John Montgomery
REALTOR® | Co-Founder & Team Leader, The JR Group
Crye-Leike, Inc., REALTORS® | Clarksville, Tennessee
Practical Insight. Smart Strategy. Relationships Beyond Closing.
About John
John Montgomery is a REALTOR®, experienced real estate investor, author, military veteran, and community advocate who believes successful real estate decisions begin with knowledge, preparation, and trusted relationships.
As Co-Founder and Team Leader of The JR Group at Crye-Leike, Inc., REALTORS®, John serves Clarksville, Fort Campbell, and greater Nashville communities. His real estate experience spans residential and commercial properties, investment real estate, land and acreage, recreational properties, and military relocation.
Before real estate John completed a 21-year career as a United States Army officer. His military service helped develop the leadership, discipline, and strategic planning skills that continue to shape his approach to business and client relationships.
Real Estate Investing & Property Ownership
John brings a unique perspective to real estate through his personal experience as an investor and property owner. His portfolio experience includes multifamily properties, single-family rentals, and a KY Lake cabin and Destin, FL condo operated as vacation rentals.
Having owned local and out-of-state rental properties, John understands the opportunities and challenges associated with investment real estate, including property selection, rental demand, operating expenses, and long-term ownership strategies. He also helps connect investors with exceptional out-of area Realtors and property managers, recognizing the importance of having the right team in place to protect and manage an investment.
Land, Hunting & Recreational Properties
A former Kentucky land owner and lifelong outdoorsman, John brings firsthand experience to evaluating land, acreage, and recreational properties. His knowledge includes habitat management, re-wilding, land improvement, and identifying the characteristics that contribute to a property's recreational potential and long-term value.
An avid hunter and fisherman, John understands that evaluating hunting property involves much more than acreage. Access, topography, water sources, timber, wildlife habitat, and neighboring properties can all make a significant difference. He enjoys helping clients recognize these opportunities and make informed land-purchasing decisions.
Community, Service & Personal Interests
John's commitment to serving others extends beyond his military career. He has served on the Board of Directors of the Clarksville Area Chamber of Commerce, the Clarksville-Montgomery County Education Foundation, and as a leadership instructor at Austin Peay State University. He is also the author of 4 Buckets – Achieving Financial Freedom, reflecting his passion for financial education and helping others pursue financial independence.
John currently serves as an ambassador with Valor and Honor Outdoors, a nonprofit organization dedicated to sharing outdoor experiences with our nation's warfighters.
Away from real estate, John enjoys spending time with family, hunting, fishing, and ultrarunning. He has completed numerous ultramarathons, including a 100-mile trail race. These endeavors require the same preparation, perseverance, and determination required to operate a successful real estate business. With over 90% of the team’s business coming from referrals, it’s a model clients appreciate and tell their friends about.
Alongside fellow Army veteran Robert Roof, John built the JR Group on the principles of integrity, respect, professionalism, and work ethic. The team reflects their shared commitment to service and exceptional client experiences.
Whether you're buying or selling a home, exploring commercial or investment opportunities, relocating to Middle Tennessee, or searching for your next recreational property, John welcomes the opportunity to put his experience to work for you.
Request a Personalized Real Estate Review to better understand your property’s current market position, or schedule a consultation to discuss your next move.
John Montgomery, REALTOR®
Co-Founder & Team Leader | The JR Group
Crye-Leike, Inc., REALTORS®
Direct: (931) 802-1222
Office: (931) 648-2112
Email: john@thejrgrouppartners.com
Office Address: 2204-D Madison Street, Clarksville, TN 37043
Tennessee Real Estate License: #344121
Website: www.thejrgrouppartners.com
The JR Group — Your Partners in Real Estate.
