Winthrop, MA Homes for Sale

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