Josh Lipton, Agent in Chicago - Compass

Josh Lipton

Broker | President, Lipton Luxury Living

Chicago Agent Magazine - Rookie of the Year, City of Chicago (2015)

Chicago Association of Realtors - Top Producer (2015-2018)

Chicago Association of Realtors - Top 1% (2017, 2018)

Crains - Chicago's Most Influential Residential Real Estate Brokers (2018)


Josh Lipton has been consistently praised in the press:

Featured in Crain's, Chicago's Most Influential Real Estate Brokers, March 2018

Chicago Tribune, Modern home in Chicago high-rise, April 2018 and Lincoln Park home with two parking spaces: $2.2M

Chicago Agent Magazine, ,"Who's Who" in 2018, 2017, and and 2016.

Chicago Agent Magazine, Rookie of the Year, 2015 and Reigning rookies of the year share advice for new agents, 2016

Chicago Agent Magazine, My Style: Josh Lipton, Broker/Attorney,

Social Media

Facebook_CIR_BLK Instagram_CIR_BLK Linked_In_CIR_BLK Updated_Zillow_Icon


First-Time and Experienced Buyers and Sellers, Developers and Builders, Professional Athletes and Entertainers, Investors and 1031 Exchanges, Corporate Relocations, Multifamily Properties, Value-Add Opportunities, Land Acquisition and Off-Market Opportunities


Indiana University - Kelley School of Business, 2006

Indiana University - Maurer School of Law, 2012


Josh plays a role in numerous local charities including The Chicago All-Stars Project, Jewish United Fund and The Superhero Collective, where he is a board member.

About Josh

Since entering the residential real estate industry five years ago, Josh Lipton has quickly climbed the ranks amongst Chicago’s top producing agents. After being named Rookie of the Year in 2015, Lipton has been recognized annually by the Chicago Association of Realtors as a Top Producer, earning the Top 1% distinction in 2017 and 2018, and was selected as one of the 2018 Most Influential Residential Real Estate Agents in Chicago by Crain’s. Lipton’s professional experience and background as a licensed attorney has prepared him to embrace one of the often-unacknowledged truths about real estate: The business is less about property than it is about people. Holding both business and law degrees, Lipton has a keen understanding of the many nuances buyers and sellers may encounter during any given transaction. His business acumen, negotiation skills and broad transactional experience lend him the foresight needed to navigate the complex real estate market and strategically improvise and advocate for his clients.

Lipton’s hands-on, consultative approach combined with his tenacity, candidness and friendly demeanor has led to a business largely driven by referrals and repeat clients. “Oftentimes, buyers have a preconceived notion of what kind of property they think they want and in what neighborhood; however, I always tell my clients, “You don’t know what you don’t know, and encourage them to think outside the box by placing their trust and confidence in my judgment.” The son of an interior designer, Lipton also has a knack for creating an overall vision of a property, helping clients appreciate its true potential and future value with minor renovations or a complete facelift.

Part of what makes Lipton’s approach so successful is candidly setting and managing expectations from the get-go, by distilling the home buying and selling processes to their simplest terms and providing candid guidance, insight and sound reasoning every step of the way. “I don’t necessarily tell my clients what they want to hear, I tell them what they need to hear. Any agent can simply write an offer, but often the highest offer is not the winning offer; the human element is vital and must not be overlooked.”

The aspect Lipton loves most about real estate is that just as no two properties are the same, each client is motivated by different objectives, which is why he takes the time to thoroughly connect with every client on a personal level. Lipton understands that his clients are the lifeline of his business, and his ultimate success relies on each client’s complete satisfaction. “At the end of the day, nothing is more rewarding than knowing I turned a stressful and overwhelming process into an enjoyable and memorable experience.”

Josh and his wife, Jordyn reside in Roscoe Village with their daughter, Leni, and her four-legged brothers, Hank and Levi.


I have now worked with Josh on two separate transactions...once on the buy-side and once on the sale-side. Josh not only meets but exceeds expectations. Before hiring him on the sale side I interviewed several other brokers and Josh was the only 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 only 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!!! - Sold a Condo home in 2018 in 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 only 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 front of the right people. Josh is also very responsive and 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 and his stellar marketing skills ranged from a high impact brochure, 3D dollhouse tour, and front page placement in the Tribune’s Luxury Home real estate section. All of this and his attention to detail resulted in our getting an offer within 3 days! - Sold a Apartment home in 2017 in Park West, Chicago, IL.

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


Josh Lipton’s Listings

Josh Lipton’s Recent Transactions

Recent Sales
Recent Rentals