Billy Howard’s life and career have been shaped by service, leadership, and a genuine desire to help others.

Growing up in Virginia, Billy developed discipline and determination through wrestling. He attended Longwood University on a wrestling scholarship, graduated and was commissioned as a Second Lieutenant in the United States Army.

Billy served for more than 21 years as an Army Aviation Officer and UH-60 Black Hawk helicopter pilot. During his military career, he supported combat and contingency operations around the world and served in numerous leadership positions before retiring as a Lieutenant Colonel. While serving, he also earned a master’s degree in Information Resource Management from Central Michigan University.

Following his military retirement, Billy continued supporting government and national security missions as a technical program manager overseeing complex intelligence and technology programs. He later transitioned into technology sales, helping provide intelligence software used to identify threats and support government missions around the world. He began as an individual sales representative and eventually advanced to Senior Vice President, leading the company’s government sales organization.

Outside of work, Billy has a lifelong passion for fitness, particularly distance running, and has completed multiple marathons. He credits both wrestling and running with teaching him the value of preparation, patience, and perseverance.

While Billy was working remotely and traveling extensively, he and his wife, Stephanie, spent nearly a year searching for the right place to begin their next chapter. After visiting The Villages through the Lifestyle Preview Plan, they immediately knew they had found something special. They were drawn to the people, activities, amenities, and remarkable sense of community. Soon afterward, they sold their home in Northern Virginia and became proud full-time residents.

Billy and Stephanie have three grown children, who have each built successful lives of their own in Virginia, North Carolina, and Colorado. After careers that took Billy and Stephanie across the country and around the world, they feel incredibly fortunate to now work together as real estate partners with Properties of The Villages.

Billy feels truly privileged to serve a community that has brought so much joy and fulfillment to his own family. He is passionate about helping others discover the friendships, activities, opportunities, and genuine sense of belonging that make life in The Villages so extraordinary.

For Billy, the greatest reward is helping people find not only a home, but also a lifestyle and overall experience that can enrich their lives for years to come.