MEET EILEEN WINFREY
Orlando’s Premier Luxury Real Estate Strategist
For buyers and sellers of luxury properties in Orlando and Central Florida, Eileen Winfrey delivers unmatched expertise, market insight and a record of success in the $1M+ home market. With over $190M in closings, Eileen has navigated discerning buyers and sellers through high stakes transactions with discretion, precision, expert guidance and exceptional results.
As a seasoned luxury home marketing and negotiation specialist, Eileen brings a strategic, data-driven approach to pricing, positioning and selling high value properties even in complex, shifting markets. Accreditations such as Luxury Home Marketing Specialist, Certified Staging Professional and multiple Top Producer distinctions reflect her commitment to excellence. With Eileen, luxury real estate isn’t simply a transaction, it’s an elevated experience.
“Eileen is terrific, she sold our house at the 1st open house showing, less than a week on the market! Also, when the buyer delayed the closing she negotiated a payment from them to help the cost of our rental.” - Satisfied Luxury Seller
Whether representing buyers seeking exclusive Orlando luxury homes or sellers looking to position a high-value property for maximum return, Eileen provides a calm, strategic presence and a proven plan for success.
WHY WORK WITH EILEEN
Eileen provides strategic representation for Orlando’s luxury buyers and sellers
Luxury real estate requires more than experience, it demands strategy, discretion as well as an unwavering focus on results. Eileen offers a refined, highly personalized approach designed specifically for buyers and sellers of high value and luxury homes in Central Florida.
Eileen is a calm expert in high stakes transactions
Clients trust Eileen for her ability to navigate complex, high dollar transactions with confidence and precision. She provides clear guidance, measured advice, and steady leadership in competitive and shifting markets, ensuring her clients make focused, informed decisions.
Eileen offers white glove service without showmanship
Eileen knows luxury is not how loudly a transaction is marketed but by how smoothly a transaction proceeds from start to finish. Her clients receive attentive, responsive service with meticulous attention to detail, privacy and timing. Every step of the process is handled with professionalism and discretion.
Eileen prioritizes intelligent pricing, positioning and negotiation
In the luxury market, pricing and presentation are everything. Eileen utilizes deep market insight and data driven analysis to position high end properties correctly from the start, protecting the value while attracting qualified, serious buyers. Her negotiation style is deliberate, strategic and focused on securing optimal outcomes for both her buyers and sellers.
Eileen creates custom marketing for high value properties
No two luxury home sellers, or clients, are the same. Eileen develops tailored marketing strategies for each property, combining elevated presentation, professional staging guidance, targeted exposure, and private showings designed to reach the right buyers, not the masses.
Eileen operates as a trusted advisor for discerning clients
Executives, investors and luxury homeowners alike choose to work with Eileen time and again because she becomes a trusted advisor through the real estate transaction process. Her clients value her discretion, honesty and ability to anticipate challenges before they arise resulting in the rare luxury of smoother transactions and stronger results.
For those seeking expert representation in Orlando’s high end real estate market, Eileen Winfrey is recognized for delivering clarity, confidence, results and luxury at every level.
ORRA Top Producer - Gold
2026 President - Women's Council of REALTORS® - Orlando
2026-2027 ORRA Board of Directors
2025-2026 Florida Association of REALTORS® Director
29 Years Experience Selling Residential and Investment Properties
ORRA Military Advisory Council (MAC) Accredited
Buyer's Representative (ABR®)
Military Relocation Professional (MRP)
Performance Management Network (PMN)
Certified New Home Sales Professional (CSP)
ASP® Home Staging
Certified Relocation Specialist (CRS)
Excellence in Professionalism ~ Gold Key Certification
Ready to elevate your luxury real estate experience? Reserve your strategic consultation today.
