Taste is a mysterious, subjective kind of a thing. One person’s “yuck” is someone else’s “aha!” One homebuyer’s teardown is another’s fixer-upper. When Cain Semrad and Damen Seminero first locked eyes on their future vacation home, they looked past the chain-link fence, the frog-filled pool, and the undeniably peculiar architecture, and all they saw was a quirky gem, screaming to be loved.

In 2013, Cain and Damen drew a two-hour travel circle around their home base of New York City. The couple had been together for 17 years and had reached the point where they were ready to trade in the weekend whirligig of the city social scene for a little relaxation. In their minds’ eyes, they saw themselves lounging on the veranda of an early 19th–century Greek Revival. After searching and rejecting for a year and a half, they came to an uncomfortable realization: such antique houses tend to have depressingly low ceilings and less-than-ideal locations. Then, while spontaneously checking out a town called Pleasant Valley, Damen and Cain stumbled upon: It.

Located at the end of a long driveway on eight elevated, heavily wooded acres, the strange four-bedroom house—the original structure was built in 1967 by the owner of a local millwork company—vanquished the couple’s Greek Revival dreams. Once they discovered that the site was surrounded by farms and protected wetlands, they pulled out the checkbook.

“During the two months prior to closing, we noticed the astounding amount of acorns on the property and named it ‘Acorn Hill,’” Cain recalls. By the time they moved in, the house had become simply “The Hill.”

To some observers, the home’s jolie-laide architecture might suggest a monster emerging from the primordial muck. “To us, it just appeared unconventional and unusual,” clarifies Cain.

The pair set about updating the home with fearless sledgehammering bravado. The scope of their involvement is nothing short of extraordinary. Their professional lives—Cain is the senior art director at fashion conglomerate Phillips-Van Heusen and Damen is the chief technology officer for Jonathan Adler—hardly suggest they might morph into construction super-heroes. But that’s exactly what happened.

No task was too daunting. In order to insure the house, they were obliged to chop down 220 trees, 50 of which they lopped themselves. “I ran out and bought a chainsaw,” recalls Damen, who did most of the hacking. “Cain read the brochure in order to prevent me from killing myself.” (A local company named Out on a Limb took care of the rest.)

The tree felling was a nice warm-up for the exterior rehab. “We designed the pool deck and outdoor area one month after we closed, on a napkin at the local diner,” Damen recalls. Their inspiration for the outdoor space came from the existing house and woods. The dilapidated pool house had sunk five inches into the mud. Brought back to its former splendor—with the help of local handyman/landscaper Dimitri Markou—it revealed itself to be a mini version of the main house. With a hand from artisan Gerry Doucette of Custom Decks, they surrounded the pool with a wood walkway. An unobtrusive aluminum fence allows the area to integrate with the forest.

After completely revamping the garage, they next installed a new program of exterior lighting and restored the original pagoda lights to their former glory. For the final touch, Damen says, they “restained the house and adjacent structures using one color, instead of the previous seven.”

Landscape work followed: First Cain and Damen painstakingly refurbished the brick walkways. Then they dug out and exposed many of the natural outcroppings of granite bedrock. The goal? “To make it look less Camp Crystal Lake,” says Damen, alluding to the fictional location of the Friday the 13th movies.

Then came the house itself. Looking at Damen and Cain—they are both on the small side—it’s hard to imagine them doing the literal heavy lifting. “Each piece of lumber for the twenty-foot-long beams was cut in the garage, and the finished beam was carried to the house, by us,” boasts Damen. “We measured ten times so we would only have to cut once. To install them we climbed up ladders, at opposite ends of the room, with levels. Once they were firmly bolted, we sanded and stained them.”

They also refinished the stairs, added the kitchen backsplash, and installed the medicine cabinets, the bathroom mirrors, all light fixtures, and cabinet hardware. They even restored the fireplace by faux-painting the bricks one by one.

“We take time to consider every moment in our home. That’s what makes the potentially incongruous parts jell.” —Damen Seminero, resident

Cain is a minimalist who avoids gaudy hues, while Damen tends toward a more exuberant style. A balance was achieved throughout the house. “Damen is the design instigator,” Cain admits. Says Damen: “We are both creative, with strong points of view, but I know what piece I want and for which location. Cain knows what color it should be. He also told me when to stop, if I started going overboard, and kept us non-fussy.”

“We worked hard, knowing the payoff would be our perfect retreat. We had no idea how much fun we would have.” —Damen Seminero

Once Damen had installed rugs and furniture, Cain brought in the finishing touches: “I came in at the end and added a layer of art, books, and decorative objets,” he says, noting that he likes to personalize guest rooms with tablescapes, à la David Hicks.

The couple enjoy sharing their rural idyll—and the local charm—with weekend guests whenever they can. “The Hill is located in one of the most beautiful corners of the Hudson Valley,” Damen points out, “with rolling hills and woods, oodles of quaint fairs, festivals, and farm stands.”

Cain, who hails from a small town in Nebraska and grew up surrounded by cornfields, is mesmerized by the environment: “My Instagram posts went from New York City street-style shots and art openings to obsessively photographing the amazing insects, flora, and geology on the property. I am having a total Charles Darwin moment.” Damen, who grew up in Chicago, is similarly bewitched: “After so many years of city living,” he notes, “we are digging the delights of the changing seasons.”

There is one dissenter, he adds. “Jack, our fifteen-year-old beagle, seems more at home diving for pizza crust on the streets in the East Village. He would rather snuggle up inside on a sheepskin rug than chase squirrels.”

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One Couple's Imagination Goes Wild at a 1967 Weekend Retreat