5 Oregon Luxury Retreats from Cannon Beach to Bend

With the ocean as its backdrop in Cannon Beach, this custom-built beachside residence pairs modern design with a deep focus on materials and craft. Floors are built with 1 1/4-inch-thick plywood for exceptional strength, while the kitchen is constructed from Baltic birch—chosen for durability and the absence of unpleasant odors. Premium German and Italian hardware by Salice and Blum adds refined function, and modern-style white oak doors finished in waterborne lacquer echo the clean lines throughout. Quartz countertops continue across the home, complemented by high-end Café appliances. Outside, an outdoor kitchen features stainless steel cabinets and quartz counters, set beside a waterproof front deck designed to take in sweeping ocean views, plus a rear deck for quieter moments. Fully furnished and equipped, it’s ready for immediate, beach-forward living.

In the heart of downtown Newberg, The 1888 Building offers a rare chance to own a piece of local history at the prominent corner of 1st and Meridian Street. Constructed in 1888, this iconic corner building has anchored the city’s commercial core for generations, combining historic character with modern versatility. The mixed-use layout is thoughtfully suited to daily life in a walkable district: ground-floor commercial space envisioned for a restaurant, tasting room, retail, or hospitality concept, with two established residential units above. Currently operating as successful short-term rentals, the upper-level residences add built-in income potential while original architectural details and strong street presence underscore the property’s enduring appeal. With its visibility, legacy, and flexible configuration, it’s a landmark setting for those drawn to the rhythm of Oregon Wine Country’s most vibrant downtowns.

Set on 10.27 acres in Estacada, this custom retreat balances modern comfort with an unmistakably outdoor rhythm. Inside, three bedrooms and two spa-like bathrooms feature heated floors, while a chef’s kitchen pairs stainless steel appliances with quartz countertops and a hidden pantry. The stone fireplace anchors the living space, framing sweeping pond views that shift with the light. In the primary suite, direct deck access and an ensuite that flows into the closet and laundry make daily routines feel quietly effortless. Outdoors, a pond with fountain and dock—complete with a paddle boat—sets the scene for slow mornings and unhurried evenings, with landscaped grounds suited to gatherings or starlit time by the fire. A detached bonus room and art studio invite games, a bar, or creative work, and the heated shop adds a climate-controlled car bay, RV hookups, and EV readiness.

In Bend, this custom Mt. Modern residence pairs contemporary architecture with the natural beauty of the High Desert. A distinctive palette of barn wood, oxidized metals, and weathered steel accents is balanced by vaulted ceilings that bring volume and warmth to the interiors. The layout centers on a chef’s kitchen with top-of-the-line appliances, flowing into a spacious dining area and comfortable living space, all designed with mindful indoor/outdoor integration. Practicality is equally considered: an oversized 3-car garage is paired with a heated driveway and a dedicated Sprinter van garage bay for gear and adventure days. Set on the property, a detached 610 sq ft private ADU adds flexibility with its own 1.5-car garage—ideal for guests, rental income, or a private studio. Step outside to Phil’s Trail, with Mt. Bachelor and downtown Bend within easy reach.

Commanding views from Pronghorn, this timeless residence frames fairway, lake, and Cascade Mountain panoramas with exceptional craftsmanship throughout. Soaring exposed beams and a dramatic floor-to-ceiling stone fireplace set the tone for an entertainer’s dream floor plan, while indoor-outdoor living spaces invite long evenings under Central Oregon skies. The gourmet kitchen is thoughtfully appointed with solid-surface counters, a butler’s pantry, and an expansive bar for effortless gathering. A private main-level primary suite offers its own stone fireplace and a spa-like bath; the level also includes a guest suite and a dedicated office. Upstairs, a third en suite is joined by a media room and additional dual home-office space overlooking the lake and course. Full golf membership is included, along with a member’s club, restaurants, pools, pickleball, a fitness center, and 24-hour gated security—peaceful seclusion with easy access to Bend.