When you meet Ashleigh and hear her stories of growing up in the postcard-pretty foothills of the Blue Ridge Mountains, you’ll sense right away her genuine love and deep reverence for Rappahannock County. Her grandfather Ray T. Cannon, a real estate broker, and father Jimmy Cannon, a realtor and farmer, were both instrumental in preserving Rappahannock’s land and traditions, and Ashleigh’s commitment to conservation, farming, and real estate are a genuine extension of her family’s values. While holding on to history and carefully envisioning the future, Ashleigh was instrumental in developing and revitalizing Sperryville’s River District, encouraging entrepreneurship and supporting small business owners in creating spaces to keep neighbors and families delighting in Rappahannock’s local treasures. She’s also an active community volunteer, serving as a past Board member of the Headwaters Foundation and establishing the Women’s Committee for the Rappahannock Farm Bureau. Ashleigh loves to spend her free time gardening with her daughter, exploring and cooking Southern cuisine, shopping for antiques, and studying the architectural features of old homes. If you are hoping to find “that sweet spot” in Rappahannock, a place that blends the beauty of the past, present, and future, let Ashleigh put her creative energy, business acumen, and local heritage to work for you.
My fondest memories are of times spent with my father and grandfather, riding around Rappahannock and surrounding counties looking at land and farms, seeing cattle and horses, corn and soy bean fields, and learning the long history of the farms and the people that owned them from past generations.
Fighting the Good Fight
I graduated from Radford University and have a background in Senior Care and Marketing. I’m passionate about fighting Alzheimer’s disease- which my educational background ensures I am well suited to fight for the cause.
My daughter and I often visit our favorite local chef on Monday evenings for amazing greens and other delicacies. Best of all? My daughter has learned so much about where her food comes from.
Ashleigh Cannon's Listings
Ashleigh Cannon's Customers
I wanted to express my gratitude for the outstanding service that I received from your agent, Ashleigh, during the recent sale of my rental property on Sperryville Pike. Ashleigh is a gem! She made the process seamless and easy. She exhibits unparalleled professionalism while always being down to earth and approachable. Ashleigh’s work made this transaction far exceed my expectations. I would certainly refer anyone in need of an agent to your office.- Linda D.
You were critical in helping us get the deal done. Being nervous first-time home buyers, you made the experience as painless as possible. You answered every question we had and kept reassuring us throughout the whole process keeping our confidence where it needed to be to get it done smoothly. And not only did we have a great Realtor, but we made our first friend and we’re so excited to start the rest of our lives here! We seriously can’t thank you enough for what you’ve done for us.- Eric and Aleyna
My husband and I closed on a property last week on Nethers Road in Sperryville. We were referred to Ashleigh Cannon of Cheri Woodard Realty by an old friend, also a resident of Sperryville. From the moment we met Ashleigh, she had our best interest in mind. Our contract was not an easy one. Ashleigh had nothing but a positive and professional attitude through some very trying negations. I can not say enough about her as an agent and now friend. I look forward to making our new home another special piece of Madison and Rappahannock history thanks to Ashleigh Cannon.- Leigh & William G.
I knew Ashleigh would be an awesome Realtor to sell my home, and she was! Ashleigh listened to me and offered great advice. An added bonus, she has an infectious smile and is such a fun person to be around. Because of Ashleigh’s experience and background in marketing, my home went under contract in a day with multiple offers, and over the asking price. Ashleigh made the whole selling process an easy and pleasurable experience, and now I have a great friend! Highly recommend!!- Elizabeth W.