Oregon’s real estate landscape is a picturesque fusion of natural beauty and eclectic urban charm, with lush forests, mountain backdrops, and Pacific coastline framing many of its properties. From sleek modern builds in Portland to secluded timber lodges in Bend, the market offers a blend of rustic tranquility and high-end innovation that reflects the state’s progressive character.
Now, let’s dive into five of the most expensive houses currently making waves in Oregon’s luxury market.
5. Wilsonville, OR – $6,495,500
Commanding 62 acres of private countryside in Oregon, this $6,495,500 English Manor estate offers 12,254 square feet across four levels with 5 bedrooms and 7 bathrooms. Originally built in 1988, the home includes a finished basement, two kitchens, a wine cellar, library, home theater, sauna, and a guest apartment above the attached garage. The grounds feature a red barn with stalls, pool and hot tub with pool house, outdoor kitchen, tennis and sport courts, and 17.6 acres of water rights.
Where is Wilsonville?
Wilsonville, Oregon, is located along the Willamette River, just south of Portland. Originally a farming community, it developed into a suburban center with major employers and tech companies. The city features planned neighborhoods, parks, and shopping centers. It also serves as a gateway to the Willamette Valley wine region.
Main Entrance
Brick and stone create a dramatic facade at the main entrance, framed by a grand staircase-style gable and rounded balcony above the arched doorway. Multiple dormer windows and symmetrical bay windows add dimension across the front elevation. Well-kept hedges and mature landscaping line the curved path up to the door.
Living Room
Two-story windows dominate the formal living room, curving along the wall to bring in outdoor views and daylight. A sectional sofa faces a white fireplace accented with marble and decorative molding, centered beneath a tray ceiling. Chandelier lighting and hardwood floors complete the bright and elegant interior.
Kitchen
Warm-toned wood cabinetry and exposed beams frame the kitchen, where tiled countertops and dual islands define the workspace. A mix of open shelving and glass-front cabinets adds storage above the wraparound counters and stainless steel refrigerator. Patterned backsplash tiles contribute subtle character beneath large windows.
Family Room
An expansive sectional wraps around the center of the family room, with a red brick fireplace anchoring one end and a rounded window nook lining the other. Natural wood trim and ceiling beams match the cabinetry, shelving, and furniture throughout the space. Greenery just outside the windows offers a soft backdrop for the cozy setting.
Pool Area
An in-ground pool sits at the rear of the property, enclosed by a black metal fence and surrounded by wide concrete decking with brick trim. The main house rises beyond a manicured lawn, showing off its symmetrical brick design and upper-level balcony. A poolside structure nearby offers shade and dining space under a covered roof.
Source: Peggy Hoag @ Hoag Real Estate via Coldwell Banker Realty
4. Medford, OR – $7,900,000
This $7,900,000 California-style modern estate in Oregon offers 8,293 square feet of living space, including 4 bedrooms and 6 bathrooms, set on 2.14 acres with panoramic views of the Siskiyou Mountains. The property includes a main residence, guest house, arboretum, artisan studio, and extensive outdoor amenities such as an infinity pool, putting green, and open-air kitchen. The layout features multiple kitchens, meditation rooms, a wine tasting area, gym, and climate-controlled greenhouse, with convenient access to Rogue Valley Airport.
Where is Medford?
Medford, Oregon, lies in the Rogue Valley and serves as a commercial and medical hub for southern Oregon. It grew rapidly with the arrival of the railroad and the rise of the pear industry. The city is near Crater Lake and surrounded by vineyards and outdoor recreation areas. Downtown Medford includes theaters, breweries, and public art.
Living Room
Deep in the heart of the main living area, a blue sectional faces a sleek slate fireplace crowned with a bold abstract painting. Floor-to-ceiling windows frame panoramic views, while a grand piano anchors the open layout behind glass partitions. Accents like sculptural driftwood, velvet chairs, and a ring chandelier round out the scene with visual balance.
