10 Exclusive Oregon Estates Showcasing Luxury, Privacy, and Natural Beauty

Located in the exclusive Ranch at the Canyons, Painted Rock is a luxurious retreat surrounded by natural beauty and serenity, featuring 2.5 miles of private Crooked River frontage and close proximity to Smith Rock State Park and Redmond Airport.

Listing details: Designed for multi-family living, the home offers a gourmet kitchen, two luxurious primary suites, and various flexible spaces including guest rooms, game rooms and offices. A standout feature is the wall of windows that opens to stunning canyon and river views, embodying a perfect blend of privacy, grandeur, and the beauty of Oregon’s high desert.

MK Ranch is the definition of Tumalo tranquility with nearly 60 acres of privacy for the equine and ranch enthusiast. Expansive views from the Cascades to the Ochocos and the wonder of the regular wildlife this property is truly a gem of Central Oregon. Two legal parcels combine to create one expansive property. The main house at 3,700 SF on the ridge overlooks the valley, pastures & hay field. Nestled on the lower parcel is a second 1863 SF home, where the successful short and long-term rental history coupled with barn stall rentals, provides income potential.

Listing details: 14 stall barn with sprinklered indoor and outdoor arenas. 45 acres of irrigation keeps the pastures & hay field lush. 1,650 SF shop. The orchard and 20’ x 30’ greenhouse are perfect for the gardener. Rarely does a property like this come along, where the sunlight rises to greet you with incredible eastern views and shines from the Cascades to create a peaceful, country life dreams are made of.

Nestled in the gated Skyline Ridge Estates, this fully furnished 20-acre retreat offers breathtaking views, privacy, and space for horses and farm animals—just 30 minutes from downtown and 10 minutes from the Silicon Forest.

Listing details: Located in Lincoln High’s top-rated IB district, the home boasts radiant heated floors, soaring ceilings, and European-inspired finishes. A chef’s kitchen, wine cellar, gym, and multiple outdoor entertaining areas make this estate truly special. Plus, a 1,789 sq ft detached garage offers endless possibilities. Move-in ready—price includes all furnishings!

Luxury ranch with turnkey cattle/horse operations located in Crook County- the Cowboy Capital of Oregon. Built around the original homestead, this ranch offers 103 acres with 98 acres of gravity fed flood irrigation- no pumping fees! 

Listing details: Fenced and cross fenced for efficient cattle rotation and/or haying operation. Stock ponds in most pastures. Corral with equipment and load out chute. Easy winter feed set up with concrete bunks. Productive high quality hay fields. Cascade Mountain views from all points on the ranch! 2 homes plus ADU. 3700+ sq ft Owner’s home (see attached features list), 1100+ sq ft Ranch manager’s home, and well appointed studio. 13 stall horse barn with runs and arena. Two 3 car garages, large shop with 14′ doors and 1/2 bath. Two machine sheds… farm equipment available on separate agreement. This offering has so much more than can be listed here.

Located below the northern side of Tillamook Head, this home overlooks Seaside Cove to give unparalleled views of winter storms, migrating whales, and some of the best surfing on the West Coast.

Listing details: Watch the ever-changing movie that is the Pacific Ocean through the large picture windows as you enjoy life in the beautifully remodeled common rooms and spacious living areas. Get a front-row seat to the show from the primary suite’s private balcony or get closer to the waves with your private steps down to the beach. This home provides a picturesque setting for life at the beach – Don’t miss out on this stunning 4 -bed, 3.5 bath coastal haven.

SPRING 2025 is the scheduled completion. Caldera Springs LOT trades welcome. This stunning home could be your Basecamp in the Pacific Northwest. Caldera Springs | Sunriver offer a secluded Resort living with easy access to skiing, lakes, and trails. Experience the beauty of nature up close, with opportunities to spot the elk herd and deer, and other wildlife roaming freely. A meticulously crafted, high-end, mountainside retreat is designed collaboratively by the partners, Olsen Brothers and Horowitz family, with custom architectural features and thoughtful details. Perfect for year-round living, vacationing, or short- term rentals.

Listing details: Every residence boasts premium finishes, custom signature features, attention to detail and impressive ‘wow factors’ throughout. Complete Listing Packet available upon request including all finish selections, floorplan, cabinet drawings, and rental prospectus. Sample board finishes are available for viewing. Call today for your private showing.

This custom home, completed by Westlake Development Group in 2022, is situated on 3.34 private acres in the coveted Stafford Hamlet of West Linn. 

Listing details: This thoughtfully designed residence serves as a stunning woodland retreat, blending contemporary style with warm, inviting details throughout.

First time on the market! This custom-built gem, crafted with European artistry, blends luxury and warmth. Rich walnut cabinets, hardwood floors, soaring 10-ft ceilings, and custom woodwork create an inviting space.

Listing details: The gourmet kitchen features three ovens, dual fridge doors & drawers, a warming drawer, and a spacious pantry—perfect for chefs of all levels. Two main-floor suites enhance accessibility, while multiple rooms open to the expansive .87-acre yard. A gated driveway ensures privacy, with an eco-friendly well for irrigation. Minutes to trails, shopping, and PDX, this home is a sanctuary designed for generations.

Catch lightning in a bottle with this once-in-a-lifetime opportunity to own a Washington County icon. Scotch Church Road Vineyard is a compendium of stories told by surfaces & spaces, starting with a meticulously restored 1964 farmhouse built to feature bricks reclaimed from the old Portland Laundry tower. 

Listing details: Your main level is an entertainer’s dream, with a kitchen built for a foodie, a living room opening to expansive outdoor spaces and an elegant master suite. A loft & full bath complement 3 quiet bedrooms upstairs while the patio level has separate living quarters with exterior entrance to great room, kitchen, bedroom, full bath & laundry. The grounds surrounding the home make for exquisite open-air enjoyment, with deck above, patio below, hot tub, fire-pit & groomed planting areas. Consider the larger features of the 15+ acre property: EVENTS~ With an intimate gathering hall that doubles as a tasting room, 2 ceremonial arches & outdoor stage, SCRV is at the heart of some of the area’s legendary memories, from weddings to corporate functions to kick-out-the-jams annual gatherings. VINICULTURE~ A vineyard of 3 varietals spreads row by beautiful row across 7 acres, leased yearly to the wine-label of the same name, such that you might choose to cultivate your own grapes, continue the lease or even purchase separately the label. EQUESTRIAN~ A shop with 3-phase 220-volt power connects to a barn with 3 generous stalls & room for more.

One-of-a-kind property in Tumalo offers privacy and serenity. Incredible Cascade Mountain views. 58.55 acres currently used for working hunting dogs – endless opportunity to create your dream estate or simply enjoy as is. 39.21 ac irrigation through TID, much of it currently in in-stream lease.

Listing details: Comfortable one level 3,016 sq ft home offers central great room and updated kitchen with granite, stainless and custom cabinetry. Primary suite includes an office, view deck with hot tub hook-up, and spacious bathroom. Two additional ensuite bedrooms. Outbuilding and dog kennel both have plumbing & electrical. Additional sheds/storage. Level pastureland and garden areas. Ideally located between Bend and Sisters.