Jackie Lewis Chronicle photo by Michael Theis

Once upon a time Jackie Bailey and David Lewis went to Boonsborough High School. They were crazy about each other and everything was great until they graduated. Jackie had received a full scholarship to the prestigious Ringling School of Art in Sarasota, Florida; and David, a scholarship to play football at Catawba College in Salisbury, North Carolina.

On the drive to Sarasota, the family car stopped in of all places SharpsburgSharpsburg, North Carolina. Jackie knew it was a sign. And the sign said TURN THE CAR AROUND! “I cried my eyes outI couldn’t stopI missed DavidI didn’t want to go to FloridaI wanted to go home.”

Now stop me if you’ve ever heard anything like this one because I hadn’t, til now. Jackie’s mom and dad did not make light of their daughter’s misery. They realized that she was seriously heartbroken and time in the Gulf Coast sun wasn’t going to fix itbut they could. So they got back into the car and headed north again.

Meanwhile, at Catawba College, the misery was mutual. After one week without Jackie, David Lewis withdrew and went home.

What happened next, you ask ? Did Jackie and David work it outfinish schoolget married. Did they live happily ever after? You bet they did.

In the fifties, Vivien and John Bailey lived in Hagerstown with their three children, John, Jr., Cheryl and baby Jackie. When Jackie was three John Bailey died of pneumonia.

Vivien eventually found love again with another great guy named Dave Van Voorhis. They married, moved to Boonsborough and within a couple of years baby Annette rounded out the family at six.

Jackie adapted to high school in style. She wrote for the yearbook and the newspaper. She joined the Future Teachers of America and to no ones surprise, was elected president of the Student Council. And as mentioned at the beginning of the show, the tiny, blonde, over-achiever fell in love.

There are few in Shepherdstown who don’t know of Jackie and DL Lewis. She’s Jackie Lewis owner/broker of Greentree Realty. David, and old friend Paul Wilmoth, are partners in the thirty five year old DL Lewis Construction. Successful ventures both.

So they returned home from North Carolina and then what? Jackie enrolled in Stevens College in Baltimore to major in fashion design and marketing. David went to Shepherd and resumed his football career and worked his way through college at General Motors. After graduating from Stevens, Jackie went to work for the Herald Mail as an editor/writer/creative director.

The two were married on January 27, 1968 and looking back on it all Jackie Lewis said “We’ve been married for forty two years and I’d do it all over again” “Seriously, I really lucked out.”

Their first year was spent in Shepherdstown and then a move back to Sharpsburg. In 1973 Eric Lewis was born, two years later Brad and Brett Lewis came along and the growing family returned to Shepherdstown and built a home at Morgan’s Grove Park. “We owned a couple of race horses and one of them paid off and we used the money to buy a four-acre lot for a whopping $4,000. Dave was still with GM and I was home with a two year old and twins.”

Dave Lewis retired from GM in ’80 to devote 100 percent to building homes and that same year Jackie, Nancy Wilson and Judy Moore went into the real estate business together. Ten years later “It was time to spread my wings.” and with the encouragement of family and friends Greentree Realty was born. “Judy Moore and Greg Didden have given me so much advice over the years. They taught me well.”

The Lewis’ lived at Ledge-Lowe for twenty seven years. Their sons grew up and went off to college from there: Eric and Brad to Shepherd, Brett to Indiana University. It was Eric who called his folks six years ago from a farm on Engle Molers Road with news of a find “You have go to see this place!!” One hundred and sixty acres with a spectacular view of the mountains. They took his advice, saw it, bought it, built a home, actually several homes, and now “We’re here to stay. We love it.”

Eric is not in real estate he just knows a good thing when he sees it. A CPA with Ours, Lawyer, Lewis in Charles Town, he’s married to Joy and they live on Engle Molers with teenagers – Chandler and Maclaine. Brad Lewis, a property manager and GreenTree agent for twelve years, his wife Jainee Tinker and Bailey (2) live in Shepherdstown. They’re expecting baby #2 on Dec. 27th – Jackie’s birthday. Brett and Elizabeth Ishler are married and live in Reston with Sophie (3 ) and Kate (1 ). Brett’s in software management. Reston is much too far away for Sophie and Kate’s grandmother, who said “I keep myself open” for babysitting opportunities.

Grandmotherly, absolutely – but still back in high school at heart – having fun and taking chances. They’ve collected Corvettes and she’s has raced, owned race horses, and lent money to young promising entrapreneurs on a hand shake. “My husband loves poker” Jackie said “and he’s good at it. We’ve vacationed near casinos in Atlantic City, Connecticut, Las Vegas, all over. I antique while he plays, but Dave will go anywhere I ask. We just spent a week at Bethany with the whole family and next year we’re going to Normandy. We’re taking Chandler. Chandler loves history.”

Jackie started “her own thing” twenty years ago and since then the firm has received many awards. The Chamber of Commerce has named Greentree the Number One real estate firm in Shepherdstown, the firm has received The Journal Readers Best Real Estate Company nomination every year and top prize two years running. And though Jackie is very proud of the success and the people with whom she works, work is clearly not her life. She’s unabashedly family-first. Just hanging out together, babysitting, family vacationsthese times are her life.

Nonetheless, here is one of the best and most successful business women in the tri-state area so the question begged asking: What is your prediction about the future health of the local real estate market? “I’m not worried about Shepherdstown. If we keep the spirit which we have, people will always come here and fall in love.” Good answer. And, with a track record like hers, you just don’t bet against Jackie Lewis when it comes to business and to love.