Tucked into Oregon’s diverse landscapes, these extraordinary estates redefine the meaning of secluded luxury. From the rugged high deserts of Bend to the lush valleys of Ashland and the dramatic cliffs near Smith Rock, each home offers breathtaking settings and impeccable craftsmanship.
Whether it’s an infinity pool overlooking Cascade peaks or a Tudor-inspired manor nestled in Eugene’s rolling hills, these properties are designed for privacy, elegance, and unforgettable views.
Step inside these stunning Oregon retreats and discover the ultimate in private estate living.
1. Thunder Ridge Estate with 40 Acres
Set on 40 acres in Bend, this 4,001 square foot estate features 3 bedrooms and 4 bathrooms with panoramic views of 10 Cascade peaks. Built for privacy and recreation, the property includes an infinity pool, entertainment kitchen, 1,800 square foot storage building, and trail access throughout a park-like setting. Listed at $4,100,000, it offers close proximity to Shevlin Park and Bend’s NW amenities with potential short-term rental opportunities.
Where is Bend, OR?
Bend, Oregon, sits along the Deschutes River at the eastern edge of the Cascade Range. It transitioned from a logging town to a center for outdoor sports, technology, and brewing. The city is a starting point for activities like skiing, hiking, and mountain biking. Bend’s Old Mill District and downtown offer shopping, dining, and cultural venues.
Living Area
Vaulted ceilings and panoramic windows define the upstairs living and dining space, centered around a stacked stone fireplace. A rectangular dining table with cushioned chairs is set near the open railing, blending into the adjacent living area. Bamboo flooring and open beam accents complete the modern-rustic design.
Lounge
Double-height ceilings and a full wall of windows in the lounge frame breathtaking forest and mountain views. White sectional seating is positioned to face the outdoor scenery, while dark stone tile flooring grounds the open-plan interior. Wooden trim around the windows and a wood-paneled ceiling add warmth to the modern design.
Bedroom
Glass double doors open to a bright bedroom with two corner windows that let in natural light. A simple upholstered bed is paired with a matching bench at the foot and neutral-toned furnishings. Soft carpet flooring and wood trim details bring a cozy feeling to this private retreat.
Outdoor Deck
Spacious outdoor deck features cushioned seating arranged around a modern firepit, with clear sightlines to the infinity pool and distant mountains. Decking material matches the surrounding natural colors, while sleek cable railings maintain uninterrupted views. Comfortable daybeds and lounge chairs create an ideal outdoor entertaining space.
Aerial View
Modern architecture defines the two-story residence, set against a rugged natural landscape with pines and rocky terrain. A large infinity-edge pool is built along the home’s main living level, overlooking miles of trees and open sky. Flat roofs, large glass panels, and dark trim create a strong, contemporary silhouette against the landscape.
Source: Stacey Nyman @ Cascade Hasson Sir via Coldwell Banker Realty
2. Ashland Villa on 80 Acres
Built in 1981 and updated in 2008–2009, this 4,793 square foot custom villa in Ashland offers 4 bedrooms and 5 bathrooms on 80.58 acres with views of Emigrant Lake and Mt. Ashland. Featuring Black Walnut floors, a chef’s kitchen with Wolf appliances, a pool, hot tub, outdoor kitchen, and a small vineyard, the property also includes a game room and a paved driveway. Listed at $2,199,000, it generates approximately $125,000 annually as an Airbnb and provides a private resort-like setting just 15 minutes from town.
Where is Ashland, OR?
Ashland, Oregon, is located in the Rogue Valley near the California border. It is best known for hosting the Oregon Shakespeare Festival, drawing visitors year-round. The city blends historic architecture with a lively arts and culinary scene. Ashland’s Lithia Park offers trails, gardens, and spaces for community gatherings.
Living Room
Sweeping iron-railed staircase curves above the living room, where a gray sectional and leather chairs form a comfortable conversation area. High ceilings with wood beams and an antler chandelier add rustic flair to the open space. Large pieces of vibrant wall art and warm hardwood floors complete the room’s bold character.
