Compare Gregory Hills vs Trails West Real Estate in Billings, MT

The median home sale price in Billings, MT sits at roughly $389,900 as of mid-2026, with available properties spending an average of 57 days on the market. Buyers looking above that median price point often find themselves comparing specific subdivisions to match their preferred home style and location within the best neighborhoods in Billings, MT.

Two areas that come up repeatedly are Gregory Hills and Trails West. Both give you solid access to local amenities, but their architectural styles, price points, and layouts are genuinely different - different enough that the right choice usually depends on what stage of life you're in and what kind of commute you're willing to accept.

Exploring Gregory Hills and Trails West in Billings

Gregory Hills is an established subdivision tucked right under the Billings Rimrock. Homes here often carry views of the Bighorn, Pryor, and Beartooth mountain ranges - the kind of backdrop that tends to stop first-time visitors mid-sentence.

Trails West sits on the West End and reflects a much more recent development footprint. The community layout puts outdoor walking routes and nearby educational campuses within immediate reach.

Parks and Outdoor Recreation

Gregory Hills overlooks a natural city park located just beneath the Rimrock. That adjacent green space gives residents a place to exercise and take in the mountain scenery without leaving the subdivision's edge.

Trails West weaves recreation into the streetscape itself. The subdivision includes multi-use trails, sidewalks, and boulevards that start at residents' front doors, and it borders the 40-acre Ben Steele Middle School campus, which adds a meaningful buffer of open space on that side of the development.

Transportation and Commute Times

Commuters in Trails West are typically looking at a 15-to-20-minute drive to reach downtown Billings. Being on the West End also means you're close to outlying commercial centers, local parks, and restaurants without fighting your way across town.

Gregory Hills runs a different direction. It offers a short drive to the city's medical corridor, local colleges, and the airport. That's a real advantage for the right buyer - and a longer haul for someone whose office is on the opposite end. Map your specific workplace from both subdivisions before you decide, because the West End and Rimrock areas feed into different major arterials and the difference adds up over time.

Real Estate Prices and Architectural Styles

The broader Billings market currently holds about 583 homes in active inventory, representing roughly a four-month supply. Gregory Hills and Trails West pull from that inventory in very different directions - different buyer budgets, different architectural eras, different expectations about what a home should look like.

Trails West consists primarily of newer construction from the 2020s, with several homes completed between 2024 and 2025. Gregory Hills is an older neighborhood built around larger, executive-style homes, many with classic brick exteriors that you simply don't see in newer subdivisions anymore.

Home Prices and Market Trends

Gregory Hills pricing spans a wide range depending on size, finish level, and view. Older or smaller homes in the subdivision have closed in the $500,000 range, while larger executive homes average around $1,200,000 in local luxury-market analyses. To put a real number on it: a 4,066-square-foot brick home on Gregory Drive South previously listed at $524,000.

Trails West runs considerably tighter. Prices generally cluster between $433,000 and $500,000 - new construction floor plans start around $433,000 to $494,000, and recent resale listings land near $470,000 to $500,000. In July 2026, active listings included a 2,241-square-foot home priced at $499,000 and a four-bedroom property on Mountain Front Avenue listed at $495,000.

Property Types and Lot Sizes

Trails West gives you options within a consistent size envelope: one-level ranchers, two-story homes, and tri-level designs, typically ranging from 1,520 to 3,200 square feet on fully landscaped, fenced lots of about 0.14 acres.

Gregory Hills is where you go when you need more room. The neighborhood is known for substantial two-story homes on spacious, landscaped lots, with some properties exceeding 4,000 square feet. Many of those homes have also been recently remodeled inside, so you're not necessarily walking into a 1990s time capsule just because the exterior is brick.

Researching Yellowstone County Civic Data

Before you go under contract on anything, verify the local boundaries and zoning regulations yourself. The official Yellowstone County government website has a detailed GIS mapping tool available to the public.

Through that portal you can look up exact school district boundaries, fire and election districts, and specific parcel data. It also links directly to property records, courthouse services, and the sheriff's office for official public safety information. These aren't details to take someone's word on - pull the data yourself or ask your agent to walk you through it.

Frequently Asked Questions

How do the HOA fees and average home prices compare between Gregory Hills and Trails West?

Average home prices in Trails West cluster around $470,000 to $500,000, while Gregory Hills sees a wider range from the $500,000s up to roughly $1.2 million for luxury properties. Exact HOA fee amounts depend on the specific property and current association budgets - verify those numbers during the disclosure period, not after.

Which Billings school districts are Gregory Hills and Trails West zoned for?

Trails West sits adjacent to the Ben Steele Middle School campus on the West End. To confirm the exact elementary, middle, and high school boundaries for any specific address in either neighborhood, use the Yellowstone County GIS mapping tool.

Are lot sizes and home styles noticeably different between Gregory Hills and Trails West?

They really are. Trails West offers primarily 2020s-built ranchers, two-stories, and tri-levels on lots around 0.14 acres. Gregory Hills features older, larger executive-style brick homes on spacious lots - a fundamentally different product.

Which neighborhood offers a faster commute to downtown Billings and the West End amenities?

Trails West is on the West End, which means immediate access to nearby restaurants and a 15-to-20-minute commute to downtown. Gregory Hills puts you closer to the medical corridor, local colleges, and the airport.

Are there still new construction opportunities in Gregory Hills or Trails West, or are they strictly resale?

Trails West continues to offer new construction through Trails West Homes, with recent floor plans starting around $433,000. Gregory Hills is fully built out - resale only, though many properties have seen recent interior remodels.

Do properties in Gregory Hills or Trails West generally carry active Special Improvement District (SID) assessments?

It varies by individual parcel and subdivision history. Check the Yellowstone County property records and courthouse services to confirm whether any active SID assessments apply to a specific home you're considering.