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$2,250,000
3 Beds 3 Baths 220224011 MLS
Welcome to an absolute equestrian masterpiece in SE Bend! This exceptional, fully operating cutting horse property balances pristine privacy w/ unmatched training facilities. Positioned beautifully among large, mature Ponderosa pines on a massive 24+ lot, this classic ranch-style estate offers substantial interior space coupled w/ panoramic mtn views+elite ranch utility. Relax on the spacious back deck to take in clear views of snow-capped Cascade Mountains. Bring your vision-the estate home features a warm, expansive ranch layout anchored by a central fireplace. Multi-level functionality with a daylight basement setup, a spacious den/office area, and a bonus room loft ideal for hosting. Residence is beautifully nestled into a grove of majestic pines, ensuring ultimate natural privacy from the road. Fully enclosed indoor arena-barn complex designed to handle year-round training, horse mgmt, & professional cutting work. Deschutes Nat'l Forest is at your fingertips to ride into sunset!

60266 Tekampe Road, Bend

Listing courtesy of Jeff Larkin Realty.

$2,250,000
2 Beds 2 Baths 220221796 MLS
This 405.81± acre Oregon Farm consists of two legal parcels: 40.81± acres that sites the 2-story 2-bedroom 1.5-bath home with its open floor plan featuring vaulted ceilings, granite countertops, wood and tile flooring, beautiful interior wood features, and a phenomenal view of the surrounding hills and valley below; a 365± acre farm parcel boasts 1.8± miles of North Fork John Day River frontage and .5± miles Rudio Creek. 295.9± acres certified water rights allow diverting water from Rudio Creek and the North Fork John Day River to irrigate your hay, pasture, and grain fields. Four center pivots, a wheel line, and some handlines support irrigation distribution. Cross-fencing aids in pasture and crop management. Fish for smallmouth bass and steelhead trout, or hunt for mule deer, Rocky Mountain elk, pronghorn antelope, upland game birds, and waterfowl, or just enjoy the wildlife and river!

40252 Rudio Road, Kimberly

Listing courtesy of Fay Ranches, Inc..

$2,250,000
220220428 MLS
Rare 10-unit investment opportunity in Ashland's Hillview Condominiums -- close to Scenic Park, Asante Ashland Community Hospital, downtown dining and entertainment. Three-year seller-carried financing available at 3.75% rate with interest-only payments and balloon at maturity. Each unit ranges from 1,034 to 1,174 SqFt with two bedrooms, one full bath, open living and dining space, high ceilings, in-unit laundry, kitchen with granite counters and all appliances included, dedicated parking, storage, and access to landscaped common areas. Ground-level units with fully fenced private backyards and poured concrete patios. Portfolio includes stable tenancy, average occupancy of 4.2 years, room for rent growth, and association-maintained exterior building components including roofs, siding, paint, and landscaping. Complete investment analysis and user guide, rent roll, association documents, title information, and additional due diligence materials available upon request.

230 Grant Street, Ashland

Listing courtesy of John L. Scott Ashland.

$2,250,000
5 Beds 5 Baths 220219651 MLS
Custom contemporary estate -- 6,161 SF of intentional architecture sitting directly on the 16th green of the RTJ Jr.-designed Resort at Eagle Point Golf Course. This is not a golf course view. This is golf course living. Wolf/Sub-Zero kitchen w/ double Wolf ovens, built-in espresso station, and walk-through pantry. Below-grade geothermal wine cellar -- 1,007-bottle capacity w/ hidden safe room. Tiered home theater w/ concrete isolation and immersive surround. Pool cabana w/ full bath and hide-a-bed. Saltwater pool w/ waterfall grotto, outdoor kitchen w/ wet bar, bocce court, putting green. One of only a few homes on the entire course with a dedicated golf cart garage -- minutes to the first tee.

32 Pebble Creek Drive, Eagle Point

Listing courtesy of RE/MAX Integrity Grants Pass.

