Ashleigh Cannon

c: 540-230-5959 e: Ashleigh@CheriWoodard.com o: 540-987-8500 Ext: 8

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.

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.

Ashleigh Cannon's Listings

Blue Sky
265 Castleton View Road,
Whorton Hollow Retreat
339 Whorton Hollow Road, Rappahannock
Creek View
23 Mill Hill Road,
Castleton View Retreat
0 Castleton View Road, Rappahannock

Ashleigh Cannon's Customers

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

Whorton Hollow, Castleton, Rappahannock County

New CWR Properties

Fair Haven

Whippoorwill Hill

Blue Sky

Little Gem in Woodville

Ashby Road

Corner Cottage

Whorton Hollow Retreat

Brookhill Farm

The Ballard Building

Castleton View Retreat

Ashleigh Cannon

Fun Facts

Fondest Memories

Fighting the Good Fight

Localvore

Ashleigh Cannon's Listings

Blue Sky

Whorton Hollow Retreat

Creek View

Castleton View Retreat

Ashleigh Cannon's Customers

Contact Ashleigh Cannon

Ashleigh Cannon

Fun Facts

Fondest Memories

Fighting the Good Fight

Localvore

Ashleigh Cannon's Listings

Blue Sky

Whorton Hollow Retreat

Creek View

Castleton View Retreat

Ashleigh Cannon's Customers

Contact Ashleigh Cannon

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