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$4,999,900
5 Beds 6 Baths 220226159 MLS
A once-in-a-generation opportunity to own one of Oregon's premier legacy estates. Encompassing approximately 1,167 contiguous acres, 15600 & 17341 SW Dupee Valley Rd offers an extraordinary combination of custom luxury living, productive timberland, open meadows, extensive road systems, & unmatched recreational opportunities. The centerpiece is a stunning new construction custom-built 5,355± SF residence, thoughtfully designed w/ quality craftsmanship, spacious living areas, & panoramic views. A second 3-bedroom, 2-bath home provides accommodations for guests, caretakers, or multigenerational living. Improvements include a large shop & addn'l outbuildings supporting ranch, timber, & recreational operations. Miles of established roads provide access throughout the property for timber mngment, ATV riding, horseback riding, hiking, hunting, & enjoying the natural beauty.A truly exceptional Oregon estate where luxury, investment, & outdoor living come together in one remarkable offering.

15600 SW Dupee Valley Road, Sheridan

Listing courtesy of RE/MAX Integrity Salem.

$4,995,000
5 Beds 5 Baths 220213779 MLS
Horseman's Dream of Central Oregon is a 35.21± acre estate w/ 18.6± acres of water rights that backs up to Bureau of Land Management(BLM) land in one of Oregon's most desirable rural areas, Tumalo. Boasting a 3,000± square foot, 5-bedroom, 5-bathroom (3 are suites) home with luxury finishes, a covered outdoor patio, & a 4-car garage. Additionally, it has a recently built (2021) 1,862± square foot hobby building w/ multiple rooms that could serve offices, two bathrooms, and a fully covered and screened outdoor kitchen. Both structures have been recently built or remodeled with impeccable care. This is the horseman's dream. The recently built (2021) indoor arena w/ 8 stalls w/runs, wash stall, tack room, a feed room, multiple hay storage areas, automatic watering system for the arena, and heated/automatic waterers. Add a trail course, Priefert hot walker, outdoor roping arena, custom pipe fencing, automatic waterers, round pen, & even a small feedlot for cattle. Come and see the dream.

66505 Gerking Market Road, Bend

Listing courtesy of Fay Ranches, Inc..

$4,995,000
5 Beds 5 Baths 220207668 MLS
Horseman's Dream of Central Oregon is a 35.21± acre estate w/ 18.6± acres of water rights that backs up to Bureau of Land Management(BLM) land in one of Oregon's most desirable rural areas, Tumalo. Boasting a 3,000± square foot, 5-bedroom, 5-bathroom (3 are suites) home with luxury finishes, a covered outdoor patio, & a 4-car garage. Additionally, it has a recently built (2021) 1,862± square foot hobby building w/ multiple rooms that could serve offices, two bathrooms, and a fully covered and screened outdoor kitchen. Both structures have been recently built or remodeled with impeccable care. This is the horseman's dream. The recently built (2021) indoor arena w/ 8 stalls w/runs, wash stall, tack room, a feed room, multiple hay storage areas, automatic watering system for the arena, and heated/automatic waterers. Add a trail course, Priefert hot walker, outdoor roping arena, custom pipe fencing, automatic waterers, round pen, & even a small feedlot for cattle. Come and see the dream.

66505 Gerking Market Road, Bend

Listing courtesy of Fay Ranches, Inc..

$4,987,000
5 Beds 5 Baths 220224796 MLS
Floating the Deschutes River? Consider launching from your own private waterfront compound with a true boat slip & two docs. Enjoy miles of boating or paddling from this legacy compound located just outside the resort area with no HOA & no CC&Rs. Yet you are an 11 minute bike ride to the resort village or the Sunriver Airport. This thoughtfully designed Frank Lloyd Wright inspired home offers timeless luxury and thoughtful design features, built for year round multi generational living or entertaining favorite guests. Close to the numerous restaurants, shops & golf & come home to one of the finest riverfront compounds in the Bend Oregon area. Resting on two separate tax lots totaling 1.53 acres with over 200' of river frontage, it includes over 2400 sq ft of garage space, has designs & foundation in place for a 2nd 2200 sq ft guest house, all wrapped in sublime landscaping behind a gated entry. Be sure to watch the 2 minute video & ask for the link to the dedicated web page

56680 Lunar Drive, Bend

Listing courtesy of Bend Premier Real Estate LLC.

$4,950,000
3 Beds 6 Baths 220222840 MLS
Featured on the cover of Build Magazine (May 2025) and as the Home Spotlight in Bend Magazine (Summer 2025), this 2024 estate is one of the newest custom homes in Ranch at the Canyons, offering luxury living with a modern organic aesthetic, smart home automation, designer lighting, and professional-grade appliances. Set on 6.5 private acres, walls of glass frame breathtaking views of Smith Rock, the Crooked River, and the Cascade Mountains. The home features a chef's kitchen, two private offices, a dedicated fitness room, guest casita, workshop, attached two-car garage, and a separate RV garage with 14-foot and 10-foot doors. The primary suite offers a steam shower and infrared sauna. A resort-style pool, multiple patios, and a courtyard fireplace complete the outdoor experience. Residents enjoy access to 1,700 acres of ranch land, trails, stocked ponds, equestrian facilities, pickleball and tennis courts, a clubhouse with fitness center and pool, and private Crooked River access.

11500 NE Canyons Ranch, Terrebonne

Listing courtesy of Cascade Hasson SIR.

$4,949,999
4 Beds 6 Baths 220198522 MLS
Perched above the Crooked River Canyon, this Ranch at the Canyons estate captures iconic views of Smith Rock, the River, and the Cascade Mountains. Stone + wood finishes add warmth, with hardwood floors, coffered ceilings, and custom built-ins. The heart of the home is a double-sided fireplace and chef's kitchen with Wolf/SubZero, 3 ovens, stone counters, oversized island, and banquette. The wet bar and seamless flow to the great room make entertaining effortless! The primary suite offers sweeping views and a spa-like bath, with a private junior suite and 2 additional ensuite bedrooms ideal for guests. Bonus room with wet bar and built-ins, plus an office with panoramic canyon and mountain views. Spacious mud/laundry room off the garage. Multiple outdoor seating areas invite you to relax and take in the surrounding landscape. Set on 12+ acres in a gated 1,700-acre community with 46 homesites, offering river access, equestrian facilities, clubhouse amenities, trails + more.

11540 NE Canyons Ranch Drive, Terrebonne

Listing courtesy of Avenir Realty.

$4,900,000
2 Beds 1 Baths 220225565 MLS
Whiteline Hay Farm is a turnkey forage operation featuring exceptional infrastructure and modern agricultural improvements designed for efficiency and productivity. The farm includes five center pivots supplied by two high-producing irrigation wells. Pivots are new (Zimmatic) or like-new (Valley Irrigation) with updated sprinkler packages, Bluetooth controls, fertilizer injection, and dedicated tanks. Three-phase power services all pivots and well pumps, which have been recently upgraded. Improvements include a large insulated shop (2019/2020) with finished office space and restrooms, a 2022 equipment shed, a 2020 service bay with concrete floors and enclosed parts storage, plus multiple hay storage buildings, including a fully fenced roadside loading facility. Well suited for timothy, orchard grass, alfalfa, and other forage crops, this is a rare opportunity to acquire a highly improved, move-in-ready farming operation.

10902 Swan Lake Road, Klamath Falls

Listing courtesy of Berkshire Hathaway HomeService.

$4,900,000
220208356 MLS
The Miller Ranch, sprawling over 3,400 acres of grass, juniper, pine and fir in the John Day River valley in Grant County Oregon. Located 7 miles east of Dayville @ MP 138 @ Mark Creek Road. Short drive of 4.0 miles along Marks Creek to the main gate. Marks Creek provides a water source for livestock and wildlife. This ranch has a long history of trophy elk & deer roaming the as the elevation climbs from 3,000' to nearly 5,400' in the timber. As you climb you are surrounded by federal land with no public access. For those who are looking for a blend of ranching, hunting or a legacy investment this is the one that checks all of the boxes. There are 6 tax lots of various sizes allowing you flexibility in ownership options. The ranch is zoned, MUR (Range) and PF (Primary Forest).The ranch has one ''small cabin'' (off grid solar powered) that works as a base camp not far from the entrance, with many other locations for a buyer to build a new home/cabin. Currently landowne

Marks Creek Road, Mount Vernon

Listing courtesy of Willow Canyon Group.

$4,500,000
4 Beds 2 Baths 220223731 MLS
This breathtaking 4,457.49-acre ranch is a rare opportunity for those seeking prime grazing land, abundant water, and incredible wildlife. Cow Creek runs year-round through the property, complemented by four ponds, lush meadows, and vast rangeland--ideal for cattle grazing. Wildlife enthusiasts and hunters will love the resident mule deer and elk, with the potential for four landowner preference tags. The custom-built 1,611 sq. ft. home (2004) offers 4 bedrooms, 2 full baths, and comfortable living with a rustic charm. The property is well-equipped with a 30x48 shop featuring four roll-up doors, plus a separate 24x48 shop with a walk-in cooler, full bath, and laundry facility. For a truly off-grid experience, a cozy 1-bedroom cabin with a loft runs on a generator and features a custom outhouse, antique cook stove, and wood stove, overlooking one of the scenic meadows. With 60 acres of irrigation water rights.

