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Michelle DeWoskin, Owner & Managing Broker

As a third generation Chicagoan to enjoy a career in real estate, I take pride in my work and service.  I guide buyers and sellers of homes and condos with my knowledge of the market, and ability to understand people.

As with life, a career is only as successful as the relationships built along the way.  Selling and purchasing real estate is exhilarating, and can also be emotional and taxing. I am sincerely dedicated to my clients throughout the process – keeping constant contact and providing thorough checks and balances.  All scenarios can result in the satisfaction of all parties.

Having worked in the arts as a professional dancer, writer, and yoga instructor, and having lived many years in both New York City and Los Angeles, I bring experience from various fields and environments which prepares me to work with, and adjust to, all that comes along.

Building a portfolio of loyal and growing partnerships with local builders and developers, I enjoy finding land and properties for community growth and improvement, where all sides of a transaction are served for the better.

I take great pleasure in the diverse and unique communities around Greater Chicago and its surrounding suburbs; and specialize in Lakeview, Lincoln Square, Roscoe Village, and North Center where I reside, run, ride, and raise my two boys.

Land and Property Prospecting and Acquisition

Our contacts with local builders and developers often provide a perfect solution for some sellers.  Ease of direct purchase offers with little to no contingencies, avoiding the inconvenience of showing your property at anytime for browsing buyers, time or financial constraints - all valid points for selling your home as is, without risking mortgage contingencies or buyer's remorse in the open market sales contract.  


Buyer’s and Seller’s Representation

Our experience with both on and off market avenues for purchases and sales provide our clients all options available for a successful transaction. Knowledge of the market for optimal price point positioning, relationships with brokers & developers, and compelling marketing strategies & products -  these are the basics for our clientele.


Expert Negotiation Resulting in Success

Our education and expertise with market analyzation are just the start of our negotiating position. We know our area markets - we respect our communities and our neighbors. Relationships come first. Trust, respect and confidence in the numbers are the pillars of a successful negotiation.


Relocation and Moving Synchronization

From researching neighborhoods, finding the right property, negotiating the purchase along with your current exit strategy - to vetting movers, arranging what stays and what goes where, transferring utilities... the list can seem insurmountable.  We can assist with placing all the pieces.  We have strong partnerships that we count on again and again; we know where to find just what you need so you can enter your new chapter confident and ready.  You are not alone.



Yep, and that...


Design and Rehab Consultation and Management

Whether juxtaposing furniture and art placement, designing a new kitchen layout, or drawing plans for new construction or gut rehab - we have the eye, the experience and the partners in each area of expertise.



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Michelle DeWoskin Properties Llc

4044 N. Lincoln Ave. #379

Chicago, IL 60618

773-432-4136 c.


"I have had the pleasure of working alongside Michelle DeWoskin for the past few years. I knew from the start that Michelle was not just the typical broker… Michelle is a trailblazer who recently launched her own independent brokerage - MDW Properties, dedicated to working with builders, contractors, developers, architects and small businesses.

Having worked with Michelle, I know her to be a thoughtful and personable real estate professional and strategist who constantly researches the market in order to leverage her knowledge in a manner that allows her to provide great insights into the details of the project. 

I admire her tenacity in finding and providing her clients real estate opportunities and properties utilizing her skills as a talented negotiator and expert researcher resulting in a superior knowledge of the real estate market. I am honored to write this recommendation and excited to see what the future has in store. Well done!"

- Wendy Calvert, Attorney, Realtor


"Michelle is an absolute go-getter. She was relentless in finding a buyer for our home. Michelle came through and accomplished exactly what she said she would."

- Scott Grzesiak, Property Seller


"Michelle is an absolute gem. She is my first call when we are planning a move. I've worked with Michelle twice now while looking for a home. Michelle stands out because working with her I feel like I've finally found someone who cared about my search and would look out for my interests during the process. For example, touring a home, unlike many other agents, she was actively engaged, asking good questions about issues that I hadn't thought of or that I had forgotten to ask. Michelle also took the time before we even began looking at homes to discuss our goals and priorities so she understood what was important to us. 

Michelle also is a great negotiator. In a particularly difficult negotiation, Michelle was calm, collected and professional even after I had become frustrated with the other side (and I negotiate contracts for a living). I was very impressed!  At the same time, I also appreciated her counsel on different options, not to mention her incredible responsiveness. The deal ultimately didn't get done but I felt like Michelle had done everything that she could to try to make it work, though in the end we eventually choose another home that Michelle had showed us. We were and are incredibly appreciative of Michelle for all of her efforts and that working with her was such a pleasure, even if the circumstances weren't always easy. 

Suffice to say, Michelle has earned my trust and as long as she has time I don't plan on working with anyone else."

- George Houhanisin, Home Renter


"Michelle was instrumental in finding a buyer and helping obtain a fair price for our building within a short period of time while the housing market was still depressed. We were very grateful for her expertise and diligence."

-Jane Zimmerman, Property Seller


"Michelle is the ultimate professional and a complete pleasure to deal with. I have used her to rent apartments in my two-flat multiple times and she has always found me good, reliable renters. She is easy to work with and understands the ins and outs of real estate. If I have a need for a realtor, I will definitely use Michelle again."

- A Carlo, Multi-Unit Owner/Landlord


"Working with Michelle was truly an excellent experience. My finance and I met Michelle while visiting an Open House. We were new to the city and looking to purchase a home in Chicago. We quickly felt very comfortable discussing our needs with Michelle and we were very impressed with her knowledge of the local neighborhoods. When we reached out to Michelle to be our agent she was immediately responsive and we were out looking at homes the very next weekend. She spent lots of time showing us a variety of places until we ultimately found a condo that we fell in love with. Michelle was an effective negotiator and was very helpful throughout the inspection and closing process. I would recommend Michelle to anyone looking to purchase a home." 

- John Phlipot, Home seller/purchaser


"Michelle is the most patient and knowledgeable agent I have ever dealt with. She works fast and is a tough negotiator. I felt that she had my best interests at heart and really understood what it was that I was looking for. I highly recommend her and would use her again if need be."

- Sonya Nieves, Home owner


"Michelle was great in helping me through the process of buying my first home. She was very professional with a personal touch. I couldn't have done it without her."

- Amanda Williamson, Home purchaser


"Michelle helped me find the perfect apartment for my family. She was very knowledgeable, prepared, and a joy to work with."

- Kim Knoper, Home renter