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Explore My Properties

Your Story Starts with the Right Home

With a deep understanding of the market and a passion for helping others, Chessica brings warmth and expertise to every step of your real estate journey. She takes the time to listen, guide, and support you—whether you’re buying your first home or making your next big move. With Chessica by your side, finding the right home becomes a meaningful experience built on trust and care.

100+

Closed Sales

$119.5K - $1.4M

Price Range

$334.7K

Average Price

$21.8M

Total Value

Chessica Reichert-Olson

Meet Chessica


With over 20 years of experience, Chessica has guided hundreds of buyers and sellers through one of life’s biggest milestones with care and confidence. She believes that real estate is more than a transaction—it’s about building lasting relationships and helping clients find a place that truly feels like home. Known for her honesty, strong communication, and personalized service, Chessica goes above and beyond to make every step of the process smooth and rewarding. Whether you’re buying your first home, upgrading, or selling, she’s dedicated to making your experience stress-free and successful.

License
#40148366

Why Clients Chose me

1
23+ Years of Experience
Licensed since 2003 with a proven track record in residential, investment, and development sales.
2
Proven Results
$4.5M in sales last year and on pace to exceed that this year.
3
Lake Property Expertise
Unique insight into lake homes from personal experience co-owning a resort and marina on Lake Vermilion.
4
Aggressive Representation
I fight for every client's best outcome with strong negotiation skills and relentless follow-through.
5
Personal Care
Real estate is one of life's biggest movesI'm there every step of the way with honest communication and true dedication.

Featured Properties

  • 4281 End Of Trail Lane For Sale

    $925,000

    4281 End Of Trail Lane, Greenwood Twp, MN 55790

    • 4 Beds
    • 3 Baths
    • 2,998 Sq.Ft.
  • 3638 Fectos Road For Sale

    $499,900

    3638 Fectos Road, Greenwood Twp, MN 55790

  • 428 Riverview Drive For Sale

    $359,900

    428 Riverview Drive, Monticello, MN 55362

    • 5 Beds
    • 3 Baths
    • 2,838 Sq.Ft.
  • 605 Main Street For Sale

    $349,000

    605 Main Street, Tower, MN 55790

    • 4,467 Sq.Ft.
  • 95536 Pine Island Pending

    $309,900

    95536 Pine Island, Greenwood Twp, MN 55790

    • 2 Beds
    • 1 Bath
    • 936 Sq.Ft.
  • 2060 Clearwater Forest Drive S For Sale

    $149,900

    2060 Clearwater Forest Drive S, Clearwater, MN 55382

    • 3 Beds
    • 2 Baths
    • 1,456 Sq.Ft.
  • 9401 Samuelson Road For Sale

    $129,900

    9401 Samuelson Road, Alango Twp, MN 55703

View All

Success Stories

"2 plus years after Chessica helped us out getting into a Vermilion coop share, she helped us out of that same share. Not a traditional real estate transaction, but Chessica mastered the process, so we didn't have to. On top of that, she had a buyer for the share within a week and at a price point we were happy with. Both transactions deserved 2 thumbs up for her effort and result. It's rare to find someone 500 or so miles away whom you can trust and rely on. Chessica is that person!"
"2 plus years after Chessica helped us out getting into a Vermilion coop share, she helped us out of that same share. Not a traditional real estate transaction, but Chessica mastered the process, so we didn't have to. On top of that, she had a buyer for the share within a week and at a price point we were happy with. Both transactions deserved 2 thumbs up for her effort and result. It's rare to find someone 500 or so miles away whom you can trust and rely on. Chessica is that person!"
Keith S.
"Chessica is awesome! Professional and Ethical. I have always been a little suspicious about agents representing the buyer. Chessica has removed my hesitations. She is responsive, attentive, and detailed. Candidly, I think she protected our interests, and I am not sure we would have been able to make the deal without her!"
"Chessica is awesome! Professional and Ethical. I have always been a little suspicious about agents representing the buyer. Chessica has removed my hesitations. She is responsive, attentive, and detailed. Candidly, I think she protected our interests, and I am not sure we would have been able to make the deal without her!"
Doug M.
"We had the pleasure of working with Chessica in our search for the perfect family cabin, and we couldn’t be more grateful for her guidance. Our criteria were centered around specific features we wanted in a lake property rather than a fixed location, which made the search more complex. Chessica navigated that challenge with ease, bringing deep knowledge not only of her primary market but also of surrounding regions. Her responsiveness, insight, and genuine enthusiasm made the process enjoyable and efficient. If you're looking for someone who listens closely, adapts quickly, and truly understands the nuances of recreational property searches, Chessica is an outstanding choice."
"We had the pleasure of working with Chessica in our search for the perfect family cabin, and we couldn’t be more grateful for her guidance. Our criteria were centered around specific features we wanted in a lake property rather than a fixed location, which made the search more complex. Chessica navigated that challenge with ease, bringing deep knowledge not only of her primary market but also of surrounding regions. Her responsiveness, insight, and genuine enthusiasm made the process enjoyable and efficient. If you're looking for someone who listens closely, adapts quickly, and truly understands the nuances of recreational property searches, Chessica is an outstanding choice."
Skrenner
"Chessica kept us well informed and was very responsible to all questions."
"Chessica kept us well informed and was very responsible to all questions."
Jared & Becky C.
"Chessica is an outstanding real estate agent! The property I purchased was less than $100K, yet I always felt that Jessica was always looking out for my best interest, as though I was purchasing a greater-than-$1-million property. Cannot say enough good things about Jessica and will refer anyone I know to buy property."
"Chessica is an outstanding real estate agent! The property I purchased was less than $100K, yet I always felt that Jessica was always looking out for my best interest, as though I was purchasing a greater-than-$1-million property. Cannot say enough good things about Jessica and will refer anyone I know to buy property."
Tim K.
"Our process was a little different because our purchase depended on 2 houses selling first. Chessica informed us every step! Absolutely! The process goes along smoothly. As I said above, my son's house had to sell-which it did within 24 hours, he purchased our home, and we bought a new house without Chessica. There is no way it could have gone smoothly as it did. Chris has continued to use Chessica's services and referred people. I (Misty) just referred my best friend, and she closed today! Thank you, Chessica. We just cannot say thank you enough, Chessica. You literally helped us get our dream home. You are such a blessing to us. We will ALWAYS use z'up and will always refer to you!"
"Our process was a little different because our purchase depended on 2 houses selling first. Chessica informed us every step! Absolutely! The process goes along smoothly. As I said above, my son's house had to sell-which it did within 24 hours, he purchased our home, and we bought a new house without Chessica. There is no way it could have gone smoothly as it did. Chris has continued to use Chessica's services and referred people. I (Misty) just referred my best friend, and she closed today! Thank you, Chessica. We just cannot say thank you enough, Chessica. You literally helped us get our dream home. You are such a blessing to us. We will ALWAYS use z'up and will always refer to you!"
Chris & Misty
"Chessica is incredible and really went above and beyond to support us in our search for a lake cabin! She should truly be a valued employee. We will definitely recommend her! Thank you."
"Chessica is incredible and really went above and beyond to support us in our search for a lake cabin! She should truly be a valued employee. We will definitely recommend her! Thank you."
Scott & Erika K.

Neighborhoods

  • Aurora
  • Cook
  • Crane Lake
  • Ely
  • Lake Vermillion
  • Orr
  • Tower
  • Twin Cities

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