$2,250,000
220216457 MLS
Prime investment opportunity in Ashland, Oregon! This 44-room motel is conveniently located just off the freeway at 50 Lowe Road, offering excellent visibility and accessibility for travelers. The property features beautiful mountain views and includes a well-maintained swimming pool, currently not open to the public, providing significant value-add potential. The property also includes a fully equipped restaurant space that is currently not in operation but offers the infrastructure needed to reopen or repurpose according to a new owner's vision. With its strategic location, existing amenities, and strong upside potential, this property presents an exceptional opportunity for investors or hospitality operators ready to bring new life and creativity to this motel.

50 Lowe Road, Ashland

Listing courtesy of Home Quest Realty.

$2,250,000
220208690 MLS
Bridgeview Vineyards & Winery - A Rare Southern Oregon Opportunity Established in 1986, Bridgeview Vineyards and Winery has grown into one of Oregon's most recognized and successful wine destinations. This business and property come fully equipped with a 160,000-gallon tank capacity, established bulk wine sales, bottling and labeling facility, and a welcoming tasting room. The sale includes not only the winery operation but also a charming two-story owner's residence overlooking ponds and vineyards, along with room for staff. Visitors from all over the world are drawn to Bridgeview for its breathtaking setting—picturesque lakes, decks over serene irrigation ponds with trout and swans, and sunsets that leave a lasting impression. Beyond its daily winery operations, the property shines as an unforgettable venue. From weddings and concerts to community gatherings, the grounds are designed to host events of every size, complete with a staging area and ample scenic backdrops.

3900 Holland Loop Road, Cave Junction

Listing courtesy of eXp Realty, LLC.

$2,249,900
4 Beds 4 Baths 220224456 MLS
Awbrey Heights! Fantastic views from your private covered decks - Peaceful relaxing views. Host gatherings around the gas fire pit. Enjoy views of 4th of July fireworks! A beautiful gas fireplace welcomes you into this elegant, yet relaxing, spacious great room with high ceilings & travertine flooring. Chef's kitchen with sleek granite countertops, generous center island, & stainless steel appliances (brand new dishwasher). Double oven & 6-burner range. Wet bar, wine fridge, huge walk-through pantry. Two New Furnaces (Nov 2025). Two year new Bar-B-Que. Laundry room. The lavish main-level primary suite with deck access. Upstairs, a generous second primary suite with views from its private deck. Downstairs, a finished daylight basement includes a two-bedrooms, a large bonus TV or gym room & a double office. Copious storage options throughout. Paver Driveway. Seller offers buyer a $30,000 credit at closing for Hot Tub replacement and stucco repair. New roof July 2026.

646 NW Powell Butte Loop, Bend

Listing courtesy of John L Scott Bend.

$2,225,000
4 Beds 3 Baths 220223305 MLS
Minutes from downtown Bend, with easy access to the airport, world-class mountain biking, BLM land, and skiing at Bachelor and Hoodoo, this rare Tumalo estate on 23.46 acres delivers the best of Central Oregon living. Wake to breathtaking Cascade Mountain views from a gated private retreat featuring a beautifully updated home with reclaimed wood flooring, an inviting living room, spacious kitchen, and main-level primary suite. Spend summer afternoons at the swimming pond and gather under star-lit skies. Mature landscaping, fenced gardens, and a vintage European greenhouse create a setting both timeless and inspiring--perfect for dinner parties, celebrations, or quiet evenings home. And the value keeps building: multiple barns, equipment storage, outbuildings, and ~20 acres of irrigation rights add serious equestrian or hobby farm potential to an already exceptional property. A one-of-a-kind blend of lifestyle, beauty, and country living.

66300 White Rock Loop, Bend

Listing courtesy of Engel & Voelkers Bend.

$2,200,000
3 Beds 2 Baths 220224306 MLS
Duncan Ranch is a working 226± acre equestrian property set across six parcels in the Sprague River Valley. This rustic, functional compound features two custom homes (1,920 SF and 1,902 SF) and is fully equipped for horses and ranching, with a roping/riding arena, large hay barn, tack facilities, outdoor kitchen, cabin, and corral. The property offers approx. 4,200-4,400 LF of private frontage on each bank of the Sprague River, known for its premier fly fishing for wild trout. Situated at 4,320' elevation, this property provides year-round access and excellent wildlife habitat. Zoned FR. Taxes $4,644.92. A true, turn-key opportunity for those looking for an authentic ranch setup with water access. Buyer to verify all water rights with OWRD. Buyer to perform all due diligence. The green conex box is attached to an outbuilding and is included. The red connex box is excluded. There are 2 domestic wells and 3 stock wells. Located in Klamath County Fire District 3 boundaries.

