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$1,499,000
4 Beds 4 Baths 220225118 MLS
Experience one of Southern Oregon's finest riverfront estates in the heart of the renowned Applegate Valley wine region. Located less than 15 minutes from historic Jacksonville, you'll enjoy easy access to acclaimed restaurants, wineries, galleries, and small-town charm. Set on 14.62 acres zoned EFU with over 700 feet of coveted Applegate River frontage, where gentle flows and the sounds of shimmering riffles create an unforgettable setting. Fish from your own shoreline, watch abundant wildlife, or simply relax by the river. The 4,899 sq ft custom home showcases soaring ceilings, dramatic natural wood beams, a sweeping oak spiral staircase, expansive windows framing breathtaking river views, geothermal heating, and spacious decks. Private guest wing, iconic Big Red Barn with horse stalls and runs, orchard, fenced pastures, greenhouse, 10.6 irrigated acres with golf course style irrigation system, and 1857 senior water rights complete this remarkable legacy estate.

2076 Upper Applegate Road, Jacksonville

$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

$575,000
3 Beds 3 Baths 220220067 MLS
Located in the scenic Applegate Valley, this 5 acre, fully irrigated rural property offers privacy, usability, and a true Southern Oregon lifestyle. The 2,726 sq ft home features 3 bedrooms and 3 full baths with a flexible split level floor plan. Light-filled living spaces create a warm and inviting atmosphere, with a heat pump for year round comfort plus wood heat in both living rooms. The new back deck is ideal for relaxing, entertaining, and taking in the surrounding mountain and territorial views. Multiple additional rooms offer space for storage, an office, hobbies, guests, or flexible use. The fully fenced property includes established pasture, irrigation rights for all 5 acres, a garden area, gated entry, dog run, RV parking, and outbuildings for added functionality. With usable acreage, room for animals and equipment, and a peaceful rural setting, this property offers the versatility, comfort, and lifestyle buyers seek in the Applegate Valley.

7680 Upper Applegate, Jacksonville

$390,000
2 Beds 2 Baths 220218405 MLS
Discover your own private sanctuary in the heart of the Applegate Valley. This beautifully maintained 2-bedroom, pus a bonus room, 2-bath home sits on a ''manicured mini oak forest'' featuring native landscaping and a park-like feel. Inside, you'll find 1,241 sq. ft. of thoughtfully remodeled living space, including a spacious, permitted 30'x10' living room addition and a versatile bonus room. The heavy lifting has already been done: enjoy a brand-new roof (with transferable warranty), a newer water conditioning system with UV filtration, and fresh front and back decks perfect for morning coffee. A standout feature is the 320 sq. ft. detached studio--beautifully updated and equipped with water and electricity--ready to become your dream art space, home office, or guest suite. Located on a quiet road just minutes from Jacksonville, this is the perfect blend of country quiet and city convenience. Back on the market at no fault of property.

84 Haven Road, Jacksonville

$649,900
3 Beds 2 Baths 220216435 MLS
From the welcoming front porch where countless memories have been made with family and friends to the light-filled interior, this home invites you to settle in and stay awhile. Make traditions of gathering, entertaining, and creating lasting moments. This elegant Craftsman home in Nunan Square offers 3 bedrooms and 2 bathrooms, with a desirable main-level primary suite. An open, airy floor plan is filled with natural light and designed for effortless entertaining. The kitchen has been tastefully updated with granite countertops, stainless steel appliances, and deluxe custom lighting conveniently controlled right from your smartphone, if you choose. Impeccably maintained, with annual hvac services, a newer roof and exterior paint. Ideally located near the park and the heart of downtown Jacksonville, you'll enjoy easy access to restaurants, shopping, and the grocery store. A home that blends comfort, style, and location--this one is a must-see.

110 Taylor Street, Jacksonville

$1,525,000
4 Beds 4 Baths 220211366 MLS
Just 2 miles from Jacksonville, this stunning hilltop estate blends elegance, privacy, and craftsmanship on 20 forested acres. This home showcases panoramic views from nearly every room. The soaring 28-ft ceilings and wall of windows create a dramatic entry. Chef's kitchen features granite counters, custom maple cabinetry, walk-in pantry, and is open to both a formal dining area and expansive great room. Main level includes two spacious guest bedrooms with private decks, office, family room, mudroom, and multiple baths. Upstairs, the primary suite boasts, private balcony, bonus area, walk-through closet, fireplace, and spa-like bath with jetted tub overlooking city lights. Additionally, is a 970 sq ft finished basement with bonus rooms. And a 3-car garage, carport, circular driveway. Enjoy outdoor living with a wraparound deck, hot tub, pool, patio, and water feature.

1661 OR-238 Highway, Jacksonville

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: