Winthrop Highlands Real Estate

Welcome to Winthrop Highlands, a charming neighborhood nestled within the beautiful coastal town of Winthrop, Massachusetts. This picturesque area is a hidden gem, offering residents a unique blend of suburban tranquility and vibrant community life, all while being just a stone's throw from the bustling city of Boston.

Winthrop Highlands boasts stunning views of the Boston skyline and the serene waters of Boston Harbor, making it an ideal location for those who appreciate both natural beauty and urban convenience. The neighborhood is characterized by its tree-lined streets, well-maintained homes, and a strong sense of community. Families and individuals alike are drawn to the area for its friendly atmosphere and welcoming spirit.

Outdoor enthusiasts will find plenty to love in Winthrop Highlands. The nearby beaches, parks, and waterfront areas provide ample opportunities for recreation, from sunbathing and swimming to walking trails and picnicking. The neighborhood also features a variety of local shops, cafes, and restaurants, offering residents a taste of the local culture and cuisine.

Education is a priority in Winthrop, with access to quality schools and educational resources that cater to families. The community is also well-connected to public transportation, making it easy for residents to commute to Boston and explore all that the city has to offer.

Whether you’re looking for a peaceful retreat or a vibrant community to call home, Winthrop Highlands offers the perfect balance of both. Discover the charm and character of this delightful neighborhood and see why so many are proud to call it home!

Newest Listings in Winthrop Highlands

$549,000

3 Beds ⋅ 1 Baths ⋅ 73564952 MLS

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.

283 Revere St Unit 2, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

$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.

$629,000

2 Beds ⋅ 3 Baths ⋅ 73563678 MLS ⋅ ['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.

$585,000

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

Sixth-floor waterfront living at Seal Harbor in Winthrop Highlands. This 2-bedroom, 2-bath condo offers 1,203 square feet of single-level living with brand new hardwood floors throughout and direct ocean views from the main living space. The living and dining rooms flow together in an open layout, with a slider out to a private balcony where the water views are the main event morning and night. The kitchen sits just off the dining area with tile flooring and ample cabinet and counter space. Both bedrooms are well proportioned with new hardwood, the main bedroom comfortably fitting a king with room to spare and the second serving easily as a guest room or home office. Two full bathrooms, in-unit laundry, central heat and air, and a garage parking space beneath the building, and additional storage is available on site. Seal Harbor is a professionally managed, 127-unit brick building with a concierge, swimming pool, tennis courts, exercise room, sauna and steam room, clubroom, elevator, walking and jogging trails, professionally landscaped grounds with a gazebo, and beach access. The monthly fee includes water, sewer, master insurance, exterior and road maintenance, landscaping, snow removal, refuse removal, and management. The location puts you minutes from Winthrop Beach and the Deer Island trails, close to shops, restaurants, and public transportation, and a short drive to Logan Airport and downtown Boston. A rare combination of water views, garage parking, and full-service amenities at this price point.

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 ⋅ ['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.

$859,900

2 Beds ⋅ 2 Baths ⋅ 73554136 MLS ⋅ ['Seal Harbor Three Condominium'] BLDG.

A rare offering at the prestigious Seal Harbor III, this exceptional corner residence captures breathtaking panoramic water views from an expansive, light filled interior and a private balcony - perfect for enjoying morning coffee, evening sunsets, or simply taking in the every changing waterfront scenery. Completely reimagined with a full gut reno in 2010, the home showcases timeless design, an open concept floor plan, and impeccable craftsmanship throughout. Thoughtfully curated with luxurious finishes and custom details, the residence is designed for both elegant entertaining and effortless everyday living. The spa-inspired primary bath features a steam shower, while the versatile second bedroom-equally suited as a den or private office-is enhanced by a striking custom leather accent wall. Seal Harbor III offers an unmatched lifestyle with exceptional amenities, including 24 hour concierge, deeded garage parking 2 spots tandem(D41T), outdoor/guest parking, heated indoor pool/hot tub, outdoor pool, storage closet, clubhouse, tennis courts and so much more.

3 Seal Harbor Unit 336, Winthrop

Listing courtesy of Listing Agent: Cathie Curran from Listing Office: Charlesgate Realty Group, llc.

$615,000

2 Beds ⋅ 2 Baths ⋅ 73535066 MLS ⋅ ['Seal Harbor'] BLDG.

Seal Harbor I Gorgeous ocean views from this sunny corner 8th-floor unit. Spacious living room with slider to a private balcony-This home features two comfortable bedrooms with large closets and beautiful views, a well-appointed kitchen with ample cabinetry and updated appliances, plus a newer washer/dryer. Enjoy resort-style amenities including an in-ground heated pool, fitness area, and a private walking path along the ocean. Winthrop offers miles of beaches, the Deer Island walking path, yacht clubs, golf, great restaurants, and easy access to Boston and Logan Airport. Includes underground parking space D11. If you love coastal living, you will love it here.......

1 Seal Harbor Rd Unit 815, Winthrop

Listing courtesy of Listing Agent: Peggie Gilbert from Listing Office: Coldwell Banker Peggy Carter Team.

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