The Most Expensive Homes for Sale in Oregon

Rapidly shrinking inventories, a severe shortage in new housing developments and a continuously growing population have made their impact on Oregon’s housing market, especially in the Portland metro area. First-time home-buyers are struggling to find affordable homes here, even middle-income earners. As prices and interest rates continue to climb, while the supply of available properties shrinks, especially as fewer buyers trade up their homes, homeownership is becoming increasingly difficult in what was once the last affordable bastion for housing on the pricey West Coast.

As Millennials enter the home-buying market in increasing numbers – and 2017 is predicted to be a big year for releasing pent-up demand from Gen Y – the Pacific Northwest is expected to see continued price expansions and ever-diminishing time spent on the market.

Dubbed the 8th hottest housing market for luxury real estate globally in 2016, thanks to a significant uptick in luxury property sales to deep-pocketed tech buyers, Portland’s luxury market was also marred by limited inventory. Although the state’s residential luxury segment has contracted noticeably, Oregon still has uber-pricey real estate up for grabs. Ranging in price from $10,000,000 to $24,000,000, the most expensive homes for sale in Oregon right now are a blend of wine country estates and sprawling working ranches.

Wine cellars and wine production facilities abound at the upper end of Oregon’s real estate market, as do endless acreages of Oregon wilderness, teaming with animals– including big game. Sprawling ranching operations showcase equestrian and cattle facilities along with show stopping high-end homes with all the swanky amenities deep-pocketed buyers might want. Pools, home theaters, game rooms, oversized suites, vineyards, gourmet kitchens and high-quality craftsmanship characterize the state’s most luxurious homes on the market right now.

As for the most expensive home for sale in Oregon at the moment, two pricey properties tied for the title. Scroll down to check out the two sprawling ranches, both of which come with dozens of bedrooms and fully functional ranching operations.


11777 Highway 238, Jacksonville

Asking price: $10,000,000

Who needs a European wine tour when you can own this stunning 4-bed riverfront wine estate in Oregon? Boasting 254 acres in Jacksonville’s Applegate Valley, this estate is a one-stop shop for wine connoisseurs. With a 5,200-square-foot top-of-line fermentation room, 6 wine tanks, barrel and case storage and a covered crush pad with a production capacity of 5,000 cases everything is ready to produce high quality wines from the 3 vineyards bursting with terroir-driven, cuvee Spanish varietals. The 2,600-square-foot wine tasting room and its outdoor seating ensures ample entertainment space for guests, should the 4,700-square-foot main home prove too small.


7900 NE Mill Creek, Prineville

Asking price: $10,000,000

Bordering the Ochoco National Forest, Mahogany Butte Ranch is a stunning 6,867-acre Oregon ranch. Miles upon miles of Mill Creek run through the expansive property along with countless seasonal creeks and springs. Mahogany Butte Ranch boasts abundant wildlife, pine forests and a bevy of ranching facilities. The luxurious 4,010-square-foot main residence has 4 bedrooms, but 2 additional homes provide ample space for friends and family. A striking feature of the property is the indoor swimming pool situated in a glass atrium that provides expansive views of Mill Creek Valley. Further high-priced extras include a gourmet kitchen, statement piece stone fireplace and a formal dining room with glass walls.


2113 Emigrant Creek, Ashland

Asking price: $10,000,000

Built in 2008, this Cotswold-style home showcases 10,916 square feet of “responsible luxury” – high quality finishes peppered with reclaimed materials and European antiquities. A year-round creek snakes through the 25.6 acres of irrigated grounds the 5-bed home is situated on. Luxurious amenities include a gourmet kitchen and bar imported from Paris, 12-seat home theater, wine cellar, spa and walk-in closets. The 10,916-square-foot home’s outdoor amenities are very luxurious and include vineyards, a swimming pool, outdoor kitchen, hot tub, built in BBQ, picnic area, patio and pool-side lounge area.


4184 Bellinger Lane, Jacksonville

Asking price: $12,995,000

This 182-acre resort-like wine estate is located in the increasingly popular Southern Oregon Wine Region. Known as the Bellinger Lane Vineyard Estate, the property oozes luxurious design and top-notch craftsmanship –  evident in the historic-barn-turned-office and its showcasing of reclaimed woods.The former barn’s second floor holds an expansive library with stunning views, making it the perfect entertainment area, especially considering its exquisite finishes such as hand railings covered in woven leather. The estate includes 4 homes, 90 acres of wine grapes and high-priced extras like a home theatre, outdoor kitchen and pool – all just 1.5 miles from historic Jacksonville.


