Josh Lipton

Josh Lipton is a top-producing real estate broker, developer, and investor serving Chicago and the North Shore. Known for his strategic insight and hands-on experience, Josh brings a rare dual perspective to residential real estate: advising clients not only as a broker, but as someone who actively acquires, develops, and sells residential properties himself.

Since entering the industry in 2014, Josh has built a reputation for guiding clients through complex transactions with clarity and confidence. Early in his career he was named Rookie of the Year by Chicago Agent Magazine, and he has since been consistently recognized by the Chicago Association of REALTORS® as a Top 1% Producer. He has also been named one of Crain’s Chicago Business’ Most Influential Residential Real Estate Agents and was included on the Wall Street Journal / RealTrends “America’s Best Real Estate Professionals” list, recognizing the top agents nationwide.

Josh’s background as a licensed attorney further strengthens his ability to navigate negotiations and complex deal structures. With both business and law degrees, he approaches every transaction with a strategic mindset, carefully analyzing risk, protecting his clients’ interests, and negotiating favorable outcomes.

What truly sets Josh apart is his ability to see value and potential where others may not. The son of an interior designer and an active real estate developer, he has a natural instinct for how design, construction, and smart improvements can unlock a property’s full potential. This perspective often allows his clients to make more confident decisions, whether they are purchasing a home, selling a property, or evaluating an investment opportunity.

Josh is known for his straightforward, consultative style and commitment to honest guidance. He believes that successful transactions begin with clear expectations and thoughtful strategy. “My job isn’t to simply write offers or list homes,” Josh says. “It’s to help my clients make the best possible decision for their long-term goals.”

Much of Josh’s business comes from referrals and repeat clients, a testament to the trust he builds through his candor, market knowledge, and dedication to delivering results. Above all, he understands that while real estate is about properties, it is ultimately about people and helping clients navigate some of the most important decisions of their lives.

WHAT CLIENTS ARE SAYING

I have now worked with Josh on two separate transactions...once on the buy-side and once on the sale-side. Josh not meets but exceeds expectations. Before hiring him on the sale side I interviewed several other brokers and Josh was the one that didn't tell me what I wanted to hear. He was very honest about how buyers would perceive my condo and made several recommendations on work he believed would need to be done to maximize profit. I trusted his opinion and not did he deliver but exceeded expectations by 5% on sale price ($470K price vs $450K valuation). He exceeded expectations in every aspect. Trust his opinion!!! - a Condo home 2018 Near North, Chicago, IL.

Josh worked as our buyer's agent, helping us find a gut rehab to buy in the Gold Coast. He worked with us not to find the right space - but also to find a team that could help us complete the job. Josh seems to have an endless network of high-quality contacts that he generously shared with us throughout the process. From general contractors to architects to flooring experts, Josh got us in of the right people. Josh is also very responsive has great attention to detail. We would work with him again in a second! - Bought a Condo home in 2018 in Gold Coast, Chicago, IL.

Josh was the consummate professional! His expertise his stellar marketing skills ranged from a high impact brochure, 3D dollhouse tour, page placement the Tribune’s Luxury Home real estate section. All of this his attention to detail resulted our getting an offer within 3 days! - a Apartment home 2017 Park West, Chicago, IL.

Josh helped me sell my house Lakeview. When I bought my home it had been on the market over a year so I was very nervous how long it would take to sell. Josh was confident it would sell quickly executed a strong marketing plan (including guidance on prep), even recommended a slightly higher asking price. We got an offer in about two weeks - I was delighted! - a Single Family home in 2017 in Lake View, Chicago, IL.

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