Kitchen
Dominating the open-concept kitchen, a waterfall island with dramatic black and white veining stretches under a row of matte pendant lights. Cabinets in white and navy line the room, set against a geometric tiled backsplash and a glossy blue range hood. Floor-to-ceiling windows and sliding doors wrap the space in mountain views.
Bedroom
Nestled within the private wing, the bedroom centers around a king bed facing a two-sided fireplace wrapped in blue textured tile. A curved chaise rests beside large windows with sweeping views, and an open doorway leads into a bathroom clad in dark horizontal tiling. Draped navy curtains and soft neutral bedding balance the bold architectural elements.
Pool Area
Perched above city lights, the backyard pool area features an infinity-edge design that visually blends into the valley below. Water features arc across the pool, flanked by a built-in hot tub and a full outdoor kitchen under a covered patio. Concrete pavers on manicured turf complete the elevated hillside retreat.
Greenhouse Dining Room
Converted into a greenhouse dining space, the glass-roofed structure includes two long tables surrounded by white chairs and lush potted plants. Hanging ferns and vines fill the steel rafters, while fans and overhead lights keep the space functional. Rows of growing containers and shelves line the edges beneath a dusk-lit sky.
3. Grants Pass, OR – $8,495,000
Priced at $8,495,000, this riverfront estate in Oregon spans 5,275 square feet and includes 3 bedrooms and 3 bathrooms. Built with intricate craftsmanship and set above the Rogue River, the property features a separate 10-acre organic vineyard, a barn with guest quarters, and a detached gym or home office. The estate includes a 15,000 square feet garden, irrigated landscaping, and multiple water features across its expansive grounds.
Where is Grants Pass?
Grants Pass, Oregon, is located in the Rogue Valley and is known for its connection to the Rogue River. The city began as a railroad stop and grew with the timber industry. Jet boat tours and river recreation are major attractions. Its historic downtown includes antique shops, local cafes, and murals.
Living Room
Tucked beneath a tray ceiling with fresco-style art, the living room features ornate crown molding, a carved stone fireplace, and a wall of built-in shelving. A mix of patterned upholstery surrounds a central rug, while a grand piano and entertainment cabinet divide the space. Natural light filters through traditional drapes and glass doors leading outside.
Kitchen
Positioned between French doors and floral wallpaper, the kitchen showcases white cabinetry with detailed trim and dual wall ovens. A hand-painted hood and colorful tile mural draw attention above the commercial-grade stove. A blue island with butcher block top and crystal chandeliers complete the layout.
Dining Room
Anchored by a carved wood dining table, the formal dining room opens to the garden through multiple French doors. Upholstered chairs in floral and velvet patterns surround the table beneath a crystal chandelier. Built-in alcoves, detailed millwork, and floral wallpaper frame the entrance to the adjacent living space.
Bedroom
Placed under a coffered ceiling with soft blue tones, the bedroom includes a four-poster bed framed by floral wallpaper and display niches. Built-in shelves, twin nightstands, and a bench at the foot of the bed create a balanced layout. An open doorway connects to an adjoining hallway and dressing area.
Bathroom
Centered around a freestanding bathtub under a decorative coffered ceiling, the primary bathroom features dual vanities topped with marble. Crystal chandeliers, gold fixtures, and floral curtains frame the garden-facing windows. A large rug lies between the vanities on marble flooring with detailed inlay borders.
Source: Deanna & Dyan, Chris Martin @ John L. Scott Ashland, Land Leader via Coldwell Banker Realty
2. Bend, OR – $9,750,000
Set against the backdrop of Central Oregon’s Cascade Mountains, this $9,750,000 estate in Bend offers 40 acres of private, fully equipped equestrian and recreational living. The 7,643 square feet main home, originally built in 1996 and fully reconstructed in 2013, includes 7 bedrooms and 9 bathrooms, alongside a 2,000 square feet guest house. The property features a 7-stall barn, indoor and outdoor riding arenas, a 2-acre pond, 20 irrigated acres, and extensive outdoor amenities for both leisure and function.
Where is Bend?
