Derek Heering — Real Estate Broker, Entrepreneur & Real Estate Executive

Derek Alexander Heering is an American real estate broker, entrepreneur, and real estate executive based in Connecticut. He is the co-founder and Head Broker of Property Twins Real Estate, an independent, family-owned brokerage with offices in Newtown and Ridgefield, Connecticut.

With a real estate career that began while he was still in high school, Heering has developed extensive experience in residential brokerage, luxury real estate, brokerage management, investment advisory, and property valuation.

Throughout his career, Heering has held leadership positions overseeing high-volume real estate teams, served as an Assistant Broker at a large real estate firm, and held the position of Director of Real Estate Valuation & Advisory at Doremus Advisors.

He is also recognized for his work alongside his identical twin brother and business partner, Kyle Heering, with whom he established the Property Twins brand in 2015.

Early Career and Professional Background

Heering entered the real estate industry at an early age, beginning his professional education while attending high school. His early exposure to real estate laid the foundation for a career spanning residential sales, brokerage operations, real estate management, and advisory services.

Over the years, Heering advanced into leadership roles within established real estate organizations, including overseeing high-volume sales teams and participating in the management and operations of larger brokerage firms.

His professional background includes serving as an Assistant Broker at a large real estate firm, where he gained experience in brokerage oversight, agent support, transaction management, and business operations.

Heering also served in a leadership capacity at Doremus Advisors, holding the title of Director of Real Estate Valuation & Advisory. His work has included real estate valuation, market analysis, broker price opinions, and advisory assignments involving residential, commercial, and investment properties.

These experiences contributed to his expertise in both the transactional and operational sides of the real estate industry.

Property Twins: From Multistate Real Estate Team to Independent Brokerage

In 2015, Derek and Kyle Heering established the Property Twins Team, building a recognizable real estate brand centered around their shared experience, market knowledge, and collaborative approach to client representation.

Over the following decade, the Property Twins Team operated across multiple states, including Connecticut, New York, and Florida, developing experience in residential sales, luxury properties, investment opportunities, and new construction.

The Property Twins name became associated with the brothers' real estate activities long before the establishment of their independent brokerage.

In July 2026, following more than a decade of developing the Property Twins brand, the brothers expanded the established team into Property Twins Real Estate, a full-service, independently owned real estate brokerage.

The transition represented the evolution of a multistate real estate team into a standalone brokerage operation, with dedicated offices, affiliated real estate professionals, marketing resources, and brokerage leadership.

As Head Broker, Derek Heering oversees the company's brokerage operations, strategic direction, agent development, and client services.

Professional Achievements and Recognition

Throughout his real estate career, Heering has been associated with significant transaction volume, leadership positions, and notable residential sales.

His reported professional achievements include:

• More than $250 million in residential real estate transactions overseen throughout his career.

• Recognition as a 2026 Runner-Up for Best Realtor in the InRidgefield Readers' Choice Awards.

• Previous recognition as part of a real estate team ranked among the top 1.5% nationally by RealTrends.

• Involvement in record-setting residential property sales in multiple towns throughout Connecticut.

• Leadership of high-volume real estate teams and experience in large brokerage operations.

• The expansion of the Property Twins brand from a multistate real estate team established in 2015 into an independent brokerage in 2026.

His experience encompasses residential sales, luxury properties, investment real estate, new construction, and real estate valuation.

Leadership and Business Philosophy

Heering's approach to real estate combines strategic negotiation, market analysis, operational leadership, and personalized client representation.

Having worked in both sales production and executive-level real estate positions, he brings a broader perspective to brokerage management, business development, and real estate advisory services.

Through Property Twins Real Estate, Heering and his brother have continued developing a family-owned business model that emphasizes professional marketing, agent development, local market expertise, and long-term client relationships.

Current Professional Roles

Co-Founder & Head Broker — Property Twins Real Estate

Leading an independent Connecticut real estate brokerage established in 2026 following the expansion of the Property Twins Team brand, founded in 2015.

Director, Real Estate Valuation & Advisory — Doremus Advisors

Real estate valuation, market research, broker price opinions, and advisory services involving residential and commercial property assignments.

Professional Focus

Heering continues to focus on growing Property Twins Real Estate, expanding its market presence, developing real estate professionals, and providing brokerage and advisory services throughout Connecticut and surrounding markets.