The Olks’s friends, Marie and Mark Meyer, wanted to give them a house portrait as a thank-you gift after having spent a vacation week in the Olks’s third house in Telluride, Colo. The Meyers found Ms. Flecke online and put her in touch with Ms. Olk to work out the details: which view of the house to focus on, what time of day and time of year to place the house, what to include or omit.

Ms. Flecke spent an hour visiting with Ms. Olk, who led her around the house, pointing out vantage points that she wanted to have included in the final portrait. The artist took photographs to use as references back at her studio. Ms. Olk asked Ms. Flecke to omit any weeds or bald spots in the yard. She also asked her “to make every plant be in bloom.”

Requests to include one thing or another, such as plants in full bloom even when they’re not, are fairly standard. Other requests less so. “I’ve added children and pets to these house portraits,” Ms. Flecke said. “I once was asked to put an R.V. in the driveway, and I did.”

So far, no request has seemed too outlandish, and she has accommodated them all.

While landscape portraiture became a common endeavor for artists centuries ago, homes were rarely the principal subjects of the paintings. The Vanderbilt family commissioned artist John Singer Sargent to paint several family portraits in the late 19th and early 20th centuries, for example, but none of Biltmore Estate, their famed 8,000-acre property in Asheville, N.C. One house portrait painter of note, albeit fictional, was Charles Ryder, the narrator of Evelyn Waugh’s novel “Brideshead Revisited.” He was not taken very seriously as an artist, but his vocation was a convenient vehicle for exploring Brideshead Castle and the world it represented.