Kitchen
Custom kitchen features distressed pale cabinetry, a large center island, and stainless steel appliances tucked into a wall of cabinets. Dark countertops contrast with the light cabinetry, while a plate rack and detailed trim emphasize the traditional style. Hardwood flooring and recessed lighting bring a clean, functional finish to the spacious layout.
Bedroom
Exposed wood beams line the vaulted ceiling in the bedroom, anchored by a large dark wood bed against a light gray wall. Full-length windows open to sweeping views of hills and valleys, complemented by a fireplace along one side. Rich wood flooring ties the bedroom’s rustic and elegant elements together.
Bathroom
Tile floors and a deep soaking tub are paired with a glass-enclosed walk-in shower in the primary bathroom. A vintage-style wooden vanity with a marble top adds character beneath a full wall mirror. Large windows bring in natural light while crown molding frames the clean, traditional finishes.
Pool Area
Rectangular pool is set within a manicured garden space, surrounded by trees and open to mountain views. Stone coping and grassy borders frame the water, with a simple white bench offering seating nearby. The rear elevation of the home features a two-story covered patio with decorative balustrades overlooking the pool.
Source: Dallin E George @ Home Quest Realty via Coldwell Banker Realty
3. Hilltop Estate with Panoramic Views
This 4,127 square foot custom estate, built atop a hillside, offers 4 bedrooms and 6 bathrooms on 13.46 acres with sweeping views of the Cascade Mountains and valleys. The home features luxury amenities including an in-ground pool, hot tub, sauna, chef’s kitchen with Subzero and Wolf appliances, and a study with a custom bar and wine cellar. Listed at $2,100,000, it also includes a crow’s nest loft, built-in vacuum system, and dual furnaces with heat pumps for year-round comfort.
Where is Prineville, OR?
Prineville, Oregon, is one of the oldest communities in Central Oregon, founded along the Crooked River. Originally a center for ranching and timber, it now includes technology and data centers in its economy. The city hosts the Crooked River Roundup, a long-running rodeo and horse racing event. Prineville is surrounded by public lands, offering fishing, hiking, and camping opportunities.
Living Room
Stone fireplace anchors the cozy living room, framed by wood-paneled walls and a rustic ceiling beam. Three armchairs and a curved sofa are grouped around a round wood table, positioned near a built-in shelving unit. A yellow accent wall with a mounted TV adds warmth to the lodge-inspired design.
Kitchen
Rustic wood cabinetry fills the spacious kitchen, complemented by a large granite-topped island with seating for two. Exposed beams stretch across the ceiling, and multiple windows bring in views of the surrounding landscape. Pendant lights over the island add an elegant, craftsman-style touch to the space.
Breakfast Nook
Glass-topped round table with four wicker chairs creates a charming breakfast nook next to a large window. Shelves filled with colorful dishware line one side, adding casual character to the corner. Bright natural light and panoramic views make this a cheerful, relaxed spot for everyday dining.
Bathroom
Natural stone walls and a freestanding tub create a spa-like feel in the bathroom, paired with a large walk-in stone shower. Wood cabinetry with granite countertops offers ample storage and rustic detailing. Slate flooring and neutral tones blend with greenery accents for a seamless, earthy design.
Pool Area
Rectangular pool sits on a stone patio with lounge chairs and dining areas arranged nearby, surrounded by open views of forested hills. A covered patio extends from the house, providing shaded seating and outdoor entertainment space. Wide skies and natural scenery complete the tranquil setting.
Source: Jessica Dawn Lay @ Signet Realty via Coldwell Banker Realty
4. Masterpiece Overlooking Smith Rock
Set within the exclusive Ranch at the Canyons community, this 6,000 square foot home offers 4 bedrooms and 6 bathrooms with sweeping views of Smith Rock, the Crooked River, and the Cascade Mountains. Featuring stone and wood accents, a chef’s kitchen with Wolf appliances, multiple fireplaces, a luxurious primary suite, and an upscale bonus room, the home sits within a gated 1,700-acre community with trails, ponds, a clubhouse, and equestrian facilities. Listed at $5,200,000, the property offers luxury living surrounded by nature.
Where is Terrebonne, OR?
