They Built Three Homes Together. Now She Must Do It Alone.

Sarah-Mai Miller and Heath Miller lived in 10 different houses and apartments in 17 years. The couple owned three of those houses — an 1800s saltbox in Greenport on Long Island and a modern cozy cabin and a glass cabin, both in a town called Milan in upstate New York.

The couple’s ventures in real estate were a natural extension of their jobs as creative directors. Together, they founded Chalk 242, a creative ad agency they’d named after the address of their first apartment in New York City, a prewar building on the Upper West Side. For the Millers, the lines blurred between work, play and home.

The two houses in Milan were nicknamed Maitopia and Mailan, a nod to Ms. Miller’s name. But they bore her husband’s out-of-the-box touches, like a lap pool within two steps of the backdoor of Maitopia, and, most curious to Ms. Miller, a bathtub in the middle of the tiny home. “I saw the designs for the tub and was like, ‘Really?’” she recalled.

In February 2023, Mr. Miller, 47, died in a head-on collision on a rural, dark road on the North Fork a few miles from their Greenport home. Mr. Miller was driving. His friend who was in the passenger’s seat, and the two occupants of the other car died.

Mr. Miller’s death left his wife stricken with grief, reliving every memory of what they had built together. The night Heath died, Sarah-Mai called her parents, who drove through the night to be with their daughter. Other friends and family members offered their support and presence in the coming days and weeks. Ms. Miller eventually went back “home” to her native Ohio after the informal celebration of Heath’s life in his hometown, York, Pa., where some of his family still lives. She returned to the saltbox home in Greenport weeks later to see if she could be there alone. She had a little company, Rufus, their dog. “It was so empty,” she said. “Every day was a reminder of how quiet it was.”

She lasted four days. It was time to let go, she thought. She listed the home. And then she listed Mailan, the ‘cozy-modern glass house’ upstate. And then she and her husband’s business partner, Max King, decided to sell Rest Co., a boutique hotel that her husband helped create out of a chicken coop. Piece by piece, Ms. Miller has spent a year shedding much of the property that they bought and renovated so she can pick up the pieces.

“I don’t think grief ends,” Sarah-Mai said. “But it changes.”

Doing What They Loved

The Millers met when they worked at the Columbus, Ohio, headquarters of Express, the clothing retailer. Mr. Miller’s job was running the creative direction for the brand, which included working with models and stylists for photo shoots, while Ms. Miller was hired as an internet coordinator, a novel title at the time that included dressing mannequins.

Mr. Miller had helped interview his future wife for her job and wanted to pass on her for a more experienced candidate. Ultimately, the person in charge of Customer Relationship Management overruled him.

Two months later, they began dating, Ms. Miller said, recalling how Mr. Miller’s nattiness was a bit intimidating. “I grew up in small-town Ohio where there’s no such thing as fashion,” she said. “Heath was stylish. He cared about his appearance.”

That carried over to the décor of his apartment. The first time Ms. Miller visited, he apologized for the “mess,” she recalled, laughing. “It was the cleanest and nicest apartment I’ve ever seen.”

Less than a year later, the couple moved to New York. Their first apartment in the city was on 242 West 104th Street, which they renovated shortly after buying it, applying a mix of modern aesthetics with old-school New York grace, plus a dash of industrial.

They got married in Turks and Caicos in June 2008, which happened to have been their first vacation spot together more than a year earlier. Heath’s son, McKenzie, who was 12 at the time and from Heath’s previous marriage, was also in attendance. They’d return to Turks and Caicos many times after their wedding, staying at the same hotel and going to their favorite beaches.

New York was a cultural initiation. In addition to trying out as many new restaurants as they could, they loved frequenting museums and art exhibitions, where they sought inspiration for their jobs. This inspiration would eventually spill into many areas of their lives — home décor, wardrobe and the business they were planning.

By this time in their careers, having grown weary of corporate power and the way stakeholders sometimes dilute creativity, the newlyweds talked a lot about doing work that they both loved as opposed to work they thought they needed to do. “A good idea is going to be polarizing,’” Sarah-Mai recalled Heath saying, a philosophy that would one day factor into their attitudes around designing their living spaces.

Chalk 242 was born.

Maitopia

While they were building their business, the Millers were looking for a second home, out of the city. They were flexible on locations within a two-hour radius and eventually found a three-acre parcel of wooded land on Willow Glen Road in Milan, with an adjacent stream. Mr. Miller had no technical know-how, but he was determined to design the home himself, Ms. Miller said. “It paired with his design aesthetic and background,” Sarah-Mai said. “Something just clicked for him. He could see it really clearly.”

Within a year of purchasing and clearing the land, Mr. Miller had come up with the designs for the home, featuring a one-bedroom lofted structure with a peaked roof and that lap pool that they could jump in just by opening the back door. The giant pivot door that swings open to the small pool, for instance, took Mr. Miller, three of their friends and a contractor to install.

Mr. Miller seemed to be on to something. The peaked roof, negative space and glass windows, like hefty fragments of a geometric puzzle made what is essentially a one-room, tiny house feel more spacious.

And they kept it bare: “When you’re going from one location to the next, you’re always bringing this stuff with you, and you don’t want to be surrounded by stuff. You just want to be in a place that’s welcoming and clean.” That made it easy when they decided to rent it out through online booking sites.

One of their frequent renters was Tina Roth-Eisenberg, the designer best known for her blog Swiss Miss. Ms. Roth-Eisenberg started posting pictures of Maitopia to her social accounts whenever she rented it, stunned by the creativity and attention to detail. In an Instagram post dated Nov. 12, 2021, she wrote, “I’ll never forget the moment when we entered the driveway, in spring of 2016. There she was, this modern, tiny beauty. As we got out of the car my daughter noticed the Swiss cross” on the shed “and jokingly said, ‘This house was waiting for you, mommy!’ It felt like fate, but she later learned that Mr. Miller had hung it there because he enjoyed the graphic appeal of the cross, its clean lines. Ms. Miller had been a fan of Ms. Roth-Eisenberg for years and they soon became friends.

By 2020, they had bought the lot across the road and constructed a new home that they called Mailan. They found an eager buyer for Maitopia: Ms. Roth-Eisenberg. Wanting to give an offer in person, Ms. Roth-Eisenberg met the couple in the city with a houseplant and illustrations of Maitopia that her children had made. “It felt like an adoption,” Ms. Roth-Eisenberg said. “Like I adopted this labor of love.”

Mailan

As a child growing up in Ohio, Ms. Miller had seen a glass house and told her mother she wanted to live in one just like it. Mr. Miller had always been obsessed with the glass house that the architect Philip Johnson had constructed in New Canaan, Conn., which seemed to rise out of the grass, equal parts stately and understated.

Mr. Miller’s creation was smaller, but it was grander than Maitopia with two bedrooms, two full baths, plus an open living room area with wood floors and wood slat paneling along the exterior. She relished the view that was the wood-burning stove looking out onto the pool, and the woods beyond it. Those woods contained “fun little elements,” Ms. Miller said, “like the treehouse that Heath and his son, McKenzie, had built. Heath was a creative. He had to always create or else he’d get restless.”

The Salt Box

Greenport on the North Fork of Long Island was a different vibe, neither woods nor straight beach, neither rural or suburban. The Millers had vacationed in Mattituck, a quick drive from the house in Greenport they’d eventually move to, and was recommended to them by family friends who had vacationed there.

Unlike Maitopia and Mailan, which they built from scratch, the Salt Box had been standing since the 1830s on a decently busy intersection where the Main Road meets Rt. 48, or what’s locally called the North Road. The Salt Box’s age, nearly 200 years old, and its shaker-style minimalism are what first attracted the couple. The wide-plank floors were originally part of the home, some of them over a foot wide, as was the impressive Dutch colonial style entrance with its stalwart trim.

When it came to the renovation, which began in April 2021 and was completed later that November, the Millers wanted to pay homage to the architect who built it, though they didn’t know who that was.

The important thing was that it exemplified simplicity and coziness, while permitting the modern theme that the couple had grown to love. They moved the kitchen from where the second bedroom downstairs currently stands, to the living room, incorporating the wood fireplace, while making the second room downstairs a library/study, replete with two high back chairs, a gas fireplace and built-in shelves that Mr. Miller constructed. “It was our dog Rufus’ favorite room. At night, when she slept in there, we’d put the fireplace on low and keep her comfortable whenever it was cold,” Ms. Miller said.

It was one of her favorite rooms, too. “All the homes we built had an intimate vibe to them,” Sarah-Mai said. “Heath was an extrovert and I’m an introvert, and our home was a space that felt like ours. If we did entertain, the space lent itself to smaller groups.”

But it was mostly just the two of them, plus Rufus, cooking meals, playing chess or cozying up by the fireplace. When they ventured out together, they enjoyed riding around the island.

Mr. Miller was out with his friend, William Price, whom he didn’t get to see often. Mr. Miller wanted to show off some of his favorite spots, and Ms. Miller stayed home to give them space and time to catch up. Mr. Price, who was a passenger in Mr. Miller’s Tesla, died, as did Peter Smith and Patricia O’Neill, passengers in a 2020 Ford Explorer.

Before Mr. Miller died, he and his wife talked about where to move next. They considered Charleston, after enjoying a two-month road trip down south when they were closing on the salt box. Ms. Miller is now thinking about Paris or staying put in Ohio or settling into her apartment in New York City. “I’m still learning not to get attached to things,” she said, remembering how she and her husband went from project to project. (She also lost Rufus, who was eight years old, in December.) “At that time, we said, ‘We need to keep going. We need to keep moving. We were collecting houses and memories.’”

Recently, she bought a saltbox-style home 20 minutes from her parents’ place in Ohio. She is about to start renovations.