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203-832-7677

Property Twins Team

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Derek Alexander Heering, Head Broker

Growing up in a real estate family, Derek’s passion for the business began early. While still in high school, he took the initiative to attend real estate school, laying the foundation for a long and successful career. Over the years, Derek has built a wealth of experience, serving as Assistant Manager for one of Florida's largest private real estate companies, leading a high-performing team as Team Leader and Manager in Connecticut, and co-founding The Property Twins with his twin brother Kyle. Derek’s career has been shaped by learning from some of the best in the industry. Their mentorship has fueled his drive to bring his clients a high level of professionalism, innovation, and market expertise. Operating all over the United States, Derek specializes in real estate advisory services, helping buyers, sellers, and investors navigate complex transactions, identify lucrative opportunities, and maximize returns. With a proven track record of overseeing $150+ million in real estate transactions, Derek has the expertise to guide clients through even the most complex deals. His deep industry knowledge, invaluable connections, and client-first approach set him apart in the competitive market. In early 2025, Derek became a partner and co-launched Ever Realty Partners at Weiniger Realty, expanding the team's already established presence in New Jersey. 

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Kyle Heering, Licensed Real Estate Salesperson

Growing up in a family deeply rooted in real estate, Kyle Heering was immersed in the industry from a young age. Having worked in his family-owned offices before becoming an active sales associate, Kyle has honed a wealth of knowledge and experience, making him well-equipped to manage any real estate transaction. As part of Property Twins Real Estate with his twin brother Derek Heering, Kyle serves clients across Connecticut and Florida, specializing in everything from first-time home buyers to high-net-worth individuals and celebrities. Whether you’re buying or selling, Kyle is dedicated to providing personalized service and expert guidance for all your real estate needs. Contact him today to start your journey.

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Stephanie Heering, Licensed Real Estate Salesperson

I was born in Syosset (Long Island) New York, and I relocated to Ridgefield at a toddler.  I attended Ridgefield Public Schools from Kindergarten through High School; graduating from Ridgefield High School in 1980.Married in 1983, my husband, Robb and I raised our 4 sons locally.  Our identical twin sons, Derek and Kyle are the founding members of Property Twins Real Estate.Excellence In Ridgefield Area Real EstateStephanie and the Property Twins create and develop successful relationships between buyers and sellers of residential homes from starter to luxury throughout Connecticut, New York, and Florida. Our mission is to provide each of our clients with extraordinary quality of service in the buying and selling of real estate and to always act with honesty and integrity. When working with us, we will share every insight that 20+ years brings to each sale, whether obtaining the best possible price for selling your home or negotiating the best possible price when purchasing your home. Stephanie has unrivaled familiarity with current on and off-market properties and trends that having a solid career in real estate exemplifies. When representing first-time buyers, move-up buyers, investors, corporate executives, self-employed business owners, and celebrities, each client’s needs will be met with discretion and utmost privacy. Stephanie is very active in all things Ridgefield. She is a Justice of the Peace, a board member of the Ridgefield Chamber of Commerce, and the Ridgefield Commemorates America at 250.  She is also the Co-Founder of the local non-profit Angel of Ridgefield and resides in Ridgefield.          

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Robb Heering, Licensed Broker Associate

        After four decades as one of Fairfield County's most trusted and recognizable real estate attorneys, Robb Heering of Ridgefield has announced that he will wind down his law practice and pivot his distinguished career toward residential and commercial real estate. He will join his wife, Stephanie, and twin sons, Kyle and Derek, as part of The Property Twins Team at Houlihan Lawrence in Ridgefield, Connecticut. Heering has represented thousands of buyers and sellers throughout his 40-year legal career. Known for his practical guidance, deep market knowledge, and client-first approach, he has played a central role in countless residential transactions statewide. "This transition is not about stepping away — it's about stepping forward," said Heering. "After decades helping clients navigate the legal side of real estate transactions, I am excited to bring that experience directly into the brokerage arena and work alongside my family to deliver an even higher level of service." Heering is no stranger to the real estate brokerage business. In 2005, he founded a real estate franchise company that grew to more than 110 offices spanning 22 states and 3 countries. After successfully exiting the company in 2012, he returned his focus to real estate law, continuing to handle a high-volume closing practice and serving as a trusted advisor to buyers, sellers, and Realtors throughout the region. Now joining The Property Twins Real Estate — a dynamic and fast-growing real estate firm — Heering brings unmatched transactional insight, negotiation experience, and market perspective developed over thousands of deals. His transition represents a unique convergence of legal expertise and brokerage strategy, positioning the team to offer clients an expanded level of guidance from contract to closing. Robb's sons Derek and Kyle said "we are thrilled to welcome Robb to the team, his reputation, deal making experience, and dedication to clients elevate what we can offer in today's competitive real estate environment." The move reflects broader shifts within the real estate industry, where clients increasingly value integrated expertise and strategic guidance throughout the buying and selling process. Heering's background as both a seasoned attorney and former brokerage founder uniquely positions him to meet those evolving expectations. Heering will serve clients as part of The Property Twins, focusing on helping buyers and sellers navigate complex transactions with clarity, confidence, and proven expertise.

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142 North Street, Ridgefield, CT 06877
203-832-7677
REB.0795639 (Derek Heering, Head Broker)

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