Betsey Little Real Estate

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Bend, OR
Betsey Little Real Estate

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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.

11/10/2026

Not many laundry rooms can compete with the view outside the window. This one can.

Warm terracotta tile floors, beautiful natural light, and Smith Rock framed perfectly beyond the glass. Even the most practical room in the house has a remarkable sense of place.

Set on 3.89 acres at Ranch at the Canyons, 10436 NE Sage Lane is full of thoughtful details and unexpected moments like this one.

10436 NE Sage Lane | Terrebonne, Oregon

Listed by Betsey Leever Little & Lynn Larkin
Cascade Hasson Sotheby’s International Realty

11/07/2026

Nearly 40 acres in Powell Butte, and there’s quite a bit to love about this one.

The 3,000-square-foot home offers bright, open living spaces, a kitchen with quartz countertops, and a private first-level suite with its own entrance and living area. Outside, the property is fully fenced with a barn, heated tack room, paddocks, additional outbuildings, and direct access to BLM land.

And the views? Mountains in every direction.

All within a gated community just beyond the Pronghorn turnoff, approximately 15 minutes from Bend.

16264 SW Majestic View Lane, Powell Butte, Oregon
Offered at $885,000
3 Bedrooms | 3 Bathrooms | 3,000 Sq Ft | 39.83 Acres

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

For more information or a private showing, please reach out.

11/02/2026

NEW PRICE | $2,725,000

A little more possibility at a new price.

Set on 7.46 acres above Tumalo, this Winston Ranch estate offers the kind of space that invites you to imagine life a little differently.

Panoramic Cascade Mountain views, a heated pool, private theater, beautiful gathering spaces, and a remarkable wood-paneled office are just the beginning. A finished workshop, 44-foot RV bay, and open pasture make room for everything else.

Five bedrooms, 5,528 square feet, and a setting that feels wonderfully removed without being far from Bend.

20180 Winston Loop | Bend, Oregon
5 Bedrooms | 4 Bathrooms | 5,528 Sq. Ft. | 7.46 Acres
Now Offered at $2,725,000

Call for a private tour!
Betsey Leever Little (541)301-8140

10/29/2026

A few familiar addresses have found their way into the Fall 2026 Luxury Lookbook.

This latest edition from Cascade Hasson Sotheby’s International Realty celebrates the individuality of exceptional properties across Oregon and Southwest Washington. We’re pleased to see several of the Central Oregon homes we represent among them.

Featured properties:

Betsey Leever Little

* 1596 NW Wild Rye Circle, Bend
* 19100 Macalpine Loop, Bend
* 20180 Winston Loop, Bend

Lynn Larkin & Betsey Leever Little

* 65810 Pronghorn Estates Drive, Bend
* 22936 Ghost Tree Lane, Bend
* 11500 NE Canyons Ranch Drive, Terrebonne

Lynn Larkin, Betsey Leever Little & Karen Wilson

* 21725 Rickard Road, Bend
* 20361 Rock Canyon Road, Bend

From distinctive architecture to remarkable settings, these properties represent the variety of homes and lifestyles found throughout Central Oregon.

Explore the Fall 2026 Luxury Lookbook and discover the full collection. Link in bio!

Betsey Leever Little (541)301-8140
Lynn Larkin (808)635-3101

Cascade Hasson Sotheby’s International Realty

10/26/2026

Most people know Smith Rock for its dramatic cliffs, hiking trails, and unmistakable place in the Central Oregon landscape. Fewer know what lies just beyond it.

Ranch at the Canyons is a private, gated community in Terrebonne, where approximately 1,700 acres of working ranchland, custom estates, and protected open space share a remarkable setting along the Crooked River.

With just 46 landholdings, ownership here includes access to equestrian facilities, a historic clubhouse, tennis courts, stocked ponds, and private stretches of the river.

We’re featuring four distinct opportunities within the ranch, from established custom residences to a canyon-rim homesite ready for its next chapter.

11500 NE Canyons Ranch Drive
11750 NE Canyons Ranch Drive
10436 NE Sage Lane
11330 NE Canyons Ranch Drive, LH 13

Each property brings something different to the conversation, but the setting is what connects them.

Ranch at the Canyons | Terrebonne, Oregon

Reach out to learn more about available properties or arrange a private tour.

Featured properties listed by Betsey Leever Little and Lynn Larkin of Cascade Hasson Sotheby’s International Realty.

Betsey Leever Little (541)301-8140
Lynn Larkin (808)635-3101

10/26/2026

Ten acres in The Highlands at Broken Top. Nearly 10,000 square feet of custom architecture. And a connection to the Central Oregon landscape that extends well beyond the walls of the home.

At 19100 Macalpine Loop in Bend, Oregon, the great room and dining spaces open to expansive outdoor living areas, with Cascade Mountain views providing a remarkable backdrop.

The property is equally considered when it comes to recreation. A saltwater pool and spa, private pool house, golf simulator, basketball and bocce courts, outdoor kitchen and established grounds offer plenty of reasons to spend time at home. Direct access to Phil’s Trail brings another side of Bend life right to the gate.

What stands out is how these elements work together. The acreage provides privacy, the architecture creates a natural connection between indoor and outdoor spaces, and the location keeps the best of Bend close at hand.

For those exploring luxury real estate in Bend, Oregon, particularly private acreage estates and homes in The Highlands at Broken Top, this is a property best understood in person.

19100 Macalpine Loop | Bend, Oregon 97702
5 bedrooms | 8 bathrooms | 9,971 SF | 10 acres

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

Address

650 SW Bond Street, Suite 100
Bend, OR
97702

Telephone

+15413234823

Website

https://www.cascadehassonsir.com/bio/betseylittle

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