Winthrop Homes with Other (See Remarks) Style

Welcome to Winthrop, Massachusetts—a hidden gem nestled along the picturesque coastline of Suffolk County. Just a stone's throw from the bustling city of Boston, Winthrop offers a unique blend of serene suburban living and vibrant urban accessibility. This charming seaside town boasts stunning waterfront views, inviting parks, and a tight-knit community that welcomes newcomers with open arms.

Winthrop is known for its rich history and diverse culture, with tree-lined streets that showcase a delightful mix of architectural styles. From classic New England homes to modern townhouses, the real estate market here features a variety of options to suit any lifestyle. If you’re searching for homes with a distinctive flair, you’ll find that Winthrop has an array of properties that embrace the "Other" style—an eclectic mix that reflects the town's unique character. These homes often combine traditional elements with contemporary designs, creating spaces that are both functional and aesthetically pleasing.

Residents enjoy easy access to beautiful beaches, recreational activities, and a vibrant local dining scene. Whether you’re taking a stroll along the scenic shoreline, enjoying a day at the park, or savoring fresh seafood at one of the local eateries, life in Winthrop is a delightful experience.

With its perfect blend of coastal charm and urban convenience, Winthrop, MA, is not just a place to live—it's a community to thrive in. Explore your options today and discover the home of your dreams in this enchanting coastal town!

Newest Winthrop Homes with Other (See Remarks) Style

$769,000

3 Beds ⋅ 3 Baths ⋅ 73530174 MLS

Welcome to coastal living at its finest in this truly unique and beautifully appointed townhome residence. Spanning three expansive levels, this exceptional three-bedroom, two-and-a-half-bath home seamlessly blends comfort, style, and privacy in the one and only seaside community of Winthrop 02152 Privately situated with its own separate entrance, this rare offering lives like a single-family home and features direct access to an enchanting secluded backyard retreat — a perfect escape for relaxing, entertaining, or enjoying quiet moments outdoors.Inside, thoughtfully designed living spaces are filled with natural light and offer the ideal balance of elegance and functionality. Just one block from the beach, enjoy the very best of coastal living while remaining only minutes from Boston, Logan Airport, and public transportation for an effortless daily commute.A

189 Shirley St Unit 1, Winthrop

Listing courtesy of Listing Agent: Nicole Bettano from Listing Office: Lantern Residential.

$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.

$950,000

4 Beds ⋅ 2 Baths ⋅ 73509670 MLS

Wake up every single morning to beautiful, unobstructed water views from this home; sitting proudly on a rare, oversized lot. Positioned directly across the street from the water, this property offers the ultimate coastal lifestyle with endless space to expand, entertain, or build your dream outdoor oasis. Inside, you will find a couple of freshly painted bedrooms to offer a clean start, while the rest of the home is a blank canvas ready for your design ideas and style updates to make this home into your dream coastal escape. Whether you're planning thoughtful updates or a full transformation this is a unique chance to secure both location and land in a premier seaside neighborhood. Bring your vision and unlock the full potential of this remarkable coastal property. Now offered at a new improved price, this is a great opportunity for an oversized lot and water views on the market. Washer, dryer, and refrigerator are being left as gifts!

118 Sunnyside Ave., Winthrop

Listing courtesy of Listing Agent: Donna Scalfani from Listing Office: William Raveis R.E. & Home Services.

$549,900

2 Beds ⋅ 2 Baths ⋅ 73504907 MLS

MAJOR NEW RENOVATION IN 2023.......EXCITING 2 BEDROOM, 2BATH UPSCALE CONDOMINIUM AT WINTHROP CENTER. Stunning oak floors and state of the art quartz and stainless kitchen, fully applianced with subway tile accents and an over sized island with pendant lighting. All open to a generous living area and access to an exclusive deck for personal outdoor space. A beautiful main suite with an amazing custom marble bath along with another room as a 2nd bedroom or bonus room. Incredible guest bath has stackable laundry as well. Basement storage and off street parking provide all the extras you hope for! A very convenient location near restaurants, coffee shops, banks, bakery, schools and lots more! Discover all of the natural beauty of WINTHROP by the SEA, WHERE PRIDE OF OWNERSHIP CAN BE YOURS!

35 Somerset Ave. Unit 3, Winthrop

Listing courtesy of Listing Agent: Sharon Tallent from Listing Office: Compass.

$1,450,000

6 Beds ⋅ 6 Baths ⋅ 73499355 MLS

Set on a highly desirable corner lot at Sargent & Johnson Ave, this truly one of a kind home offers exceptional space and versatility. Welcoming foyer opens to a spacious living room, while the dining room features a covered porch with ocean views perfect for enjoying sunset evenings. The first floor also includes a bedroom and full bath, plus a kitchen with direct access to the backyard and one of two driveways. Just off the kitchen, a stunning glass walled sitting room overlooks the home’s standout feature: a large 40K gallon indoor in-ground pool. Additional highlights include a generous garage with expansion potential above. Second floor offers multiple baths, including a primary suite with private bath. The third floor functions well as an in-law suite with its own bedroom, full bath, and living area. Previously operated as a successful legal bed and breakfast, this property presents endless possibilities. Updates include roof 2023, newer pool liner. Perfect opportunity for ADU.

100 Sargent Street, Winthrop

Listing courtesy of Listing Agent: Elizabeth Ferrara from Listing Office: Cottage Hill Real Estate.

$599,000

3 Beds ⋅ 2 Baths ⋅ 73486365 MLS

Wonderful opportunity to own a coastal Winthrop home with tremendous potential. A welcoming mudroom opens to a spacious foyer and a large living and dining area with great flow for everyday living. A bonus front room offers flexible space for a home office, playroom, or an expanded open-concept layout. The kitchen leads directly to the back deck for warm-weather entertaining. Upstairs features two bedrooms, a smaller third bedroom, and a full bath. The lower level includes an opportunity to finish basement offering generous bonus space ideal for a family room, guest suite, gym, or creative studio. A small fenced-in backyard below the deck provides room for pets, gardening, or flexible outdoor use. Steps to the beach, coffee shops, restaurants, and public transportation, this home is sold as-is and ready for its next owner to bring their vision to life with meaningful long-term investment potential.

47 Highland Ave, Winthrop

Listing courtesy of Listing Agent: Elizabeth Ferrara from Listing Office: Cottage Hill Real Estate.

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