Living in Upper Skyway, Colorado Springs: The Real Deal

Upper Skyway is one of southwest Colorado Springs' distinctive foothill neighborhoods, offering mountain views, established homes, mature landscaping, and incredible access to trails and open space.

Tucked into the hills above the city, Upper Skyway feels removed from the busier parts of Colorado Springs while still keeping downtown, the Broadmoor area, restaurants, shopping, and everyday conveniences within easy reach.

If views, outdoor access, and a home with a little more personality are high on your list, Upper Skyway deserves a look.

Upper Skyway Homes & Real Estate
Real estate in Upper Skyway is anything but cookie-cutter. You'll find established homes, custom properties, mid-century architecture, remodeled homes, and larger residences positioned to take advantage of city and mountain views.

Lots, floor plans, age, condition, and updates can vary considerably from one property to the next.

Because of the area's age and terrain, buyers should look beyond the finishes. Roofs, sewer lines, foundations, drainage, retaining walls, electrical and plumbing systems, HVAC, and previous renovations can all deserve extra attention.

And on the west side, the lot itself can be just as important as the house sitting on it.

Location & Outdoor Living
Outdoor access is one of Upper Skyway's biggest advantages.

The neighborhood sits near Bear Creek Regional Park, North Cheyenne Cañon, Stratton Open Space, and Section 16, providing access to miles of hiking, biking, and Colorado open space.

You're also convenient to the Broadmoor area, Old Colorado City, downtown Colorado Springs, Highway 24, and I-25.

Schools
Upper Skyway is generally served by Cheyenne Mountain School District 12, although buyers should verify the school district and individual school assignments for a specific property.

School boundaries and assignments can change, so we always recommend confirming current information directly with the district before purchasing a home.

Military & PCS Relocation
Upper Skyway can also be considered by military buyers, particularly those commuting to Fort Carson or Cheyenne Mountain Space Force Station.

We help military and VA buyers compare southwest Colorado Springs neighborhoods based on commute, budget, property characteristics, financing, and future resale.

The Trade-Off, Because We'll Be Straight With You
Foothill living comes with considerations you won't necessarily encounter in a flat, newer subdivision.

Sloped lots, drainage, retaining walls, driveway grades, wildfire considerations, wildlife, insurance, and winter conditions may all be worth evaluating depending on the property.

But for buyers who want character, views, mature landscaping, outdoor recreation, and a southwest Colorado Springs location, those trade-offs may be completely worth it.

Buying or Selling in Upper Skyway?
Crystal Sisler and Shawn Bedel of Everyday Properties & Investments, powered by eXp Realty, help buyers and sellers throughout Upper Skyway and Colorado Springs.

With 7+ years of real estate experience and more than 300 families helped, our experience includes sellers, buyers, military and PCS relocation, VA buyers, investments, and relocation.

We also own Everyday Staging, with professional home staging included in our listing packages to help our sellers stand out online and in person.

Browse Upper Skyway homes for sale or connect with Crystal & Shawn to talk about your next move.