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200 Belle Fiore Lane, Ashland
$26,000,000
7 Beds ⋅ 19 Baths ⋅ 220223434 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is for sale for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,400+ sqft; it has four levels, 5 bedrooms, 19 bathrooms, a 4-stop elevator, vineyard, 2 bedroom 2500+ sqft carriage house, 4-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard with 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

4311 SW GREENLEAF DR, Portland
$25,000,000
8 Beds ⋅ 11 Baths ⋅ 24631430 MLS
This iconic Tudor Revival estate in Portland’s West Hills has been reborn through a nearly $20 million renovation, blending historic charm with the ultimate in contemporary luxury. Originally crafted in 1930 by celebrated architect Roscoe D. Hemenway, the 25,568-square-foot residence has been meticulously transformed by JHL Design and Green Gables Restoration with a reimagined interior seamlessly blending timeless elegance with top-of-the-line designer amenities, showcasing imported materials and handcrafted finishes. Perched on 3.26 stunning private acres, the property offers some of the best panoramic views of Portland’s skyline and four majestic mountains in the metropolitan area, creating an extraordinary setting for both grand entertaining and everyday living. This storied property, built as the estate of the day in 1930, is the estate of today with a winning combination of historic architecture and modern amenities to be enjoyed for generations to come.

4311 SW GREENLEAF DR, Portland

83584 TROY RD, Wallowa
$19,800,000
3 Beds ⋅ 2 Baths ⋅ 251575010 MLS
In the Nez Perce language, the word 'Powwaka' has been translated as 'high, cleared ground, from where a view could be had'. There is no better way to describe the Powwatka Ranch in NE Oregon. Located on Powwatka Ridge in the Blue Mtns, about an hour north of Wallowa, OR lies 9,457 acres of pristine ranch land, stretching almost 10 miles from north to south. Consisting of approximately 4,800 acres of timber, 600 acres of meadows, and 4,000 acres of canyon lands, nearly 2 miles of Grande Ronde River frontage, the Powwatka Ranch truly does have it all.Over 4 decades of thoughtful land management with a focus on wildlife, water, grassland, and timber health have resulted in what can best be described as a private nature preserve. Manicured forests and lush, expansive meadows cover the upper portion of the ranch, flanked by steep canyons dropping off both sides of the ranch to the river and creeks below. A well-maintained road network provides access to all parts of the ranch.Wildlife management has been a priority and the abundance of game provides proof of this wildlife haven. The ranch is located in the Sled Springs unit and qualifies for 5 LOP Tags each for elk and deer.The ranch has almost 6 ½ miles of live water; approx 1 & 2/3 miles of Grande Ronde River; almost 3 miles of Mud Creek; 1 ¼ miles of Wildcat Creek; and ¾ mile of Buck Creek. Many springs and ponds are located throughout the ranch, providing reliable sources for both wildlife and cattle. Numerous improvements are located throughout the ranch. Lodging includes an owner's home, two guest cabins, managers home, ranch hand home, and guest duplex. Shop, multiple barns and 2,950' paved airstrip with 2 hangars.The breathtaking scenery, abundant water, wildlife, and quality improvements perfectly complement each other to create a genuine legacy ranch property. The Powwatka Ranch is an extraordinary offering that is truly one of a kind!

83584 TROY RD, Wallowa

331 METZ HILL RD, Oakland
$15,500,000
5 Beds ⋅ 4 Baths ⋅ 305448302 MLS
Nestled in Oregon's scenic Umpqua Valley, this extraordinary 2,670-acre ranch offers a rare blend of luxury, tranquility, & commercial potential. Atop a prominent knoll stands a grand 7,936-sqft Tudor-style mansion that commands sweeping 360-degree views of rolling pasture, woodlands, & distant hills. The home's 3-levels are a testament to craftsmanship & attention to detail featuring 5 spacious bedrooms, 4 full bathrooms, 2 powder rooms, custom millwork, stained-glass accents, chandeliers, & multiple fireplaces for an atmosphere of timeless elegance. Seeking a quiet reading space? Step into the charming, castle-like library. The rolling ladder & private balcony enhances its storybook feel. The basement is a haven for wellness. It features a hot tub, tanning bed, sauna & steam room, & fully equipped exercise room. Prefer a drink? Head to the full bar or select a bottle from the wine cellar. The kitchen offers style & functionality with a built-in Sub-Zero refrigerator, custom copper range hood, ample workspace, & storage. Currently operating as a working cattle ranch, the property includes a general-purpose building with a Helicopter hangar & landing pad, caretaker's apartment, meat-processing room, & workshop. A state-registered, one-mile private airstrip caters to aviation needs with potential for further development. Conveniently located along Interstate 5 & close to Historic Oakland. Heaven's Gate Ranch is fully approved by the county for destination resort development with civil engineering, site maps, & utility designs already completed. The new owner will receive comprehensive documentation including plans for a 100-room hotel, restaurant, convention center, & 200-lot residential subdivision—providing an advantage for streamlined development & customization. These approvals & plans save years of work & expense. Heaven's Gate Ranch marries majestic living with the rare potential to craft a world-class destination resort. It is a once-in-a-lifetime opportunity.

