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Eileen Winfrey Orlando Agent Buyer Seller

Meet Eileen~


  • About Eileen Winfrey

    Eileen is a highly skilled Real Estate Sales and Marketing professional with exceptional experience and 30 years of working with happy buyers and sellers. Her ability to manage projects and employees, using sound judgment, discretion, and strong leadership skills, is well proven.


    Eileen’s reputation as a skilled negotiator precedes her as she fiercely protects her clients’ interests while keeping every transaction professional and positive. It’s for this reason 90% of her business comes from referrals and why clients return to her again and again as well as recommending her to friends and family. With nearly 30 years of experience, hundreds of homes sold, and a proven track record of satisfied buyers and sellers, Eileen knows how to deliver results. She lists and sells properties while also mentoring, coaching, and training fellow agents. Specializing in Luxury Residential Real Estate, Buyers, Sellers, Relocation, New Construction, Vacation Properties & Military Relocation, Eileen has been the recipient of multiple industry recognitions including:


    *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


    Eileen launched her real estate career in 1996 in Atlanta, GA, after spending several years in property management. Throughout nearly three decades in real estate, she’s trained at the corporate level in brokerage management, agent training, new home community marketing, agent recruitment, and the sale of a wide range of properties from luxury single-family homes and new construction to investment opportunities, owning her own company for 12 years. Eileen recently joined the iAD Group.  


    Beyond real estate, Eileen is an active community leader and volunteer, serving with organizations like the Women’s Council of REALTORS®, ORRA, Harbor House, Base Camp, and Runway to Hope. When Eileen's not helping clients, she enjoys riding her Harley with her husband Mark, spending time with their daughters Alexa and Haylee, and doting on their 4 mini-dachshunds.

Eileen Sells Orlando

Your Professional Real Estate Consultant

House hunting is easier and more efficient than when you utilize the right tools and Eileen's superior ability to match you to your dream home is all you need.

  • How Will A Buyers Rep Help Me?

    With my extensive knowledge of the Orlando market, industry insights and almost 30 years working with buyers, my team is best suited to help you gain financing, advise you on local neighborhoods, help determine your individual purchasing power and prioritize your list of essential features necessary in your new home. We'll save you valuable time by finding properties that best suit your desires and will only show you the most promising ones. Rest assured, I specialize in matching buyers with their dream homes by identifying properties that align with individual preferences while honoring a home buying budget. 


    Once you've found a place that catches your eye, we'll look at comparable properties in the area to help determine your purchase offer. Then we'll negotiate on your behalf with the seller to make sure you get the most favorable terms possible.

  • Find Your Dream Home

    Begin the search for your dream home now! Click "here" to get started today

Selling a home on your own can be a daunting and time consuming task so having a trusted Realtor, with over two decades experience, by your side is a must.

  • How Will A Sellers Rep Help Me?

    With nearly 30 years experience in working with sellers, my goal is to facilitate your new home search process well beyond what you would be able to achieve on your own while providing valuable knowledge that makes your current home stand out to potential buyers, assuring your ability to get to get the highest possible return on your most valuable investment. Throughout our collaboration, I will guide you through the intricacies of contracts, inspections and closing procedures, ensuring a seamless and even enjoyable home selling experience. 


    Rest assured, I am committed to providing you with peace of mind, knowing that every aspect of your home sale is meticulously managed and personalized to meet your specific needs facilitated by my vast experience of being a Realtor.

  • Home Valuation

    Get your current, personal, home valuation now! Click "here" to get started

My top-notch customer service and commitment to our clients is second-to-none.

Market Expertise

Market knowledge goes beyond simply knowing the neighborhoods. Ask me about the school district, available parking, or standard bedroom sizes in the area.

Client-Focused

Your time is valuable. That's why I will take the time upfront to understand your unique wants, needs and dislikes to ensure the rest of our time together is productive as possible.

Responsive

You have questions and I have answers. I'll make sure that you feel confident and empowered when it comes to make important real estate and purchasing decisions.

Referral Network

This industry is all about who you know. I can connect you with the top mortgage brokers, real estate attorneys, home inspectors, home stagers, and more.

Eileen Sells Orlando