34 | CAPE COD LIFE | MAY 2026 capecodlife.com | CAPE COD LIFE | 35Gather TogetherBy Leslie HattonPhotography by Edward Glick, BluWater Photography.This sprawling Cape Cod home was quite literally designed for big family gatherings—especially the multi-generational kind—where there’s room for everyone to spread out, yet no one ever feels far from the fold. And that’s because the owners, themselves parents to four active children, have an innate understanding of all that a family would want, need, and enjoy doing in a vacation rental. Scott Cheyne, chief operating officer at Pretty Picky Properties shares that, “Rain or shine, this home was made to be a playground. It was designed to be a place for making memories because that’s what vacations on the Cape are all about.” With multiple bedrooms and several thoughtfully designed living spaces, the home which was recently renovated, easily accommodates families of all sizes. A walk away from Nauset Beach, popular restaurants, shops, and summer’s favorite treat—ice cream—you may just park your car in the driveway of this Orleans home and leave it idle during your stay. From an outside glance, the home welcomes you with its quintessential Cape Cod feel—a front porch swing, comfortable Adirondack deck chairs, an American flag and lush blue hydrangeas. But the simplicity is a bit deceiving as the elaborate property is a multi-structure compound that consists of a main house, guest cottage, pool cabana, office/recreation center, and a freestanding snack shack. Inside, the home offers everything from spots where you can enjoy a leisurely morning coffee and the Wordle, to a friendly game of pool. Cheyne reflects on Cape vacations of years gone by, when families would cram into small spaces and share bedrooms and a singular bathroom. Not the case at the home affectionately named Northern Exposure. Sporting a total of five bedrooms and five full baths and three half baths, the property offers ample space for a group of twelve to enjoy. The main house has four decadently prepared bedrooms, each with its own full bath—no waiting in line for the shower here! Upstairs, the king primary suite is pure indulgence, with a grand ensuite, a gas fireplace for cozy nights, and a balcony that overlooks the whole compound—the perfect perch for grandparents.A private stairway leads to two more upstairs suites: one bedroom contains a king-sized bed, the other contains a queen—every guest getting their own little slice of luxury. On another floor, three queen beds share a stylish ensuite, perfect for kids, friends, or anyone who wants to crash in comfort. And the guest house located just steps away? A cozy queen bedroom that has its own full bath, giving visitors their own peaceful hideaway.
36 | CAPE COD LIFE | MAY 2026 capecodlife.com | CAPE COD LIFE | 37The pièce de résistance of this property: its many spaces and opportunities for having fun, in whatever form that may take for each individual guest. For those who love to plan and prepare a meal, the well-appointed kitchen in the main house is a dream. Stainless steel appliances, granite countertops, and a large island flow into a dining room/family room that has a gas fireplace and a pool table. If you need a moment for an important call or meeting, there’s a building off the main house with an office/recreation room complete with a television, half bath, and a bar as well as a pop-a-shot and large table for games. A favorite for the younger ones is the snack shack located off the pool area with a freezer, hot dog machine and a sliding serve window for endless hours of outdoor fun alongside the large saltwater heated pool and oversized hot tub. Take your grilling skills to the next level in the expansive rustic stone outdoor kitchen. The home itself is so well outfitted that many families find just as much joy staying in, cooking together, playing lawn games, or unwinding after a day in the sun. It’s the kind of vacation haven where both adventure and togetherness come together easily. To see additional images and to learn about all that Pretty Picky has to offer, such as full provisioning and concierge services, visit prettypicky.com and search for Northern Exposure: 010-OB. Alternatively, you can email [email protected]’s your vacation. Get Picky! ®Leslie Hatton is the editor of Cape Cod LIFEccmnh