331 METZ HILL RD, Oakland

25500 CAPE VIEW LOOP, Gold Beach
$13,789,586
4 Beds ⋅ 4 Baths ⋅ 406650755 MLS
EXQUISITE PISTOL RIVER OCEAN VIEW ESTATE FOR THOSE WITH DISTINCTIVE TASTE! Incredible opportunity to own this private retreat. Embrace the freedom and breathe in the beauty of this coastal land spreading over three tax lots covering 354 acres. The oasis is located above the pristine beaches of Pistol River. This exceptional coastal retreat seamlessly combines beauty, tranquility, and adventure. Sellers have significantly improved the infrastructure of the property with a stunning ocean view Custom Home that is professionally decorated with 4 bedrooms, 3 baths, 3,508 sq ft being sold fully furnished. Complementing the home is an ocean view 900 sq ft porch, a 2,070 sq ft garage with generator and cement bunker, and 7,500-gallon water tanks. There is a 110-mph wind shear on the structure of the house to comfortably handle storms. Included are architectural plans for a 13,000 sq ft main home with a 5,000-gallon water tank. The estate includes a 1,265 sq ft 1 bedroom, 1 bath Caretaker’s Cottage with garage offering ocean views from the living room and large deck. Additional improvements are miles of ATV trails, manicured roads, 2 fishing ponds, one with bear tree carving, rifle range, three barns with equipment to maintain the estate and house the fishing boats, RV’s and more, 600-gallon propane tanks, 3,000-gallon septic, 5 drilled wells, and a cell tower lease with 15 years remaining. Too many improvements to list. Whether relaxing in your hot tub, discovering the rock formations, walking the sandy beach, finding tidepool treasures , riding your ATV on miles of trails, or witnessing the stunning sunsets, this is the ultimate Oregon Coast experience where forest, valley, and the Pacific Ocean merge! Additional homesites are cleared. Buyer to do due diligence with the county for permits. Owner will carry with 30% down. Prequalified buyers only.

25500 CAPE VIEW LOOP, Gold Beach

200 Belle Fiore Lane, Ashland
$12,000,000
7 Beds ⋅ 19 Baths ⋅ 220223437 MLS
Chateau at Belle Fiore is one of Oregon's most extraordinary estates. Spanning over 17,400 sqft across 4 levels, this French-inspired masterpiece offers 7 bedrooms, 19 bathrooms, and exceptional craftsmanship throughout. An elevator services all floors, including an 8,000 sqft lower level with a wine room, game room, gentleman's lounge, multiple wine bars, and expansive entertaining spaces. Premium finishes include custom cumaru flooring, granite surfaces, and intricate architectural detailing. Set on 17+ acres, including 12+ irrigated acres and a producing vineyard, the estate is ideal for private enjoyment, weddings, retreats, and special events. Exterior features include hand-chiseled golden granite, a hand-cut slate roof, custom copper gutters, dormers, and downspouts. A 2,500+ sqft carriage house, 4-car garage, prep kitchen, and grand gathering spaces complete this iconic estate. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

Fishhole Creek RD, Bly
$12,000,000
6 Beds ⋅ 8 Baths ⋅ 213194239 MLS
Aspen Ridge Ranch, in South-Central Oregon, between Klamath Falls and Lakeview, offers privacy on more than 3,598+/- deeded acres, plus an adjoining 11,718+/-acre USFS grazing allotment. Owned and improved continuously since 1975, the ranch features a 7,000+/ sq ft log lodge with multiple gathering areas, ensuite bedrooms, a commercial kitchen, and five 1,250+/ sq ft log cabins for luxurious retreats. Operating off-grid with hydro power and propane generators, it emphasizes sustainable living. Water is abundant from five reservoirs, and Fishhole Creek, with senior water rights supporting irrigation and 800+/- cow equivalents seasonally on both deeded and USFS lands. Diverse wildlife, including elk, deer, and waterfowl, provides hunting and fishing opportunities. Secluded, yet reachable: commercial flights available at Medford, Redmond, and Reno, plus nearby private air options.

