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Jerry Olson
Chairman's Club 2023
REALTOR®
(269) 484-4578
VCard Icon 

Jerry is top notch and a person of highest integrity and experience in SW Michigan.

J Drier, Three Oaks, Mich | Home Seller

Sidney Williams, New Buffalo Michigan | Home Seller

Should have been better with certain details of sale. In particular that the survey l was paying for was only for the carve out acreage being sold. And l was not allowed to personally meet with the survey company as l repeatedly requested.

Sidney Williams, New Buffalo Michigan | Home Seller

Jerry was very informative and professional with all aspects of our transaction.He was always eager to hear what we needed and make us happy in the process and also making sure the new owners were very happy with the property they were purchasing. Jerry takes pride in himself and his company. I have spoken very highly of Jerry and highly recommend him to all of our friends needing someone to assist in the "perfect" home.Mike Reisig

Mike Reisig, Baroda Michiga | Home Seller

Jerry was extremely knowledgable, and thoruough and followed through with interest and concern for all parties. He was always in communication and extremely reliable.Aditionally Jerry is extremely effective and credible in navigating the emotions and expectations that come into every real estate transaction.

Charles Greco, Chicago, IL | Home Buyer

Jerry understands the local market from his years of experience. As a first time home buyer Jerry found a perfect fit for my financial needs. Love the house!!

Braxton Schroeder, Galien Mi. | Home Buyer

Our experience with Jerry and Maggie was exemplary from start to finish! We would highly recommend them to anyone buying or selling!

Heather Hanson, Union Pier, MI | Home Seller

I had switched my listing to Jerry and Maggie Olson after a disappointing experience with another agency. I am extremely happy with their service. They are very experience, knowledgabe and professional. They went above and beyond to keep me me informed and to keep my home prepared for showings. They even cleared my porch entrance for a showing and a inspection after a snow storm. ( a service I'm sure most agency's would not do.) I highly recommend them . I currently have a other home listed with them. I feel confident I will have another positive experience.

Deb Flower, Harbert Mi. | Home Seller

I will highly recommend Jerry and Maggie Olson for you real-estate needs.Their professionalism from the start of the listing to the final closing was orderly and well managed.You will not be disappointed.

Jim Passios | Home Seller

Jerry is very professional, knowledgeable, considerate, understanding and quick in action. We will definitely go back to Jerry for any future real estate needs. Thank you!

Helena Sledz, Sawyer MI | Home Buyer

Got the job done.

Allan Ryden, Arizona | Home Seller

Great work Jerry thanks a bunch, stop by for a drink sometime

Scott Burkholder | Home Buyer

Jerry Olson is an extremely knowledgeable and professional person, who is will to go above and beyond to ensure that your entire experience is an excellent one.He is a true gentleman.

BAC/Bridgman | Home Buyer

Jerry was responsive and professional from the very beginning! We were working with another realtor at the time but Jerry just won us over immediately.

Mike and Carolyn Niles MI | Home Buyer

Jerry is very passionate about helping others. He listens to you and has a long history of a strong sales record. Would recommend Jerry to anyone.

The Evelyn Gothberg Trust | Home Seller

Jerry's wealth of experience in the real estate business and professionalism in handling the unique challanges of selling our property were critical in accomplishing a successful transaction. We really appreciate all of the time and effort he and Maggie put into selling our house. They are very kind, compassionate people.

Jennie Koebel, Galien, MI | Home Seller

Jerry is well regarded and has an outstanding reputation / well deserved.

Michael Sheridan / Chicago | Home Seller

Jerry has handled other RE transactions for me in years past. He is always at the top of the game professionally. I always recommend him to others whenthe occasion arises. In my book, he is the best of the bunch at what he does.

John Olson, Sawyer | Home Buyer

Jerry is a real stand-up guy, and made the journey into my first home purchase simple and enjoyable.

Derek, New Buffalo | Home Buyer

Jerry Olsen is the BEST Harbor Country Real Estate Agent, PERIOD! He has the history, knowledge and understands the community.

James Wagner | Home Buyer

Jerry Olson (and his wife Maggie) were super to work with. Always professional,knowledgeable and helpful. Felt like they worked in our best interest all thetime. Experience counts. Thanks, Jerry, you were great.

Diane Holzer, Burr Ridge, IL | Home Seller

Jerry Olsen did a great job for us. We had four showings the first day the house was on the market and three offers. The closing was four weeks later. Jerry’s knowledge of the market, his communication and follow up we’re excellent. I would absolutely use Jeri Olsen again if the need arises.