Terrebonne, Oregon, is a small community in Central Oregon near the Crooked River. It is best known as the home of Smith Rock State Park, a popular spot for rock climbing and hiking. Agriculture remains an important part of the local economy. Terrebonne also serves as a gateway to outdoor recreation across the region.
Living Room
Stone fireplace with a heavy wood mantel creates a strong centerpiece for the living room, surrounded by leather sofas and soft armchairs. Large windows and French doors bring canyon views directly into the space, while exposed wood beams add depth to the ceiling. Neutral tones and a textured rug soften the stone and wood elements.
Kitchen
Rustic kitchen features dark wood cabinetry, natural stone accents, and a large central island topped with a thick slab of stone. High-end stainless steel appliances are built into the cabinetry wall, while an oversized stone range hood defines the cooking space. Warm lighting and rough-hewn details blend with smooth counters for a sophisticated but natural feel.
Dining Room
Formal dining area includes a dark wood table with six leather chairs placed beneath a simple iron chandelier. Built-in hutch with display shelves and tall windows draped with terracotta curtains frame views of the landscape. Exposed beams overhead continue the natural, lodge-style aesthetic.
Bedroom
Wood-framed four-poster bed stands across from a stone fireplace in the bedroom, with built-in bench seating tucked under tall windows. A painted ceiling beam design and rich hardwood flooring complete the rustic luxury feel. French doors lead directly to a private balcony with canyon and mountain views.
Bathroom
Primary bathroom centers around a large freestanding bathtub set within a stone-topped surround, facing a wide arched window that overlooks the cliffs. Dual vanities with dark wood cabinetry and stone countertops line opposite sides of the room. Warm neutral walls and tile floors keep the space serene and connected to the outdoor setting.
Source: Laura Blossey @ Avenir Realty via Coldwell Banker Realty
5. Tudor-Style Estate in Coburg Hills
Located in Eugene’s gated Cloud Nine Ranch community, this 6,775 square foot Tudor-style home offers 7 bedrooms and 6 bathrooms with panoramic sunset and city views. Built for multi-generational living, the property includes a gourmet kitchen, multiple living areas, a separate guest unit, and two laundry rooms on a spacious knoll. Listed at $2,499,900, the home also features a 3-bay garage, fenced yard, and access to a shared community well.
Where is Eugene, OR?
Eugene, Oregon, is located at the southern end of the Willamette Valley near the confluence of the McKenzie and Willamette Rivers. It is home to the University of Oregon and has a strong connection to sports, arts, and environmental activism. The city features an extensive network of parks, bike paths, and public spaces. Eugene also hosts events like the Oregon Country Fair and the U.S. Olympic Track and Field Trials.
Kitchen
Vaulted white ceilings with exposed beams highlight the expansive kitchen, featuring cherry-toned cabinetry and a large central island with a cooktop. Hardwood flooring ties the entire space together, while a tiled backsplash and updated appliances add functionality. A bright breakfast nook sits just off the kitchen, surrounded by bay windows.
Breakfast Nook
Small round table with four chairs anchors the cozy breakfast nook, placed beneath a hanging light fixture. Windows wrap around the space, bringing in views of the front courtyard and surrounding greenery. Natural light floods the area, creating a welcoming atmosphere for casual dining.
Dining Room
Wood columns with arched beams frame the formal dining room, where a long table and leather chairs are placed under two ornate chandeliers. A trio of windows along one wall brightens the space, paired with tile flooring and neutral walls. Architectural woodwork gives this room a unique, traditional character.
Bathroom
Double vanity with white cabinetry and tiled countertops lines one side of the bathroom, with a large mirror and warm lighting above. Raised platform bathtub is tucked into a bright corner surrounded by windows that frame views of the trees. Tiled floors and step-up design create dimension in this airy, sunlit space.
Courtyard
Private courtyard is framed by the pink and white exterior of the home, accented with maroon timber details under the peaked gables. A red wooden picnic table sits at the center of the courtyard, surrounded by potted plants and well-maintained landscaping. Multiple entrances open into the courtyard, blending indoor and outdoor spaces.
Source: Alison Cramer @ Icon Real Estate Group via Coldwell Banker Realty