23125 Sprague River Road, Sprague River

Listing courtesy of USLANDCO LLC.

$2,200,000
3 Beds 2 Baths 220224294 MLS
Duncan Ranch is a working 226± acre equestrian property set across six parcels in the Sprague River Valley. This rustic, functional compound features two custom homes (1,920 SF and 1,902 SF) and is fully equipped for horses and ranching, with a roping/riding arena, large hay barn, tack facilities, outdoor kitchen, cabin, and corral. The property offers approx. 4,200-4,400 LF of private frontage on each bank of the Sprague River, known for its premier fly fishing for wild trout. Situated at 4,320' elevation, this property provides year-round access and excellent wildlife habitat. Zoned FR. Taxes $4,644.92. A true, turn-key opportunity for those looking for an authentic ranch setup with water access. Buyer to verify all water rights with OWRD. Buyer to perform all due diligence. The green conex box is attached to an outbuilding and is included. The red connex box is excluded. There are 2 domestic wells and 3 stock wells. Located in Klamath County Fire District 3 boundaries.

23125 Sprague River Road, Sprague River

Listing courtesy of USLANDCO LLC.

$2,200,000
4 Beds 5 Baths 220224209 MLS
Golf course views in Caldera Springs! Custom-built by Pineriver Homes, this exceptional home showcases quality craftsmanship and timeless mountain style throughout. The open-concept floor plan features a gourmet kitchen with chiseled-edge granite countertops, copper farmhouse sink, coffered wood ceiling and high end appliances. Adjacent dining area includes a bar with ice maker and wine refrigerator. The vaulted great room features tongue-and-groove wood ceilings, distressed hickory hardwood floors, and a floor-to-ceiling stone fireplace with built-ins. An oversized mudroom/laundry room leads to the 3 car garage with epoxy floors and built-in cabinetry. Enjoy outdoor living with golf course views, a paver patio, built-in BBQ area and fire pit--ideal for entertaining and relaxing. 4 bedrooms plus a bonus room with a wet bar and built in bunk beds. Additional features include central vacuum, zoned heating, wood windows, and exceptional attention to detail throughout.

56820 Dancing Rock Loop 49 Unit 49, Bend

Listing courtesy of Cascade Hasson SIR.

$2,200,000
220217055 MLS
Rare opportunity to acquire a turnkey stand-alone restaurant with drive-thru in a highly visible Bend location near the signalized intersection of NE Hwy 20 and NE 27th Street. The ±3,492 SF building sits on a 0.51-acre parcel and is zoned Commercial General (CG), allowing for a variety of retail and restaurant uses. Originally constructed in 1996, the property offers an efficient restaurant layout with a drive-thru lane, ample onsite parking, and strong street visibility. The sale includes furniture, fixtures, and equipment (FF&E), providing a plug-and-play opportunity for an owner/user or investor looking to reposition the asset. The site benefits from strong regional retail synergy and is shadow-anchored by Walgreens and Wilco, with traffic counts exceeding 15,000 vehicles per day along the NE Hwy 20 corridor. The existing tenant is scheduled to vacate prior to or upon sale, creating a rare chance to immediately occupy or redevelop the property.

62080 NE 27th Street, Bend

Listing courtesy of Compass Commercial Real Estate.

$2,199,000
3 Beds 4 Baths 220221747 MLS
Premier Rogue Riverfront estate with 96+ ft of frontage in Anglers Cove subdivision. This custom home offers 3,207sf, 3 bdrms, 3.5 baths, soaring 24' great room ceilings, artisan plaster walls, knotty alder doors & stunning reclaimed hand-hewn logs from 1800s Pennsylvania buildings. Designed for luxury living & entertaining, the home features a gourmet kitchen w/Wolf 48'' gas range-6 burners & griddle w/double ovens, Sub-Zero refrigerator, wine cooler, granite counters, 10-ft ceilings throughout w/solid core doors, zoned HVAC, dual tankless water heaters, security system & Wi-Fi-controlled lighting & irrigation supplied by river rights. Enjoy heated patios w/roll-down screens & Bluetooth audio overlooking the Rogue River. The 1,478sf attached garage includes a large RV bay w/50-amp service, water, sewer hookups, workshop area, gated entry, Generac backup generator & beautifully updated landscape lighting. Rare blend of craftsmanship, privacy, technology & premier riverfront living.