Fishhole Creek RD, Bly

65255 Swalley Road, Bend
$11,900,000
3 Beds ⋅ 3 Baths ⋅ 220207865 MLS
This +/- 118 acre property located less than 20 minutes north of Bend, Oregon straddles the rugged Deschutes River canyon for over a half mile. The house is perched on the edge of the river canyon in a prime location to capture river, forest, and unobstructed canyon and cascade mountain views from Mt Bachelor to Mt Jefferson. Built in 1973, the house serves as a place holder for this spectacular homesite as current restrictions would not allow construction perched on the rim today. The song of small rapids below adds to the ambiance. On the north end of the property the sheer canyon walls open, providing access to the river for swimming, fishing, floating or just chilling by the water. Ownership of both sides of the canyon protects the breathtaking view from external encroachment. Redmond Airport is only 18 minutes away. The property may qualify for a land partition and CUP(s) for additional dwellings. Buyer to do all due diligence with Deschutes County and other land use agencies.

65255 Swalley Road, Bend

64095 Tamoli Lane, Bend
$10,850,000
7 Beds ⋅ 7 Baths ⋅ 220229854 MLS
Forty acres, Cascade views, and a home that welcomes you the moment you arrive. Rebuilt to the foundation in 2013 by Norman Building and Design and refined with recent updates, this 7,643 sq ft, 4-bedroom residence centers on a Great Room where walls of glass frame the mountains beside a Montana Moss stone fireplace. The reimagined kitchen was made for gathering, and the primary suite offers its own fireplace, steam shower, secluded deck, and hot tub. Downstairs: wine cellar, theater, gym, game room, and wet bar. Crestron and geothermal keep life effortless. For the horse lover, a glass-wrapped 60x180 indoor arena, 80x200 outdoor arena, 12 paddocks with loafing sheds and automatic waterers, and a 4-stall barn with a loft. 35 irrigated acres include 20 in orchard grass hay, with boarding and hay operations. A 3-bedroom caretaker's cottage completes a rare Central Oregon legacy property.

64095 Tamoli Lane, Bend

16799 Highway 66, Ashland
$10,775,000
12 Beds ⋅ 10 Baths ⋅ 220210683 MLS
AUCTION: Bidder registration deadline: 1 December. Starting bids expected between $3.5M-$5.5M. Set amid pristine wilderness along the historic Green Springs Highway, New Frontier Ranch is a storied 958-acre legacy property where Old West heritage meets boundless possibility. Anchored by a 1910 farmhouse that once served as a stagecoach stop, the ranch unfolds across irrigated meadows, forests, creeks, and two reservoirs framed by views to Mount Shasta and Mount McLaughlin. A grand event hall, museum building, three log cabins, and a private campground create a ready foundation for hospitality, while a preserved ghost town adds a rare sense of discovery. Miles of trails invite hiking, horseback riding, and ATV adventures, with fishing and hunting close at hand. Grandfathered destination resort approvals open the door to a lodge, spa, weddings, retreats, and festivals, or a singular private wilderness estate.

16799 Highway 66, Ashland

7619 SE 17TH ST, Vancouver
$10,000,000
5 Beds ⋅ 7 Baths ⋅ 428974194 MLS
Beyond the gates of one of the most exclusive waterfront communities lies a once-in-a-lifetime estate offering an extraordinary blend of grandeur, warmth, and resort-inspired living. Privately gated and perfectly positioned on a rare level waterfront lot with its own sandy beach, south-facing backyard, and shared deep-water dock capable of accommodating virtually any size vessel, this remarkable 15,785 SF residence captures breathtaking sunsets and panoramic river views unlike anything else on the Columbia. Designed to live large while still feeling intimate and inviting, the home was thoughtfully crafted for both elevated entertaining and comfortable everyday living. A dramatic grand staircase creates an unforgettable first impression, while soaring spaces, walls of glass, rich architectural detail, and multiple gathering areas bring warmth and sophistication throughout. The residence features 5 bedrooms, 7 full and 1 half baths, dual staircases, elevator access to every level, and a luxurious upper-level primary retreat with private balcony overlooking the water.The main level offers beautifully scaled living and entertaining spaces including formal dining, executive office, elegant lounge areas, and a full bar designed for hosting on any scale. The lower level rivals a private luxury resort with home theater, game room, indoor lap pool and spa, sauna, commercial-grade fitness studio, and a fully equipped indoor/outdoor bar and kitchen experience. Expansive walls of doors open seamlessly to the waterfront grounds, creating effortless year-round indoor/outdoor living.Rarely does a property offer this combination of scale, privacy, level waterfront living, beach access, boating lifestyle, and proximity to both Portland and Vancouver. This masterpiece estate was built by Lake Oswego-based Avgerakis, one of the most sought-after luxury builders in the Pacific NW - widely recognized for their top quality, state-of-the-art construction techniques and innovative designs.

