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$795,000
3 Beds 3 Baths 220224732 MLS
Nestled in the heart of Southern Oregon's premier wine country, and close to the historic town of Jacksonville, this property on 4.98 acres offers the perfect blend of rural charm and functional infrastructure. The property features a magnificent, classic wood barn set against a backdrop of mature landscape, sweeping valley and mountain views. The home boasts bright, inviting living spaces, a spacious upstairs primary suite, a light-filled sunroom, and a private entrance leading to 2 downstairs bedrooms, 1 full bathroom and studio. Enjoy unique access to the Applegate river, IRRIGATION WATER RIGHTS dated from 1876 and the natural beauty of the surroundings. Bring your horses or enjoy it as a peaceful country retreat. A true Applegate gem waiting for its next chapter.

7935 Upper Applegate Road, Jacksonville

$890,000
4 Beds 3 Baths 220223492 MLS
Situated in the lovely Stagecoach Hills neighborhood, this multi-level residence embodies limitless possibilities with its panoramic views of the mountains and valley. The property's interior shines with exquisite hardwood floors and a gourmet kitchen equipped with a high-end Wolf range, complemented by elegant tile and granite accents, alongside a spacious butler-style pantry. The primary suite, nestled on a private upper level, offers serene seclusion and features a stone fireplace, a sitting room area, and an updated bathroom with a large stone shower, heated tile floors, and dual sinks. The residence also features an in-ground pool / spa with expansive decking, perfect for creating unforgettable experiences. This multi- level design features French doors that leads to 3 additional bedrooms and guest bath

443 Conestoga Drive, Jacksonville

$569,000
3 Beds 2 Baths 220222554 MLS
Perched atop a private hill just outside of Jacksonville, this one-of-a-kind retreat offers breathtaking views stretching across mountains, valleys, and Southern Oregon skies. Situated on just over 40 acres, this 3-bed, 2-bath home was designed to embrace its incredible setting with expansive windows, multiple outdoor viewing areas, and a deck perfect for stargazing or soaking in unforgettable sunsets. The main living space is open and inviting, while the downstairs wood stove helps heat the entire home. The lower level includes a single-car garage and additional living space, creating a functional layout with room to spread out. Private, peaceful, and truly unforgettable--this is your chance to own a rare hilltop sanctuary just minutes from the charm of Jacksonville. Please no drive-bys.

1528 Morton Way, 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

$649,999
4 Beds 3 Baths 220222192 MLS
Tucked into the highly sought-after Little Applegate Valley, this exceptional Southern Oregon lifestyle estate offers a rare blend of privacy, natural beauty, recreation, and valuable water resources (Irrigation rights 1857 priority). There is an irrigated organic orchard and berries. This setting feels more like living in a private park than a traditional rural property, with mountain biking, hiking, and outdoor adventure accessible directly from Grouse Creek Road. Enjoy nearby fishing, boating, and paddling at Applegate Lake, while remaining just minutes from historic Jacksonville with its renowned dining, wineries, festivals, and vibrant community atmosphere. This is a 4 bedroom, 3 bathroom, open-concept home with soaring vaulted ceilings. With hardwood floors, tons of natural lighting, and a big kitchen, this home has everything you could need for your own private retreat. Sitting on 8+ acres of land, bordering BLM land, with incredible views, this property checks all the boxes

4046 Little Applegate Road, Jacksonville

$1,700,000
2 Beds 3 Baths 220220012 MLS
Butterfly Hill is a LEED Silver certified, self-sustainable eco-luxury masterpiece in a gated community outside Jacksonville. This three-wing home delivers abundant sweeping views, open-concept living space & stunning folding glass doors which open directly to outdoors blending nature with the eco-luxury lifestyle. The kitchen stuns with a large tasking island, custom cabinetry, walk-in pantry and sleek cooking zone. Primary suite demands awe with a bank of windows facing the mountains & spa inspired bath. Flexible secondary suite with Murphy bed is a perfect multi-use haven. 8-year-old Hügelkultur gardens, drought-tolerant native plantings, and a 15,000-gallon rainwater collection system supplies irrigation and dedicated fire suppression tank, solar power, KVA 20 generator and extensive fire hardening measures secure this home for years to come. Private hiking trails, wildlife, views and space without feeling endlessly remote.

