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.

Number 3 in Oregon. Not the region. The whole state.I’ve been named a 2026 professional, ranked third among individual ...
06/10/2026

Number 3 in Oregon. Not the region. The whole state.

I’ve been named a 2026 professional, ranked third among individual agents in Oregon by sales volume. The ranking is built on 2025 closings, independently verified, with $53 million in residential sales and another $13.5 in off market closings (*does not include land closings).

I am still taking it in.

A number like this is never really about the number. It is about the families who trusted me with one of the biggest decisions of their lives, the sellers who let me into their homes, and the buyers who let me help them find the right one. Every closing behind that figure belongs to them.

I love this work, and I love doing it here. Thank you to everyone who has been part of the journey.

I’ve spent my career across Central Oregon representing exceptional homes with care and attention, and getting to know the people and places that make this area what it is. As an agent at Cascade Hasson Sotheby’s International Realty, I am grateful to do this work alongside clients and colleagues I admire.

06/06/2026

Ranch at the Canyons is one of Central Oregon’s most extraordinary communities, and 11500 Canyons Ranch Drive is one of its finest estates.

Built in 2024 on 6.5 private acres, this 8,022 sq ft home was designed for the way people actually want to live. Chef’s kitchen, steam shower, infrared sauna, guest casita, three private offices, full gym, resort pool and spa, and an RV garage. As a 1/46th owner of 1,700 acres, the lifestyle comes with it: clubhouse, vineyard, fishing, equestrian center, pickleball and tennis, and miles of private trails.

Featured on the cover of Build Magazine, May 2025, and selected as the Home Spotlight in Bend Magazine, Summer 2025.

This is the one you stop comparing others to.

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

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Ranch at the Canyons luxury estate for sale in Bend Oregon. Custom home with Smith Rock views, resort pool, guest casita, and equestrian access. One of the newest custom homes available in Ranch at the Canyons, Central Oregon luxury real estate, Cascade Hasson Sotheby’s International Realty.

06/03/2026

There are homes you read about. And homes you have to walk through.

This is the second kind. The kind where every room feels considered, where the light shifts through the morning and the spaces respond to it. Where a tour that was supposed to take thirty minutes quietly becomes an hour. Where guests linger in doorways because leaving a room feels like a decision.

19100 MacAlpine Loop. The part that takes a full walkthrough to appreciate.

Videography by

19100 MacAlpine Loop | The Highlands at Broken Top
5 Bed | 6 Full & 2 Half Bath | 9,970 SF | $8,750,000

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



Betsey Leever Little and the team at Cascade Hasson Sotheby’s International Realty represent luxury homes across Central Oregon including Bend, Tumalo, Sunriver, Powell Butte, and the resort communities of Pronghorn and Broken Top.

05/28/2026

Some homes you tour. This one you settle into.

Set above downtown Tumalo on just over 7 acres, this Winston Ranch estate opens to 180-degree Cascade Mountain views from nearly every room. Mornings start slow with coffee and a full view of the range. Afternoons drift toward the pool. Evenings find their way into the private movie theater or the office and den wrapped in spectacular woodwork.

Freshly updated throughout with new paint, hardwood flooring, new carpet, and a reworked primary ensuite, the home feels both timeless and ready. The ground-level primary suite frames the mountains with a large walk-in closet, soaking tub, and dual vanities. A finished shop with workspace and a 44’ RV bay add rare flexibility, while a 1-mile private loop invites long walks under big skies.

Upscale rural living, without the work.

20180 Winston Loop, Bend, Oregon
Offered by Betsey Leever Little
Cascade Hasson Sotheby’s International Realty

Winston Ranch living, framed by the Cascades and built for the kind of life that slows down in all the right ways. This Tumalo luxury estate brings together mountain views, refined updates, and rare acreage just minutes from Bend.

✨ Life on the Deschutes ✨Tucked along one of the most scenic stretches of the Deschutes River, 865 SW Theater Dr offers ...
07/18/2025

✨ Life on the Deschutes ✨
Tucked along one of the most scenic stretches of the Deschutes River, 865 SW Theater Dr offers a front-row seat to nature’s beauty—right in the heart of Bend. Imagine launching your kayak from your backyard, sipping coffee as deer wander by, or watching the river glow golden at sunset.

This is more than a home—it’s a sanctuary, where water, wildlife, and refined living come together. Just minutes from the Old Mill, yet a world away.

Now available. Contact me to experience it in person. 541-301-8140

🌲 Awbrey Glen Evenings Hit Different ⛳️Bend’s private gem, the Awbrey Glen Golf Course, offers more than just a game—it’...
06/07/2025

🌲 Awbrey Glen Evenings Hit Different ⛳️
Bend’s private gem, the Awbrey Glen Golf Course, offers more than just a game—it’s a lifestyle. With panoramic fairways, peaceful surroundings, and a vibrant community, it’s the kind of place you’ll never want to leave.

Now available: a new opportunity to live right here—just listed at 3013 NW Melville Dr.

Contact for more information: [email protected]

Just Listed in NWX 🌿Live where Bend buzzes—in the heart of Northwest Crossing! This charming Craftsman-style home offers...
06/07/2025

Just Listed in NWX 🌿
Live where Bend buzzes—in the heart of Northwest Crossing! This charming Craftsman-style home offers the privacy of a detached residence with all the perks of low-maintenance living. Vaulted ceilings, hardwood floors, a cozy gas fireplace, and a stylish, functional kitchen set the tone. Outside, relax under the covered deck or garden in your lush, fenced yard.

💫 2 Beds | 2 Baths | Private Yard
🚶‍♂️ Blocks to shops, parks & eateries
✨ HOA covers all exterior: painting, roof repair, sidewalk, tree trimming, lawn, gutter cleaning, landscaping, snow removal, water & more!

📍2555 NW Shields Dr. | Bend, OR

🏔️VIEWS FOR DAYS in West Hills!Welcome to 2049 NW Trenton Ave, where dramatic Cascade Mountain views, glowing sunsets, a...
05/29/2025

🏔️VIEWS FOR DAYS in West Hills!
Welcome to 2049 NW Trenton Ave, where dramatic Cascade Mountain views, glowing sunsets, and endless skies set the stage for elevated Bend living.

This exceptional home in Bend’s coveted West Hills neighborhood features:
✨ Vaulted ceilings + sun-filled open living
🛏 3 bedrooms | 🛁 4 beautifully updated bathrooms
🛌 Private guest quarters – perfect for extended stays
🌿 Trex decks, hot tub, fire pit & raised garden beds
🔋 Paid-off solar panels
🚐 RV parking + oversized driveway
🛠 Detached 832 SF garage/shop w/ unfinished flex space above

Whether you’re entertaining under the stars or enjoying a quiet evening surrounded by nature, this home blends comfort, flexibility & breathtaking views.

📍Offered at $1,625,000.

Address

650 SW Bond Street, Suite 100
Bend, OR
97702

Telephone

+15413234823

Website

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