From the pastoral woodlands of New Hampshire to the contemporary shoreline of Naples, Guy and Christina “Chris” Inslee enjoy the best of two starkly different worlds. Here, they drink in panoramic views of the Gulf of Mexico and Naples Bay from their perch on Gulf Shore Boulevard. “It’s like an alter ego—I kept pinching myself for the first 10 years we lived in Naples,” says Chris. “I’m glad to have the combination of historic New England and a modern high-rise.”
Near Portsmouth, New Hampshire, sits a thoughtfully—sometimes painstakingly—restored 1790s farmhouse called Hillside Farm nestled among maple, oak, and tulip trees on five and a half acres studded with granite boulders. It’s where they also relax and reconnect with their grown daughters, Blair and Paige, though they are never truly far apart. All four Inslees work together at their Inslee Wealth Management office in Portsmouth—one of the earliest family advisory practices at Merrill Lynch—founded by Guy and Chris in 1986. Chris was named among Forbes’ national list of the top 10 “Best-In-State Women Advisors” for 2024.
For years, Guy and Chris worked from both locales while Paige attended Community School of Naples. Today, their daughters conduct business from the Portsmouth office, though the firm has clients along the Eastern Seaboard and throughout the country.
“The bicoastal connection we have is special,” Chris says. “We love both places equally. That’s our new problem,” Guy adds.
Relevant Restorations
Guy and Chris have immersed themselves in historic properties—and learning how to restore them—since they married. In the 1990s, they traveled all over—think Monticello, Williamsburg, Mount Vernon, and many more—to learn about period proportions, sizes, materials, and colors. “It was important to us to restore with the right sensibilities—to have a sensitive eye toward restoration,” she says. “We wanted to learn the obligations and the benefits of living in an older home. It wasn’t point, click, and ship.”
The couple lovingly restored a 12,000-square-foot Vermont home—a Federal brick stagecoach stop—with a guest cottage and extensive formal gardens where the family resided for 25 years. Known as Coach Hill, it earned a statewide historic architectural installation award for the hand-turned, custom woodwork created by Guy and a talented local carpenter. Chris is the first to praise Guy’s creative genius. “He’s the driver of this,” she notes.
When the couple wanted to live closer to his sister in Portsmouth, Merrill Lynch welcomed an office in the quaint city. In New Hampshire, they owned the third floor of the historic Custom House, where 27 chests of tea delivered by the British East India Company were hidden in 1774 in the aftermath of the Boston Tea Party. In 2021, they bought Hillside Farm in the Kensington community after it immediately caught Chris’s eye—and captured her heart. At one time, it was home to 100 beehives and five acres of apple orchards surrounded by a stone fence. A 102-foot barn had connected it to the neighboring farm during the contentious presidential election of 1800 (Thomas Jefferson versus John Adams). The neighbors shouted political arguments to each other across the property in support of their opposing candidates, according to a local history book. That barn is no longer extant, though a white English barn with a stone foundation that was built into the hillside as a cider house remains, in addition to a circa-1860 yellow equipment barn attached to the house.
“The natural beauty is something we fell in love with the first time we visited the property,” Chris says. It also had the characteristics they’ve come to appreciate in centuries-old homes, including a covered porch with a swing, a welcoming kitchen, pine plank flooring, and bucolic vistas.
From day one, the hands-on Guy faced an arduous task, and though the home and grounds are an elegant picture of refinement, restoration of the barns is not complete. “This is the fifth old home renovation that I’ve lived through, and they’re never done,” he says wryly.
As with any mature house—especially one that’s more than 230 years old—many changes were made through the decades. Guy undid less-than-favorable modifications and added some of the couple’s own. “Someone had made the kitchen into two rooms with two fireplaces,” he says. Guy and his helpers took down an unworkable three-story chimney with a hammer and chisel, saving the bricks for a careful rebuild. “I took them down one by one,” Guy says. He also designed the pool and patio and collaborated with a hardscape designer to move 8,000 cubic yards of dirt. “Along the way, we found 3,000 to 4,000 stones” buried in the ground, he says, noting that New Hampshire’s moniker is, after all, the Granite State.
