COL(R) T.W. Cannon

  • Colonel T.W. Cannon (RET) REALTOR®

    T.W. Cannon has spent a life time career in the service of this Nation. He has over 30 years of leadership, training and management experience as a now retired Army Colonel and senior executive. His expertise was in the areas of leadership coaching, counseling, organizational development, change management and facilitation.  His federal career experience was in the Senior Executive Services and included service within the Department of Army, Department of Homeland Security, Department of the Treasury and the Library of Congress. His military career saw him move up the ranks in positions of staff and command responsibilities in the United States and Europe.  He has both a Bachelor of Arts Degree and a Master’s Degree.  He is also a graduate of the Army War College, Strategic Studies, located in Carlisle barracks, PA. TW also holds a certificate as a certified Leadership Coach from George Washington University, Washington DC.  Since his military retirement, he worked as a management consultant,  and educator to assist others in becoming self-reliant. 

    T.W. has moved thought out these United States working and living in in CA, ID, VA, MO, AL, GE and now FL.   During all the changes of stations he became very experienced at buying and selling single family homes.   He has used Professional Real Estate agents in all but one of these transactions.  The last move he did as a For Sale by Owner (FSBO) and used the buyer’s agent to facilitate the transaction.   The process of relocating and transitioning a family with six (6) children was no easy task.  Finding adequate housing in the right location that was within his budget constraints required research and planning.  It was always an adventure when reassignment orders were issued and received. He learned early on the key to a successful move was planning, organizing and keeping a positive attitude. Knowledgeable area real estate professionals were always a key factor to a successful move for his family.

    He said he had no idea after his retirement his children would be his biggest contribution to the military.  After deployments to Iraq and Afghanistan his son Jacob is now a Captain with the 4Th Infantry Division at Ft Carson Colorado. His daughter Penny is also a Captain in the Army Medical Service Corp and is assigned to an Army Reserve Hospital unit in Utah. 

    T.W.’s oldest daughter’s husband, Stuart, holds the highest enlisted rank as an Army Sergeant Major and they are assigned to Ft. Shafter, HI.   It’s hard to keep track of them and even harder to keep track of the 19 grandchildren he now enjoys. A birthday roster on an excel spread sheet is highly valuable.

    TW and his wife Gina finally settled on retirement in Florida for the purpose of being closer to her now 92-year-old mother.  These girls had been separated for about 15 years due to work schedules with only intermittent visits as vacations permitted.  Bringing them together, living in the same town of Naples, has been a wonderful experience.  The Cannons were catching the vision of the phrases heard so often as “living the dream” and “another day in paradise”.   The Cannons are totally enjoying the Naples South West Florida experience. The tax advantages of full time residency in Florida is an added benefit and was also a consideration.

    TW and his wife live in a single-family home in Heritage Bay Golf and Country Club, Naples FL. They enjoy the golf, pickle ball, the fitness center, swimming pool, community activities and social amenities provided by the resort club environment. Additionally, learning to SCUBA dive, boating, hiking and biking keep them active and busy all year around. 

    TW is so very knowledgeable in the aspects of home ownership and transitioning to new environments.  He knows the South West Florida area and can share his enthusiasm, professionalism and experience to all who are interested in home ownership and in living, working and/or recreating in South West Florida. The Cannons are “living the dream!”



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9250 Corkscrew Road, Suite 8

Estero, FL 33928


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