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$410,000
2 Beds 1 Baths NEW Status 73555750 MLS 902 SqFt.
Coastal living at its best! Just steps from the beach, this beautifully maintained 2-bedroom, 1-bath condominium offers the perfect blend of charm, comfort, and convenience. The bright, open-concept living and dining area flows seamlessly into a spacious kitchen featuring rich cabinetry, granite countertops, and large penninsula—ideal for entertaining. A sun-filled enclosed porch provides the perfect spot to enjoy your morning coffee or unwind after a day by the ocean. Additional highlights include low condo fees, ample street parking, generous private dry storage in the basement, and a small four-unit association. Whether you're looking for a year-round home, weekend retreat, or investment opportunity, this move-in ready condo offers an unbeatable location just moments from Winthrop's beaches, restaurants, and Boston.

25 Winthrop Shore Drive Unit 1, Winthrop

$489,900
3 Beds 1 Baths ACTIVE Status 73553580 MLS 1,036 SqFt.
Welcome to 16 Underhill Rd. #3, a beautifully updated 3-bedroom, 1-bath condo offering 1,036 sq. ft. of move-in ready living space. This bright and inviting home features modern updates, a functional layout, and private laundry in the basement for added convenience. Enjoy your own private deck, perfect for relaxing or entertaining. The property also includes a private garage plus ample additional parking—a rare find. Ideally located just moments from the beach, you'll love the convenience of coastal living with easy access to local shops, restaurants, and commuter routes. Whether you're looking for a primary residence or a low-maintenance lifestyle near the ocean, this turnkey condo is ready for its next owner.

16 Underhill St Unit 3, Winthrop

$499,900
1 Beds 1 Baths ACTIVE Status 73551484 MLS 947 SqFt.
Wake up to SPECTACULAR SUNRISES over the Atlantic and fall asleep to the soothing sound of OCEAN WAVES in this affordable OCEANFRONT UNIT at Seal Harbor Condominiums! Offering UNOBSTRUCTED OCEAN VIEWS from EVERY ROOM, this beautifully maintained home delivers the ultimate coastal lifestyle while being a short drive to Boston & Logan Airport! Gleaming HW FLOORS flow throughout the OPEN CONCEPT LIVING & DINING AREAS, where a PRIVATE BALCONY provides the perfect setting to relax w/the ocean as your backdrop. The updated kitchen features SS APPLIANCES, GRANITE counters, w/a FULL HEIGHT BACKSPLASH complementing the stylish cabinetry. A SPACIOUS BEDROOM & UPDATED FULL BATH with a wall of closets complete the space. Experience RESORT STYLE LIVING w/exceptional amenities including an inground pool, fitness center, sauna, steam room, tennis courts, clubhouse, beautifully manicured gardens w/a gazebo, scenic oceanfront walking paths, recreational facilities & the convenience of a 24/7 concierge!

1 Seal Harbor Unit 210, Winthrop

$495,000
2 Beds 2 Baths ACTIVE Status 73550972 MLS 879 SqFt.
This like-new 2-bedroom, 2 bath condo at 34 Underhill Street delivers the finish level of new construction at a fraction of the cost. Gut renovated and converted in 2020, every detail was approached with care, from the white shaker kitchen with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including gas cooking, to the wide plank hardwood floors that run throughout the entire unit. The primary bedroom features a custom walk-in closet with built-in shelving and drawers, and direct access to a full bath. The open living area is bright and generously sized with recessed lighting and mini-split systems for year-round comfort. Ground-floor entry with private access adds convenience rarely found in condo living. Set steps from the Winthrop coastline with the Boston ferry, Rt. 1A, and Logan Airport all just minutes away, this is a turnkey home in a location that continues to attract buyers who want coastal living without sacrificing quality.

34R Underhill St Unit 3, Winthrop

$499,900
1 Beds 1 Baths EXTENDED Status 73542366 MLS 623 SqFt.
LAST ONE BEDROOM UNIT. Discover the perfect blend of modern design and seaside charm at 140 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This one-bedroom home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you’ll find engineered hardwood flooring, recessed lighting, and a bright, open-concept layout ideal for everyday living or entertaining. The contemporary kitchen features double-stacked soft-close shaker cabinets, quartz countertops, and stainless-steel appliances, creating a clean and timeless look. Enjoy the comfort of central heating and cooling, elevator access from the elegant lobby, and garage parking. Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston’s best-kept secrets.

140 Shirley Street Unit 330, Winthrop

$499,000
1 Beds 1 Baths ACTIVE Status 73536723 MLS 683 SqFt.
Welcome to Unit 405 at The Somerset, Winthrop’s premier boutique condo community, where coastal charm meets modern design. This bright, open 1-bedroom, 1-bath home features a spacious living and dining area perfect for relaxing or entertaining plus a flex area for those who work from home. The kitchen blends style and functionality with quartz countertops and stainless steel appliances. Enjoy a pet-friendly building, a fitness studio, elevator access, and a resident lounge ideal for connection or remote work. Located in the heart of downtown Winthrop, steps from local shops and restaurants, and with a quick, easy commute to downtown Boston via the Blue Line or seasonal ferry, Unit 405 offers the perfect combination of seaside living, modern comfort, and effortless city access.

