About Us



The goal Up-North Living Real Estate is to “Live your best life Up-North!” and to help others to do the same as well. Things are changing and being tied to a desk was no longer a productive use of my time in this business. Over 90% of buyers now begin their search online instead of coming into an office. Think about where you looked for the property recently. My guess is it was on your phone, tablet or computer. I absolutely love getting out and about in the nearby communities instead of watching the world go by behind a desk.

I have put together an informative, competitive and user friendly website for buyers and sellers.  I have created a mobile office that can come with me anywhere if need be.  Truly looking into the future of Real Estate and what buyers and sellers are looking for. Putting into action what I know will work in today’s world. Great customer service is what I strive for. Prompt replies and great communication is what you can expect when we work together.

I grew up in the Chicago area and like many of you fell in love with Wisconsin at a young age.  Some of my best memories are visiting my Great Aunt Ellen on Golden Lake down in Oconomowoc.  I was fortunate enough to buy my first property in the Northwoods in 2001. In 2004 I made the big move and have been a full time resident ever since. The biggest unexpected bonus the Northwoods gave me was meeting my husband Rob Benson who is a lifelong resident and grew up on the Manitowish Waters chain. Lucky him getting to grow up here and lucky me for meeting him and now having an amazing family close by. It almost makes me a local!

I understand buying and selling a second home or transitioning to the Northwoods as I have been in those positions myself and would love to help you navigate the waters .

So let’s talk and let me help you “Live Your Best Life Up-North!”

Sheri Benson
Broker Owner

  • Wisconsin Real Estate Brokers License
  • Board of Directors, Greater Northwoods Association of Realtors 2016-2017
  • National Association of REALTORS
  • Wisconsin REALTORS Association
  • Northwoods Association of REALTORS
  • Member of Presque Isle Chamber of Commerce
  • Member of Manitowish Waters Chamber of Commerce

Local Expert

Professional Staging & Photos

Online / Print Marketing


We enlisted the help of Sheri to sell our lake cottage. Sheri was very familiar with the area and helped us properly assess the market value of the cottage. Sheri also provided us with suggestions to improve our property’s overall visual depiction. She even helped us obtain contractors to perform the minor work she suggested to improve the property. Sheri was always very responsive to communication either by email, text messages or by telephone.

Most importantly Sheri was able to help us obtain a fair price for our property. We highly recommend Sheri as a real estate agent for anyone looking to sell their property in the North Woods.

Chris and I want to thank you for all your help in finding our dream cottage. We were so impressed with the way you handled the whole process, from writing up the offer, shepherding us through the financing paperwork and closing. We even closed early!!! You gave us all the information we needed and you gave us honest answers to all our questions. If someone asks us if we know of someone to help them in their home search we would not hesitate to name you as a reference. Once again we would like to thank you for everything you did.

We were referred to Sheri by friends who live in the Northwoods, after we bought our cabin we know why. Sheri was relaxed, real, thorough and all encompassing throughout the search for our cabin.  When we found our Goldilocks and it was time to negotiate, Sheri listened to what we had to say, and gave her suggestions. We are extremely pleased we chose to work with Sheri Benson and now have a Northwoods cabin where we can come to slow life down and share with our family for generations to come. We highly recommend speaking with Sheri before you embark on your own house hunting adventure, you won’t be disappointed.

Stephen Krezinski

Sheri was very instrumental in helping us find our dream property in Presque Isle. We shared with her our list of wishes that we visualized for our north woods retreat. Although we lived out of state, she consistently emailed us any listings she felt met our criteria. In less than three months, she had found the place that we fell in love with immediately. Through the process, she was always available to guide us and promptly answer any questions that we had. To this day, she is still happy and more than willing to be of assistance, when needed. Working with Sheri was such an enjoyable experience that we now consider her our friend..

John & Cindy Monaghan