Heather Wells
Luxury Property Broker
Heather Wells is a long-time Sotheby’s luxury real estate advisor with 19 years of experience in residential, investment, and new development sales. She has represented over half-a-billion dollars in closed transactions, previously working at Sotheby’s International Realty serving the Bay Area (San Francisco), and now based in Bend, Oregon, entering her sixth year with Cascade Hasson Sotheby’s International Realty. She has built a reputation for strategic precision, discretion, and an elevated client experience across luxury custom homes, new construction, pre-construction opportunities, and complex land acquisitions throughout Central Oregon.
Academic & Strategic Background
- Harvard Business School, Concentration in Real Estate Investment and Development
- University of Colorado Boulder, Dual degrees in International Business and Political Science
- Heather’s foundation integrates global business perspective, investment analysis, and high-level advisory expertise.
AI & Technology Leadership
Heather is recognized as a leading AI and luxury-technology strategist & futurist within her firm and across the Sotheby’s network. She is not simply an early adopter - she is a builder of proprietary AI systems designed specifically for luxury real estate.
Innovation in Execution
- Architect of proprietary AI workflows and custom OpenAI GPTs
- Creator of the “Dirt-and-a-Dream” GPT, a proprietary AI model engineered, optimized, and refined through deep industry expertise and real-world deployment across substantial luxury, land, and new construction transaction volume.
- Developer of AI-powered marketing and buyer-targeting frameworks
Proven Results
- Luxury listings positioned to sell in as little as 30 hours
- Multiple offers above list price, including in higher-inventory conditions
- Premium-level marketing deliverables created from minimal assets, including raw land
Her work represents applied, repeatable innovation that directly enhances advisor performance, client outcomes, and market share.
Advisor & Brand Impact
In 2025, Heather led some of her firm’s most heavily attended and highest-impact AI workshops, mentoring advisors on practical AI adoption strategies designed to generate measurable ROI.
Her focus includes:
- Cross-market collaboration
- Technology leadership
- Luxury brand evolution
- Advisor-ready AI playbooks
- Scalable AI-powered marketing systems
Positioning luxury real estate at the intersection of strategy, technology, and refined execution.
Sold a Single Family home in 2021 in Awbrey butte, Bend, OR. - Highly likely to recommend - 5 stars
Heather Wells sold our home in Awbrey Butte in late August of 2021. Her knowledge of the market in Bend, her strategy and her personality impressed us. She is always professional, upbeat and optimistic. She is agile in adapting to shifts in the market and helped us navigate those changes to our advantage Before listing, Heather's prep was thorough. She helped with staging, making useful suggestions, and provided an amazing photographer to document the house beautifully. After open houses she always provided us with detailed descriptions of who visited, questions asked and how serious they might be. Once in Escrow, after the inspection Heather worked with our buyer's agent to resolve issues smoothly and equitably. Most importantly, in preparation for the appraisal, she was prepared to the max with over 60 comps to justify pricing and she spent the whole time helping measure every room with the appraiser, all the while talking up the property and demonstrating its' value. How many agents will do that? Heather Wells is a consummate professional and we couldn't have been happier with the results. Thank you, Heather.
user4093730
Sold a Single Family home in 2022 in Redmond, OR - Highly likely to recommend - 5 stars
Heather is a brilliant and fabulous realtor with a work ethic like no other. If you want data, she'll geek out with you on spreadsheets all day! If you don't want spreadsheets (after looking at houses all day for example), she'll summarize information for you in a clear and concise way, that helps you make the best decision. She is upfront, honest, and SUCH a genuine person. She helped us get the best price possible for our home, and I truly believe in her abilities. I've recommended her to several friends and will keep doing so.
Jordan King
