Winthrop Real Estate

Welcome to Winthrop, Massachusetts – a charming coastal gem nestled in Suffolk County, just a stone's throw from the bustling city of Boston. Known for its picturesque waterfront, Winthrop boasts stunning views of the Atlantic Ocean and the Boston skyline, making it a perfect blend of serene living with urban convenience.

With its rich history dating back to the early 17th century, Winthrop has maintained its quaint, small-town charm while offering modern amenities. The town is characterized by its friendly community, beautiful parks, and a vibrant local culture. Residents enjoy a variety of recreational activities, from sunbathing on the sandy shores of Winthrop Beach to exploring the scenic trails of the nearby Belle Isle Marsh Reservation.

Winthrop is also known for its diverse dining scene, with local eateries serving everything from fresh seafood to international cuisine. The town’s annual events, such as the Winthrop Beach Festival and the Winthrop Art Walk, foster a strong sense of community and provide opportunities to celebrate local talent.

Families are drawn to Winthrop for its excellent schools and safe neighborhoods, making it an ideal place to raise children. With easy access to public transportation, commuting to Boston for work or leisure is a breeze, allowing residents to enjoy the best of both worlds.

Whether you’re looking for a cozy seaside home or an investment property, Winthrop offers a unique lifestyle filled with charm, community, and coastal beauty. Discover the magic of Winthrop – where every day feels like a vacation!

Newest Listings in Winthrop

$835,000

6 Beds ⋅ 4 Baths ⋅ 73597515 MLS

COASTAL LIVING WITH INCREDIBLE POTENTIAL! This two family duplex is a must see for any contractor, savvy buyer or owner occupant looking to build equity with improvements. Each side features three levels of living space; three bedrooms, 1.5 bathrooms, in-unit laundry hook ups and separate utilities. Off street assigned parking for two cars and on street with a permit. Ideally located just steps to the ocean, public transportation to the Blue Line, and fun eateries. Whether you envision converting the property into two individual condos, living in one while collecting rental income from the other or adding this property to your investment portfolio, the possibilities are worth exploring, This two family needs updating and the asking price reflects the work needed. Bring your vision and unlock the potential.

11-15 Sturgis Street, Winthrop

Listing courtesy of Listing Agent: Mary Ann Cash from Listing Office: Charlesgate Realty Group, llc.

$365,000

2 Beds ⋅ 1 Baths ⋅ 73597184 MLS

A corner unit with a private balcony, this inviting 2-bedroom, 1-bath condo offers comfortable, low-maintenance living in one of Greater Boston’s most desirable seaside communities. Enjoy a bright, functional layout with flexible living space and the added benefit of outdoor enjoyment. Just minutes from Winthrop’s beautiful beaches, local restaurants, shops, and cafés, with convenient access to Boston. Whether you’re a first-time buyer, downsizing, or looking for coastal living, this is a wonderful opportunity to make Winthrop home!

200 Governors Dr Unit 19, Winthrop

Listing courtesy of Listing Agent: Mohamed Moutawakil from Listing Office: MS Golden Realty LLC.

$865,000

2 Beds ⋅ 3 Baths ⋅ 73596710 MLS ⋅ ['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. Unit is listed for sale and lease!

1001 Shirley St Unit 2, Winthrop

Listing courtesy of Listing Agent: Vincenzo Caraglia from Listing Office: Sciaraffa Real Estate, LLC.

$649,900

3 Beds ⋅ 2 Baths ⋅ 73596573 MLS

Coastal charm. City connections. Welcome to Winthrop. Set in this oceanside community with convenient access to Logan Airport and downtown Boston, 19 Beal Street pairs classic colonial character with modern living. Hardwood floors, an original staircase, and arched doorways bring warmth to the main level, which includes a bright enclosed front porch and dining room. The eat-in kitchen offers oak cabinetry, a gas range, a breakfast bar, and a sun-filled dining area. Upstairs are three bedrooms and a full bath, while the finished lower level adds a family room, a second full bath, and a kitchenette. An elevated deck overlooks the private fenced yard with a fire pit. Enjoy Winthrop's beaches, Ingleside Park, the Deer Island walking path, and the shops and dining of Winthrop Center, with the Blue Line and Winthrop ferry offering connections to Boston. A coastal setting with the city within reach, don't miss your opportunity to experience this special town.

19 Beal St, Winthrop

Listing courtesy of Listing Agent: Christine Goldstein from Listing Office: Lyv Realty.

$889,000

3 Beds ⋅ 2 Baths ⋅ 73596305 MLS

Welcome to 115 Read Street! Experience the perfect blend of modern luxury, style, and convenience in this stunning new construction townhouse style condominium in the heart of Winthrop! This beautifully designed 3-bedroom, 2-bath residence offers a spacious, open-concept floor plan featuring a sun filled living area, elegant dining space, and a gorgeous kitchen complete with top of the line appliances and quality finishes throughout. Enjoy the warmth and ambiance of electric fireplaces, generously sized bedrooms, and the comfort of your own private entrance. Thoughtfully designed across multiple levels, this home offers the ideal combination of space, functionality, and privacy. Additional features include off street parking, separate basement storage, and beautifully landscaped grounds. Ideally situated just minutes from Winthrop's beautiful beaches, local restaurants, shops, and downtown Boston, this exceptional property offers the best of coastal living with easy access to the city. Don't miss this incredible opportunity to own brand new construction in one of Winthrop's most desirable communities!

115 Read St Unit 2, Winthrop

Listing courtesy of Listing Agent: Michael Cimmino from Listing Office: Real Broker MA, LLC.