1030 Anglers Place, Shady Cove

Listing courtesy of Windermere Trails End R.E..

$2,198,000
4 Beds 4 Baths 220218913 MLS
The premier, corner unit is under way. This home faces open sky on two sides, the Old Mill in the foreground and the sweeping mountain views beyond. The Eight at the Old Mill was designed for the buyer who doesn't want to choose between a great location and a smart investment. The main residence offers 3 bedrooms and 2.5 baths above a fully independent ADU with its own private entrance, full kitchen, full bath, and laundry. Live above, rent below, or let both units work as short-term rentals. No overnight rental restrictions and clear of the City of Bend's 500-ft STR rule. Some finish selections remain, a rare chance to make it truly yours. Designer touches: white oak floors, JennAir appliances, quartz counters, a linear gas fireplace, and artisan tile work in every bath. EV-ready 2-car garage and HOA-maintained grounds complete the picture. Steps from the Box Factory, Crux, the Deschutes River, and the Old Mill District, this is where living well and investing wisely meet.

204 SW Log Court, Bend

Listing courtesy of Cascade Hasson SIR.

$2,195,000
4 Beds 4 Baths 220222261 MLS
Welcome to one of the newest homes in Black Butte Ranch, built in 2023. This single-level floor plan features two separate living areas divided by a see-through fireplace, and also includes a dedicated office, butler's pantry, and spacious dining area. The luxurious primary suite includes a large bathroom with a soaker tub and walk-in closet. There is also a second master bedroom with its own en-suite bathroom on the opposite side of the house. All bedrooms are generously sized with great natural light. Exterior highlights include a metal roof, paver driveway, covered front and back patios, and a 3-car garage with RV door. With its turnkey condition, flexible layout, and location in one of Central Oregon's most sought after resort communities, this property has excellent potential as a short term vacation rental on platforms like Airbnb and VRBO. Whether as a primary residence, second home, or income-producing rental, this is a rare opportunity to own a nearly new home on The Ranch.

13759 Partridge Foot, Black Butte Ranch

Listing courtesy of eXp Realty, LLC.

$2,195,000
3 Beds 3 Baths 220220779 MLS
PRICE REDUCED! Luxury 24.95-acre estate showcasing unobstructed Three Sisters mountain views. Outdoor living takes center stage with a swim spa perfectly positioned toward the range, a tree-lined paved driveway, full perimeter fencing, tranquil pond with fountains, and outdoor rock fireplace for sunset entertaining. This 3 bed, 2.5 bath residence offers refined comfort, highlighted by a primary suite with sauna, soaking tub, and a Byzantine marble river pebble shower. The chef's kitchen features slab granite countertops and high-end appliances. Equestrian amenities include a beautiful barn with 4 bays for horses or vehicles, an additional 2-bay garage, abundant storage, and a finished 14x36 loft with balcony and bath--perfect for guests or rental income. A detached 3 car garage and covered car port offer abundant parking. A brand-new 16x20 heated/cooled studio overlooks the pond, creating a serene workspace. Seller obtained transferrable option to pursue groundwater irrigation rights

67167 Highway 20, Bend

Listing courtesy of Berkshire Hathaway HomeService.

$2,195,000
4 Beds 4 Baths 220219782 MLS
Located just outside Ashland, this property offers a rare blend of natural beauty, water, quality improvements, and convenience. The custom built home is thoughtfully positioned to capture expansive views across the surrounding valley and toward distant mountains. This elevated country estate draws from a Northwest lodge aesthetic, offering welcoming living spaces, a spacious multilevel layout and a seamless indoor outdoor connection with expansive outdoor living spaces. A picturesque stretch of Neil Creek framed by mature trees adds character and tranquility. Gently rolling topography, lush pasture, and water rights support a variety of Ag uses. A recently constructed 5,000 SF barn complements the property and offers outstanding flexibility for equipment, hobbies, or recreational use. Ideal as a homestead or simply an elegant place to enjoy connection to the outdoors, this is a property that captures the essence of Southern Oregon living while remaining just minutes from Ashland.

