I'm often asked, "Have you seen anything really special lately?"
The answer is almost always yes.
I spend much of my time touring acreage and equestrian properties, helping buyers find the places that truly fit the life they want to create in Central Oregon.
Some homes stand out because of the setting. Others because of the care that went into creating them. And every so often, there's one where you can tell the owners truly understood the land and how to live on it.
Right now, buyers have more choices than we've seen in quite some time, and there are some genuinely compelling properties on the market. Here are a few of the listings that have caught my attention recently.
Sisters
67167 Highway 20
For the buyer who wants the acreage lifestyle without a renovation list, this property delivers. The 25-acre estate has been beautifully cared for, with outdoor living at the center of the experience—from the swim spa and pond with fountain to the outdoor rock fireplace. The main home is impressive, but the additional spaces are what make this property so versatile: a barn with apartment, detached three-car garage, and a heated and cooled studio overlooking the pond. Every part of the property has been considered, allowing the next owner to simply arrive and enjoy. 24.95 acres | $2,195,000 | Berkshire Hathway
16465 Suntree Lane
This is a legacy property in the truest sense. Set within the Deschutes Land Trust's preserve on 67 acres, this property offers three single-family homes, remarkable privacy, and a setting that is nearly impossible to recreate with dramatic Three Sisters views and direct access to Whychus Creek. Properties with this kind of history, scale, and location rarely come along. 67.53 acres | $9,750,000 | Engel & Volkers Portland Rose City
Bend
64629 Horseman Lane
Located in one of Tumalo's most desirable corridors, this nearly 10-acre property offers the opportunity to create something truly personal. The single-level home captures Cascade Mountain views and offers updated systems throughout, while the interiors provide a wonderful foundation for your own vision. Outside, mature landscaping, white vinyl fencing, a paved drive, and a well-appointed three-stall barn with tack room create a strong foundation for acreage living. The combination of privacy, views, and location is what makes this property stand out. 9.77 acres | $1,550,000 | LIVOregon
21837 Repine Drive
If you're imagining small acreage done exactly right, this one is worth seeing. There is a level of care and intention here that is difficult to find at this scale. The turnkey single-level home is surrounded by lush landscaping, including an orchard, vegetable gardens, and cutting gardens. The property also offers a barn with flex space above, thoughtful fencing and cross-fencing, and incredible mountain views. It feels private and peaceful while still being minutes from town. 9.66 acres | $1,299,000 | Bend Premier Real Estate
20055 Pacific Heights Road
This is one of the most memorable properties I've experienced recently. Located just minutes from downtown Bend, it feels completely removed from the pace of town. The home itself is a showstopper, with an incredible use of reclaimed barnwood, steel, and natural materials throughout. The design feels both dramatic and warm, with true indoor-outdoor living and a custom roll-up door connecting the kitchen to the patio and beyond. It's the kind of home that makes you imagine the life you would live there—and honestly, it's one I'd choose myself in a heartbeat. 9.88 acres | $2,499,000 | PENDING
22333 Nelson Road
For the serious equestrian buyer, this property deserves attention. Every part of the setup has been carefully considered, and the caretaker's home adds flexibility for staff, family, or guests. The equestrian facilities include an 80x186 indoor arena with fresh footing, a 175x250 outdoor arena, and a grand prix field with pond and bank. The property was previously home to World Cup hunter/jumper rider Gail Greenough, adding another layer of significance to this equestrian offering. 16.87 acres| $1,550,000 | Cascade Hasson Sotheby’s
24166 Dodds Road
Thirty-four acres with breathtaking Cascade Mountain views and an equestrian setup designed for serious use. The home itself is remarkable, with a main-floor primary suite and thoughtful details throughout. The property includes a seven-stall barn, two outdoor arenas, round pen, ten paddocks, COID irrigation covering 22 acres, and direct access to miles of BLM trails. The infrastructure is already in place, allowing the next owner to focus on enjoying the lifestyle this property makes possible. 34.22 acres | $1,999,000 | LIVOregon
Prineville
3900 SE Riverview Road
Set behind a gated, tree-lined drive, this custom lodge-style home offers privacy, space, and convenience just minutes from town. The home has the feeling of a true mountain retreat, with soaring ceilings, floor-to-ceiling windows, a stone fireplace, and a mezzanine overlooking the great room—a perfect spot for family game nights, sleepovers, or simply taking in the views. The 32-acre property offers room to spread out, with a heated shop, four stalls, RV hookups, and fenced/cross-fenced acreage. It’s a place designed for gathering, relaxing, and enjoying the freedom that comes with acreage living. 32.69 acres | $1,890,000 | Cascade Hasson Sotheby's
Redmond
20799 NW ONeil Highway
This is a true opportunity to create a family legacy property. With complete privacy and the space to shape the land around your vision, it's the kind of place that invites you to think long-term. There is a nostalgic charm here that is hard to find. The home has a warmth that immediately draws you in, with an attached garage shop and temperature-controlled shop adding both character and functionality. 15.16 acres | $1,459,000 | Fahlgren Group
Central Oregon's acreage market continues to attract buyers looking for something beyond a traditional home—privacy, space, and the ability to create a lifestyle that feels uniquely their own.
The properties that resonate most are the ones where the home, the land, and the lifestyle all work together. With the selection available right now, there are some truly compelling opportunities for buyers looking for acreage in Central Oregon.
If one of these caught your eye, or you'd like to explore what else is coming to market, I'd love to help.
Heather Osgood
Cascade Hasson Sotheby's International Realty
*Data from Oregon Datashare on 8/3/26.
