Office Number
EX 8
Cell Phone

Ashleigh Cannon

Realtor ®

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.

Fun Facts

Fondest Memories

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.

In Our Clients' Words

Aimee M.

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Ashleigh Cannon

We were so fortunate to find our real estate agent, Ashleigh Cannon, to lead us through our journey of finding a home with some acreage. Ashleigh was professional, communicative, and caring throughout the entire process. Ashleigh helped make our home buying process stress free and we found the perfect house for us!

Shelley & Scott N.

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Ashleigh Cannon

Thank you for your hard work and knowledge of the market! You were present every step including helping to pick out colors! We appreciate your tenacity and passion and encouraging us everyday! This day has finally come, hallelujah 🙌🙌🙌!!

D & B K.

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Ashleigh Cannon

We can’t thank Ashleigh enough for all her hard work and dedication in selling our home and helping us find a new home to keep our family in beautiful Rappahannock county. From the moment we met her, we knew we were in good hands. Ashleigh’s knowledge of the market and her attention to detail were truly impressive. She took the time to understand our needs and worked tirelessly to ensure that our home sold quickly and for a great price. Ashleigh’s professionalism, positivity, and unwavering support made the entire process smooth and stress-free. We highly recommend Ashleigh to anyone looking for a dedicated and knowledgeable realtor.