Point Shirley Homes for Sale

Welcome to Point Shirley, a hidden gem nestled in the charming seaside town of Winthrop, Massachusetts. This picturesque neighborhood, located in Suffolk County, offers a unique blend of coastal beauty and community spirit, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle near the water.

Point Shirley is renowned for its stunning waterfront views and easy access to the sandy beaches of Winthrop. Residents enjoy leisurely walks along the shoreline, breathtaking sunsets, and a variety of outdoor activities, from fishing to kayaking. The friendly atmosphere and tight-knit community make it easy to feel at home, while the proximity to Boston provides residents with the best of both worlds: a serene retreat and vibrant city life just a short drive or ferry ride away.

For those looking to make Point Shirley their home, there are a variety of charming houses for sale. Whether you're searching for a cozy beach cottage, a modern family home, or a luxurious waterfront property, Point Shirley offers diverse real estate options to suit every lifestyle and budget. Many homes feature stunning views, spacious yards, and easy access to the beach, allowing you to embrace the coastal lifestyle fully.

With its rich history, beautiful scenery, and welcoming community, Point Shirley is more than just a place to live—it's a place to thrive. Explore the homes for sale today and discover the perfect property to start your new chapter in this enchanting seaside haven.

Newest Point Shirley Homes for Sale

$729,900

4 Beds ⋅ 2 Baths ⋅ 73548082 MLS

Cape-style home in Point Shirley, steps from the beach and within Winthrop's most walkable stretch of coastline. Built in 1900 and updated with a remodeled kitchen featuring granite counters and recessed lighting, plus a remodeled full bath with a tiled tub and shower. Original hardwood floors run through the main level and all four bedrooms, paired with bay windows that bring in natural light and water views. The main level includes a living room with a fireplace, a formal dining room, and a sunroom that opens to a screened porch. Central air and forced air heat keep the home comfortable year-round. A full basement with sump pump offers storage and utility space, and a paved driveway provides two off-street parking spaces. Ocean views and public beach access nearby. Enjoy the best of coastal living, where the beach is just steps away & commuting to Boston is easy with quick access to the ferry, T stations, Rt. 1A, Logan Airport.

52 Pebble Ave, Winthrop

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

$855,000

3 Beds ⋅ 3 Baths ⋅ 73526371 MLS

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

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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