Helena Woodruff

Agent Details

About Helena

A Vermont resident since 2018, Helena brings a blend of local insight, marketing expertise, and hands-on real estate experience to every client she serves. Known for her persistence, strategic approach, and calm confidence, she is dedicated to helping you navigate your next real estate transaction with clarity and success. Helena’s own home-buying journey—purchasing in the midst of the Covid-19 market—gave her firsthand experience with the resilience and negotiation skills required to secure the right property in challenging conditions. Since then, she has expanded her expertise by acquiring and managing her own investment property: a duplex in Elmore, VT, which she personally staged and transformed into a thriving two-unit short-term rental. Her growing STR business allows her to offer practical, real-world guidance to both new and seasoned investors throughout Vermont – highly focused in Stowe, Waterbury and Warren. Originally from Minnesota, Helena earned her Bachelor’s degree in Communication and Journalism, followed by a Master’s in Strategic Communication Management. Before entering real estate, she served as Marketing Director for a high-growth financial publisher in both Florida and Vermont—experience that sharpened her skills in branding, market strategy, and high-impact communication. Helena’s passion for real estate, paired with her financial literacy, marketing background, and strong negotiation skills, makes her a powerful advocate for buyers, sellers, and investors alike—whether you’re exploring residential or commercial opportunities.

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