5293 Highway 66, Ashland

Listing courtesy of John L. Scott Medford.

$2,195,000
4 Beds 4 Baths 220216107 MLS
Wake up to the view that golfers chase all day - the 5th green of the Big Meadow course at Black Butte Ranch. This 4,400+ sq ft retreat sits front row to the action, blending lodge style with modern comfort. A floor-to-ceiling stone fireplace anchors the great room, framed by vaulted knotty pine ceilings and wood-wrapped windows. Celestial windows brighten the dining area overlooking a courtyard with a water feature and mini falls. The open kitchen features Corian counters and a built-in Sub-Zero fridge. Two primary suites--one on each level--offer flexibility, with the upper suite enjoying a private deck. A finished room above the garage, separate from the home, works beautifully as a studio, guest quarters, office, or game room. Hardwood floors, two laundry rooms, updated baths, entertainment sized golf-facing decks, and sold furnished. Life on the Big Meadow Golf Course green never looked so good. Just bring your clubs and a tooth brush.

71059 Bracken Lane, Black Butte Ranch

Listing courtesy of Central Oregon Realty Group.

$2,185,000
3 Beds 3 Baths 220221690 MLS
Set directly along the Deschutes, where the cadence of rapids becomes part of daily life, this Westside Rick Wright home offers a rare, immersive connection to the water - each room oriented to the view, with floor-to-ceiling windows that draw the river inside. Positioned at the end of the street on the canyon's edge, the setting captures long stretches of river while maintaining privacy, with immediate access to one of Bend's most sought-after areas for swimming, fishing, and paddling, yet just an ~8 minute walk along the river downtown. The home blends contemporary updates with function, including a heated driveway, stainless appliances, wool carpet, and Hunter Douglas shades, and framed by Pozzi wood windows. Living spaces extend to decks - one river-facing, another set among treetops - plus a bonus room, sunroom, and pocket office. Two-zone heating and cooling, solar, instant hot water, EV outlet, built-ins, 311 sq ft of storage, and a riverside hot tub complete the offering.

1991 NW 1st Street, Bend

Listing courtesy of Cascade Hasson SIR.

$2,175,000
3 Beds 3 Baths 220219491 MLS
Crooked River Rim Horse Ranch offers 97.94± elevated acres overlooking the Crooked River Valley, positioned just 10 mins from Prineville. This horse property combines substantial infrastructure with convenient access. The 2,265± sq ft single-level home (2003) provides practical year-round living. An attached 832± sq ft garage includes a heated/cooled loft for workspace or guests. Horse infrastructure includes: main barn with 13 stalls, tack areas, feed room, and integrated living quarters. A 12,000± sq ft covered arena. A 175' round pen and an additional small round pen complete the setup. Welded pipe corrals and feedlot with 250± feet of bunk space support livestock handling. Water security is solid: 6.1± acres of irrigation rights through Ochoco Irrigation District, two domestic wells, and freeze-protected troughs ensure reliable year-round operation. A 4,320± sq ft hay storage and shop building includes an enclosed heated workspace. Built for a serious horse person to enjoy.

2300 S Main Street, Prineville

Listing courtesy of Fay Ranches, Inc..

$2,150,000
4 Beds 4 Baths 220226146 MLS
What defines luxury living? It is the perfect blend of elevated design, effortless comfort, & peace of mind, which are exactly what this beautifully updated Awbrey Butte home offers. Step inside the interiors showcasing a vaulted great room with beamed ceilings, custom casework, & an impressive built-in wine bar. Significant capital updates like a new roof, recent exterior paint, new HVAC, & custom deck railings ensure your everyday is made more enjoyable. Dedicated spaces easily cater to work-from-home needs, game room fun, & flawless entertaining with a home office, bonus room, dual living spaces with fireplaces, plus a versatile lower-level flex room with exterior access. Unwind daily in the private sanctuary of the main-level primary suite that leads to the outdoor hot tub & a spa-like bath complete with heated floors. Epic adventures await from this location just minutes to Downtown Bend, NorthWest Crossing, scenic trails, & golf. Embrace the remarkable lifestyle you deserve!