Wayne Krahn. Tinley Park IL | Home Seller

Jerry, I knew you would do a great job for me but I had no idea anybody would go so far above and beyond as you did. I can't thank you enough for all your hard work with a difficult property.

Donald Prosser Battle Creek, Mi. | Home Seller

Very happy with Jerry Olson's handling and sale of our property.

Albert Schuck | Home Seller

Very comfortable with the sale.

Mary Balducci | Home Seller

Jerry Olson and his partner Maggie Olson are both top-notch. I never had to worry about anything in managing the sale of our property, and they got us a great price. There were of course a few twists and turns along the way as we got through all of the contingencies and through a lengthy period before closing (we required a delayed closing), but the Olsons completely took care of anything that cropped up. No ball was ever dropped. They also helped line up some of the work that had to be done at the property to prepare it for showing. This was especially helpful as I was managing the sale from a distance.The property was a vacation home, which family members used sporadically over the course of the summer when it was being sold. The Olsons were always very respectful of their privacy and ensured that any necessary visits to the property by prospective buyers and others did not interfere.Pricing was a little tricky, because there really were no exactly comparable properties available. Jerry Olson initially spoke of a sales price range, rather than trying to pick a specific price, which made sense to me. He then zeroed in on a price level that turned out to be just right, as we received a successful offer within a week at the asking price. I had the impression that Jerry had a very good "feel" for what the market would bear and could evaluate the somewhat comparable properties in a way that yielded the right results for ours. His deep knowledge of the local market paid off.Overall, I was very impressed by the Olsons' professionalism and appreciated all they did for us. It was a pleasure working with Jerry and Maggie Olson.

Ruth Hansen, Virginia | Home Seller

I can't say enough good things about Jerry! He was so helpful & gracious in every way!I would recommend him to everyone who is looking for real estate.Thank you Jerry Olson.

Michael Coman Agency, MO. | Home Seller

Jerry Olson was personable, knowledgeable, and very professional. He knows the market in southwestern Michigan. I would recommend him to handle your listing and sale of your property.

Pat Rosenfeld , Kihei, Hawaii | Home Seller

Jerry and Maggie were wonderful to work with in selling my home. Both are caring, professional people. I will always recommend them to anyone buying or selling a home.

Cheryl, Buchanan | Home Seller

We had multiple offers on our home. The one we originally accepted, had some glitches that we were in agreement with, but the deal fell thru. We relisted and had an offer in 3 days. Jerry helped put the deal together and closed it for us. I am very please with his communications and availability, as this was really important to us.Thanks Jerry and Maggie.

Dave Thomas, Three Oaks, MI | Home Seller

My husband and I both thought Jerry did an exceptional job with our property purchase! He is extremely knowledgeable about the area, property zoning, closing process, etc. and, at the same time, is such a great person to work with. It was honestly a pleasure doing business with him. We were lucky he was part of the team!

Susan Wilson, Sawyer Michigan | Home Buyer

We were referred to Jerry Olson by another business owner in the Harbor Country area, and he more than lived up to the recommendation. We appreciated Jerry's friendly personality and no pressure approach. He cut through difficult questions with easy to understand answers. His knowledge of the area was extremely helpful. It was a pleasure to do business with Jerry!

Ginna and Louie Anderson, South Bend, IN | Home Buyer

Jerry is a very honest man and real estate broker. Our family has known him for many, many years. I trust him and his opinion. His years of sales and reputation should speak for itself. Jerry not only tries to sells your real estate, he gives you ideas to help you get a better deal. You can count on Jerry and his staff.

One of the few honest real estate agents around! A true gentleman and class act business man. I would not have been able to close on this house if it were not for his amazing negotiating skills, determination, and knowledge of the community. I plan on continuing to use Jerry in all my future real estate transactions. I HIGHLY recommend Jerry to anyone looking in the Southwest Michigan area.

Jerry Olson and his team provided exceptional customer service and knowledge throughout the entire purchase process of our new home. If you are interested in purchasing a property in Harbor Country I would highly suggest you consider you meeting with the Olson team.

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 05/16/2026. The listing information on this page last changed on 05/16/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 05/16/2026 4:08:08 PM EST) or MichRic (Michigan Regional Information Center) (last updated Sat 05/16/2026 4:03:16 PM EST) or NIRA MLS (last updated Sat 05/16/2026 4:04:46 PM EST) or IRMLS (last updated Sat 05/16/2026 4:07:18 PM EST). Real estate listings held by brokerage firms other than Cressy & Everett Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Agency License Information: Cressy & Everett Real Estate is licensed in the states of Indiana and Michigan.



Agent License Information: Jerry Olson is licensed to sell real estate in the state of Michigan.

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