Cover Article | By Jocklyn Mundy
Our November Featured Family’s journey spans Special Weapons and Tactics (SWAT) service, the hosting of a syndicated TV show, being featured in national magazines, and entrepreneurial ventures. Most importantly, they are a couple who possess a remarkable combination of humility, compassion, and a genuine desire to serve others without seeking recognition. Meet Tom and Dawn Stroup.
Tom and Dawn are both from military families. Tom was born in Washington State, but most of his family is from Missouri. Dawn is originally from Plattsburg, New York. Her family is spread out all over the country, and when they get together, they enjoy meeting in the scenic surroundings of Lake Champlain, New York.
Dawn is a graduate of Northern Arizona University with a Major in Business and a Minor in Fashion Merchandising. After college, Dawn pursued opportunities as a Buyer in Orlando.
Tom’s journey to Central Florida had its challenges. Tom left high school to serve in the Army. Once out of the Army, he found himself in Kentucky, juggling two demanding manual labor jobs to provide for his family. A chance encounter with a stranger brought about a life-changing moment. Out of nowhere, an older man in a truck pulled up and said, “The police department is hiring,” then he drove off. Although it was a strange encounter, Tom knew it was a message that could not be ignored. With a newfound purpose, Tom earned his GED, cut his hair, and secured a position with the local police department. In time, Tom decided to leave Kentucky and move to Central Florida to be closer to family.
Tom believes in the power of the spoken word; he says, “Everything you say to people matters and could have the power to change their lives.” He has received wisdom from the least expected people and believes more people would also if they’d just listen.
When asked how he and Dawn first met, Tom, with a sly smile, recalls “Dawn and I met in 1982 in downtown Orlando at church,” he hesitates then clarifies, “Church Street Station”. Their connection flourished, and three years later Tom and Dawn were married at First Baptist Church in Orlando. Tom’s son Jarred was 9 at the time, and the three of them moved into the area now called “Waterford Lakes”.
Dawn had been a Buyer for Jacobson's Department Store since shortly after she moved to Orlando. Over her 17-year tenure, she cherished her role as the junior department Buyer and forged deep bonds with her colleagues. She has continued to maintain these relationships to this day. After the store’s closure in 1999, Dawn channeled her expertise into jewelry design and sales for a prominent supplier to Disney, a role she enjoyed for 15 years.
Tom began his career in Orlando as a Corrections Officer at the Orange County Sheriff’s Office before advancing to the role of Deputy Sheriff. During his tenure, he also dedicated himself to the SWAT (Special Weapons and Tactics) team as an operator. Ultimately, Tom earned the distinction of SWAT Commander, where he served for 8 years. Three decades later, he concluded his distinguished service at the Orange County Sheriff’s Office, retiring with the esteemed rank of Captain, and had his Master’s Degree in Criminal Justice from UCF.
A few years after getting married, the Stroups moved to Mt. Dora. Here they founded “Architectural Salvations,” a small side business crafting furniture from reclaimed architectural elements. Dawn’s design background combined seamlessly with Tom’s exceptional craftsmanship. Their creations, often sourced from old houses, churches, and historic structures slated for demolition, caught the attention of notable publications, including a feature in Bob Vila’s American Home magazine.
Tom also ventured into television, hosting NBC’s reality series “School Pride,” which spotlighted the transformation of underserved public schools across the U.S. Tom said, “I really enjoyed working on the School Pride project; seeing the impact we had on the communities was very fulfilling.” He also played a notable role in “Stars Earn Stripes” on NBC, a competition merging military drills with celebrity challenges.
During this time, he continually worked with the Sheriff’s Department, which took him all over Orange County. One of his duties was Marine Patrol on the Butler Chain. It was during this time that Tom and Dawn fell in love with the distinct and rustic feel of Windermere.
In the fall of 1999, Tom discovered a house in downtown Windermere. Most people would only see a small home that needed a lot of attention, but they saw so much more. They saw a unique 1920’s historic home with loads of character on a large double lot with beautiful trees, and it even had a separate workshop for Tom! It was perfect! They purchased their home in the fall of 1999, and with the help of friends and family, they transformed the space and moved in March 2000.
Over time, the Stroups have meticulously updated and restored their historic Windermere cottage, ensuring its preservation and original style and character. They added two spacious porches, which have become favorite spots for the couple to relax and greet neighbors. Word of Tom’s carpentry expertise, combined with Dawn’s flair for design, has spread. Their home frequently draws visitors eager to admire their quaint cottage.
Tom and Dawn did not take long to become an integral part of the Windermere community. Dawn has a deep sense of empathy and care for the struggles and challenges faced by others. She is quick to lend a helping hand and offer support to those in need, and she does not hesitate to make personal sacrifices to ensure their comfort and happiness. She says, “Nothing makes me happier than helping someone else.”
Tom is always quick to lend a hand, whether for neighbors, Family Church, or helping his friend, George Poelkner, work on restoration and design projects. Tom helped George with the restoration of the Old Windermere Schoolhouse. They also worked to rescue the historical materials from the former Windermere Police Station before it was torn down. George and Tom skillfully repurposed these salvaged pieces into unique designs that are now used in the new Police Department Building. Among those designs is a magnificent large conference table, as well as end tables that are featured in the Police Department lobby.
For years, Tom made it a priority to attend the Windermere City Council meetings and now serves on the board. He feels strongly that being an active participant in local governance is his civic duty. Tom says, “To bring about positive change and ensure the well-being of the community, it’s essential to be actively involved.”
Blessed with good health in retirement, the Stroups lead extremely active lives. They host a community walk that meets at the Town Hall every Monday at 5 pm. Everyone is welcome to join, regardless of age. Tom and Dawn love spending as much time as they can with their son, Jarred, who has dedicated 17 years as an Osceola Firefighter/Paramedic, their daughter-in-law, and their four beloved grandchildren.
Dawn, who was once deeply involved in competitive rowing, participating in both sweep rowing and sculling for 15 years, now finds solace in regularly practicing hot yoga. Tom maintains a disciplined daily exercise routine, complemented by his cold plunge. Family remains central to their lives; since their move to Windermere, 12 other family members have also chosen to call Downtown Windermere home.
The Stroups’ actions consistently speak louder than words. Tom and Dawn’s lives are a testimony; they radiate the essence of their faith and put others before themselves, showing love, compassion, and empathy. Tom says, “We want people to know we are Christians without asking.” We do Tom, and Windermere is forever grateful!
We would like to thank Anna Sells Lakeside for bringing you this month’s cover article.