400 Coyote Run, Jacksonville

$849,000
4 Beds 4 Baths 220219145 MLS
An Everyday Getaway! That is what it's like living on this Tuscany style homestead. 4 scenic acres, 3,511 sq.ft. multi-level home, full of warmth & artistic detail. Earthen plaster, frame built w/ straw-bale insulation, a Kachelofen masonry woodstove & eco-conscious features. The main level offers a primary bd that opens to a pleasant deck w/ view of surrounding mountains Living & dining areas, kitchen & laundry. Upstairs includes a bd w/ convenient 1/2 bth, while the bright daylight basement provides bonus rooms, sauna, bth & generous cold storage. The 2,066 sq.ft. ADU combines living, entertaining & creative space w/ an integrated shop & a garage w/ laundry. Permitted for vacation rental, this unique building adds fun & diversity of living choices. Land offers a beautiful mix of rolling & level terrain w/ mountain views & dotted w/ oaks. A wonderful home base w/ the fenced garden, animal areas, play structure, decorative pond & multiple outbuildings & outdoor living spaces.

8150 Upper Applegate 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

$629,808
3 Beds 2 Baths 220219807 MLS
Picturesque little valley backing up to BLM land & Sterling Dutch trail on 43.20 acres. Rich in history dated back to 1856 homestead in Sterling Creek nestled in Southern Oregon. Charming log style home, Knotte pine doors, vaulted rough cut beams and Knotte pine ceilings. Enter in to the great room/dining room through a lg cedar deck for entertaining and beautiful landscaping w/dbl doors, Vermont cast iron fireplace w/cooking plate. Open staircase to 3rd bdrm or great office. Vaulted wood ceilings in primary suite, 3 lg closets and bath. 2nd bdrm off back of home w/open kitchen, lg walk in pantry w/ hickory cabinets and glass fronts. Milgard dbl pane windows. French doors to a covered patio. Beautiful property w/fruit trees, grape arbor, fenced garden and Dog Park. 3 sheds, slate walkways and great well! Super charming property close to Jacksonville

7484 Sterling Creek Road, Jacksonville

$599,000
4 Beds 2 Baths 220219015 MLS
Nicely set back off the highway you will find this well constructed Bavarian style home, built by a master builder from Germany. Sits on just under 3 acres with spectacular views of the Siskiyou mountains. Located in the middle of the Applegate wine country near Ruch and a short 15 min drive to Historic Jacksonville. This 3404 sq. ft. , 4 bed plus office has all the space you would want for everyday living and entertaining. Main living is upstairs, offers a covered porch to enjoy the views year round. Large patio off lower level for outdoor entertaining. The two car garage is detached with upstairs living area. Paved driveway offers ample parking. The 2 wells offer plenty of water for landscape/gardening and household use. Well flow from 2017 on file, good flow production. Slightly sloping land is mostly open pasture with mature landscaping around the house, fenced and gated.

8330 Hwy 238, 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

$1,250,000
3 Beds 3 Baths 220217685 MLS
This exceptional 40.97-acre estate features a beautifully remodeled home w/modern luxury & contemporary design. Nestled in a private valley with 360-degree views, the custom estate offers turn-key elegance. The 2-story floor plan centers around a chef's kitchen w/professional-grade appliances, sleek finishes, & open-concept layout. The main level also includes a dining room, private office, & expansive windows that frame the panoramic views. The master suite offers a luxurious retreat, w/two additional guest bedrooms, guest bathroom, second living area, and balcony completing the upper level. The property includes ample room for open pasture, with approximately 10 acres ready now & ideal for horses or livestock. The mature landscaping, sprawling lawns, & multiple patios offer a peaceful, private setting perfect for enjoying the beauty of the Applegate Valley. This well balanced property and turn-key estate is ready for its next owners to call it home.

7499 Highway 238, Jacksonville

$3,995,000
4 Beds 6 Baths 220203312 MLS
A true masterpiece in Southern Oregon, 1st time, extraordinary Mediterranean estate captures sweeping views of the Jacksonville Mountains & glittering city lights. Set on 5 private park-like acres w/city water, ±5700 SQ FT of luxury on main level, ±3484 SQFT private lower level; ideal for entertaining, additional living/guest quarters & lg detached private guest Casita--designed & built by Mike Pagnini--showcases unmatched craftsmanship and timeless elegance. Highlights include 4 luxurious primary suites, 6 baths, a Pebble Tec pool & spa, guest casita, & a 12-car garage. Inside, grand living spaces feature soaring dome ceilings, 8 fireplaces, and French doors opening to stunning outdoor living areas. Chef's kitchen, wine cellar, theater, & fitness rooms complete the experience. Ideally located near Rogue Valley International-Medford Airport w/Million Air Medford for private jet access, & minutes from the Britt Music & Arts Festival, Oregon Shakespeare Festival, & renowned wineries.

321 Pair A Dice Ranch Road, 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: