Diane “Dee” Martin Montgomery, 69, died early Friday morning June 19 following a short illness at the Dartmouth Hitchcock Medical Center in Lebanon, N.H.
Dee was born on Oct. 16, 1945 in Elizabeth, N.J., the daughter of Franklin Armstrong and Olive (Smyth) Martin.
Dee received a Bachelor’s Degree from Middlebury College where she was an active member of the Tri Delta Sorority, women’s field hockey team, National Honors Society, and French Club. Dee went on to further her education with two years of graduate studies at NYU with a focus on banking and finance. Upon completion, Dee became one of the earliest women to become a commercial loan officer for Manufacturers Hanover at Rockefeller Center, where she met (in an elevator!) and later married Robert “Bob” Montgomery. She said yes when proposed to while on the back of his motorcycle. After moving to Boston, Dee became a commercial loan officer for New England Merchants Bank “at the Pru”.
After running a couple of ski houses in the late 1960s, Dee and Bob moved to Killington, Vt. in 1971 and subsequently founded the Montgomery Co., a full-service real estate company. Dee opened the first full-service bank (the Howard Bank) in Killington. In addition to real estate and banking, Dee was a partner in several businesses, oftentimes wearing many hats including account manager and chief communications liaison. Dee was, without question, the integral component to the success of these businesses. Dee’s patience and uncanny ability to manage employee/employer relationships is what kept these businesses together. For Bob, she was not only a wife for 45 years and a best friend for 47 years, but also a business partner for 44 years.
During her years in Killington she was one of the founders of Sunday School at the United Church of Christ, an early member of Killington Women’s Club, and an original trustee of the Killington Mountain School where she also taught and tutored in French and Spanish.
Midlife, Dee realized one of her true passions was helping young adults plan for college and helping them decide which school may be best for them. She eventually became a private college counselor for Strategies for College of Rutland, Vt., where she worked with juniors and seniors at several different high schools throughout the state. With her love and passion for working with students ever present, Dee continued to offer her services to friends and family later in life. It was her wish to start a Killington Educational Scholarship as a means by which to give back to the community that had given her so much joy.
Dee was extremely proud of the success of her two sons. The unconditional love and support Dee showed her family was indescribable. Dee enjoyed spending time in South Bristol and Venice, Fla. with family and friends. Dee was an exceptional cook, an avid tennis player, and enjoyed boating, sailing as well as showing off her green thumb at her Killington and South Bristol properties.
In addition to her parents, Dee is predeceased by brothers, George and Peter.
She is survived by her husband of 45 years, Robert “Bob” of Killington, Vt. sons, Robert W. “Whit” of Killington, Vt., and Brian and wife Jen of Melrose, Mass.; grandson, Davis, and granddaughter Taylor, both of Melrose, Mass.
Memorial service to be held at 11 a.m. Sat., June 27 at The United Church of Christ, Rt.4, Killington Vt.
Memorial donations may be made to the Diane M. Montgomery Killington Scholarship Foundation, C/O Killington Elementary School, 686 Schoolhouse Rd., Killington, VT 05751.
Arrangements are under the direction of the Cabot Funeral Home in Woodstock, Vt.
An online guest book can be found at cabotfh.com