Bend, Oregon, sits along the Deschutes River at the edge of the Cascade Range. It was once a logging town and has grown into a center for outdoor sports, craft brewing, and tech startups. The city offers access to skiing at Mount Bachelor and trails throughout the high desert. Its downtown mixes historic buildings with modern shops, restaurants, and galleries.
Living Room
Floor-to-ceiling windows frame a panoramic view of snow-capped peaks, as the living room centers around a tall stone fireplace with a timber mantel. A white sectional and armchairs line the seating area atop a textured rug and wood plank flooring. Vaulted ceilings with exposed beams and a metal chandelier complete the open yet rustic setting.
Kitchen
Custom cabinetry and a deep red range define the kitchen, backed by white subway tile and a decorative tile inlay. Marble countertops run along both walls, flanking a farmhouse sink and extending to a small service bar. Exposed beams and dark wood trim blend with traditional finishes to connect the kitchen with adjacent spaces.
Dining Room
Three walls of glass surround the dining area, where a wooden table and wicker chairs are arranged below a small chandelier. Expansive views of a pond, trees, and distant mountains create a natural backdrop in every direction. Built-in ceiling beams and a wood floor visually tie the space to the rest of the main floor.
Bedroom
Glass doors and angled windows wrap around the primary bedroom, offering views across the lawn and trees. A wrought iron bed rests on a patterned rug, paired with classic armchairs and a tufted bench. Exposed ceiling beams and chandeliers add architectural character to the bright, simple layout.
Bathroom
Glass panels enclose a walk-in shower with dual rain heads and beige tile walls in the primary bathroom. A wide soaking tub with a wood base sits below corner windows that face out to trees and open fields. Marble tile flooring and open shelving add balance and storage to the serene layout.
Source: Karen A Wilson, Betsey Leever Little @ Cascade Hasson Sir via Coldwell Banker Realty
1. Sisters, OR – $19,500,000
Located in Oregon, this $19,500,000 equestrian estate spans 190 acres and includes a main residence with 14,666 square feet of living space. The property features 8 bedrooms and 10 bathrooms, along with two additional cabins, an indoor arena, a 12-stall barn, and a 9-bay shop. Built with legacy in mind, the estate includes over 120 acres of deeded water rights and was designed for both luxury living and equestrian use.
Where is Sisters?
Sisters, Oregon, is a small city located at the base of the Cascade Mountains, near the Three Sisters peaks. It developed from a ranching and logging town into a hub for outdoor recreation and tourism. The city hosts events like the Sisters Rodeo and the Sisters Folk Festival. Its downtown area features Western-themed architecture and local artisan shops.
Great Room
A towering stone fireplace rises at the center of the great room, surrounded by leather and upholstered seating on a patterned rug. Vaulted ceilings with exposed trusses and two chandeliers emphasize the room’s height and symmetry. Wood double doors and arched openings connect this space to the entry and adjacent halls.
Kitchen
Rustic wood cabinetry and a stone hood frame the kitchen, where granite countertops and a central sink island define the layout. Arched windows wrap around the adjacent dining area, bringing in views of trees and distant mountains. Exposed beams and chandeliers span both sections, tying together the open-concept design.
Home Office
Custom woodwork fills the home office, from the large built-in shelving units to the detailed executive desk at the center. Double glass doors open toward an outdoor view, while recessed lighting and a large chandelier illuminate the interior. Neutral carpet softens the floor against the richness of the wood finishes.
Home Theater
Balcony-style railings and wall sconces give the home theater a classic cinema feel, with rows of leather recliners facing a large screen. Wood paneling, curtains, and elevated seating complete the immersive atmosphere. Soft lighting from recessed fixtures highlights the architectural trim around the ceiling and walls.
Bedroom
Tall arched windows wrap the outer wall of the primary bedroom, casting light across the neutral carpet and dark wood furnishings. A dome chandelier hangs over the bed, and seating is arranged by the windows for a view of the landscape. Rich drapery and carved furniture add a formal, traditional tone.
Source: Brian John Ladd, Erin Martin @ Cascade Hasson Sir via Coldwell Banker Realty
