By Ben McCarthy
It’s Tuesday and Maggie Sheehan is getting calls about a home in Raymore, MO. She’s making plans to make the drive from her Brookside home the next day to check out the property and see if she wants to buy it.
All of it.
In cash.
If she buys the property, it could be a three- to four-month process to turn it all around and getting the contents sold to new owners. What she can’t sell, will end up donated to local organizations, like the Rose Brooks Center. Everything on the property will usually end up with a new owner, but sometimes Sheehan will find a certain item that she can’t part ways with.
“My greatest ‘find’ is probably a first edition of Gone With The Wind,” Sheehan said. “I just found it hiding in a bunch of books and decided I was going to have to hold onto it.”
It’s one of the perks of working for herself since 2000 and growing Whole Estates throughout the metro area. She says her favorite part of taking on a new property is the moment where she gets to grab the keys from the title company and go look through everything for the first time. Right now, she’s keeping tabs on prospective properties from Sugar Creek, MO to Roeland Park, KS. She’ll find and buy properties anytime something enters her radar, even doing so on Christmas Eve.

“I’ve purchased almost 300 homes over the last 23 years, even ones with holes in the roof,” Sheehan said. “I’ve just always liked houses: we used to drive along I-70 to Colorado and I’d see an old, abandoned farmhouse on the way and I would just want to pull over and take a look inside.”
Sheehan didn’t have any real estate experience when she launched Whole Estates in 2000, but her entrepreneurial spirit had been on display around town even as a small child.
“There was a flower shop at 70th and Troost that used to dump the flowers they didn’t want in the back and I would go pick through them, put them in my wagon and sell them door to door,” Sheehan said.
Some of her first business forays included Maggie’s Helping Hands, which operated like a precursor to Uber and helped seniors get to the grocery store, doctors appointments, and other daily errands. Maggie’s Natural Creations was an organic dessert line featured at the now defunct Wild Oats Market on Broadway in midtown. Maggie’s mom, Peggy Sheehan, operated Sheehan’s Irish imports in Westport for decades, starting in the mid-80’s.
In the 90’s, Sheehan began purchasing and repurposing antiques, collectibles and household items. Through this, Maggie saw a niche where she could turn her love for old houses into a steady business.
“I discovered there was a huge need for people to have someone not just purchase individual contents from a home, but to help sell the whole estate as well,” Sheehan said. “Maybe someone had just passed or a family member was going into an assisted living facility – I could work with the family or the power of attorney so they don’t have to deal with a realtor or worry about having an estate sale.”

She still works from her home in Brookside, where she’s been for 28 years (near her childhood home at 61st and Charlotte). Sometimes she’s juggling up to three estates at a time, although she admits it does stretch her a bit thin. She’s surprised that more people don’t insist on a work-from-home or remote arrangement, and values the ability to conduct business on the go, wherever it takes her around town.
“I’ll sign some contracts on the hood of my car,” Sheehan said. “I work a lot around Brookside and Waldo, but I’m (frequently) traveling all over the city and finding new properties. I wouldn’t want to change that.”
Because Sheehan is a unique one-stop shop for people in the market, she has been able to thrive while still flying under the radar. Relying heavily on word of mouth referrals, and a basic website, she has bypassed much of today’s technology and tools. She’s kept the same landline phone number that she had 23 years ago, and works with many of the same contractors to rehab some of the more drastic reclamation projects she takes on.
“I go to folks who have a familiarity with these older houses and know what to look for,” Sheehan said. “I’m still the general contractor who has to buy all the materials, pick the paints, and get everything going.”
The concern I have is that in a housing development investors come in and purchase property at a distressed rate to be later rented which can open the door to individuals of questionable abilities. It is difficult if not impossible to vet individuals of questionable ethics due to the laws of the land and state.