Inside the Mind of Luxury Real Estate Agent Brian Milton

The elite agent is sharing everything from what makes him tick to stellar advice.
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Photograph by Julia D’Agostino

If you’re familiar with the Fairfield County and North Westchester luxury real estate markets, you know the name Brian Milton. A founding agent of Compass Greenwich and Compass Westchester, creative-thinking Milton has a natural ability to see beyond four walls. He was on the ground in both areas before Compass established offices there, wanting to challenge himself to grow with this company. Selling nearly 750 million in real estate over the past 11 years, Milton’s track record of success speaks for itself.

Now, here’s the chance to get to know the elite agent who serves captains of industry, young families, and everyone in between. Find out what makes him tick, his advice for buyers or sellers right now, and much more.

Living room with herringbone floors

Photograph Courtesy of Compass

What is your life motto?

My motto is whoever I deal with, I expect to see them in business or in a personal way again one way or another. So whatever we do in the original deal, I’m prepared to speak to it again on the follow-up transaction in the future. It’s about long-term relationship building and it works really well.

How did you decide to get into real estate?

Real estate was a total 180-degree career change for me. I was inspired to do something different when life began with my family and we had our first child.

How has your approach to real estate changed over the years?

From the onset, I aimed to create a different approach from the traditional platform of an agent doing business in just one town. I started out in one town as a base, in the area where I grew up, Armonk, NY. It evolved to relatable markets in addition to the state of Connecticut and into a luxury brand that offers services that clients are looking in or looking to sell in. From day one, I’ve tried to come up with new ideas and value-added services to always be one step ahead of the competition.

More evolving in the future will be a subset of what has already been created. Bringing in additional people around me to work with new buyers and sellers in multiple markets. I’ve expanded, and now I am deepening. I always want to be the brand people call for, but able to serve each market in a successful way with really good people around me. This included my move to Compass three years ago, which was a strategic move to expand my network in multiple markets around the country. I had built my career with the same company for 14 years, which was a great experience, but was ready for a change. This move to Compass has taken business to an entirely different level and has worked primarily based on the broad reach of Compass in addition to its forward-thinking business model.

How would you describe your relationship with clients?

Confidential, interactive, informative, available at all times, proactively giving them information that provides a service of value not found on the internet. That is what continues to build the business. People realize that there is a relationship with facets of business that they never thought was part of the service of being an agent. It surprises them and is effective in achieving their goals.

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Photograph by Julia D’Agostino

What do you love about the NYC suburbs and why have you focused your business there?

It’s what I can relate to. It’s the architecture, landscape, and homes that frequently need updating and a fresh look. I love seeing the before and after and providing my insight for what can be done in a home for the clients who don’t have that vision.

The suburban move is generally about solving for additional space and room to grow. I can articulate what could work for a buyer that would enhance their lifestyle by moving to the suburbs, speaking to the amenities of multiple markets. I know what markets would work for certain buyers, taking into consideration distance to Manhattan or what’s desirable in their commutes. Also, a lot of my business is working with people who are buying secondary homes in the suburbs and it’s equally rewarding to find them a place in the country to escape the city day-to-day. Weekend houses provide a lot of opportunities, especially in today’s climate and that’s where an additional part of my service comes into play.

What was it like growing up in Westchester County?

Growing up in Northern Westchester, the Armonk and Bedford area, was joyful. It was an experience that created lifelong friendships that are hard to replicate. It’s been wonderful watching Armonk evolve. Through the years, it has become an even more refined community, but still has the same quaint characteristics that it had when I was growing up.

Inside the Mind of Luxury Real Estate Agent Brian Milton

Photograph Courtesy of Compass

What are some characteristics of Westchester County and Fairfield County you love?

The beach towns, Old Greenwich and Westport are two great communities where people really enjoy the lifestyle of coastal living. The Northern Westchester suburbs with rolling lawns, open space, lake clubs, and privacy is another area that I am particularly fond of in an entirely different way.

And outside of real estate, what are some of your favorite activities?

Spending time with the family, sports activities with the kids and my wife, traveling when time or circumstances allow. I love sports: baseball and football are two of my favorites. For teams, I’m a Yankees and Giants fan. I’m also a painter, I enjoy oil painting and have an artistic background. Since I was young, it’s always been enjoyable and somewhat therapeutic just to pick up a paintbrush and paint a landscape or a portrait. That is sort of what inspired me to have a vision in real estate and architecture.

Inside the Mind of Luxury Real Estate Agent Brian Milton

Photograph Courtesy of Compass

If you weren’t a real estate agent, what would you want to be doing?

I would definitely be involved in home development in some way, shape, or form. I truly enjoy watching something being built from the ground up or being restored. The before and after, the creative aspect of real estate development and architecture is what keeps my blood flowing. So, it would definitely be something along those lines.

Early in my career, I surrounded myself with builders and watched houses being built. I educated myself on the process of what a house is, how it’s created, and the different components that go into it. It’s paid dividends in being able to educate buyers that aren’t familiar with that. This is an extremely valuable service that people appreciate and come back for, and many recommend me to others for this reason.

Modern home with glass walls

Photograph Courtesy of Compass

Is there a certain style of architecture you most enjoy?

I have a love affair with most styles in various ways. Specifically, I like the simplicity of modern architecture—lots of glass, indoor-outdoor perspective of interior space and its relationship to nature. I’ve become a student of all types of architecture, from older homes that have been renovated as well as being fluid in the language of new construction to somewhere in between, like mid-centuries. I appreciate all that they are in their existing form and what they could be if someone is willing to take on a project.

And this interest in architecture is something you’ve really taken up on your own, right?

It’s a natural instinct for me and I think it’s because I have an artistic background to see things that aren’t there yet and create. Then combining that with people skills, which is a lot of our business.. The process needs to be organic with patience and many explanations. It’s pivotal to make someone feel comfortable with the process of buying real estate and understanding what they are pursuing. It comes naturally to me and I enjoy every minute of helping people turn the chapters in their lives.

Rustic chic living room

Photograph Courtesy of Compass

Here’s a bit of a rapid-fire to pick your brain about real estate currently. What practices or lessons from the times of COVID-19 do you think could be here to stay?

Fully vetting and qualifying buyers before showings to know that they are ready and able to buy.

What is your top advice for buyers right now? And for sellers?

For buyers, see as many places as you can so you are educated walking into the right one and be prepared to bid on the one you like because others are going to be ready as well.

For sellers, prepare yourselves with a plan of where you are going in case the right deal happens before you expect it to.

What are you hearing from clients who currently want to move from New York City to the suburbs? Give us a peek into their mindset.

The mindset of buyers is much more open to looking further out of the city now than they were pre-COVID. That’s based on the thought process of not feeling like they have to go to the office 5 days a week, could be 2-3 days now. Pools are key for the current buying market moving out here because they are uncertain of the ability to travel or use their club amenities. Having their own recreational space and tennis, or the potential for it, is also a big draw.

Inside the Mind of Luxury Real Estate Agent Brian Milton

Photograph Courtesy of Compass

Lastly, what are your musts in life?

Taking care of my wife and four children, and enjoying my personal family time with them. I thrive on our own personal projects within our family’s home. Now on our third renovation project, some family members are more patient with my creative spirit than others. Beyond that, my must has always been to be at the top of the industry in a very crowded arena and maintain a love and passion for it.

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Photograph by Julia D’Agostino

With a deep knowledge of luxury inventory, both on and off-market, Brian Milton serves his clients above and beyond their expectations. However, it’s his design and construction knowledge that helps people not only find a home they love, but create it. Visit or follow him on Instagram to see Milton’s current listings and get in touch to work with him..