Josh Lipton

Josh Lipton

Broker | President, Lipton Luxury Living

Social Media

Facebook_CIR_BLK Instagram_CIR_BLK Linked_In_CIR_BLK Updated_Zillow_Icon


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)



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


Indiana University - Kelley School of Business, 2006

Indiana University - Maurer School of Law, 2012


Josh plays a role numerous local charities including The Chicago All-Stars Project, Jewish United Fund The Superhero Collective, where he is a board member.
About Josh
Since entering the residential real estate industry in 2014, Josh Lipton has quickly climbed the ranks amongst Chicago’s top producing agents and hasn't looked back. After being named Rookie of the Year by Chicago Agent Magazine in 2015, Lipton has been recognized annually by the Chicago Association of Realtors as a top 1% producer and was selected as one of the 2018 Most Influential Residential Real Estate Agents in Chicago by Crain’s. In 2021, Lipton was included on the Wall Street Journal's Real Trends "America's Best Real Estate Professionals" List, an accolade bestowed upon the top 1.5% of more than 1.4 million licensed Realtors nationwide. 

Lipton’s professional experience and background as a licensed attorney have prepared him to embrace one of the often-unacknowledged truths about real estate: The business is less about the property than it is about people. Armed with both business and law degrees, Lipton has a keen understanding of the many nuances buyers, sellers and developers 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 daughters, Leni and Summer. 


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.


Josh Lipton’s Listings

Compass Coming Soon
6 BD
5.5 BA
Listed By Compass
5 BD
3.5 BA
4,200 SF
Compass Coming Soon
1632 North Leavitt Street

Chicago, IL 60647

5 BD
4.5 BA