7619 SE 17TH ST, Vancouver

4415 NE 259TH ST, Ridgefield
$9,000,000
4 Beds ⋅ 3 Baths ⋅ 751170809 MLS
Imagine a lifestyle where mornings begin with mist rising over a private lake, afternoons are spent wandering vineyard rows and evenings unfold beneath spectacular sunsets. This extraordinary Ridgefield estate blends luxury living with the romance of the land, offering endless possibilities across its picturesque grounds. AG-20 zoning, valuable water rights and extensive infrastructure create opportunities for hospitality, equestrian, agricultural and entrepreneurial pursuits.Custom built in 2022, the gated 4,989 SF, 4BD/3.5BA residence with 5-car garage embraces breathtaking lake views through soaring windows and abundant light. An open floorplan features a dramatic two-story fireplace, gourmet kitchen with quartz countertops, large island and expansive butler's pantry. The private main floor primary wing offers a luxurious ensuite bath with a soaking tub and enormous shower, gym and spa sanctuary with sauna, massage area, Himalayan salt wall and tranquil lake views. Effortless entertaining with an indoor outdoor flow from the house to a covered patio with fire table and outdoor kitchen. Bask in the beauty & privacy of the property in the outdoor hot tub.A second 3,602 SF, 3BD/2.5BA residence (currently an AirBnB) with 3-car garage offers multigenerational living, guest accommodations or rental potential.Approximately 15 acres of vineyard, primarily Pinot Noir, grace the landscape alongside a winery with 3,000 SF production facility and 5,000 SF warehouse. A 1,640 SF tasting room, two timber-framed pavilions totaling 3,036 SF, lakefront stage, floating gazebo deck, trellised patios and event infrastructure invite unforgettable celebrations. Explore walking trails, practice on your private driving range or simply savor the serenity of open space, water and nature. Minutes from I-5, Portland and Vancouver, yet a world away. One of Ridgefield's largest remaining land offerings, where the beauty of the land is matched only by the possibilities it inspires.

4415 NE 259TH ST, Ridgefield

19100 Macalpine Loop, Bend
$8,750,000
5 Beds ⋅ 8 Baths ⋅ 220219311 MLS
Ten acres inside the gates of The Highlands at Broken Top, where Cascade mountain views frame every west-facing room & privacy is absolute. This estate was designed to host a life at full scale. A great room with vaulted timber beam ceilings & wood-burning fireplace opens to a main kitchen with onyx backlit backsplash & full prep kitchen. The main-level primary suite offers an infrared sauna, steam shower, fireplace, dual closets, & private patio, alongside three additional ensuite bedrooms, guest quarters, & a private office. The lower level adds a golf simulator, gym, and flex game room. Outside, a solar-heated saltwater pool & spa, outdoor kitchen, Alfa pizza oven, bocce court, gas firepits, & wood-burning fireplace with surround sound. The pool house with wet bar, & pass-through bar connects to heated RV/shop. Kitchen garden, greenhouse, & basketball court complete the grounds. Phil's Trail at the gate. One of a kind private homesites in The Highlands.

19100 Macalpine Loop, Bend

41221 SE VAN LAKE RD, Prineville
$8,700,000
3 Beds ⋅ 3 Baths ⋅ 351135247 MLS
Logan Butte-96 & Tackman Ranch offer a rare opportunity to acquire approximately 6,700± deeded acres across two complementary Central Oregon ranches. The 96 Ranch includes 3,500± deeded acres with approximately 10,000 acres of Forest Service lease, 6,000 acres of BLM lease, and 1,100 acres of private grazing lease, featuring irrigated and sub-irrigated meadows, strong water rights, and a center pivot supporting a high-capacity cattle operation. Tackman Ranch adds approximately 3,190± deeded acres plus 1,820± acres of BLM grazing allotment, with 90± acres of irrigation rights, creek frontage, barns, shops, fencing, utilities, and a prime homesite. Together, these properties provide exceptional scale, operational flexibility, strong grazing capacity, direct access to public lands, and outstanding mule deer and Rocky Mountain elk habitat, all just over an hour from Bend. A unique opportunity to own a legacy ranch with production, recreation, and long-term investment value.

