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Mentoring the Marketplace

About Each Influencer

Having influence is not about elevating one's self, but about lifting others and mentoring them through inspiration.

Local Influential-Chicago introduces residents to local area influencers who are making a difference in the lives around them by following their passion and believing in themselves, despite obstacles that are presented along the way. Behind each and every establishment is someone inspirational who has a unique story to share.

Each story is compelling, sharing a unique path to success. Our featured local influencers provide inspiration and words of wisdom for residents who share their passion for leading a success-driven lifestyle, both personally and professionally.

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PENNY O'BRIEN of NAPERVILLE | Top Naperville Real Estate Agent

Penny O'Brien, Top Real Estate Agent In Naperville, Local Influential-Chicago


This Top Real Estate Agent Loves Mentoring New Agents and Brings Her Confidence and Determination as She Helps Her Clients throughout Every Step of the Real Estate Process

Penny O’Brien’s clients always comment on her boundless energy and her intense work ethic. When she meets clients, she brings her confidence and determination to do her best work. She listens to what is important to them and the results they'd like to achieve.

O'Brien's rise in the ranks of Naperville real estate has been lightning fast, selling $53 million in 2021, her 8th year in the business. Penny was the #1 agent at Baird & Warner Naperville in 2021. Year to date for 2022, the Penny O’Brien Group has $46 million in written and closed sales and 86 transactions. Mainstreet Organization of Realtors recognized her as among the Top 1% in Sales and Transactions. She was awarded Glancer Magazine’s Readers’ Choice award in 2020, 2021 and 2022. She works with two full time agents, Karen Sanders, Mia Dehnoo and a full time transaction coordinator, Leslie Lathrop. They each have our own clients, but they support each other & complement each other’s skill set.

Sellers often can't envision what it takes to get their home ready for the market. O’Brien puts them at ease, sets the timeline and recommends her team of contractors to seamlessly ready the home. The results are in. Her listings receive an astounding 200% more showings than the average agent. She believes in strategic pricing, offers a price range, and discusses the different outcomes. Her listings sell for 2.9% over the market average. She is a consummate communicator. The Penny O’Brien Group’s services include complimentary professional staging, drone photography, dazzling videos and top-notch innovative marketing—in fact, 35 percent of the group’s clients come from marketing.

“I’m honest, confident and determined, and will explain to clients what it takes to get the job done,” O’Brien says. “The reason to work with an agent doing a lot of business is because they have the reputation, people, marketing and processes in place to make the transaction as seamless as possible.”

I am proud to call Naperville home for 22 years. I love sharing my enthusiasm & knowledge of Naperville with its many neighborhoods & 2 school districts.

This summer, the Penny O’Brien Group is proudly sponsoring the Naperville Park District Concert Series.


  • Seller Representative Specialist SRS

  • Buyers agent

  • Relocation Specialist

  • Pricing Strategy Advisor PSA

  • Real Estate Negotiation Expert RENE

  • Certified Staging Consultant CSC


"New agents always ask what I did to become a top producing agent so quickly. Lots of agents keep this close to the vest. I am willing to share my knowledge, give pep talks & provide opportunities. I love mentoring new agents! I am happy to speak at meetings & over share. It is my way of giving back. I was a new agent just 9 short years ago! You learn something from every agent you talk to. Never stop learning." -Penny O'Brien


  • #1 Agent Baird & Warner Naperville 2021

  • Glancer Magazine - Reader's Choice Award 2020,2021,2022 - Best Realtor

  • Baird & Warner Top 1% & Founder's Club

  • Top 1% in Sales & Transactions Mainstreet Organization of Realtors

  • Chicago Agent Magazine Who's Who 2019 - 2022

  • Chicago Magazine Top Realtors

  • #13 In Naperville for Social Media - Property Sparks


Penny O’Brien-Broker

Baird & Warner

836 W. 75th Street

Naperville, IL 60565

(630) 778 1855(office)

(630) 207-7001(cell)


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