Real Estate Educator REALTOR® Leader Industry Speaker

Windy Bailey Educating Professionals. Developing Leaders. Elevating Real Estate.

Based in Colorado Available Nationwide

Practical real estate education informed by years of industry leadership, advocacy, and hands-on experience. Windy brings complicated subjects into focus and helps learners turn information into confidence and action.

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Windy Bailey speaking at a podium beside the Colorado state flag

About Windy

Education that is useful, engaging, and memorable.

Windy Bailey is a Colorado REALTOR®, real estate instructor, and industry leader who believes effective education should be useful, engaging, and memorable. Her teaching approach connects complex concepts to real-world decisions and encourages active participation—not passive note-taking.

Windy teaches pre-licensing courses at Bowen Real Estate School and practices as a REALTOR® with Red Bow Realty. She served as 2025 President of the Pikes Peak Association of REALTORS® and is the 2027 President-Elect of Women’s Council of REALTORS® Colorado. Her broader Colorado and national REALTOR® leadership includes committee service on fair housing and federal taxation policy.

Earlier in her career, Windy led a Colorado Springs brokerage branch, growing it to more than 200 agents while coaching and mentoring the professionals who built it. That experience shapes how she teaches: every lesson ties back to the decisions agents, brokers, and leaders actually face. She also holds an MBA with a concentration in real estate.

Windy is based in Colorado and available for teaching and speaking engagements throughout the United States.

01

Useful

Content tied to real transactions, real clients, and real decisions, so learners leave with something they can apply on Monday.

02

Engaging

Discussion, scenarios, and participation in place of slide-reading. Learners work through the material, not just past it.

03

Memorable

Complicated subjects brought into focus with clear structure and stories from the field that make key points stick.

Education & Speaking

How Windy works with your organization

Real Estate Education

Real-world instruction designed to make challenging material understandable and relevant, for pre-licensing students and practicing real estate professionals.

Invite Windy to teach

Leadership & Industry Speaking

Presentations and facilitated conversations about REALTOR® leadership, advocacy, service, and professional growth for associations, brokerages, and conferences.

Request speaking availability

Curriculum & Course Development

Development of original learning experiences and materials for real estate professionals. Course details will be added here as they are developed and approved where necessary.

Courses in development Discuss a curriculum project

Who Windy works with

  • REALTOR® associations
  • Real estate schools & education providers
  • Brokerages & teams
  • Conferences & leadership events

Areas of experience

  • Pre-licensing fundamentals
  • Fair housing & inclusive practice
  • Association leadership & governance
  • Advocacy & RPAC
  • Brokerage growth & team leadership
  • Negotiation & client service

Leadership & Credentials

A track record of service to the industry

Selected leadership

  1. 2027
    President-Elect, Women’s Council of REALTORS® Colorado
  2. 2025
    President, Pikes Peak Association of REALTORS®
  3. 2024
    President-Elect, Pikes Peak Association of REALTORS®
  4. 2023
    Fair Housing Policy Committee, National Association of REALTORS®
  5. 2023
    Fair Housing Education & Events Planning, Colorado Association of REALTORS®
  6. 2022–23
    State Liaison, Women’s Council of REALTORS® Colorado
  7. 2022
    Federal Taxation Committee, National Association of REALTORS®
  8. 2021
    Chair, Diversity & Fair Housing, Pikes Peak Association of REALTORS®
  9. 2020
    President, Women’s Council of REALTORS® Pikes Peak

Recognition & programs

  • RPAC Hall of Fame, Colorado Association of REALTORS®
  • National Leadership Institute Graduate, Women’s Council of REALTORS® (2021)
  • Leadership Academy Graduate, Colorado Association of REALTORS® (2020)
  • Leadership Academy Graduate, Pikes Peak Association of REALTORS® (2019)
  • Athena Award Finalist, Colorado Springs Chamber of Commerce (2019)
  • Entrepreneur of the Year, Women’s Council of REALTORS® (2018)

Designations & certifications

  • CRB
  • CRS
  • GRI
  • ABR
  • SRES
  • MRP
  • RENE
  • PSA
  • C2EX
  • AHWD

Education

  • MBA, Real Estate concentration, Columbia College
  • Bachelor’s degree, Business Administration & Management, University of the Incarnate Word

Contact & Booking

Bring Windy to your next class, conference, or professional development event.

Based in Colorado. Available nationwide.

Share a few details about your event or course and Windy will follow up to discuss availability, format, and goals.

Prefer email? homes@myagentwindy.realtor

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