Robert T. Montgomery

Killington, VT

Robert “Bob” T. Montgomery, 81, passed away peacefully on February 7, 2026, at his home in Killington, Vermont, surrounded by loved ones.

Born on February 17, 1944, in Tombstone, Arizona, to Beatrice and Robert Montgomery, Bob lived a full and vibrant life marked by entrepreneurship, storytelling, deep family devotion, and an unwavering love for celebration.

He is survived by his sons, Robert “Whit” Montgomery (Kelli) of Killington, Vermont, and Brian Montgomery (Jen) of Andover, Massachusetts; his cherished grandchildren, Gracyn of Killington, and Davis and Taylor of Andover; his sister, Mrs. Judy Fulkerson; many loving cousins and extended family; and his devoted companion, Betty Sabotka, who remained faithfully by his side.

He was predeceased by his beloved and cherished wife, Diane “Dee” Montgomery, who passed away in June 2015. We find peace in knowing he now rests once again with Dee — his best friend and the love of his life.

Bob attended Parsons College, earning a degree in Political Science. In 1971, Bob and Dee moved to Killington and began what would become a remarkable legacy in real estate and development, founding The Montgomery Company, a full-service real estate company. Most recently, he proudly led The Killington Group, continuing his lifelong commitment to the growth and vitality of the region. He took immense pride as a businessman, developer, and true visionary. His entrepreneurial spirit, coupled with unwavering tenacity, helped shape the Killington community so many enjoy today.

Bob’s favorite place on earth was his family’s coastal property in South Bristol, Maine — the setting for his legendary “Toast on the Coast” gathering. True to his spirit, he believed it was better to enjoy the party while he was here, rather than after one passes. Winters often found him in Venice, Florida, but no matter where he traveled, family remained his compass.

“GrandBob” was there for the big life moments of his grandchildren — hockey games, sporting events, school concerts, graduations — or something as simple and meaningful as a first haircut. Showing up mattered to him. Being present mattered.

He loved music — especially listening to “The King,” Elvis Presley — and he always had a good story ready to tell. Bob believed deeply in his guiding words:

“Live each day to the fullest, as we are all just penciled in.”

Bob also co-authored his memoir, with Hank Haskell of Maine, Born at the Right Time, Life lessons that you and your family can learn from, capturing reflections from a life well lived.

When Dee passed, an unimaginable void was left in his life. Betty Sabotka helped fill that space with companionship, care, and steady love.

Above all else, family was everything to Bob. His legacy lives not only in the businesses he built, but in the memories created, the traditions carried on, and the love that remains.

He was a man who built things — businesses, communities, traditions, and stories — but more importantly, he built a family rich in love, loyalty, and presence.

One thing is certain: there will be a huge void left in the hearts of his family and his community.

A private burial will take place this summer on his property in South Bristol, Maine, where he will be laid to rest beside Dee.

A local celebration of Bob's life will be announced at a later date.

In lieu of flowers, we encourage those who wish to honor Bob's memory, to purchase his memoir, Born At The Right Time, life lessons that you and your family can learn from. All proceeds will be donated and split between Dee's foundation, The Diane M. Montgomery Killington Scholarship Foundation and The Killington Community Events Fund, which is being established in Bob’s honor to support and fund summer events in Killington. To purchase copies of Bob’s memoir or for more information on how to contribute, please contact: Bmontyme@gmail.com

171 Estabrook Rd. Killington, VT 05751

Life is short… Have Fun

Arrangements are under the direction of Clifford Funeral Home