27. Biddeford, Maine
If you still want to enjoy white Christmases after you retire, Biddeford, Maine could be an ideal destination for you with its warm summers and traditional, snowy winters. Looking like a truly picturesque, storybook coastal town, Biddeford has all of the lighthouses, barns, and rocky beaches you could ask for. Fans of seafood will find an abundance of inexpensive, fresh local lobster and several local chowders. Biddeford has a rapidly growing local brewery and vintner scene, with Banded Brewing, Lorne vineyard, and Round Turn gin distillery being popular spots for nightlife and fine local microbrews.
Despite the historic and picturesque setting, the median home price in Biddeford is only $223,000, making it extremely inexpensive by East Coast and oceanfront standards. While Biddeford is relatively small, it is quite close to the large city of Portland, meaning many amenities and access to excellent health care facilities is only a short drive away. Retirees should be prepared to either buy a snowblower or hire some neighborhood shoveling help, as Biddeford is subject to the occasional lake effect snow and Nor’easter storm. The beautiful autumn leaf scenery is definitely worth the rare winter storm, though.