Your Trusted Partner in Appalachian Land & Property Acquisition
About Our Team…
At Highland Heritage Realty, we introduce buyers from across the country to the unmatched opportunity and natural beauty of Kentucky’s Appalachian region. From private mountain retreats and working farms to timberland, development tracts, and income-producing properties, we help you invest with confidence in a place where land still holds its value and your vision has room to grow.
For those ready to trade congestion for open space and lasting value, Highland Heritage Realty offers a direct path to life in Appalachia. We specialize in connecting out-of-state buyers and investors with the region’s most remarkable land, farms, and distinctive properties—places where you can build, retreat, or create sustainable income surrounded by breathtaking scenery.
Jennifer Travers Skidmore, ALM
Principal Broker/ Owner
Jennifer Skidmore is a licensed real estate broker and the Principal Broker and Owner of Highland Heritage Realty, with offices in Barbourville and London, Kentucky. She serves clients throughout southeastern and central Kentucky, specializing in commercial real estate, redevelopment initiatives, and strategic real estate investment advisory work that supports long-term economic growth.
In her real estate practice, Jennifer works with commercial property owners, developers, investors, and community stakeholders, advising on site selection, property feasibility, adaptive reuse, and the repositioning of underutilized assets. Her work frequently intersects with economic development efforts, including downtown revitalization, tourism-driven redevelopment, and rural investment strategies. She provides market-informed guidance to support acquisition, redevelopment, and long-term portfolio planning.
Jennifer holds a Bachelor of Science in Elementary Education from Union Commonwealth University and a Master of Liberal Arts from Harvard University, where she focused on Museum Studies and Nonprofit Management. Her academic background and professional experience in education, nonprofit leadership, and community development contribute to a comprehensive understanding of regional history, land use, and value creation across Appalachian communities.
Beyond brokerage operations, Jennifer is actively engaged in regional leadership and public service. She serves as a board member of the Knox County Tourism Commission, where she supports initiatives promoting heritage-based tourism and economic development. She is also a board member of the Challenger Learning Center of Kentucky, contributing to STEM education and experiential learning programs across the Commonwealth. In addition, she serves on multiple leadership and advisory committees for Bluegrass REALTORS®, participating in professional development, diversity, and industry-focused initiatives.
Jennifer maintains strong ties to the communities she serves and approaches real estate as both a transactional discipline and an economic development tool, emphasizing stewardship, long-term value, and regionally aligned growth.
Weldon Lester
REALTOR®
A lifelong resident of Barbourville, Kentucky, Weldon Lester offers clients an authentic understanding of the region and a deep appreciation for the land that defines it. As a REALTOR® with Highland Heritage Realty, he specializes in land tracts, guiding buyers and sellers through opportunities that range from recreational acreage to homesteads and investment properties throughout southeastern Kentucky.
Weldon holds a Bachelor’s degree in Biblical Ministry and brings a strong foundation of integrity, service, and leadership to his work. In addition to his real estate career, he has a professional background as an Advanced EMT, equipping him with calm decision-making skills, attention to detail, and a steady presence—qualities that serve his clients well throughout every step of the transaction process.
Alexandra Travers
Office Manager
Alexandra Travers is the Office Manager at Highland Heritage Realty and plays a vital role in the seamless day-to-day operation of the brokerage. As the organizational backbone of the office, she oversees administrative coordination, supports agents throughout each transaction, and helps ensure that every client interaction reflects the professionalism and care that define the Highland Heritage Realty brand. Her strong attention to detail, efficiency, and welcoming presence help create a smooth and positive experience from the first inquiry to the closing table.
Born in Kentucky and deeply connected to the region through generations of family heritage, Alexandra takes great pride in being part of a company that celebrates Appalachian land, legacy, and community. Her behind-the-scenes leadership allows the team to focus on serving buyers, sellers, and investors at the highest level, and her commitment to excellence makes her an essential part of the brokerage’s continued growth and success.
