Office Number
540-987-8500
EX 8
Cell Phone
540-230-5959

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.

Localvore

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

Joan & Tony K.

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Ashleigh Cannon

We had the pleasure of working with Ashleigh as our Realtor, and I can’t recommend her highly enough!  From start to finish, Ashleigh was professional, attentive, and incredibly knowledgeable about the housing market.  She took the time to understand our needs, whether it was finding the perfect home within our budget but that checked off all the necessary “boxes” or navigating the complexities of the buying and selling process.  Her communication was prompt and clear, always keeping us informed and confident in every decision.  Ashleigh’s negotiations skills were top-notch, securing us a fantastic deal not only on the house we bought in Boston, VA but selling our home in Springfield, VA.  Her warm, approachable demeanor made the entire experience stress-free and enjoyable.  If you’re looking for a dedicated, trustworthy and results-driven realtor, Ashleigh is the ONE!  And because she was so wonderful to work with, she’s become a life-long friend.

Patricia U. & Casey E.

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Ashleigh Cannon

We can’t thank Ashleigh Cannon of Cheri Woodard Realty enough for the excellent care and effort she recently put into helping us sell our Castle Spring property!  A huge and overwhelming project with plenty of bumps along the way was met at every step with “we’ve got this!”.  Her knowledge, professionalism and people skills made this a pleasant experience for all, buyer and seller alike.  And her use of innovative marketing – arial drone, square footage calculations, etc… Highly recommend Ashleigh Cannon to help you will all your real estate needs!

Ben K.

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Ashleigh Cannon

Ashleigh Cannon has been simply exceptional in helping us purchase our home. Her in-depth knowledge, constant availability, and sincere dedication made the process much easier to navigate. With her expert guidance, we’ve been able to find the perfect home that matches our needs and dreams.

We truly couldn’t ask for a better realtor.