41221 SE VAN LAKE RD, Prineville

21080 NE RIBBON RIDGE RD, Newberg
$8,500,000
3 Beds ⋅ 3 Baths ⋅ 391451544 MLS
The crown jewel of Ribbon Ridge. At the summit of the acclaimed Ribbon Ridge AVA sits a property unlike any other—the original homestead of the Ridge and now, a rare offering of history, elegance, and world-class vineyard potential. This 41-acre estate combines legacy and luxury in one of Oregon wine country’s most desirable and tightly held sub-appellations. With 8 acres of organically farmed vineyard already in production and the ability to plant a total of 15-20 acres on prime hillside ground, this is a once-in-a-lifetime opportunity to establish or expand a premium wine brand on the AVA’s most enviable positions. The modern 3,000 sq ft custom farmhouse is both refined and functional—designed with hospitality, lifestyle, and versatility in mind. An irreplaceable property, unmatched in provenance, position, and potential.

21080 NE RIBBON RIDGE RD, Newberg

11777 Highway 238, Jacksonville
$8,500,000
4 Beds ⋅ 3 Baths ⋅ 23696912 MLS
Welcome to Red Lily Vineyards, one of the most acclaimed vineyards in the esteemed Applegate Valley of Southern Oregon. Renowned for its exceptional wines and captivating scenery, Red Lily Vineyards presents an alluring mix of established wine and agri-business with great opportunities for event and hospitality expansion. It's not just a business; it's a gateway to an extraordinary experience and a haven for those seeking a rare and sought-after investment and lifestyle opportunity. This 255-acre ranch and estate boasts strong water rights, breathtaking river frontage, a state-of-the-art winery, mature vineyards, and an expanses of quality irrigated land for vineyard and agricultural expansion plus perhaps the most iconic and well-trafficked wine tasting experience in Southern Oregon. Nestled atop a secluded knoll, commanding picturesque views of the Applegate Valley, is the main residence, a quintessential American cedar shingle-style home boasting over 4,000 square feet of living space. The second home, known as the winemaker's house, is a delightful farmhouse that has been thoughtfully updated. With its well-established reputation and a wealth of infrastructure, Red Lily provides an excellent platform for business expansion. This includes options for expanding vineyard and agri-business operations, developing a hospitality business with a focus on events such as destination weddings, as well as on-site accommodations like bed and breakfast and cabin rentals. An additional estate dwelling and farm-to-consumer sales are also relevant opportunities. This rare gem offers an unparalleled setting with 3,300 feet of Applegate River frontage and convenient access to incredible outdoor activities. The phenomenal location is a short commute from all the conveniences of Jacksonville and Medford and is centrally located within Southern Oregon. The offering is a hybrid sale that includes the business, brand, and real estate. Owner terms may be available. Thank you!

11777 Highway 238, Jacksonville

3355 Kircher Road, Chiloquin
$8,444,000
3 Beds ⋅ 2 Baths ⋅ 220217420 MLS
Kircher's World Class Fly Fishing Ranch is a unique property that sits on the Waterfront of two of the best Trout Fishing Rivers in the Northwest. River Frontage includes +/-3 miles of the mighty Williamson and the meandering Sprague Rivers. The main Ranch Home sits just up river from the confluence of these two beautiful waterways. When it comes to Big Trout, the Williamson and the Sprague have consistently produced monster fish in large quantities, +24 inch Rainbows are common with Wild Trout up to 10 pounds. Fisherman from around the world have successfully fished these top quality wild fish. A day spent on the river is what I like to call, ''a free day.'' Free to breath in the purest of Oregon air with maybe a slight scent of the forest. Free to please your eyes with views that few have seen in person. Free to feel the adrenalin when that monster rips your fly from the surface. Free Days always add days to our lives.

