From helicopter pilot to realtor to You Tuber, James Dean has seen plenty. He also sees what you should and shouldn’t do in today’s real estate market.

He came to Teller County after 20 years as a Chinook helicopter pilot in the United States Army. Since moving to Divide 12 years ago, buying and selling the dream of mountain living in the Pikes Peak region has become his passion. His company is the James Dean Mountain Homes Team.

He maintains a You Tube channel—Living in Woodland Park— that focuses on the Teller County lifestyle. It is an abundance of information for both local and out of town buyers as well as established residents.

Recently, the Courier sat down with Dean to get feel for real estate market trends heading into the high season.

“The state of the Teller County Market is currently balanced overall but leaning slightly in favor of buyers right now,” Dean said.

The market jump Teller County saw during the pandemic started to flatten in 2023. Real estate prices have not crashed, but the boom is over.

“We expect the summer 2026 season to remain flat with no significant dips or spikes in pricing,” Dean said.

Due in part to the record warm winter, the number of sales coming into 2026—from Christmas through February—was the busiest for that period in Teller County ever. But the conflict in the Middle East brought that pace to a crawl, and being so early in the season, questions linger whether that pace can resume.

Affordability pressure and higher interest rates have inevitably become a factor everywhere. With six to eight months of inventory on the market in Teller, buyers have a slight advantage.

“One thing is for certain,” Dean said, “this is not a seller’s market. Those looking to put their homes up for sale need to have realistic expectations with their pricing strategy. Prospectors with unrealistic prices are going to see their listings sit while competitively priced listings will have far more interest and sell.”

Pricing your home right in a buyer-leaning market matters because as serious buyers watch new listings coming available, they become more savvy. A competitively priced home in good condition will sell quickly. Having an overambitious price strategy on a house that needs updates or work can backfire if the home is on the market for too long. It becomes a “problem listing” after too many months on the market or too many price drops.

“I generally advise against doing major projects before putting your home on the market,” Dean said. “If something needs repair, that’s one thing, but I’m of the opinion that in lieu of spending money on big cosmetic projects, the seller is better off accounting for the need to update with competitive pricing.”

Universal advice realtors will give clients eager to sell is to get rid of clutter and highly personalized items. A fresh coat of paint often helps. Fix anything that is obviously broken, and make sure the house is clean.

“My ideal listing is one that is empty,” Dean said. “Virtual staging is a great tool. It costs very little and can really grab a buyer’s attention. After seeing the home’s AI potential in the listing, when buyers visit the home, they can imagine their own belongings in the house without having to look past the previous owner’s things.”

According to Dean, the current median sale price in Teller County is $536K with listings within 15-minutes of Woodland Park being the most desirable. Aside from proximity to town, the majority of buyers want homes around 3,000 SF, three to four bedrooms and a garage. Homes in good repair with a view are always in high demand as are homes that offer privacy and have been mitigated for fire risk.

The further out you go in Teller, the median sale price can drop significantly. Remote homes or homes in Victor and Cripple Creek will sell for substantially less than similar listings near Woodland Park.

For buyers, this is a great time to be in the market. There are currently 256 active listings in Teller County with the vast majority falling between $400K and $800K. With a strong inventory of houses, buyers have more choices, are unlikely to get into a bidding war, there is a strong value/price correlation, and sellers are more willing to negotiate.

Teller County remains a very attractive real estate market. It offers easy access to the conveniences of Colorado Springs with lower density communities and offers the mountain lifestyle at an attainable price point compared to resort towns.

“After 20 years in the Army, my wife and I have lived in a lot of places across the US and around the world,” Dean said, “and there is nowhere else that can compare to Teller County.”