Ashlen Hayward - Team

About Ashlen

As an Orlando multi-million dollar top-producing Realtor with over a decade of experience and a proven track record facilitating successful transactions for individuals and investors, Ashlen thrives in helping her clients meet their personal, lifestyle, and financial goals with real estate. Her specialization in single family luxury residential properties allows buyers and sellers to choose a home that suits their priorities from all of the wonderful lifestyle options that Orlando has to offer; from golfing, to a pool, gated golf cart communities, nature trails, restaurants, proximity to Disney World, or simply a return on investment. Additionally, with her vast expertise in new construction and working with builders, Ashlen guides buyers through the process of building their dream home.

Ashlen’s expertise extends beyond traditional real estate transactions as she is also an investor, STR owner, Airbnb Superhost, and Resort & Second Home certified through the National Association of Realtors. Through Oak Avenue Real Estate, she is able to find her clients specialized real estate investment opportunities while helping individuals grow and sell their real estate portfolios throughout Central Florida. She has mastered the art of maximizing returns and creating unforgettable guest experiences. Ashlen is a member of the Global Council of the Orlando Regional Realtor Association and is pursuing a master’s degree in International Affairs and Leadership, further enriching her global perspective and enhancing her ability to serve the diverse global Orlando clientele. In addition, Ashlen, along with Oak Avenue, meet the needs of their client’s coastal Florida lifestyles by offering buyer expertise and representation in Palm Beach County.


A native of Missouri, Ashlen began her career in New York City as a former fashion merchandiser/editor and founder of the “Global Editorial Destination of Swimwear Fashion”. She seamlessly transitioned her eye for luxury design, client-centered customer service and business acumen to real estate. Beyond her professional achievements, Ashlen takes pride in being a devoted mom of two and a loving wife. When she is not orchestrating deals, you may find her on the ski slopes of Park City, cooking, driving her Vespa, or somewhere by the sea. Wherever your Florida property dreams may take you, Ashlen is your trusted guide to unparalleled living experiences.