3355 Kircher Road, Chiloquin

21358 OAK LN, Aurora
$7,900,000
3 Beds ⋅ 2 Baths ⋅ 488126157 MLS
Rare and Remarkable Opportunity! Two Homes. 51.41 acres. 34 acres of Vineyard. Turnkey Winery and Vineyard. WATER RIGHTS. 600 gallon per minute irrigation well. Domestic well 70 gallons per minute. Aurora Vineyards stands as a premier vineyard and winery estate in the heart of Oregon’s Willamette Valley. Recognized for its notable blend of high-quality wine production and vibrant event hosting capabilities, serving both local and destination clients. Tasting room blends rustic elegance with modern comfort, offering chef-prepared cuisine, award winning wines, and live music in a relaxed yet refined setting. Guests enjoy indoor seating and a spacious outdoor deck overlooking a waterfall and pond, creating a memorable experience for casual visitors and wine club members alike. Sale includes the entire real estate holding, all vineyard plantings, the winery facility and hospitality infrastructures, and all associated inventory and equipment. The property encompasses a modern, fully equipped winery, with on-site production capabilities for all stages of vinification. The on-site venue and event spaces provide a picturesque backdrop for weddings, private celebrations, and corporate gatherings. Surrounded by vineyards and manicured gardens, the venue features elegant architecture, bridal and groomsmen suites, and seamless flow into reception areas—making it a turnkey destination for unforgettable events. After 25 years of vision and dedication to his customers and the land, the owner is retiring from his passion of thriving vineyard, winery and event venue which has cultivated widespread acclaim for award winning wines and a proud reputation for quality. This transition marks the end of an era—and the beginning of a rare opportunity for a new owner to carry forward this legacy built on craftsmanship and quality. All buildings and details in document section.

21358 OAK LN, Aurora

65930 Mariposa Lane, Bend
$7,900,000
7 Beds ⋅ 9 Baths ⋅ 220204494 MLS
An architectural masterpiece in Bend's coveted Golden Triangle. Set on 9.77 private acres behind custom gates, this Northwest style estate by Norman Building & Design offers sweeping Cascade Mountain views. Walls of glass frame the high desert, anchored by a grand stone fireplace & massive beams. Chef's kitchen w/ slab granite & sculptural hood opens to dining & copper-topped wine bar. Steps lead down to a wine cellar & tasting room. Main-level primary suite w/new gas fireplace, spa bath & panoramic mountain views. Dramatic breezeway connects to a 2,095 SF guest house. Enclosed parking between both garages for 11 cars or 9+2 RVs. Expansive patios, fire pit, water feature & salt water hot tub under the stars. Well appointed main-level office with Mtn. views, exquisite wood finishes & timeless craftsmanship define this legacy estate--secluded yet minutes to downtown Bend. Only 25 min. Redmond Airport, Near golf, Mt Bachelor, equestrian estates & world class recreation.

65930 Mariposa Lane, Bend

503 Quail LN, Grants Pass
$7,600,000
3 Beds ⋅ 2 Baths ⋅ 635648947 MLS
Set along a rare, low-bank stretch of the Rogue River within a federally designated Wild and Scenic corridor, this approximately 18-acre estate offers nearly 1,500 feet of river frontage and a lifestyle defined by privacy, beauty, and connection to nature. Inspired by an English Country estate and crafted with exceptional attention to detail, the residence features custom millwork, artisan details, hand-scraped walnut floors, a hand-carved Carrara marble fireplace, and a chef’s kitchen with Sub-Zero and DCS appliances. Outdoor living unfolds across manicured grounds with bluestone pathways, a 15,000 SF deer-fenced garden, gazebo, and private riverfront park with sandy beach access. Additional amenities include a climate & humidity-controlled greenhouse, barn with guest quarters, detached gym/studio, and fully climate-controlled garage. Located in the heart of the Rogue Valley, this is a rare opportunity to own a legacy estate in one of Southern Oregon’s most sought-after riverfront settings.

