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993 Shirley St, Winthrop
$815,000
5 Beds ⋅ 4 Baths ⋅ 73466654 MLS
Located in Winthrop’s highly desirable Point Shirley, this renovated single-family home offers generous living space, a flexible layout, and an unbeatable beachside location while still close to Boston & everyday conveniences.The main level features a renovated open floor plan with hardwood floors & tons of natural light, where living & dining flow seamlessly into a spacious, remodeled kitchen with granite countertops, upgraded cabinetry, stainless steel appliances, recessed lighting, shiplap details & a breakfast bar, perfect for everyday living or entertaining.Two bedrooms on the first floor offer added convenience, including a main bedroom with an en-suite full bath. Upstairs, you’ll find additional bedrooms & bathrooms, offering plenty of flexibility for home offices, guest rooms, or growing households, all featuring hdwd floors, natural lighting & ceiling fans. Enjoy Atlantic views, walks to the beach, off street parking & easy access to local amenities in this move-in-ready home.

993 Shirley St, Winthrop

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

1001 Shirley St Unit 3, Winthrop
$775,000
2 Beds ⋅ 3 Baths ⋅ 73573609 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. 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.

1080 Shirley St, Winthrop
$650,000
3 Beds ⋅ 3 Baths ⋅ 73486096 MLS
1080 Shirley St presents a rare two-family property with two separate structures, offering exceptional flexibility for owner-occupants or investors seeking strong rental potential. Ideally located just steps from the ocean in Winthrop, the property enjoys beautiful water views and a true coastal setting. The front unit features a spacious sunroom that fills the home with natural light, along with a bright and inviting living area. Originally built in 1930 and well maintained over the years, the property offers a combined 2,278 square feet of living space across both units, providing comfortable living and income potential. Outdoor space offers the perfect place to relax and enjoy the ocean breeze. Located moments from beaches, the marina, parks, restaurants, and local shops, the home also offers convenient access to public transportation and an easy commute to Boston. A rare chance to own a versatile coastal property in one of Winthrop’s most desirable seaside locations.

1080 Shirley St, Winthrop

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

54 Townsend, Winthrop
$620,000
4 Beds ⋅ 2 Baths ⋅ 73406145 MLS
Welcome to this delightful charming home located in the highly sought-after Point Shirley section of Winthrop.With 7+ rooms, 3+ bdrms, and 1¾ baths, this lovingly maintained home offers timeless character and stunning views. Begin your day on the charming front porch perfect for morning coffee, a good book, or an evening beverage while soaking in the coastal scenery. Inside, the living room features rich woodwork, wainscoting, and hardwood floors, creating a warm and inviting space.The updated kitchen combines modern convenience with classic charm, showcasing the original tall glass-front cabinets. A slider leads to a private backyard deck with pergola, ideal for entertaining or relaxing in your own outdoor oasis.The main floor also includes two versatile rooms one currently used as a home office and the other as a dining room. Upstairs, you'll find 3 rooms, offering incredible views and the potential to create a stunning primary suite. Don't miss this one! This is a keeper.

54 Townsend, Winthrop

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

19 Maryland Ave, Winthrop
$610,000
3 Beds ⋅ 1 Baths ⋅ 73434616 MLS
Discover your very own coastal retreat within 19 Maryland Ave. in Winthrop-By-The-Sea where the direct OCEAN VIEWS & serene salt water air will captivate you! If seaside living is what you're after, then look no further. Situated 3 houses from the water, this move-in ready, charming, 3 bedroom home is ready for you to start your next chapter. The layout offers your choice of a 1st or 2nd floor primary bedroom & the open concept living/kitchen area leads directly to a light-filled sunroom w/ oversized windows & direct access to the level, fenced-in backyard w/ a paver patio that begs for Fall fire-pits. This home isn't just a place to live-being steps from Yirrell Beach; offering breathtaking sunsets; & front-row seats to Boston’s elaborate & Winthrop's private July 4th Firework displays visible from the backyard/sunroom & seawall steps away, this home offers the best of Winthrop! Public Trans. is a short walk away making access to Boston a breeze! Don't miss this slice of paradise!

19 Maryland Ave, Winthrop

Listing courtesy of Listing Agent: Nikki Palladino from Listing Office: Lyv Realty.

86 Undine Ave, Winthrop
$450,000
1 Beds ⋅ 1 Baths ⋅ 73463015 MLS
This offering is about the land, the view, and the opportunity to own an affordable single-family property in an exceptional location. Located in Point Shirley, one of Winthrop’s most sought after waterfront neighborhoods, this shovel ready property sits above the Atlantic with wide open views of the ocean, Boston skyline, and the iconic Winthrop water tower. Walkable to the beach, yacht clubs, Winthrop Landing, and the ferry, with an easy commute back to the city. The existing single-family structure is currently dilapidated and presents a buyer with two paths: restore the home or pursue new construction. Zoning Board of Appeals approval has already been granted, making this a fully entitled, shovel-ready opportunity. A buyer simply needs to pull a building permit and begin construction. Existing structure is intended for tear down. Zoning Board of Appeals approval has already been granted and the project is fully entitled.

86 Undine Ave, Winthrop

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

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