25405 SE Bear Creek Road, Prineville

Listing courtesy of Cascade Hasson SIR.

$4,500,000
220221221 MLS
Recently remodeled and improved, +-108,000 Sf. Industrial Complex on 7.49 General Industrial zoned acres located on the corner of Agate Rd. and Ave. G. The property is served by rail, multiple truck entry points, and a strong electrical system. The interior of the building is served by multiple roll up doors and has newly remodeled offices. The property is comprised of 3 tax lots and 3 separate buildings. Due Diligence materials on file including Environmental report, survey, etc. Notice: No warranty or representation, express or implied, is made as to the accuracy of the information contained herein; all information contained herein is subject to change, errors, and to your independent verification.

8380 Agate Road, White City

Listing courtesy of Merit Commercial RE, LLC.

$4,500,000
220211416 MLS
Formerly used as a full-service auto dealership and repair facility, the 21,301 SF building sits on 2.68 acres and features a tiled showroom, multiple offices, a fully insulated clear-span service garage with windowed roll-up doors, and a separate repair bay. The second-floor storage and attached garages add utility, while the rear ±0.68 acres remain undeveloped—ideal for future expansion or fleet parking. Located along and having direct access too Hwy 62 with over 35,000 vehicles per day, the property offers outstanding visibility. Adjacent to BMW, Volkswagen, Nissan, RAM, Jeep, Dodge, Chrysler, Fiat, and Honda dealerships, enhances its strong auto-centric synergy. Light Industrial zoning, abundant parking, and Opportunity Zone benefits make this a very rare high-exposure Medford offering ready for immediate use or redevelopment.

1492 Burl Crest Drive, Medford

Listing courtesy of RE/MAX Platinum.

$4,500,000
4 Beds 2 Baths 220197433 MLS
This breathtaking 4,457.49-acre ranch is a rare opportunity for those seeking prime grazing land, abundant water, and incredible wildlife. Cow Creek runs year-round through the property, complemented by four ponds, lush meadows, and vast rangeland—ideal for cattle grazing. Wildlife enthusiasts and hunters will love the resident mule deer and elk, with the potential for four landowner preference tags. The custom-built 1,611 sq. ft. home (2004) offers 4 bedrooms, 2 full baths, and comfortable living with a rustic charm. The property is well-equipped with a 30x48 shop featuring four roll-up doors, plus a separate 24x48 shop with a walk-in cooler, full bath, and laundry facility. For a truly off-grid experience, a cozy 1-bedroom cabin with a loft runs on a generator and features a custom outhouse, antique cook stove, and wood stove, overlooking one of the scenic meadows. With 60 acres of irrigation water rights.

25405 SE Bear Creek Road, Prineville

Listing courtesy of Cascade Hasson SIR.

$4,500,000
11 Beds 6 Baths 220173098 MLS
Exclusive 4 Home Opportunity to own a Rogue River Frontage Property with a Boat launch, an inground pool, and 4 homes all on 34.07 EFU acres. This property has it all! Air strip, helicopter pad, 2 Airplane hangars, completely fenced and cross fenced. The property has a shooting range, a lake with a waterfall, a second pond with a number of additional shops and garages. This property has the potential of being an income generating property or a multifamily setup. Do you need a caretaker's live in quarters, well that is another option for this amazing investment. The Sellers have added an outdoor entertainment area with high quality features well worth making the river front setting incredible. The property is on Modoc Road but the main home sits on the low bank river. The irrigation pumps keep the water flowing onto the property and if you choose will keep it plush green all year. This property is a must tour! All information is deemed accurate, Buyer to perform their own due diligence

12214 Modoc Road, White City

Listing courtesy of More Realty.

$4,400,000
3 Beds 1 Baths 220227396 MLS
The Rockpile Ranch is a rare opportunity to own your own hunting and cattle ranch with a river running through it. 6725 acres located on the Eastern edge of the Ochoco mountains between Izee and Dayville, Oregon, the ranch boasts incredible hunting and fishing opportunities, very nice improvements, timber, and privacy. The ranch is completely off-grid and is set up to be extremely easy and efficient. Powered by a new solar system, the ranch infrastructure and buildings come to life. The main home/cabin sits next to a partial remodeled historic cabin, built in 1892. Cabin is in solid condition and is charming and rustic. The Bunkhouse/Man Cave was just completed and boasts a wood stove, large picture windows, a fridge, and a a nice porch to relax. The ranch also has a shop/garage and a large historic horse barn. There is a good set of working corrals as well. Ranch qualifies for 4 LOP tags for Deer and 4 LOP tags for elk in the highly coveted Ochoco Unit.

