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Five years ago, Nicole Tirapelli moved to Nantucket with her two young children. She had visited the Massachusetts island, with its quaint, maritime vibe, several times as a tourist and fantasized about living there though she was not particularly nautical. Trained as a chef and the onetime owner of a wedding cake bakery, she spent much of her professional life helping her father run a Ford dealership near Chicago.

“She was the cutest person ever working in a car sales job,” said her friend Meg Piercy, 41, a Chicago designer who owns the company MP Interiors and bonded with Ms. Tirapelli over a shared love of vintage artifacts.

After schools closed during the pandemic, Ms. Tirapelli, who is now 48, relocated to the island community of Siasconset (commonly known as “Sconset”). She bought a two-bedroom cottage a few blocks from the ocean and fixed it up with Ms. Piercy’s help. She helped manage local estate sales filled with captivating secondhand objects and became known on the Nantucket Consignments Facebook group as “the furniture lady.” Upon obtaining a real estate license, she applied what she knew about automobile sales to her new life selling houses.

As her son, Jack, now 14, and her daughter, Lily, now 16, matured, she looked for a house in Sconset with separate bedrooms for the children and found one that had been on and off the market for several years because of its poor condition.