1804 NW Remarkable Drive, Bend

Listing courtesy of Cascade Hasson SIR.

$2,150,000
3 Beds 3 Baths 220224480 MLS
Experience exceptional craftsmanship in this custom contemporary home by Timberline Construction, one of Oregon's premier luxury builders, designed in collaboration with renowned Bend architect Brandon Olin. This stunning single-level home showcases soaring ceilings, walls of south-facing windows, one-of-a-kind chestnut hardwood floors, hand-selected granite, an oversized island, and a chef's kitchen with a butler's pantry. The open floor plan seamlessly connects to a spacious partial wraparound deck, creating effortless indoor-outdoor living. Situated on a desirable corner lot in Tetherow, the home offers 3 bedrooms, a dedicated office, media/flex room, 3 full baths, and a tandem 3-car garage. A rare opportunity to own a home where exceptional design, premium materials, and timeless quality come together.

19450 Bainbridge Court, Bend

Listing courtesy of eXp Realty, LLC.

$2,150,000
4 Beds 4 Baths 220222154 MLS
Private gated riverfront estate on the North Umpqua featuring a true collector's garage/shop with polished floors, abundant natural light, and capacity for up to 12 cars, an exceptional setup for collectors, boats, and recreational gear. Direct access to a rare, gentle stretch of usable shoreline with private boat access, set along a natural wildlife corridor known for world-class steelhead fishing. The Frank Lloyd Wright inspired main residence showcases natural materials, dramatic light, and intentional design to capture sweeping river views, complete with an outdoor kitchen and a newer 50 year roof. Additional guest house, plus detached studio with full bath connected to an oversized 2 car garage, and full RV hookups. All set on meticulously maintained, private park-like grounds with a stocked pond. Entire property irrigated from the river with valuable water rights and not in flood plain. Furniture negotiable.

2546 Fisher Road, Roseburg

Listing courtesy of Pine-Rok Realty.

$2,150,000
3 Beds 3 Baths 220217549 MLS
This exceptional, private single-level residence offers 3 BD/3 BA spread out across 2,844 SF and situated on 9 + acres, including a large pasture with a picturesque barn. Residents enjoy sweeping views along the Big Deschutes River as well as snow-capped Mt. Bachelor. The property is part of an exclusive community of 7 homes on a private lane, with protected marshlands ensuring ongoing scenic views. The property is unsurpassed when it comes to wildlife viewing, creating a harmonious balance between nature and tranquility. Bring your horses or alpacas, they will feel at home too. Inside this home, you will find no flaws! Inside, each room offers panoramic views, including the oversized primary suite with a Vermont Castings wood-burning fireplace, spacious sitting area & direct access to the backyard, river, & hot tub. The land is perfect for keeping animals, starting a garden, or embracing a small-scale homestead lifestyle. Let the photos do the talking as you discover this property.

55635 Gatehouse Lane, Bend

Listing courtesy of Cascade Hasson SIR.

$2,150,000
5 Beds 4 Baths 220217393 MLS
Experience elevated living in Black Butte Ranch with this beautifully updated golf course home. Perfectly positioned along the 14th fairway of Big Meadow Golf Course. This light-filled retreat features an open-concept design, vaulted ceilings, and high-end finishes throughout. The stylish kitchen flows seamlessly, ideal for entertaining. While the spacious primary suite offers a peaceful, spa like escape, enjoy serene golf course views from your private upper deck. (There Is A Place) BBR is one of Central Oregon's premier resort communities, with access to golf, dining, pools, and endless recreation. Offering the perfect blend of luxury and lifestyle, designed with gathering in mind, this home offers the perfect setting for entertaining family and friends. Whether it's holiday celebrations or summer nights under the stars, this home was made to bring people together.

13210 Hawks Beard GH 234/235 Unit GH 234/235, Black Butte Ranch

Listing courtesy of Stellar Realty Northwest.

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