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$777,000
2 Beds 2 Baths 220222465 MLS
Custom round home designed and built by architect Clair Killen, positioned to capture panoramic views of Dutchman Peak and Little Grayback Mountain. The lower-level solarium provides exceptional space for year-round gardening and plant cultivation. Backing to BLM land, the property offers privacy, direct access to miles of public land, and a network of neighborhood trails, including a trail from the property that connects to the Sterling Mine Trail system. A gardener's paradise with two wells, extensive water storage, and two greenhouses with underground power. Multiple outbuildings and an ADU provide flexibility for guests, multigenerational living, rental income, hobbies, or workspace. Whether you're a gardener, homesteader, artist, or outdoor enthusiast, this property offers the space and infrastructure to bring your vision to life.

9595 Sterling Creek Road, Jacksonville

$1,995,000
7 Beds 5 Baths 220218653 MLS
Don't miss this once-in-a-generation opportunity to own Applegate River Retreat, a true Southern Oregon legacy estate. This extraordinary riverfront sanctuary spans nearly 20 private acres with 420' of Applegate River frontage in the heart of the Applegate Valley wine country. Thoughtfully transformed, the property features 3 beautifully finished homes accommodating 21+ guests, 2 RV sites, an authentic Finnish sauna, game room, fitness/yoga studio, reclaimed pastures, forest trails, private swimming holes, and multiple river access points. Perfect for creating lifelong memories with family and friends, hosting unforgettable gatherings, or simply escaping to nature's beauty. Steps from Red Lily Vineyards and Devitt Winery, and just minutes from historic Jacksonville and the renowned Britt Music & Arts Festival. Swim, fish, kayak, hike, relax beneath towering trees, and experience one of Southern Oregon's most remarkable private retreats. Start your legacy today. Truly one of a kind!!!!

11677 Highway 238, Applegate

$399,000
2 Beds 2 Baths 220211931 MLS
Full of cherished memories & ready for new beginnings. Well loved 2bd, 2bth cedar-sided home offers character & opportunity. Central living area featuring open beam ceiling & dramatic floor-to-ceiling windows & open to kitchen creates an inviting gathering space. 2 distinct wings add personality & flexibility, with a wet bar & open balcony, the other offering a private main-level bedroom, cozy den & unique upstairs bd w/ ''peek-a-boo'' loft. Front & side decks, plus covered rear patio for outdoor enjoyment. Large carport w/ attached shop provides excellent workspace & storage w/ additional storage found throughout the property. Detached ADU includes bth, kitchenette, loft sleeping & its own covered porch. Set a comfortable distance from the main home for added privacy. Fenced areas for small animals, ample parking & direct BLM land access enhance the property's appeal. A wonderful opportunity for someone ready to bring fresh vision & renewed life to a home filled w/ charm & potential.

812 Left Fork Humbug Creek Road, Applegate

$430,000
2 Beds 1 Baths 220204243 MLS
Private & Charming Mini-Farm on Humbug Creek in the Applegate Valley. Cross a creek through the forest up to your own private little hobby farm homestead on 11.2 acres backed by 4,900 acres BLM. Unique, cozy custom built cedar sided home with dramatic architectural angles, custom details & rustic charm. Central wood stove, vaulted ceilings, stone & bamboo flooring throughout. Detached laundry room with additional storage & covered firewood area. Turn-key fenced & terraced garden area sports 3 automated greenhouses (one solar), mature fruit trees, blueberries, animal corrals & a chicken coop. Spacious workshop w/ vaulted ceiling is set up for wood stove, a previously certified kitchen & view into the attached hothouse. Hike up the hill to gorgeous views. A dreamy must see!

2231 Humbug Creek Road, Applegate

$1,950,000
3 Beds 4 Baths 220201540 MLS
Experience the perfect blend of luxury, privacy, and natural beauty with over 500 feet of pristine Applegate River frontage in the heart of Southern Oregon's renowned Applegate Valley Wine Region. Behind a gated entrance, this exceptional estate showcases a custom-built 4,510 SF residence thoughtfully designed to capture the tranquility of its remarkable setting. The park-like grounds feature mature landscaping, a hobby vineyard, and picturesque river views that create a true retreat. Inside, an inviting open-concept floor plan combines elegance and comfort, highlighted by abundant natural light, beautiful Italian tile flooring, and expansive windows that bring the outdoors in. The gourmet kitchen is designed for both everyday living and effortless entertaining. Guests and extended family will appreciate the separate 1,188 SF guest accommodations, providing flexibility and privacy. A rare offering where refined living meets the unmatched beauty of the Applegate River.

13587 OR-238, Applegate

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: