Meet Cyndee Haydon, Madeira Beach Waterfront Real Estate Expert | Florida Realtor Leader | Published Author
Cyndee Haydon isn’t just a Madeira Beach real estate expert—she’s a Madeira Beach resident who lives the waterfront lifestyle she helps her clients find. After helping dozens of clients discover the unique charm of “Mad Beach,” Cyndee and her husband Jack made it their home in 2018, drawn by the walkability, community vibe, and proximity to John’s Pass. In a serendipitous turn, the exact waterfront property she’d placed on her 2016 vision board became their first Madeira Beach home—proof that she practices what she preaches about the power of clarity and intention in real estate.
With over 20 years of experience and $230+ million in sales, Cyndee has built a reputation as one of Florida’s most accomplished and innovative real estate professionals. She specializes in waterfront homes, beach condos, and short-term rental investments along Florida’s 26 miles of Gulf Coast beaches—from Clearwater Beach to St. Pete Beach. But what truly sets Cyndee apart isn’t just her impressive sales record; it’s her commitment to education, innovation, and creating exceptional experiences for every client she serves.
Why Waterfront Properties and Beach Living?
Expertise That Delivers Results
Waterfront & Beach Properties: 195+ waterfront and beachfront properties sold in Madeira Beach, Indian Rocks Beach, Indian Shores, Clearwater Beach, St Pete Beach, Belleair Beach, Redington Beach, Redington Shores and North Redington Beach. Those sales totaled $136 million, representing 43% of all their real estate sales.
Beach Condos: 146 condos sold totaling $65+ million, with deep knowledge of buildings, HOAs, rental restrictions, and investment potential throughout Tampa Bay.
Short-Term Rental Investments: 89 properties sold totaling $81+ million since launching this specialty in February 2010. Cyndee was among the first REALTORS® in the Tampa Bay area to specialize in vacation rental investments, helping clients purchase STR properties that they rented on Airbnb and Vrbo, ensuring they met their income and equity goals. She has countless client testimonials and success stories of buyers who purchased the right property and achieved excellent returns later when they sold so it was a win-win, even in today’s challenging market of higher interest rates and prices, she helps clients find smart short-term rental options.
Luxury Properties: 28 properties sold over $1 million in the last five years, with her highest sale at $6.49 million, which has earned her the Certified Luxury Home Marketing Specialist (CLHMS) Guild designation based on proven results.
A Pioneer in AI-Powered Real Estate
Long before artificial intelligence became a buzzword in real estate, since 2005, Cyndee has been exploring how technology could deliver better client experiences and results. As an international keynote speaker, she addressed brokers in Lisbon, Portugal in 2023 about leveraging AI for business operations and agent success. She regularly trains fellow REALTORS® through programs like “AI Advantage for Realtors: Out Work, Out List, Out Last” and the “Opportunity Generator Masterclass,” teaching agents how to create more valuable information for consumers.
Her AI-driven approach produces measurable results, as evidenced by studies that have shown AI-optimized listing descriptions generate 200% more inquiries and helps properties sell 23% faster. But Cyndee doesn’t use technology to replace the human touch, she uses it to enhance personalized service, giving clients more time, better insights, and superior marketing while maintaining the relationship-first approach that defines her business.
National & State Leadership
Current Roles (2025):
- Florida Realtors® Secretary and Executive Committee
- Vice Chair, NAR Regulatory Issues Forum
- Women’s Council of Realtors, Florida Leadership Identification Chair
Past Leadership:
- 2023 NAR Chair of Insurance Committee –
- 2019-2026 NAR Board of Directors (six consecutive years)
- 2020 President of Pinellas Realtor Organization / Central Pasco Realtor Organization (the “COVID President,” recognized for steady leadership through crisis)
- 2019 President of Leadership Pinellas – 2022 Florida Realtors District 6 Vice President
- 2022 President, Women’s Council of Realtors Tampa
- 2021-2023 Stellar MLS Board of Directors
- Multiple terms on Florida Realtors Executive Committee (2019, 2020, 2022, 2025)
- 2021 NAR Leadership Academy Graduate
Awards & Recognition
Cyndee’s exceptional service and production have been honored repeatedly:
- 2024 Women’s Council of Realtors Florida Member of the Year
- 2022 Florida Realtors Associate Realtor of the Year
- 2022 Florida CRS (Certified Residential Specialist) of the Year
- 2022 Women’s Council of Realtors Florida Entrepreneur of the Year
- 2021 Realtor of the Year – Pinellas Realtor Organization / Central Pasco Realtor Organization –
- Ranked #313 among Florida Realtors by RealTrends (Top 1.5% of Realtors
- 2017-2025 RPAC Golden R / President’s Circle / Hall of Fame
Professional Certifications & Designations
Cyndee holds an impressive array of specialized certifications that demonstrate her commitment to expertise across multiple real estate specialties:
- CRS (Certified Residential Specialist),
- PMN (Performance Management Network),
- CIPS (Certified International Property Specialist)
- SRS (Seller Representative Specialist),
- PSA (Pricing Strategy Advisor),
- SRES (Seniors Real Estate Specialist),
- ePRO (Digital Marketing Certification),
- RSPS (Resort and Second-Home Property Specialist),
- MRP (Military Relocation Professional),
- CRB (Certified Real Estate Brokerage Manager),
- C-RETS (Certified Real Estate Team Specialist),
- GREEN (Green Designation),
- AHWD (At Home With Diversity),
- RENE (Real Estate Negotiation Expert)
- Golden Key, and
- CLHMS** (Certified Luxury Home Marketing Specialist)
She has also achieved CE2X, demonstrating commitment to continuing education excellence.