10 Somerset Unit U405, Winthrop

$485,000
1 Beds 2 Baths ACTIVE Status 73535636 MLS 591 SqFt.
Stunning water views from every angle make this exceptional condo truly one of a kind. Enjoy breathtaking sunsets over the Boston skyline and harbor from the comfort of your own home. Nestled in the charming seaside community of Winthrop, you'll experience the perfect balance of coastal living and city convenience. The ferry is just one block away, offering a scenic and stress free commute to Boston. Unit features tasteful upgrades, including a custom kitchen marble backsplash, quartz countertop and boasts not one, but two private decks featuring Trex decking. Unit 7 is widely considered the premier residence in the building, featuring the largest private waterfront-facing deck an ideal setting for morning coffee, outdoor dining, or simply taking in the spectacular views. Vinyle double hung windows with thermopane glass. Just in time for summer, this rare offering presents an incredible opportunity to enjoy, waterfront living at its finest.

600 Shirley St Unit 7, Winthrop

$495,000
ACTIVE Status 73530360 MLS 1,900 SqFt.
Priced to Sell! This is your opportunity to purchase a versatile 2 unit commercial building located in Metcalf Sq in the Central Business District. The CB district allows for many possibilities such as mixed use & retail/office, etc.. and is a blank canvas for any investor, business owner or developer to transform/redesign this property to suit their needs with loads of potential to increase revenue. Current use is Office space, featuring a 1st floor unit w/great exposure, full windows, open layout suitable for office or possible retail. The 2nd fl unit has character & is bright and sunny w/2 large open areas, vaulted ceilings, (2) private offices, loft area, kitchenette and a private enclosed porch. The front entry is warm & inviting with 2 common restrooms, a nice size yard and a full walkout basement. Winthrop is a wonderful place to open/relocate a business or to invest in. there is meter-less street parking & municipal lots nearby.

11-13 Pauline St, Winthrop

$495,000
2 Beds 2 Baths UNDER AGREEMENT Status 73529956 MLS 903 SqFt.
Gut renovated and converted in 2020, this upper-level 2-bedroom, 2-bath condo at 34 Underhill Street brings new construction finishes to one of Winthrop's most sought-after pockets. The white shaker kitchen is fitted with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including electric cooking. Wide plank hardwood floors & high ceilings run throughout, and recessed lighting and energy efficient mini-split systems keep the space comfortable year-round. The primary bedroom includes a custom walk-in closet with built-in shelving and drawers and direct access to a full bath. Upstairs positioning means added privacy and elevated sight lines in a building where no detail was overlooked. The Boston ferry, Rt. 1A, and Logan Airport are all minutes away, and the Winthrop coastline is right at your doorstep. Turnkey condition, standout finishes, and a location buyers keep coming back to.

34 Underhill St Unit 4, Winthrop

$499,000
2 Beds 1 Baths ACTIVE Status 73529631 MLS 1,006 SqFt.
Ultimate beachside living awaits in this stunning top-floor condo with direct ocean views and two private decks! Located across from Winthrop Beach, you can wake up to the sights and sounds of the Atlantic right from your bed. The sun-drenched interior features high ceilings, hardwood floors, and an abundance of windows that flood almost every room with natural light and ocean breezes. The layout boasts an updated, functional eat-in kitchen and a modernized bathroom. For added flexibility, a lower-level bonus room with a large walk-in cedar closet makes the perfect home office or guest space. Convenient amenities include deeded parking and in-unit laundry. Whether you are sipping morning coffee on the deck listening to the waves or enjoying a stroll along the shore, this stylish coastal retreat makes every day feel like a vacation—all just minutes from downtown Boston!

52 Trident Ave Unit 52, Winthrop

$485,000
2 Beds 1 Baths ACTIVE Status 73515219 MLS 913 SqFt.
Welcome home to this pristine and exceptionally well-kept two-bedroom, one-bath condominium in the heart of Winthrop’s vibrant 02152 community. This inviting home offers comfortable living along with private outdoor space—perfect for relaxing, entertaining, or enjoying coastal breezes. Conveniently located with easy access to Orient Heights, major highways, Logan Airport, and downtown Boston. The location of 43 Sagamore makes commuting simple while still enjoying the charm of a seaside town. Winthrop Beach is just moments away, offering the perfect setting for everything coastal living has to offer. A wonderful opportunity to own and become part of this welcoming waterfront community. Ask about available mortgage options.

43 Sagamore Ave Unit 1A, Winthrop

$475,000
1 Beds 1 Baths UNDER AGREEMENT Status 73514946 MLS 623 SqFt.
Discover the perfect blend of modern design and seaside charm at 140 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This one-bedroom home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you’ll find engineered hardwood flooring, recessed lighting, and a bright, open-concept layout ideal for everyday living or entertaining. The contemporary kitchen features double-stacked soft-close shaker cabinets, quartz countertops, and stainless-steel appliances, creating a clean and timeless look. Enjoy the comfort of central heating and cooling, elevator access from the elegant lobby, and garage parking. Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston’s best-kept secrets.

140 Shirley Street Unit 230, Winthrop

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