503 Quail LN, Grants Pass

29951 SW OLD WELL RD, West Linn
$7,500,000
4 Beds ⋅ 4 Baths ⋅ 596471429 MLS
Architectural ambition meets unrivaled privacy. This once-in-a-generation custom estate spans 10 private acres in West Linn, where bold design, modern luxury, and elevated living converge in an atmosphere of unmatched exclusivity. Created by Street of Dreams award-winner Westlake Development Group and architecturally designed by Scott Streitberger, this 7,500 sq ft concept is as rare as it is remarkable. Renderings by Envision Studio offer a striking starting point for those ready to build a legacy.Wrapped in blackened stone, smooth panels, and glass, the design makes a statement from every angle. Towering ceilings, a dramatic two-story entry, statement lighting, and full-height windows deliver maximum drama and natural light. The chef’s kitchen is a true showpiece featuring dual islands, sleek cabinetry, and seamless indoor-outdoor flow designed for entertaining. A rooftop sky deck and 4-car glass-fronted garage round out the lifestyle-forward vision. Interior renderings showcase a floating staircase, executive office with forest views, and a signature glass-enclosed wine display anchoring the main living space.The primary suite overlooks the Willamette River, offering commanding views, a spa bath retreat, and private terrace. But the crown jewel? 100 feet of deeded Willamette River frontage with a private gangway and oversized dock already in place - a feature so rare it elevates this opportunity into a category of its own. Water rights and access to a shared high-output well are also included.The property offers ample space to bring your dreams to life: an infinity-edge pool, sport court, vineyard rows, or luxury guest pavilion, there’s room for it all! Tucked behind a gated private drive and surrounded by forest, this estate offers total seclusion just minutes from downtown and within the top-ranked West Linn school district. Time remains to personalize the finishes and build your legacy.

29951 SW OLD WELL RD, West Linn

67480 Cloverdale Road, Bend
$6,999,000
6 Beds ⋅ 7 Baths ⋅ 220223667 MLS
Experience luxury country living on 25± acres between Bend & Sisters, Oregon. This exceptional equestrian estate offers breathtaking views of the Cascade Mountains, & surrounding countryside. The 9,075 square-foot custom home features 6 bedrooms, 6.5 bathrooms, soaring cedar ceilings, hardwood floors, a gourmet kitchen, library, office, game room, guest suite, & a private apartment for guests or staff. Outdoor amenities include a pool, hot tub, pool house with steam room & sauna, and beautifully landscaped grounds. Equestrian improvements are highlighted by a 170' x 90' indoor arena with stalls, tack rooms, paddocks, kitchen, full bath, & viewing loft. The property is fenced & cross-fenced, includes approximately 11 acres of irrigation, two RV hookups, & may qualify for approval to host up to eight weddings annually, subject to county requirements. A rare opportunity to own a premier Central Oregon equestrian & lifestyle property just minutes from recreation, dining & outdoor adventure

67480 Cloverdale Road, Bend

300 49 Rd Silverlake Hwy, Chiloquin
$6,900,000
4 Beds ⋅ 2 Baths ⋅ 788754662 MLS
Approx. 1.5 miles of Williamson River frontage — one of Oregon's premier fly fisheries, renowned for trophy native redband trout. Five contiguous parcels totaling ±1,011 deeded acres offering sub-irrigated pastures fed by the Williamson River, timbered uplands, and diverse wetland habitat. The main ranch features a rustic cabin and four livable structures total. Cattle corrals and loading chute in place. Good road systems throughout. All utilities off-grid. EFU-G zoning with farm-use special assessment. Available as a complete assemblage or in two separate offerings: The Ranch (±931 acres) and The 80-Acre Parcel (±80 acres). Strong conservation easement potential. Scale, water, and river frontage rarely come available in the Klamath Basin. Buyer to verify all.

300 49 Rd Silverlake Hwy, Chiloquin

15530 DIAMOND HEAD RD, Lake Oswego
$6,725,000
6 Beds ⋅ 6 Baths ⋅ 601096255 MLS
Diamond Point - At the Intersection of Architecture + Art. A stunning example of architectural art that perfectly captures the spirit of its era while being timelessly modern. Originally designed in 1965 by Kenneth G. Walter and meticulously updated & preserved through a sensitive renovation by Emerick Architects, this home is more than a residence, it is an experience.Tucked away at the edge of a quiet road, the home feels like being transported to a stylish sanctuary resembling a space found Hollywood Hills,yet remains firmly rooted in its lush Pacific Northwest landscape. Designed to contour the terrain, the structure maximizes both privacy and connection to nature, essentially "floating" above Lake Oswego at the tip of Diamond Head Road.Inside, the home reveals beautiful mid century modern architecture that frames breathtaking lake views.Vaulted tongue-and-groove wood ceilings with exposed beams draw the eye upward, while floor-to-ceiling walls of glass invite the outdoors in. The transitions are seamless; local basalt rock walls blur the line between indoor comforts and the natural surroundings. For the entertainer, the home offers an abundance options: a large main living area with a signature MCM sunken conversation pit wrapped around a cozy fireplace, a dining room that is open to the kitchen where a folding glass wall opens the home to the fresh forest air, a lower-level rumpus room complete with a custom bar and outdoor patio access.Every detail has been curated for an elevated life—from the custom walnut kitchen cabinetry, bespoke built-ins and designer fixtures to the preservation of the high quality vintage details throughout. With six bedrooms, six baths, and 213 feet of lake frontage including a private dock and boat house, this is a rare opportunity to steward a significant piece of Pacific Northwest architecture in one of the most prestigious areas. Just minutes to downtown LO shopping&dining.

