On the Market: 5 Homes for Hosting a Picture-Perfect Holiday Gathering

By Grace Cassidy To herald the arrival of the holiday season, we’ve prepared a five-course feast of current listings across our regions that feature spectacular dining and gathering spaces for celebrating with family and friends. Bon appetit! The Hamptons, N.Y. Photo: Marissa Wagoner, Douglas Elliman Photography 359 Meadow Lane, Southampton, NY | $25,000,000 Sited on over five acres of land on Southampton’s Meadow Lane, this 6,200-square-foot bayfront retreat is ideal for entertaining, especially around the holidays. There are five bedrooms, six full bathrooms and two half-baths, providing ample space for hosting. Sliding glass doors in the dining room offer easy egress for a post-meal stroll outside. Long Island, N.Y. N Chestnut Hill Drive, Upper Brookville, NY | $7,800,000 This Upper Brookville home was designed with entertaining in mind. Situated on five private acres of land, the home includes seven bedrooms, seven full bathrooms and two half-bathrooms, as well as a kitchen equipped with brand-new marble countertops, gas range, pot filler, farm and prep sinks and center island. The nearby dining room offers ample space to accommodate all your guests, while walls of French doors bring natural light indoors. Massachusetts 53 Countryside Road, Newton, Mass. | $6,188,000 With a two-story foyer, floor-to-ceiling windows, a chef’s kitchen with commercial-grade appliances, a finished lower level and attached outdoor gazebo, this Newton home offers endless entertaining opportunities. Inside nearly 10,000 square feet, there are seven bedrooms and eight full bathrooms, allowing plenty of space for your guests to stay. Florida 1091 Hillsboro Mile, Hillsboro, Fla. | $33,000,000 Found on over an acre of land with 130 feet of private white sand beach frontage in beautiful Hillsboro, this nearly 10,000-square-foot retreat can be an ideal hub for family gatherings around the holidays. There are six bedrooms and six full bathrooms, a well-equipped kitchen, formal and informal dining spaces, as well as ample covered outdoor living space for enjoying the Florida weather. Texas 3808 Potomac Avenue, Highland Park, Texas | $17,500,000 Located in Highland Park, just north of downtown Dallas, this incredible 10,720-square-foot modern farmhouse-inspired estate features walls of windows, soaring ceilings, a sleek and stylish kitchen and an elegant, light-filled dining room. The Calcutta marble-clad bar and spacious patios elevate your options for entertaining. The home features six bedrooms, eight full bathrooms and three half-baths, offering plenty of space for overnight guests.