1500 Northsore Road, Lake Oswego

Asking price: $15,000,000

One of the most luxurious properties in Oregon, this 13,462-square-foot home on Oswego main lake is a showstopper. Built in 2006, the 6-bed home sits on the waterfront and takes maximum advantage of its coveted location – an infinity pool and hot tub sit right on the water, opening expansive views of Lake Oswego.  The boathouse, complete with boat lifts, can be accessed through the home. A stand-out feature is the estate’s little promontory stretching into the lake with a quaint rotunda at the end. But this home isn’t just about maximizing that coveted waterfront location – it’s also chockfull of luxurious amenities like a media room, in-home fitness center full bar, game room, 4-stop elevator, generous outdoor entertaining space and 5-car garage.


61794 Tam McArthur Loop, Bend

Asking price: $15,000,000

On the market fully furnished, this 5-bed home is located in Bend’s Broken Top neighborhood in a gated community. Built in 1995, the home blends high-priced international art and local artisan creations throughout the property. Basking in golf course and lake views along with Cascade Mountain vistas, the 7,538-square-foot home also showcases a bevy of big-ticket extras like the spa-style heated pool and hot tub with pool-side lounge dotted with artwork. Additional pricey features include nine fireplaces and a fitness center, a guest house, heated driveway and 3-car garage.


33561 Parrish Creek Road, Wheeler County

Asking price: $15,995,000

Located in the Ochoco Mountain Range, Long Valley Ranch offers 16,441 acres of stunning Oregon wilderness. Highly private and secluded, the ranch has had only 3 previous owners and hasn’t been on the market in 68 years. Lush valleys alternate with timbered mountains and wildlife thrives here – including elk and mule deer. Long Valley Ranch holds one 3-bed, 2-bath ranch-style home, barn, corrals and additional outbuildings. Initially listed for $21,755,000, the property underwent two price cuts since May 2016.


1707 SW Schaeffer Road, West Linn

Asking price: $18,000,000

The consummate entertainer’s dream home, this stunning 14-bed wine and horse estate blends old world formal luxury with the comforts of a modern home, such as state of the art security and a professional grade kitchen with all the bells and whistles. Known as Villa de l’or, the 16,359-square-foot home showcases a private club-like bar, home theater, fitness center, “Benihana”-style outdoor kitchen, pool and “pool salon”.  The 35-acre estate also boasts a 4-acre vineyard that currently produces 50 cases of wine, with the possibility of expansion. A Tuscan-style wine building with temperature-controlled wine storage and tasting facilities rounds out the Oregon wine experience.  A stable and horse arena and very extensive parking complete the resort-like experience just 30 minutes from downtown Portland and Portland International Airport.


County 1400 Road, Pilot Rock

Asking price: $24,000,000

For those chasing the times of old Clint Eastwood movies, this 34,497-acre ranching estate in the Blue Mountain Range is the ideal property. But outdoors types and extreme sports lovers will also covet the estate – thanks to its size and varied landscape the property is teeming with game and everything from skiing to mountain biking to climbing is a possibility. Dubbed the Ukiah Main home, the main residence is a 9-bed mountain home with a 4,900-foot paved, private runway. 7 more homes are situated on the property, including a 4-bed guest house, a 3-bed managers home, 3 ranch homes with a total of 13 beds, the 3-bed Cowboys Home and the Ukiah Cowboy house, outfitted with bunkbeds for 6.  The non-contiguous property is bordered on two sides by national forests and holds an array of ranching facilities.


16400 Jordan Road, Sisters

Asking price: $24,000,000

Covering close to 508 acres of stunning vistas, Cable Creek Ranch is a 4-home ranching estate with luxurious amenities. The 8-bed, 14,666-square-foot main residence features high-end amenities like the theater and wine rooms, private gym, wet bar, fire pit and 6 guest suites. A further 5-bed, 6,263-square-foot guest home ensures visitors have plenty of luxurious, private space. The property also holds a 3-bed manager’s home and 2,800-square-foot farm manager’s home. A 4,234-square-foot recreational barn and a 29,374-square-foot indoor arena join Cable Creek’s swanky extras along with a full range of ranching facilities and structures, including a 0.25-mile race track with bleachers.

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In order to determine which were the most expensive homes for sale in Oregon, we looked at all residential properties listed for sale, taking into account condo, co-op, single- and two-family homes. All package deals were excluded.

Eliza Theiss

Eliza Theiss

Eliza Theiss is a senior writer reporting real estate trends in the US. Her work has been cited by CBS News, Curbed, The Los Angeles Times, and Forbes among others. With an academic background in journalism, Eliza has been covering real estate since 2012. Before joining PropertyShark, Eliza was an associate editor at Multi-Housing News and Commercial Property Executive. Eliza writes for both PropertyShark and CommercialEdge. Reach her at [email protected]

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