William “Billy” P. Lessa

WINSLOW – William “Billy” P. Lessa, 53, passed away on Jan. 15, 2025, surrounded by the love of his family. He was born on July 20, 1971, in New Bedford, Mass. Billy grew up in Acushnet, Mass., and later made his home in Winslow, Maine.

Billy’s life was a testament to perseverance, dedication, and love for our family. After owning his business DBT Land Design for over 15 years, he went on to pursue a higher education earning his Bachelor of Science in Mental Health and Human Services from the University of Maine, Augusta. He went on to become a Licensed Alcohol and Drug Counselor (LADC), driven by his passion for helping others overcome addiction.

Family was Billy’s greatest joy and his highest priority. He found happiness in the simple and profound pleasures of life—riding his Harley, fishing, boating, driving his classic Ford Galaxie and spending time along the coast. Known for his unwavering honesty and boundless wisdom, he was a man who could fix anything, solve any problem, and always knew just what to say.

Billy’s humor, strength, and unforgettable phrases—like “jumping out of windows,” “30 seconds or less,” and “two weeks”—will forever echo in the hearts of his family and friends. He was the definition of a real man, earning respect and admiration from everyone who knew him.

Billy is survived by his wife, Tara and their children, Danny and his wife Alexandria, Billy and his wife Courtney, and Tim “Bird”. He was a proud grandfather to Dyson, Easton, and Madison. He is also survived by his sister, Teresa and her children, Beth, Jay and Jordan. Billy was predeceased by his parents, William and Rita; as well as his brother, Alan.

Billy’s passing leaves an unfillable void in the lives of those who loved him. Tara, his wife, remembers him as her heart and soul. We will continue to honor his legacy and will hold him in our hearts until we meet again.

Arrangements are under the care of Dan and Scott’s Cremation and Funeral Service, 488 Farmington Falls Road, Farmington, Maine, where memories, photos, and condolences may be shared at dsfuneral.com.