About High Desert Property Management
Trusted by Central Oregon property owners for over a decade.
Our Story
Serving Central Oregon Since 1999
High Desert Property Management operates with a simple mission: to provide Central Oregon property owners with professional, reliable management they can trust. Over the years, we've grown into one of the region's most respected property management companies.
Over the years, we've built our reputation on honest communication, meticulous attention to detail, and a genuine commitment to protecting our clients' investments. Today, we manage hundreds of properties across Bend, Redmond, Sisters, Prineville, Culver, Metolius, and Madras — from single-family homes to multi-unit complexes.
Our team lives and works in Central Oregon. We understand the unique dynamics of this market — from seasonal rental trends to the nuances of each community. That local knowledge, combined with proven systems and technology, allows us to deliver results that out-of-area management companies simply can't match.
What Drives Us
Our Core Values
Integrity
We believe in transparent communication, honest reporting, and doing the right thing — even when no one is watching. Your trust is the foundation of everything we do.
Local Expertise
We live and work in Central Oregon. Our deep knowledge of local rental markets, seasonal trends, and community nuances gives your property a competitive edge.
Owner-First Approach
Your investment goals drive every decision we make. From maximizing rental income to minimizing vacancy, we treat your property as if it were our own.
Where We Work
Our Service Area
We proudly serve property owners and tenants across seven Central Oregon communities. Each market has its own character, and we bring specialized knowledge to every one.
The People Behind HDPM
Meet Our Team
Our experienced team is dedicated to making property ownership simple and stress-free.
Craig Bramscher
President
Craig leads HDPM's strategy and technology adoption, working directly with owners to make sure their investments are performing. He's passionate about bringing a smarter, more transparent approach to property management in Central Oregon. When he's not at the office, you'll find him tinkering with technology, fly fishing, or playing pickleball — ideally with his family, including his four children.
Mathew Free
Property Manager
Mathew is hands-on with every property in his portfolio, from tenant screening and leasing to inspections and renewals. He's thorough, responsive, and takes pride in keeping properties in top condition. Owners appreciate his straightforward communication style and his knack for solving problems before they escalate.
Penny Free
Property Manager
Penny brings a sharp eye for detail to everything she does, whether it's coordinating a move-out, reviewing a lease, or walking a property. She's known for being organized and easy to work with, and she makes the move-in and move-out process as painless as possible for both tenants and owners.
Cheryl Waterman
Maintenance Coordinator
Cheryl is the hub of all maintenance activity at HDPM. She coordinates repairs, manages vendor relationships, and keeps track of every open work order across the portfolio. If something needs fixing, Cheryl makes sure the right person is on it quickly and the job gets done right the first time.
Brody Bramscher
Inspector / Maintenance Technician
Brody handles property inspections and hands-on maintenance work across the HDPM portfolio. He conducts move-in and move-out inspections, routine property checks, and tackles repair jobs directly. He's quick, capable, and takes care of properties like they're his own.
Kennedy James
Assistant Property Manager
Kennedy supports the property management team with tenant communication, leasing coordination, and day-to-day operations across the portfolio. She keeps the details organized so owners and tenants always know where things stand.
Alberto Flores
Maintenance Technician
Alberto handles hands-on maintenance and repair work across HDPM-managed properties. From routine fixes to turn work between tenants, he keeps homes in great shape and gets jobs done right the first time.
Ashley Bessey
Office Support
Ashley keeps the Redmond office running smoothly — fielding calls, supporting owners and tenants, and making sure paperwork and scheduling stay on track for the whole team.
Always Here to Help
Meet Our AI Agents
When the office is closed or our team is tied up on another call, our AI agents step in — so you always get answers, day or night.
Leesa
Leasing
After hoursAsk for Leesa for anything leasing — current availability, application questions, and scheduling tours — whenever our leasing team is away.
541-406-6409
Sally
General Questions
After hoursSally is a friendly first stop for general questions about our services, your account, and how we work — perfect for when the office is closed or everyone is on another call.
541-548-0383
After office hours, ask for Leesa for leasing, Sally for general questions, and Max anytime — he’s available 24/7 for maintenance.
Ready to Work With Us?
Whether you own one property or twenty, we'd love to show you what professional management looks like. Get in touch for a free consultation.