$869,000

3 Beds ⋅ 2 Baths ⋅ 73596306 MLS

115 Read St Unit 1, Winthrop

Listing courtesy of Listing Agent: Michael Cimmino from Listing Office: Real Broker MA, LLC.

$379,000

73596053 MLS

Build your Point Shirley home on a lot that already has Winthrop Zoning Board approval for a single family. The zoning work is finished, so you can go straight to design and permitting. Go up two or three stories and the upper floors open to ocean views and a clear line to the Boston skyline. Mornings on the water, evenings watching the city lights, and Logan and downtown Boston only minutes away. Located beside 54 Otis St. Also offered as land MLS 73594294. Fully approved lot for single family build, variance recorded with registry of deeds.

Lot 190 Otis Street, Winthrop

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

$629,900

2 Beds ⋅ 1 Baths ⋅ 73595832 MLS

HOME SWEET HOME! Are you ready to become a homeowner in the coastal Town of Winthrop? This well-priced, move-in ready Cape offers two bedrooms, a separate study, one full bath, dining room and an eat in kitchen. Situated on a 3,313 sq. ft. lot, this property also features off-street parking and a convenient location close to schools, shopping, Ingleside Park and the center of Town. With bus service to the Blue Line right on the corner, this home offers comfort, convenience and excellent value. Whether you're a first time homebuyer, downsizing or looking for a home to make your own, 96 Marshall St. is an opportunity you won't want to miss!

96 Marshall Street, Winthrop

Listing courtesy of Listing Agent: Mary Ann Cash from Listing Office: Charlesgate Realty Group, llc.

$625,000

3 Beds ⋅ 2 Baths ⋅ 73595787 MLS

This wonderful seaside home is ready to welcome its next owner! Located less than a block from Winthrop Beach, this lovingly updated single-family home blends modern style with warmth, comfort, and functionality. The stylish granite-topped kitchen features stainless steel appliances and an island, creating an inviting space for everyday living. Outdoor enjoyment is just as appealing, with a private yard offering room to relax, enjoy the outdoors, and take advantage of ample storage space. A welcoming porch extends the living area and provides a seamless connection between indoor and outdoor spaces. Ample parking is a bonus, including a second driveway. Enjoy the best of beachside living in a fantastic location and community just steps from the beach. Easy to show—don’t miss this opportunity!

17 Hawthorn Ave, Winthrop

Listing courtesy of Listing Agent: Luca Amara from Listing Office: LA Realty and Property Consulting, LLC.

$849,000

6 Beds ⋅ 2 Baths ⋅ 73595333 MLS

Work and Relax from one Prime location in Winthrop - between 2 great beaches, with proximity to the Orient Heights blue line MBTA subway to the airport and downtown Boston, and quick access to Route 1A to I-90 and I-93. Recently renovated 2-Family with new eat-in kitchens, stainless steel appliances, granite countertops, new bathrooms, new decks. The upper unit has 3 bedrooms, 1 bathroom, direct access deck from sliding patio doors off the kitchen - perfect for the alfresco meal and beverages; the first first floor unit has 2 bedrooms, 1 bathroom, rear deck out the common corridor. Separate electric & gas/heat. Just a mile to each beach, either Donovan beach or Winthrop beach, public amenities, golf course, boat club, and so much more. Great for an owner occupant and have your tenants pay your mortgage, or a pure investment, or both.

50-52 Bowdoin St, Winthrop

Listing courtesy of Listing Agent: Mac Chinsomboon from Listing Office: Coldwell Banker Realty - Boston.

$1,995,000

5 Beds ⋅ 4 Baths ⋅ 73594447 MLS

Truly exceptional waterfront Victorian, with glorious city and water views and direct private access to Boston Harbor and beyond, is historic yet fresh, sophisticated yet wonderfully livable! Head out on your boat to explore beaches and islands, restaurants and bars, or relax and enjoy spectacular water views from almost every room. The bespoke water-facing chef's kitchen, with a welcoming island, bar sink and beverage fridge, and suite of Bosch appliances, is an inviting place to gather, cook and linger. Adjacent, the family room beckons, sliding doors bring the outdoors in, and connect to a deck just steps to your own beach. Natural light changes with the day and seasons; the moody grays of winter will be perfectly offset by a cozy fire in the living room. Of course there's a dining room, inviting guests for memorable celebrations, family gatherings, and holidays! Upstairs five bedrooms are paired with more water views, a roof deck, and three tiled baths with elevated finishes. Charming original details go hand-in-hand with the 2026 updates, including ducted heating and cooling, highly efficient replacement windows, on-demand hot water, 400-amp electrical, hardwood flooring, new kitchen and baths, and more. Bonuses include a two car garage awaiting your roof deck and a clean, dry lower level media room w/ high ceilings! Close to restaurants, Winthrop Yacht Club, Winthrop Golf Course, five minutes to the blue line, 10 minute drive to Logan Airport and Boston. Enjoy coastal living with easy city access! Anticipated completion November 2026.

119 Washington Ave, Winthrop

Listing courtesy of Listing Agent: Nellie Aikenhead from Listing Office: Aikenhead Real Estate, Inc..

$379,000

73594294 MLS

Buildable lot beside 54 Otis St with Winthrop Zoning Board approval for a single family home. Build up and the second and third floors deliver ocean views plus a direct line to the Boston skyline. The zoning work is done, so a buyer can move straight to permitting. Minutes to Logan and downtown Boston. Also listed as a single family as separate MLS. Fully approved lot for single family build, variance recorded with registry of deeds.

Lot 190 Otis Street, Winthrop

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

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Winthrop Real Estate

Newest Listings in Winthrop

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