From sketching and drafting ideas on graph paper to refining plans with a computer-aided design program to swinging a sledgehammer, Guy is always actively involved in the structural work. At one time, he was chief painter, but he’s relinquished that role. “I might have been an architect if it wasn’t for what I do,” he says. “[Home restoration] helps get creative juices going.”
Guy believes the home, located at the top of a hill, was originally four rooms: two on the bottom and two on top. With changes made over time, it’s now “north of 5,000 square feet,” he estimates, and it has four fireplaces.
Two of the Inslees’ thoughtful transformations have made the home a true retreat. Guy designed a bedroom wing off the second floor of the library; it has a fireplace and wraparound French doors that provide spectacular views of the sunrise and sunset and the valley below. The restoration of the kitchen and its four-sided fireplace make it the home’s central hub.
“On mornings at the farm, I make coffee, and we wander the property,” Guy says. “We will see six or seven turkeys; we have foxes, deer, bobcats.”
Through the Generations
Guy has long been guided by the unseeable tug of his family’s rich ancestral line that’s intertwined with the earliest days of America’s founding. “My family came over at a variety of different points but all very early,” he says, noting the earliest ventured to the New World via the Caledonia and Mayflower. His people traversed the tides of history; they were inventors, naval commanders, soldiers, and farmers. His ancestor, Dr. James Craik, was Surgeon General of the First Continental Army during the American Revolution alongside General George Washington, later becoming his friend and personal physician. Guy also is a descendent of Major General Alexander Macomb, Commander in Chief of the United States Army from 1828 to 1841 and recipient of a Congressional Medal of Honor.
He grew up in a house that his great-grandfather built in the late 1800s, and his parents went on to buy and rehabilitate a historic property. “I got the love for old homes from them,” he says.
Before they met, Chris had become adept at basketmaking, and her creations hang throughout the New Hampshire home; some are four decades old. On their team, she is the colorist and the decorator. In their Vermont home, which had an incredible 80 windows, she created all the window treatments with historic-print fabrics. She will do so again at Hillside Farm.
The home is full of heirloom antiques and portraits of Guy’s storied ancestors. “Most of the portraits were handed down. Some we found at auction. In some way, shape, or form, they are somewhat significant to me,” he says.
As an associate member of the National Society of Colonial Dames of America in New Hampshire, Chris is also fascinated by—and appreciative of—the people, places, and events that shaped America. The couple revere the past through the homes that have stood sentinel as they sheltered so many ancestors and have done their part to restore them and bring them into the twenty-first century.
There’s a balance between keeping the old and upgrading to the new, Guy says. “I want to live here; I don’t want to live in a museum,” he says. “We wanted a place where we can gather and stay connected as a family.”
At Home in Naples
Before the Inslees moved to Naples more than two decades ago, Chris had a well-established track record of community volunteerism and leadership. “I have been on boards consecutively for 40 years with one interest or another in philanthropy.”
While living in Vermont, she was involved in several organizations. One of the highlights was serving as president and founding member of the Junior League of Champlain Valley. She naturally embraced The League Club in Naples, a 630-member organization comprising past and current members from Junior League chapters around the globe. “It has such a range of interests and such support for the community,” she says.
Chris jumped into the local organization, becoming a board member and vice president of communications, then public relations chair. She’s also served as public relations chair for the club’s popular Naples Tables fundraising event since the tablescaping extravaganza’s inception in 2019.
Guy, too, spends his time in service on various boards. He served on the Park Plaza board during two hurricanes and was president when Hurricane Ian struck. When they joined the Country Club of Na- ples, he sat on the membership committee for two years during the COVID pandemic.
“It’s important to give back and know where your talents can be beneficial,” Chris reflects about the couple’s charitable endeavors.
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