Betsey Little Real Estate

Betsey Little Real Estate Specializing in listing & selling amazing properties in Central Oregon. For questions or property tours contact me anytime at (541) 301-8140.

Visit my website https://www.cascadehassonsir.com/bio/betseylittle to view MLS listings in Central Oregon. Originally from Southern Oregon - Medford, Betsey is a fifth-generation Oregon Real Estate Broker. Betsey currently resides in Bend and has partnered with Deb Tebbs, Founder of Cascade Hasson Sotheby’s International Realty. As an accomplished real estate agent, known for her commitment to her

clients, and tireless work ethic, Betsey started her career in Fort Worth specializing in high-end, custom boutique homes. Estate properties, golf communities, development opportunities, acreage offerings, ranches, or legacy property are something that really excites and inspires Betsey in her career. Betsey offers comprehensive and thorough service working alongside her clients to find unique properties. She has a proven track record for minimizing the time a property is on the market while consistently receiving top value for sellers. The value of relationships and working as a team with all clients is Betsey's top priority. She graduated from Oregon State University and has a profound love for the state of Oregon and the Northwest. When Betsey takes off her real estate hat you can find her taking hikes in the backcountry, fly fishing, riding horses which have all been her passion since childhood.

The rooms at Winston Loop have plenty to hold your attention. And then you look outside.Set on 7.46 acres above Tumalo, ...
08/30/2026

The rooms at Winston Loop have plenty to hold your attention. And then you look outside.

Set on 7.46 acres above Tumalo, the home opens to sweeping Cascade Mountain views that have a way of becoming part of nearly every space. It’s one of those rare settings where the relationship between the house and the land feels just as important as either one on its own.

20180 Winston Loop | Bend, Oregon
5 bedrooms | 4 bathrooms | 5,528 sq. ft. | 7.46 acres
Offered at $2,850,000

Listed by Betsey Little
Cascade Hasson Sotheby’s International Realty

Living at The Ranch at the Canyons means owning a beautiful home, but it also means becoming part of a place that has be...
08/25/2026

Living at The Ranch at the Canyons means owning a beautiful home, but it also means becoming part of a place that has been intentionally preserved.

Nearly 1,700 acres are shared among just 46 landholdings. The Crooked River runs through the Ranch. Pastures remain in agricultural use. Horses, wildlife, vineyards, ponds and trails are part of the landscape, with Smith Rock rising just beyond it all.

There is space here, but there is also stewardship. The things that make this land extraordinary have been given room to remain that way, and ownership comes with the opportunity to be part of protecting what has made this place so special in the first place.

11500 NE Canyons Ranch Drive offers a particularly beautiful way to experience it. A modern home thoughtfully connected to the landscape, where the views, the quiet and the larger story of the Ranch are part of everyday life.

For more information or a private showing:
Betsey Leever Little
Cascade Hasson Sotheby’s International Realty
541.301.8140
[email protected]

08/22/2026

I’ve walked through this entry more times than I can count, and it still gets me.

Maybe it’s the scale. Maybe it’s the way the light moves through it. Or maybe it’s because it does exactly what a great entry should do. It changes the pace the minute you walk in.

At 19100 Macalpine Loop, there is a lot to take in. Nearly 10,000 square feet, 10 acres, Cascade Mountain views, a pool and pool house, golf simulator, batting cage and so much more.

But I keep coming back to this part.

19100 Macalpine Loop | Bend, Oregon
Offered at $8,750,000

Betsey Leever Little
Cascade Hasson Sotheby’s International Realty

Two Westside homes closed today, and I love how differently they tell the Bend story.At 1370 NW Mt Washington Drive, it’...
08/21/2026

Two Westside homes closed today, and I love how differently they tell the Bend story.

At 1370 NW Mt Washington Drive, it’s NorthWest Crossing living in all the ways people love it. A front porch, mountain views, a smaller footprint, and a neighborhood that makes walking out the door part of the routine.

At 19509 Meadowbrook Drive, there’s more room to spread out. Four bedrooms, a big backyard, and trails just beyond it for bikes, dogs, kids, or whatever happens to be coming along.

Different neighborhoods. Different rhythms. Both unmistakably Bend.

Congratulations to my sellers and the new owners of both homes. A very good day on the Westside.

Betsey Leever Little
Cascade Hasson Sotheby’s International Realty

Staging by Leighton Elizabeth Interiors

08/20/2026

A little look at what never made it to market.

We were preparing 6565 & 6331 SW Yew Avenue for its debut when the right buyer found it first.

More than 40 acres along the Deschutes River, Cascade Mountain views, irrigated pasture, and this beautiful barn. The kind of Central Oregon property that makes it very easy to dream a little.

Now sold, before it was ever listed.

Congratulations to our sellers and the new owners. We couldn’t be happier for everyone involved.

Listed by Betsey Leever Little & Karen Wilson
Cascade Hasson Sotheby’s International Realty

Address

650 SW Bond Street, Suite 100
Bend, OR
97702

Telephone

+15413234823

Website

Alerts

Be the first to know and let us send you an email when Betsey Little Real Estate posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Betsey Little Real Estate:

Shortcuts

Share

Category