Killington, VT – Robert “Bob” T. Montgomery, a prominent figure in the Killington real estate and development scene, passed away peacefully at his home on February 7, 2026, at the age of 81. His death marks the end of an era for the community he helped shape, leaving behind a legacy of entrepreneurship and a commitment to the region’s growth.
Born on February 17, 1944, in Tombstone, Arizona, to Beatrice and Robert Montgomery, Bob Montgomery’s life was characterized by a vibrant spirit and a dedication to building connections. He moved to Killington in 1971 with his wife, Diane “Dee” Montgomery, and together they founded The Montgomery Company, a full-service real estate firm that became a cornerstone of the local economy. Montgomery’s influence extended beyond business, as he was known for his storytelling and love of celebration, particularly his annual “Toast on the Coast” gathering at his family’s property in South Bristol, Maine.
A Legacy in Killington Real Estate
The Montgomery Company quickly established itself as a leading force in Killington’s burgeoning real estate market. More recently, Bob Montgomery led The Killington Group, continuing his lifelong dedication to the area’s vitality. His entrepreneurial spirit and tenacity were instrumental in shaping the Killington community as We see known today, fostering development and attracting investment to the region. He took immense pride in his role as a businessman and a visionary, according to those who knew him.
Montgomery’s commitment to the area wasn’t solely focused on development. He believed in enjoying life to the fullest, a philosophy reflected in his famous gatherings and his dedication to family. His “Toast on the Coast” became legendary, a testament to his belief in the importance of community and shared experiences. He often said it was better to enjoy the party while one was here, a sentiment that encapsulated his approach to life.
Family and Early Life
Bob Montgomery received a degree in Political Science from Parsons College. He is survived by his sons, Robert “Whit” Montgomery (Kelli) of Killington, Vermont, and Brian Montgomery (Jen) of Andover, Massachusetts. He also leaves behind his cherished grandchildren, Gracyn of Killington, and Davis and Taylor of Andover, as well as his sister, Judy Fulkerson, and devoted companion, Betty Sabotka. He was predeceased by his beloved wife, Diane “Dee” Montgomery, who passed away in June 2015. Those who knew the couple often spoke of their deep connection and shared love for life.
The loss of Bob Montgomery is deeply felt within the Killington community, and beyond. His contributions to the region’s development and his unwavering commitment to family and friends will be remembered for years to come.
In lieu of flowers, the family requests that those wishing to honor Bob’s memory consider purchasing his memoir, Born At The Right Time, which offers life lessons for families.
Funeral arrangements are under the care of Clifford Funeral Home & Cremation Service. Further details can be found at www.cliffordfuneralhome.com.
As the Killington community mourns the loss of a true visionary, the impact of Bob Montgomery’s work will continue to be felt for generations. The future of The Killington Group and the ongoing development of the region will undoubtedly be shaped by the foundation he laid.
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