Meet the Team

    Best of the Northwoods
    Best of the Northwoods

    Meet the Team

      Welcome to Windseeker Realty! Your trusted Guide and Realtor for the Bayfield Peninsula and shores of Lake Superior. We understand buying, selling or renting a home, condo, vacant lot or commercial property is more than just a transaction. At Windseeker Realty our clients come first. Whether you’re a first time buyer or seller or have bought and sold before, we are here to help navigate you through all your real estate adventures – big or small. We take great pride in the relationships we build and work relentlessly on the client’s behalf to help them achieve their real estate goals. We dedicate ourselves to providing exceptional, personalized service for each of our clients. We’re always striving to lead the field in research, innovation, and consumer education. With our extensive knowledge and commitment to providing only the best and most timely information to our clients, we are your go-to source for real estate industry insight and advice for Northern Wisconsin: Bayfield, Washburn, Cornucopia, Herbster, Port Wing, Ashland, La Pointe, and Iron River.


      Our philosophy is simple: clients come first. We pledge to be in constant communication with our clients, keeping them fully informed throughout the entire buying, selling or renting process. We believe that if you’re not left with an amazing experience, we haven’t done our job. We don’t measure success through achievements or awards, but through the satisfaction of our clients.

      Jenna Galegher - Windseeker Realty



      Raised on a 4th generation farm in the Red River Valley of North Dakota, I learned the value of family, commitment and hard work. I earned my Bachelors in Business Management at North Dakota State University, and began my real estate career managing rental properties in Fargo, ND.

      I have experience working in healthcare, startup companies, and non-profit environments, and continuously engage in learning and educational opportunities to best serve the community around me. I found the Bayfield area through my interest in sailing and continue to race locally on Lake Superior and around the region. I now live between Bayfield and Cornucopia and raise chickens and pigs with my husband on our small hobby farm. I understand the challenges of transitioning and would love to work with you to best serve your needs for the adventures that lie ahead. Call or email me today to start your next adventure!

      Katie Barningham - Windseeker Realty



      Hailing from the Great Lakes area, I have lived in Bayfield for the majority of my life. I am a member of the Red Cliff Band of Lake Superior Chippewa and I grew up in a rural setting hunting, fishing, and learning how to provide for myself and my family. My free time is spent with my dogs in the Northwoods and taking in all this natural area has to offer. I love spending time with my large family, most of which also reside in the Bayfield area. I entered into Real Estate to combine my passion for people with my passion for this area, to help others find their forever home, and to enjoy the beauty of Bayfield that was I lucky enough to grow up in.

      Dann Tervo - Windseeker Realty



      After having grown up on Chequamegon Bay and moving away from the area for 25+ years, I had the opportunity to move back to the area and am so excited to be back home! I have worked in a variety of positions with the travel industry and collegiate athletics. Obtaining my Real Estate Sales License has enabled me to promote the Bayfield Peninsula as not only a vacation destination but a place to call home for people looking to enjoy either seasonally or year round. The pace of life, natural beauty of Bayfield County with its year round recreational opportunities, and having Lake Superior close is enough to keep me here for good. I hope to help you achieve your real estate goals and be able to call this area home!

      Brad Dryer - Windseeker Realty



      Having grown up in Ashland, I feel fortunate to have my roots in the Chequamegon Bay area. I graduated from Northland College with a business degree and went on to get an MBA from UW-Superior in 2014. I’ve had a diverse professional background, holding positions in manufacturing, construction, facilities management, and education. Most recently, I’ve been running a small garden center and landscaping business in Washburn. In my free time, I get outdoors to enjoy the four seasons—from golfing and biking in the summer to skiing and ice fishing in the winter. No matter the season, I’m always happy to simply relax near Lake Superior. Real estate has always been a passion, and I’m excited to be a member of a really enthusiastic team of real-estate professionals. I can’t wait to help our clients find their dream home, land or commercial property by the natural beauty of Lake Superior. I enjoy bringing my creativity to real estate by connecting the aesthetic of a home with the perfect buyer. From the sandy south to the snow capped trees, I am grateful to call this place home and am so excited to welcome others to Bayfield County and surrounding areas.

      Brianna Bailey - Windseeker Realty



      I fell in love with the Apostle Islands when I was young, vacationing with my family on Madeline Island. My husband and I continued to visit the area and jumped on the opportunity to own our dream hobby farm. Now we raise chickens, grow veggies, and enjoy everything the Northwoods has to offer. My career started in education, teaching preschool, high school Spanish, and abroad in South Korea. I understand the challenges of chasing your dreams and the excitement of exploring new opportunities. That’s why I fell in love with real estate. Whether buying or selling, you are starting a new adventure. It brings me great joy to help clients along their journey, and be there every step of the way no matter what challenges arise. I am also an avid lover of the arts, making jewelry and watercolor illustrations inspired by the natural beauty of Lake Superior. I enjoy bringing my creativity to real estate by connecting the aesthetic of a home with the perfect buyer. From the sandy south to the snow capped trees, I am grateful to call this place home and am so excited to welcome others to Bayfield County and surrounding areas.