15530 DIAMOND HEAD RD, Lake Oswego

41221 SE VAN LAKE RD, Prineville
$6,650,000
3 Beds ⋅ 3 Baths ⋅ 693016462 MLS
Seller is willing to carry a contract! Inquire with listing agent for details. Logan Butte-96 Ranch is a premier Central Oregon cattle and recreation ranch set in its own private valley between Logan Butte and Smokey Butte, just over an hour from Bend. The property includes 3,500± contiguous deeded acres supported by approximately 10,000 acres of Forest Service lease, 6,000 acres of BLM lease, and 1,100 acres of private grazing lease, offering exceptional scale and grazing capacity. Designed for efficiency, the ranch supports approximately 380 cattle and features irrigated and sub-irrigated meadows with approximately 79.6 acres of water rights, including a center pivot, wheel lines, and hand lines. A year-round creek and an approximately 16-acre lake provide excellent water resources. Improvements include a 2,720 sq ft main home, second residence, bunkhouse, apartment, shop, barns, corrals, and arena. Outstanding mule deer and Rocky Mountain elk habitat. Strong internal road system and quality fencing throughout.

41221 SE VAN LAKE RD, Prineville

28605 SW PETES MOUNTAIN RD, West Linn
$6,250,000
5 Beds ⋅ 6 Baths ⋅ 714297374 MLS
Residence 35 at High Grass Pointe. An extraordinary expression of modern luxury, this gated 2.6-acre estate showcases the exceptional craftsmanship of Master Builder. Offering over 7,000 square feet of sophisticated design, sweeping Mt. Hood views, and complete privacy, this remarkable new construction sets a new standard for modern living. Walls of glass, soaring ceilings, and refined finishes define the expansive great room. The luxurious kitchen features an oversized island and an exceptional working scullery, ideal for effortless entertaining. A private owners’ lounge and chic primary suite with a massive walk-in closet provide an elevated retreat. Designed for exceptional comfort and versatility, the home features a main-level guest suite, four additional ensuite bedrooms, a stylish library with walkout balcony, and a dedicated media room. The impressive fitness center includes a sauna and cold plunge, while an oversized garage offers exceptional space for automotive enthusiasts. Located in prestigious High Grass Pointe, the property is minutes from acclaimed vineyards, fine dining, golf courses, and boating. High Grass Pointe is also the site of the 2027 Street of Dreams, highlighting its distinction as a premier destination for exceptional residential design. A rare offering of architectural sophistication, exceptional craftsmanship, spectacular views, and resort-caliber amenities, this is modern luxury at its finest.

28605 SW PETES MOUNTAIN RD, West Linn

22141 NW REEDER RD, Portland
$6,250,000
4 Beds ⋅ 3 Baths ⋅ 383233553 MLS
For those seeking more than a home, this remarkable Sauvie Island estate offers a private sanctuary designed for gathering, celebrating, and creating memories for generations to come. Privately situated on 26.66 acres and just 20 minutes from downtown Portland, the property offers an increasingly rare opportunity to slow down, reconnect, and enjoy the rhythms of country living without sacrificing convenience. A thoughtfully reimagined farmhouse is surrounded by curated grounds featuring open lawns, mature landscaping, gardens, orchard trees, walking paths, and sweeping mountain views and the Coast Range. Designed around light, flow, and connection, the home lives comfortably in every season and at every scale—from quiet mornings to large family gatherings. Designed for entertaining on any scale, the estate includes a resort-style pool, outdoor kitchen, pool house, and a striking barn with cedar-clad interior. Framed by expansive Oregon skies and a setting that feels worlds away, this is a place where family, friends, and future generations can gather, celebrate, and create lasting memories.

22141 NW REEDER RD, Portland

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

The data relating to real estate for sale on this web site comes in part from the Internet Data Display (IDX) of the Southern Oregon Multiple Listing Service. Real estate listings held by brokerage firms other than our company are marked with the IDX logo and detailed information about them includes the name of the listing brokers. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information subject to change and should be independently verified. Listing content is copyright © 2018 SOMLS, Medford, Oregon. Last updated:

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