Probate Real Estate Expertise
As one of four founding members of the Certified Probate Real Estate Advisory Board, Cyndee is committed to sharing expertise and providing ongoing education to those navigating the probate process. The Board has created unique tools and co-authored six books to help personal representatives and attorneys dealing with probate and settling estates.
Cyndee holds both Certified Probate Expert (CPE) and Certified Probate Real Estate Advisor (CPREA) certifications. She brings a compassionate and knowledgeable approach to helping families navigate the emotional and complex probate process, particularly when real property is involved. Through partnerships with industry professionals, Cyndee and her team provide support, insight, and guidance to families during these challenging times. She understands that serving as a personal administrator, executor, or estate representative can be overwhelming, and she’s committed to being there every step of the way with an open, friendly, and caring approach.
Published Author of Seven Real Estate Books
Cyndee has authored seven real estate books, sharing her expertise with homeowners, investors, and families facing complex real estate decisions. Two notable titles include:
“Secret to Happy Home Selling: An Insider’s Guide to Preparing and Selling Your Home for the Best Price and Terms Without All the Stress” (Published 2017)
This comprehensive guide addresses a sobering statistic: when 1 in 5 homes doesn’t sell, homeowners need to choose the “Easy Button.” Cyndee explains the complete 12-part Home Sellers Journey and her proven 5-step Home Preparation Process. The book includes room-by-room review processes, soft staging tips, professional photo preparation guidance, and the secret 70/30 Rule that typically results in 5-20% more equity for sellers. Since most homeowners only sell their homes once every 12 years, they often have an overly optimistic view of what’s involved. This book provides the insider secrets they need to sell for top dollar.
“You’re the Probate Personal Representative, Now What? What to Do When You Are Responsible for Real Estate a Loved One Leaves Behind“
This essential guide helps executors and administrators who are seeking someone they can trust to assist with probate real estate details. The book covers 10 critical questions to ask at the beginning of the probate process, how to minimize stress as Personal Representative, helpful suggestions for working with family members, true stories of challenging situations and successful conclusions, how to prepare property for minimum cost and maximum results, and the benefits of working with a Certified Probate Real Estate Advisor.
Her other books focus on probate navigation and inspirational topics, all designed to educate and empower clients through complex real estate decisions.
Corporate Background & Innovation Mindset
Cyndee and Jack are active community advocates and long-time supporters of the Clearwater Jazz Holiday.
In a significant 2025 legislative victory, Cyndee worked directly with Florida Representative Linda Chaney since 2023 to get “lookback periods” removed from all of Florida, allowing all property owners in flood zones to have maximum ability to repair their property after storms or other events, a critical win for coastal homeowners throughout the state. If you don’t know what a look back period is ask her and how much it helped the beach communities she served recover after Hurricane Helene in 2024.
Community Involvement & Advocacy
Before real estate, both Cyndee and Jack began their careers at IBM, where they met in 1985 and developed expertise in technology systems, innovation, teamwork, and service excellence. This corporate foundation instilled a commitment to leveraging cutting-edge tools and processes to deliver superior results—an approach that continues to define their business today. Cyndee and Jack have deep backgrounds in business and computer science, giving them a unique analytical and technological edge in an industry that often resists innovation. They started their real estate business in 2005, building a resilient operation that thrived through the market crash and recovery by focusing on education, strategy, and genuine client care.
Philosophy & Approach
Cyndee’s mission is clear: “Helping people make smart, confident real estate decisions that create income, equity, and freedom”. Her approach is relationship-first and education-driven, backed by deep local expertise and data. She blends high-tech tools with high-touch personal service, delivering measurable results through strategy, clarity, and connection.
As Cyndee often says, “Smart real estate decisions start with clarity about your goals, your numbers, and your property’s story”. Whether you’re buying your first waterfront home, investing in a short-term rental property, selling a beach condo, or navigating probate real estate, Cyndee Haydon brings two decades of expertise, proven results, and genuine care to every transaction.