The Homes of Winthrop MA

Highland Real Estate is thrilled to announce our affiliation with Compass as the Highland Group at Compass. Compass’s remarkable growth has been nothing short of extraordinary. In just three years, Compass has become the top-selling office in Boston and is now the #1 brokerage in the United States. While we continue to operate from our Winthrop office, we’ve also expanded to 126 Newbury Street in Boston. With the addition of Compass’s cutting-edge technology and marketing tools, we’re elevating our commitment to exceptional customer service and attention to detail. Our marketing reach now extends across the Boston area and nationwide, providing unparalleled exposure for our sellers’ homes and enhanced service for our buyers.

Ask us about Compass's three stage marketing plan, Compass Concierge and Compass Coming Soon.

The Highland Group – Shining a new light on real estate!

Welcome to Winthrop, Massachusetts! This charming seaside village is just minutes from the vibrant city of Boston. Residents enjoy an easy commute to Boston via car, the T, or the town’s new water shuttle, all within 20–30 minutes. Winthrop is a walkable community with miles of scenic seaside sidewalks offering breathtaking views of the Atlantic Ocean and the Boston skyline. Its sandy beaches are perfect for relaxing and soaking up the summer sun. While no place can guarantee absolute safety, Winthrop offers a welcoming, pleasant, and secure environment. Boston’s real estate boom has officially reached Winthrop!

Winthrop is home to a robust school system, including full-time kindergarten and grades 1–12. With two new elementary schools and a state-of-the-art high school, the town has made a strong commitment to its children. For boating enthusiasts, Winthrop boasts three yacht clubs and three marinas, making it a dream destination for boaters.

Winthrop’s vibrant restaurant scene has earned accolades from the press, offering a diverse array of dining options. 

The homes for sale in Winthrop showcase a rich variety of architectural styles, from late 1800s Queen Anne Victorians, Colonial Revivals, Greek Revivals, Italianates, and Gothic Revivals to more modern ranches, Colonials, and luxury oceanfront condominiums. These homes reflect a blend of elegance, craftsmanship, and history, catering to a wide range of preferences.

Winthrop residents are deeply engaged in their community and take pride in their beloved “Winthrop by the Sea.” 

Come visit Winthrop by the Sea and discover why it’s such a wonderful place to call home!