A beautiful oceanside community situated at the entrance to one of the most beautiful harbors in New England! We are a peninsula of 1.6 square miles and boast some of the most spectacular views on the East Coast. On one side we have a panoramic view of the outer harbor and on the other we have the Boston Skyline and the inner harbor silhouetted against the sky. In between, we have the look of a quaint and friendly New England town with shops, parks, marinas, inns and miles of lovely beaches. An excellent public transportation system brings people to Winthrop from Boston in just 20 minutes and from the airport in five. Winthrop is also just a short boat ride away from many communities on both the North and South Shore. We like to think of Winthrop as the gateway to the North Shore. Settled in 1630, Winthrop is one of the oldest communities in the country. It was named for John Winthrop; a governor of Massachusetts and John’s son Deane Winthrop’s home, built in 1637 is now an historic site and museum.