FREE HOME LISTING
Pioneer Realty's owner, Helen, is offering one free listing in the neighborhood. Enter your information below to register. We're experts in Roscoe Village and the surrounding area with nearly 15 years of local real estate experience. Pioneer is a small local brokerage with strong roots in the community. Enjoy your burgers this weekend. We'll chat Monday about how to best market and sell your home!
Enter for a chance to win a FREE LISTING
By registering, you will will be entered in a drawing for the Pioneer sales team to sell your home for free. One local seller will be chosen at random on Monday, July 20.
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Real Estate Is Our Passion
Helen Bailey is the owner and managing broker of Pioneer Realty Group, a boutique Chicago brokerage known for thoughtful guidance, sharp market insight, and highly personalized service. With an MBA in Real Estate Finance from DePaul University and deep experience across residential sales, leasing, property management, and investment strategy, Helen brings a sophisticated, full-service perspective to every client relationship.
Warm, strategic, and deeply knowledgeable, Helen helps buyers, sellers, and investors navigate Chicago real estate with confidence. Her approach blends elevated service with practical expertise, creating a seamless experience rooted in trust, discretion, and results.
Recently Sold by Pioneer
View All ListingsAt Pioneer Realty Group, we offer comprehensive services to ensure a smooth and stress-free home-buying experience. Our dedicated team provides personalized consultations, in-depth market analysis, expert negotiation strategies, and seamless guidance through the closing process. Trust us to handle the details while you focus on finding your dream home.
At Pioneer Realty Group, we offer comprehensive services to ensure a smooth and stress-free home-buying experience. Our dedicated team provides personalized consultations and in-depth market analysis to help you make confident decisions about your purchase. From your very first meeting, we focus on understanding your unique needs and preferences so we can match you with the right properties.
We also offer expert negotiation strategies and seamless guidance through every step of the closing process. Below, you’ll find a clear outline of the steps we follow to keep you informed and supported from start to finish. Trust us to handle the details, keep things moving on schedule, and make sure the entire experience is as easy and enjoyable as possible while you focus on finding your dream home.
Start your home search now with an interactive map and customizable search options.
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Helen Bailey is the owner and managing broker of Pioneer Realty Group, a boutique Chicago brokerage built on relationships, trust, and a deep love of real estate. With an MBA in Real Estate Finance from DePaul University and years of hands-on experience in sales, leasing, property management, and investment strategy, Helen brings both heart and strategy to every client relationship.
Known for her honest guidance, practical advice, and calm problem-solving style, Helen helps buyers, sellers, investors, and renters feel confident through every step of the process. Whether she is helping a first-time buyer find the right condo, advising a seller on pricing and presentation, or walking an investor through the numbers, Helen’s goal is always the same: to make real estate feel less overwhelming and a lot more approachable.
At Pioneer Realty Group, Helen has created a small-but-mighty team that is nimble, knowledgeable, and genuinely invested in its clients’ success. Her approach is personal, collaborative, and rooted in the belief that great real estate service should feel both professional and human. We look forward to working with you!