Relocating to the Black Hills: Comparing Hill City and Custer Real Estate

The Black Hills of South Dakota offer more than just stunning granite peaks and pine-covered trails; they offer a lifestyle. Whether you're drawn to charming mountain towns, peaceful wooded properties, or wide-open spaces with room to grow, relocating to the Black Hills means choosing a place that fits your pace and your purpose.

Two of the region’s most sought-after areas are Hill City and Custer, each with its unique flavor, community feel, and real estate appeal. If you’re considering a move to the area, this comparison will help you weigh the pros and cons of both towns, whether you're looking for a quiet retreat, a vibrant artistic hub, or your next family home.

To explore more cities, property types, and insider tips across the region, check out our explore the Black Hills page.

Nestled in the heart of the Black Hills, Hill City is often called the “Heart of the Hills”  and for good reason. With its walkable downtown area, locally owned art galleries, wineries, and boutique shops, Hill City attracts both tourists and long-term residents who appreciate creativity and charm.



This town seamlessly blends small-town warmth with cultural flair, hosting events such as Sculpture in the Hills and open-air wine festivals that bring the community together year-round. It’s a place where you can grab a craft beer, admire local art, and still hit a hiking trail all before dinner.

Just a short scenic drive away, Custer offers a distinct Black Hills experience. Rooted in old-west heritage and surrounded by sprawling ponderosa pine forests, Custer feels less polished and more grounded. It’s the kind of place where you know your neighbors, your kids ride their bikes to school, and the mountains are truly your backyard.

With Custer State Park just minutes away, this town attracts nature lovers, retirees, and families who value space, community connection, and direct access to South Dakota’s most breathtaking landscapes.

Real estate in Hill City is competitive and relatively limited. Thanks to its popularity with vacationers and second-home buyers, Hill City often commands a higher price per square foot than other towns in the Black Hills. Inventory is tight, and many homes are nestled into the piney hillsides, offering mountain views and custom finishes.



You’ll find a mix of modern cabins, artist-style cottages, and the occasional luxury home designed to blend into the natural setting. If walkability, aesthetics, and a creative vibe are top priorities, Hill City real estate offers just that; however, expect to act quickly when a good listing appears.

Custer: Larger Lots, Better Value, More Elbow Room

Custer offers more variety and value for your dollar. Here, you’ll find larger lots, more ranch-style homes, and black hills cabins that are often more affordable than their Hill City counterparts. Many properties offer acreage, outbuildings, and space to garden, roam, or even raise animals, perfect for those seeking self-sufficiency or a homestead lifestyle.

Custer is also home to a growing number of retirees and remote workers, drawn by the slower pace and access to natural wonders. Whether you’re looking for a starter home, a family-friendly layout, or even commercial property, the local market remains approachable and diverse.

If your dream life in the Black Hills includes sipping wine at local art festivals, walking to dinner, and enjoying boutique living with a mountain-town twist, Hill City might be your perfect match. It’s ideal for:

• Creative professionals and artists
  
• Retirees looking for connection and culture
  
• Couples or families wanting a walkable, photogenic community
  
• Buyers seeking a vacation home or second residence with high rental potential
  
  

The lifestyle here is packed with charm — from winery tours and galleries to hiking and scenic train rides. If you're curious what day-to-day fun looks like, check out our Top 15+ Memorable Things to Do in Hill City to get a feel for the rhythm of life here.

Keep in mind: inventory moves quickly, and you’ll likely pay more for less square footage, but that premium supports a vibrant lifestyle in the cultural center of the Black Hills.

Custer is the answer for buyers who want room to breathe, open skies, and a stronger sense of frontier independence. It’s a top pick for:

• Families looking for space to grow
  
• Retirees prioritize peace and privacy.
  
• Remote workers seeking reliable internet with wild surroundings
  
• Buyers dreaming of a small homestead, cabin escape, or land-based living
  
  

Custer offers access to trails, lakes, and wildlife just minutes from your doorstep, without sacrificing the basics of a friendly, grounded small-town atmosphere.

Choosing between Hill City and Custer comes down to what kind of lifestyle you’re looking for and what type of property you want to build your life (or legacy) around.



• If you're drawn to walkability, culture, and charm, and you're okay with smaller footprints at a premium price, Hill City real estate delivers.
  
• If you value land, elbow room, and long-term value, and you're envisioning life a bit closer to the wild, Custer real estate might be the better fit.
  
  

Both towns offer something unique in the heart of the Black Hills, and both are backed by breathtaking scenery, close-knit communities, and access to some of South Dakota’s most incredible adventures.