Agent Spotlight: Jennifer Riccolo DeBower

Have you ever been inspired to start anew?

Chicago real estate agent Jennifer Riccolo DeBower has, and so she did.

“One day I woke up, and decided I should be doing what I want to do when I grow up. Never mind the fact that I was over 35,” she said. “I’m so grateful that I decided to start this business.”

Real estate was a natural career transition for this licensed attorney, who previously practiced civil litigation.

“Helping people buy and sell homes in Chicago is the perfect combination of using my legal skills and my desire to have the time and flexibility to experience a full life,” said Jennifer, who calls herself “fluent in legalese.”

We chatted with Jennifer to learn more about how the East Ukrainian Village mom of two balances her family, her Chicago real estate career…and the occasional glass of rosé. 

A beautiful home that Jennifer viewed at a fellow @properties’ agent’s broker open house

At home

@properties: What do you love most about your neighborhood?
Jennifer: I love that in the East Village, I am walking distance to the shops and restaurants around Damen and Division.

I’m also surrounded by gorgeous 1890’s architecture. The brick work on some of the homes is a thing of beauty.

@properties: Describe your own first home — what was it like?
Jennifer: My first condo in Bucktown was a fourth floor corner unit with walls of windows facing south and west. The light was my favorite thing about it. It was in an elevator building, which made it super quiet.

I had the pleasure of showing the exact unit to a client recently. It was surreal to be inside again.

@properties: When you moved into your current home, what was the first big-ticket item you purchased?
Jennifer: My husband and I converted a two flat into a single family home eight years ago. It was a gut rehab, so we were able to pick every piece of the house.

My favorite splurge was adding ipe decking to the porch. It doesn’t need to be stained and is so smooth. We never have to worry about splinters when walking barefoot.

The pork chops at El Che Bar in the West Loop are one of Jennifer’s favorite dishes

At play

@properties: Let’s say you have a full day free. Whats on your agenda?
Jennifer: I love spending a day walking through a neighborhood, popping into shops, stopping for a coffee or lunch and taking in the sights.

The perfect day would include a stop at Cafe Gelato and a seat at the chef’s counter in front of the fire at El Che Bar in the West Loop — they have the best pork chops in the city, hands down.

Bonus points for perfect weather and a glass of rosé at an outdoor cafe along the way.

@properties: How do you stay involved in your community?
Jennifer: I believe there is a season for everything in life. Right now, my kids are young. I have two boys under age six and I’m engaged with their school, which is really fun.

I’m also really looking forward to participating in the Women’s March this year on January 20. Last year, it was one of the most amazing experiences to be in the mix with so many positive and empowered people in the heart of Chicago.

In the past, I’ve been on the Associate Board of Ambassadors for The American Cancer Society and served on the board for Chicago Volunteer Doulas, an organization that provides birth support to underserved populations.

Jennifer at a home for sale in River Forest

At work

@properties: What is the one thing you couldn’t do your job without?
Jennifer: My phone. It is when talking to people —  my clients, other @properties agents, inspectors and attorneys — that the magic happens. Connecting with others allows me to advocate for my clients as best as I can.

@properties: What is your proudest achievement to date?
Jennifer: I’m proud to say that I’ve been able to win multiple offer situations for many of my clients. On the occasion that we lost, I was able to find a way to submit another offer, and my clients live in their dream home today because they trusted my plan.

@properties: What is one piece of advice you’d give to a colleague?
Jennifer: Always keep calm and carry on. Keeping my energy level calm allows me to see clearly and work effectively on behalf of my clients.

Also, consistency is key. This business requires grit and follow through, but mostly it requires consistent action every day to stay in touch with potential clients and build strong relationships.

To connect with Jennifer, visit her website, or follow her on Facebook and Instagram.

Written by Maris Callahan (Blog Editor)
Maris is the director of communications at @properties. She lives in Wicker Park and when she's not at work, she's usually cooking, reading, writing or walking the 606 with her chihuahua, Henry.