Give summer the send-off it deserves this Labor Day weekend, and invite everyone to join. Family, friends, neighbors, and even the day’s hosts are guaranteed to appreciate and thank Mother Nature for a great season among the fine comfort and style of these luxurious outdoor spaces.
Whether it is hors d’oeuvres prepared in a sleek, fully equipped outdoor kitchen, a summer cocktail at a built-in poolside bar or the warm glow of a fire crackling late into the night, these homes make entertaining guests for the unofficial end to summer an effortless night to remember.
4 Manitou Road—Westport, CT
Resting on 2 acres of riverfront land, this spectacular Westport home offers views of the Saugatuck River through nearly every window of its bright, spacious design. The classic Nantucket shingle style residence embraces its beautiful natural setting with numerous ways to spend all hours of the day and night outside. Guests can enjoy an afternoon boat road right off the property’s deep water dock, a relaxing cool-down in the heated elliptical pool, and of course, can spend time chatting on the home’s many relaxing decks and patios. There is even a full stone fireplace surrounded by comfortable couches to complete the perfect evening outdoors.
28 Ox Bow Road—Egremont, MA
This country escape is one of two homes built on 46 acres of private land located off Ox Bow Road. Numerous outdoor amenities are featured on the property, including a custom gunite pool and pool house, built-in bar, patios, gardens and exquisitely crafted retaining walls. Enjoy a day by the pool sipping on your favorite drink from the convenience of the neighboring bar, read a book under the sun and let relaxing summer days never end at this wonderful summertime oasis.
32 Lincoln Lane—Purchase, NY
Labor Day guests and residents alike will revel in the wonder of this sophisticated Purchase, NY estate. A spa-like retreat awaits those who use the property’s luxurious pool house amenities and swim in the adjacent glass-tiled pool and hot tub. Hosts can prepare the ultimate Labor Day grilled dinner while using top-notch appliances present in the home’s outdoor cooking space, which offers drawers, as well as stone counters and tables. The reception lawn, located just beyond the ground’s beautiful rose garden, only adds to the estate’s welcoming appeal.
77 Bayberry Lane—Westport, CT
This Westport home situated on 3 private acres of landscaped grounds epitomizes the perfect spot for entertaining outdoors. Complete with a pool and pool house, in addition to many terraces and an outdoor fireplace with a tropical style, this home makes it so that no one will ever want the summer to end. Catch up with old friends and make new memories at this wonderful property that keeps the season’s warmth alive.
6 Opening Hill Road—Madison, CT
This incredible 1720 estate and guest home built by the renowned architect Philip Johnson flawlessly fuses historical charm and modern luxury together as one. On the home’s 6 acres of land, visitors will find a pool and stone-walled courtyard with extensive lawn areas perfect for entertaining. Hosts of the Labor Day event never even have to set a foot inside, as a full outdoor kitchen complete with appliances and a sleek, modern style rests conveniently on the residence’s poolside patio.
40 Rolling Hills Road—Ridgefield, CT
The day will surely be peaceful at this Ridgefield nature retreat that boasts the charm of country living and comfort all in one. Enjoy a relaxing weekend listening to the sounds of waterfalls, rest in the backyard gazebo, chat on the property’s numerous decks and patios and even make a wish at the residence’s koi pond. A built-in grill, fireplace and bar complete the property, which is naturally made for all the treasures of summertime in the country.
13 Big Trail—Sherman, CT
Say farewell to summer days under the sun at this beautifully renovated 1940s country estate. The grounds offer multiple opportunities for outdoor entertainment, encouraging all to fully enjoy the remaining warm New England days to the absolute fullest. Take a dip in the property’s in-ground pool, relax in the nearby gazebo and dine under the finely built fieldstone loggia. Labor Day at this Sherman home is effortless and the best way to say goodbye to another great summer.