45074 Wind Creek Lane, Dayville

Listing courtesy of Crater Lake Realty,Inc..

$4,390,000
220224874 MLS
Exclusively offered for sale - the Lakewood Shopping Center, a well-established, value-add neighborhood retail center on 4.07 acres on hard, signalized highway intersection in White City, OR (the ''Property''). The Property features two buildings totaling ±30,110 SF, including a ±28,154 SF multi-tenant retail building anchored by Dollar Tree with a strong mix of regional and national tenants, plus one available suite for lease-up potential. A separate freestanding ±1,956 SF restaurant building is leased to Umi Sushi with an existing drive-thru lane. An additional ±0.80-acre retail pad offers future development or expansion opportunities. Positioned on a signalized corner at the intersection of the region's two highest-traffic highways, the property benefits from exceptional visibility, three full-access driveways, & convenient customer access, all located within an OZ. Buyer to perform all due diligence. Significantly more info available upon request - see attached & contact brokers.

7338 Crater Lake, White City

Listing courtesy of Merit Commercial RE, LLC.

$4,350,000
220224300 MLS
7.8-acre commercial property with outstanding visibility from I-5 and easy access from the freeway off-ramp. County C-6 zoning allows for a wide range of uses, including business park, industrial, manufacturing, warehousing, and entertainment (buyer to verify with county planning). Nearly 22,000 sq. ft. of buildings include offices, high-clearance shops, storage, and a large free-span hangar-style building offering exceptional flexibility. Currently operated as a cargo container business, the owner-occupant can vacate for an end user. The property also includes a residence and much more room for future expansion. Located on the edge of town, this is a rare opportunity with excellent access, outstanding exposure, and an attractive price per square foot. Endless possibilities for your business or investment!

2660 NW Vine Street, Grants Pass

Listing courtesy of RE/MAX Integrity Grants Pass.

$4,250,000
5 Beds 7 Baths 220223644 MLS
Overlooking Tetherow's prestigious Kidd's Corner with views of 4 fairways and situated across from the 3-acre neighborhood park in the highly sought after gated neighborhood, Tartan Druim is where you will find this impressive 6,504sf, light-filled home with detached casita. Capturing vast views throughout with features that comprise of a primary suite, guest suite, office, great room, gourmet kitchen, 2 powder rooms and mud room on the main level with 3 additional bedrooms, 2 bathrooms and 2 bonus rooms upstairs, and a 3 car garage. Graced w/high end finishes including a wood burning stone fireplace as a focal point in the great-room, built in bookshelves, wood beams, new carpet, fresh exterior paint and stain, and tons of fun touches. Kitchen amenities include an oversized island, ample storage, Dacor gas range, double ovens, Sub Zero fridge and beverage fridge. Outside enjoy the built in BBQ, gas firepit with seating area and sunken hot tub while taking in the panoramic views.

19167 Cartwright Court, Bend

Listing courtesy of Cascade Hasson SIR.

$4,250,000
6 Beds 7 Baths 220215329 MLS
Perched atop the peak of Mt. Baldy, this masterpiece occupies the most prestigious lot in Southern Oregon. Unparalleled 180-degree panorama, capturing the Rogue Valley from Table Rock to Mt. Ashland. This high-tech fortress of comfort blends security and self-sufficiency with resort-level opulence. The ''future-proof'' infrastructure includes a gravity-fed solar well with 4,000g of storage, a 26kW propane backup generator, and a 1,000g in-ground tank. An elevator connects three levels of luxury, highlighted by a main-level bifold window wall for seamless indoor-outdoor living. A 2BR/2BA guest suite with a full kitchen, while the connoisseur's lower level boasts a wine cellar, root cellar, sauna, and space for a gym or theater. A 40x16 heated pool and automated cover. 140 acres of adjoining BLM land. With a natural plateau ready additional structures. Just 10 miles from the airport.

2451 Terri Drive, Medford

Listing courtesy of eXp Realty, LLC.

