Get to Know the Broker: Jennifer Reddington of Compass

North Carolina native Jennifer Reddington, co-founder of the Georgio Reddington Team at Compass, didn’t start out selling stunning luxury properties in lower Westchester County, N.Y., and Greenwich, Conn. Indeed, she was practicing law when the real estate bug took a bite. 

Now, the University of North Carolina alum and married mother of two has been involved in more than $600 million in sales. She relies on her background in law to support her clients through advocacy, shrewd negotiations and meticulous attention to every detail in every deal.  

Commercial Observer caught up with Reddington in September for a series called “Get to Know the Broker,” where we connect with residential brokers to learn more about what makes them tick.

This conversation has been edited for length and clarity. 

Commercial Observer: What has been the biggest deal of your career so far?

Jennifer Reddington: This was not the highest dollar transaction of my career, but what made it especially meaningful was the people behind it. I was representing friends whose plans changed unexpectedly and required them to relocate internationally. Their home was still under construction, so there was a tremendous amount of preparation and strategic thinking involved in determining how to position and market the property. 

We ultimately took a private, off-market approach and developed a very deliberate strategy around pricing, positioning and presentation. The result was a record-setting sale for the home. I was incredibly proud of the outcome, but even more proud to have delivered such a strong result for friends and clients during a major life transition.

What is your career Everest? 

To continue building a real estate brand that people genuinely trust — a name that becomes synonymous with the highest level of service, attention to detail, discretion and results. 

I want people to know that when they work with our team, they are getting more than a real estate agent. They are getting a trusted adviser who is deeply invested in their goals and committed to doing things the right way. 

Who has been your biggest influence? 

Early in my real estate career, I had an incredible manager who was very hands-on and genuinely invested in my success. She pushed me, encouraged me, and made me believe that I could build a meaningful business and achieve whatever I set my mind to. That confidence was incredibly formative for me, and I still think about her influence today. 

What’s something people would be surprised to learn about you? 

Anyone who really knows me also knows I need a Diet Coke or Diet Pepsi every day. And despite working some pretty crazy hours, I don’t drink coffee. In fact, I made it through all of law school without drinking a single cup of coffee! 

What’s your go-to takeout order? 

A chicken cutlet on a roll with lettuce and onions, a side of chips, and a Diet Pepsi. Simple, but hard to beat. 

What TV show are you currently binging? 

I’m currently watching “Lioness.” I love a good CIA thriller. I’m also looking forward to the next seasons of “The Gilded Age” and “Nobody Wants This.”

What is your silliest pet peeve? 

Not answering every question in an email or text. If I send you three questions, I promise I would like answers to all three! 

What’s on your Spotify playlist? 

It’s a pretty unexpected mix: Country music because I’m from the South, classical music because I’m a classically trained pianist, and hip-hop because it gives me an energy boost. 

And, of course, Taylor Swift. Always. 

Who is your favorite architect or interior designer? 

I’m drawn to designers who create spaces with clean, classic lines and thoughtful details. I love a coastal influence and interiors that balance high-end elements with approachable, livable pieces. Not everything in a home needs to be the most expensive item in the room. 

I also appreciate designers who aren’t overly trend-driven. To me, the best spaces feel timeless rather than tied to a particular moment. 

One designer I’ve been working with a lot lately — and who several of my clients have absolutely loved — is Schuyler Grey of the Schoop. Her work really resonates with my aesthetic. 

What is your most entertaining deal story?  

There are too many to count — there’s almost always something funny, unexpected or completely unique about every transaction. 

One that always comes to mind was a bidding war in Larchmont where I represented the buyer. The home generated enormous interest, and we ultimately won against 27 competing bids. 

I will never forget getting the call that my clients had won. It was such an incredible moment. 

The story became something of a local legend, and even years later, people in Westchester still talk about that bidding war. My clients have actually had people recognize them around town because of the house they won! 

That one was a pretty memorable reminder of how emotional and competitive real estate can be — and how important it is to have a strong strategy when the stakes are high.

Amanda Schiavo can be reached at aschiavo@commercialobserver.com. 

If you’d like to be featured in our Get to Know the Broker Spotlight, please click here.