Welcome to Winn Properties Vacation Rentals!

Discover the story of Richard “Rick” Winnestaffer, an innovative entrepreneur who turned his modest beginnings into successful ventures like WinnScapes and WinnProperties. Driven by his love for real estate, Rick’s diverse business portfolio, which includes WinnRoofs and Ohio Online Auction Services, reflects his dynamic entrepreneurial spirit. A respected speaker and influential figure in his community, Rick’s infectious personality and mentorship continue to inspire others. Learn more about his journey and enduring legacy here.

Our founder, Richard “Rick” Winnestaffer, was a force in the business world. Despite starting from humble beginnings, he was determined to achieve more from a young age. His first venture began in 1981 when he established WinnScapes, Inc. in Groveport, Ohio. There are even stories about the business starting before he could drive! He continued to expand this business, diving headfirst into the landscaping world. After 12 years of building a profitable landscaping business, he ventured into real estate. Initially on a small scale, his interest in real estate grew over the years. Motivated by the potential of real estate investment, he founded WinnProperties, Inc. in 1993. This business flourished in 2000 when Rick came across the book “Rich Dad, Poor Dad.” Subsequently, he developed a highly successful real estate investment and property management company. WinnProperties expanded its portfolio to over 350 single-family homes in Columbus, Ohio, and Palm Beach Gardens, FL. Over time, he also launched other businesses, such as Winn Roofs, Winn Business Park, and Ohio Online Auction Services. He was a sought-after speaker and organized his own real estate investing seminar for many years. A true entrepreneur at heart, he was actively involved in his church and community. His passion and mentorship impacted many throughout his life. His infectious laughter and personality had a way of bringing out the best in people.

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Emily Snyder

Guest Services

Emily is the primary face of the business when working with guests in our short term rental business. She assists in the management of 3 STR properties from Florida to Tennessee. She is awealth of knowledge and a Guest Services Expert.

Emily currently lives with her husband and two children in Virginia. She has graduated from Franklin University in Columbus, Ohio with a bachelor’s degree in Business Administration. Emily has worked in various areas within real estate and rental businesses for over 5 years. She enjoys reading, spending time with her family, and going on cruises. 

Jordan Winnestaffer 

Administration Manager

Jordan wears many hats on a daily basis and helps to ensure everyone on our team is supported and organized. Jordan herself is meticulous in everything she does. Jordan assists in resident communication and management of long–term residents as well as helps to manage content creation, non–profit involvement, among many other tasks.

Jordan has a labradoodle named Scarlett she is definitely a spoiled fur child. Jordan enjoys home décor, binge watching shows, and Coopers Hawk wine tastings area few of her favorite things! She also loves Cycle Bar and spending time with her family.