$4,200,000
4 Beds 6 Baths 220227071 MLS
Welcome to your ultimate entertainer's paradise in the coveted Westgate Community! This custom-built masterpiece sits on 2.5 acres and was featured in the 2025 COBA Tour of Homes, winning accolades for Best Kitchen, Best Landscaping, & Best Value. With its modern design framed by stunning Cascade Mountain views, this home is truly spectacular. At its heart lies a jaw-dropping gourmet kitchen, complete with top-of-the-line Thermador appliances, perfect for culinary adventures. The main level features a luxurious primary suite with a spa-like bathroom, plus 2 additional bedrooms, each boasting private en-suites. Ascend to the expansive loft designed for function and fun, including a full bath, bedroom, and wet bar-ideal. Step outside to your private oasis with a underground heated 8'x44' MOD pool with fenced yard. Storage is easy with a rare 2,491 sq ft shop with 14' doors. This one-of-a-kind home perfectly blends luxury and everyday practicality, making it the quintessential retreat.

62333 McClain Drive, Bend

Listing courtesy of Cascade Hasson SIR.

$4,200,000
3 Beds 2 Baths 220206520 MLS
Got Water? We do. Now for sale a little over 1062 of organic acres with an irrigation Well that produces about 2200 gallons per minute! This incredible property boasts 2 homes, first is a 2365 ft. log cabin address 18596 Highway 140 E, the second one is18598 Highway 140 E. Which is a 1905 ft. three bed two bath home with incredible views of the valley below. This property has five pivots with upgraded sprinklers with low pressure efficient energy heads and pressurizes bowls and a VFD Drive panel and AG sense Control via your smart phone. There is One wheel line with low pressure, self-leveling sprinklers and a hay barn that holds 650 tons of hay. This Wonderful property has a red cinder pit at the top of the property with over 1,000,000 yards of red cinder rock and don't forget about the 6 livestock ponds on the property that backs up to BLM. If you love mule deer hunting, this is the place for you, there are some giant bucks that come down off the hill and feed in the fields.

18598 Highway 140 E, Dairy

Listing courtesy of Fisher Nicholson Realty, LLC.

$4,150,000
5 Beds 7 Baths 220210064 MLS
From sunrise to dusk, Smith Rock's sculpted cliffs and the Crooked River create a breathtaking backdrop for this Ranch at the Canyons residence. Designed by Norman Building & Design, the home blends refined craftsmanship with a relaxed Central Oregon spirit. Expansive windows frame panoramic views, connecting every room to the landscape. The great room, chef's kitchen, wine room, and media areas flow seamlessly for gathering, while guest suites with elevator access offer privacy and comfort. Outdoor living shines with patios for dining, a fireplace, built-in BBQ, hot tub, and lap pool. Because Ranch at the Canyons operates as a working ranch, property taxes remain significantly lower than comparable luxury properties. Expert HOA management preserves the landscape, amenities, and long-term value of this extraordinary community, just minutes from Redmond Airport and Bend.

11750 NE Canyons Ranch Drive, Terrebonne

Listing courtesy of Cascade Hasson SIR.

$4,100,000
220186315 MLS
Explore an exceptional investment opportunity in desirable East Medford. Red Tail Heights is a 35+acre parcel of vacant land ready for development. Zoned SFR-4/SFR-2 for 70+ residences, this unique property promises significant potential for developers and investors alike, made easy with planning and permitting (annexation, zone change, temporary subdivision plat) already approved. The property is available to be sold in phases. City streets and public services are accessed at three locations. Initial civil engineering work for streets, sidewalks, sewer, and storm drains are completed, along with geotechnical engineering and a a traffic study. Sweeping vistas, including views of the airport, vineyards, mountains, and city lights—along with incredible sunrise and sunset-focused lots. Convenient to amenities in Medford, Ashland, and Historic Jacksonville, this is a prime opportunity to cultivate a vibrant community in a picturesque locale!

4195 Rachel Way, Medford

Listing courtesy of Windermere Van Vleet Jacksonville.

$4,000,000
220228266 MLS
Gilchrist Historical Waterfront Resort is a rare 14.9-acre waterfront property on Hwy 97 between Bend and Crater Lake, just 15 minutes from La Pine and about 45 minutes from Bend. The resort features 21 buildings, lake access, 2 pools, 3 hot tubs, multiple waterfront patios, accommodations for 50 guests, event space for 100, and parking for 50 vehicles. Buildings have been extensively remodeled and updated. The sale includes furnishings, event supplies, tables, chairs, linens, tableware, and grounds equipment--offering a turnkey opportunity. Owners have held the property since 2006, originally as a private family compound with 17 homes. Select homes were later offered as Airbnb rentals, followed by the launch of the resort business. A spectacular waterfront property with tremendous lodging and event potential!

137930 Whitechrist Drive, Gilchrist

Listing courtesy of Sky Lodge Investments LLC.

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