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$979,000
4 Beds ⋅ 2 Baths ⋅ 73574628 MLS ⋅ ACTIVE Status
All offers due by Tuesday 9/15 at noon.Situated on one of Winthrops most desirable tree-lined streets in the most sought after neighborhood- the Maze, this charming four-bedroom home blends original character with thoughtful updates and inviting spaces for everyday living.The welcoming living room features a built-in window seat and wood-burning fireplace. An updated kitchen with butler’s pantry opens to the formal dining room with built-in china cabinet. A first-floor bedroom or den, new three-season sunroom, and oversized full bath with laundry add convenience and flexibility to your first floor plan. Upstairs are three spacious bedrooms, including an expansive primary bedroom spanning the length of the home with versatile space that offers endless possibilities for a home office, nursery, or sitting area, its a true private retreat! Or create a future primary suite by adding a private bath and walk-in closet. A partially finished basement provides additional living space, while the large walk-up attic offers tremendous potential for future expansion. Outside, enjoy a fully fenced, paved backyard with patio, built-in fire pit, and grassy area for kids and pets. A three-car driveway and detached garage with electricity heating and air conditioning, provide excellent parking and storage or flex space for a home gym. Located in the heart of the Maze, beloved Emerson Road, known for its strong sense of community and annual Block Party really is a special place to call home!

41 Emerson Rd, Winthrop

Listing courtesy of Listing Agent: Christine D'Ambrosio from Listing Office: Bowdoin Real Estate Partners.
$710,000
4 Beds ⋅ 2 Baths ⋅ 73568640 MLS ⋅ ACTIVE Status
The perfect blend of comfort, convenience, and affordability! Whether you’re a first-time homebuyer, looking to downsize, or searching for an alternative to condo living, this charming 4-bedroom home offers the space you need with the low-maintenance lifestyle you want all just one block from the beach. The main level features a comfortable bedroom and full bathroom with a convenient walk-in shower, making one-floor living a great option for a variety of needs. You’ll also find main-level laundry, an eat-in kitchen, a convenient mudroom off the entryway to store shoes and umbrellas, and split-unit heating and cooling for year-round comfort. Upstairs are three additional generously sized bedrooms, each offering great closet space, along with a second full bathroom and central air to keep the entire second level comfortable during the warmer months. It’s an ideal low-maintenance alternative to condo living, while still offering the privacy and flexibility of a single-family home within minutes walk to a playground, beaches, restaurants, coffee shops, the public ferry to Boston and yacht clubs. Don't miss out on your opportunity to own in gorgeous Winthrop by the Sea!

542 Shirley St, Winthrop

Listing courtesy of Listing Agent: Christine D'Ambrosio from Listing Office: Bowdoin Real Estate Partners.
$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.
$715,000
4 Beds ⋅ 2 Baths ⋅ 73548082 MLS ⋅ ACTIVE Status
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.
$1,199,999
4 Beds ⋅ 4 Baths ⋅ 73521657 MLS ⋅ ACTIVE Status
Nestled on a peaceful street between the shoreline of Donovan's Beach and the green space of Ingleside Park, this beautifully renovated single-family home offers exceptional flexibility and comfort across multiple levels. Thoughtfully updated from the rooftop to the lower level, the home is truly move-in ready with modern finishes and inviting spaces throughout. Sun-filled interiors create the perfect balance of open gathering areas and quiet workspaces, while large windows bring in abundant natural light. Designed for both everyday living and entertaining, the layout provides versatility for a variety of lifestyles. Step outside to an incredible outdoor setting ideal for relaxing, dining, and enjoying every season. With coastal charm, nearby recreation, and turnkey convenience, this home presents a rare opportunity to enjoy the very best of Winthrop living.

70 Edgehill Rd, Winthrop

Listing courtesy of Listing Agent: Kelvin Peters from Listing Office: Redfin Corp..
$799,999
4 Beds ⋅ 2 Baths ⋅ 73517107 MLS ⋅ ACTIVE Status ⋅ ['Seabreeze Condominium'] BLDG.
Direct Ocean Front Living. Feel like you're on vacation every day! This spacious 2 level,7 room, 4 bed, 2 bath condo is located Directly on Yirrell Beach. The sand in your own back yard. Ocean breeze and sounds of the waves crashing onto the shore, are sure to relax you after a long day.Every day the the view is different. Featuring beautiful cherry hard wood floors, Family room, Formal dining room, ( Living room-could be master bedroom) the beautiful kitchen has cherry cabinets granite countertops, stainless appliances sliders to the large deck facing the sandy yard and Beach. This is one of a kind and Direct Ocean front living. All the rooms are large with plenty of character. Walk in closets and Laundry room make this for easy living. Bus line to the Blue line and Water shuttle into Boston is just a couple minutes away at the landing next to Winthrop yacht club. Marinas, shops and restaurants add to this great community. Don't miss out on this Opportunity to live Directly on a beach

876 Shirley Street Unit 1, Winthrop

Listing courtesy of Listing Agent: James Iannuzzi from Listing Office: Amo Realty - Boston City Properties.
$1,324,900
4 Beds ⋅ 3 Baths ⋅ 73452093 MLS ⋅ ACTIVE Status
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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