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5920 Highway 238, Jacksonville
$495,000
3 Beds ⋅ 2 Baths ⋅ 220230221 MLS
Located just outside Historic Jacksonville, this 3 bedroom (plus office), 2 bath home with 1682 sq. feet is situated on 1.98 acres. Offerings include a wonderful newly painted front deck, living room with laminate flooring and skylight, kitchen w/beautiful cabinetry, newer stainless appliances (all included), dining area that adjoins the kitchen with slider that leads out to the oversized newly painted deck, perfect for entertaining! Primary bedroom has laminate flooring and ensuite bath with single sink vanity and shower. Hall bath with tub/shower combination and linen closet. Off the kitchen, you'll find a large laundry/flex room and an office that has access to the back deck. Other features include vinyl windows, newer water heater, duct work, air register, attached 750 sq. ft. garage, RV carport, fenced areas for a garden or animals. NOTE: the sellers have an assumable VA loan at 5% that they are willing to entertain offers from eligible VA buyers...Welcome Home!

5920 Highway 238, Jacksonville

Listing courtesy of Windermere Van Vleet & Assoc..

3751 Oregon 238, Jacksonville
$495,000
4 Beds ⋅ 3 Baths ⋅ 220230144 MLS
Jacksonville country home ready for a new chapter. 8+ acres, minutes to Jacksonville. Four good sized bedrooms and three full baths. There's plenty of room to enjoy country living so close to town. Lots of natural light and a wood stove add to the ambiance. Perfect for a private retreat or a new country homestead.

3751 Oregon 238, Jacksonville

Listing courtesy of KB Properties LLC.

995 Upper Applegate Road, Jacksonville
$669,000
3 Beds ⋅ 2 Baths ⋅ 220229810 MLS
Beautifully renovated dream home in the heart of wine country! Just a 10 minute drive from the Town of Jacksonville. More than 5 wooded acres surround this home. The exterior paint has been recently touched up and looks great! Enter into the open concept living area featuring timber framed vaulted tongue and grooved ceilings which are painted white. The kitchen has beautiful dove grey cabinetry, gorgeous leathered granite counter tops, tile backsplash, farmhouse sink and all stainless appliances. The roomy Primary suite is a lovely retreat with vaulted ceiling, french door access to the patio and hot tub, radiant floor heat, walk in shower and double sinks in the bathroom, and ample closet space. A spacious laundry/mud room has ample storage and counter space plus sink. The shop has been converted to an extra 750 sq ft (per owner) of living space including a full bath and bedroom, for guest quarters or entertainment space. There is even a back up Generac generator. This is a must see!

995 Upper Applegate Road, Jacksonville

Listing courtesy of Windermere Van Vleet Eagle Point.

11851 Upper Applegate Road, Jacksonville
$399,000
2 Beds ⋅ 2 Baths ⋅ 220229327 MLS
Enjoy peace, privacy, and beautiful Applegate Valley views from this special retreat on 3.31 acres. This 2 bedroom, 2 bath home offers brand new siding all the way around, a new shop, new double pane vinyl windows, new floors, a new bathroom with walk in shower and tub, and a charming custom rock chimney and wood stove for cozy evenings. All of the wood siding and most of the interior was replaced with wood milled from local timber right here in the Applegate Valley, adding unique craftsmanship and character. A large back deck looks over the river and onto the Applegate Valley. The home includes a separate office space in addition to the two bedrooms for extra versatility. The property offers a detached garage plus the new workshop/garage for vehicles, equipment, projects or hobbies. The home is super efficient and is eligible for USDA financing for qualified buyers. The craftsmanship of the home and peaceful, rural setting make it a must-see.

11851 Upper Applegate Road, Jacksonville

Listing courtesy of eXp Realty, LLC.

3919 Little Applegate Road, Jacksonville
$324,000
3 Beds ⋅ 1 Baths ⋅ 220229203 MLS
Escape to the peaceful Applegate Valley and discover the possibilities Set on approximately .71 acre, this charming 3bedroom, 1-bath cottage offers a wonderful opportunity to enjoy country living surrounded by mature trees and open space. The property features approximately 1,100 sq ft of living space small pasture area and plenty of room to bring your vision to life. Enjoy the slower pace of rural living with the beauty of the Little Applegate area right outside your door, while still being within reach of Jacksonville and Rogue Valley amenities. Whether you're searching for a primary residence, country retreat or a property to personalize and make your own, this one offers character, setting and potential. Come experience the peaceful Applegate lifestyle and imagine what you could create here!

3919 Little Applegate Road, Jacksonville

Listing courtesy of RE/MAX Platinum.

71 Yale Creek Road, Jacksonville
$975,000
4 Beds ⋅ 7 Baths ⋅ 220229003 MLS
River, Pastures, Barn, Trails & an Exceptional Home! 4,156 sq. ft. modern farmhouse w/ ADU overlooks mountains & neighboring farmland, offering a blend of comfort & functionality. The main level features a spacious primary suite, dedicated office, guest bath, formal dining room & a view-filled kitchen w/ breakfast nook that opens to a welcoming living area w/ fireplace. Upstairs are two ensuite bedrooms & a central loft-style gathering space. A large laundry/mudroom connects to an outstanding ADU w/ separate entrance, full kitchen capability, pellet stove, spacious bedroom & bath. The 3-bay garage provides abundant room for vehicles, equipment & toys. 47+ acres w/ multiple water rights, river frontage & easy potential to restore picnic areas & walking paths enhance the setting. Ideal for equestrian use w/ fenced pastures, a quality barn w/ stalls & paddock, round pen, equipment shelter & convenient access to miles of established BLM trails. Thoughtful infrastructure throughout.

71 Yale Creek Road, Jacksonville

Listing courtesy of Ramsay Realty.

640 Carriage Lane, Jacksonville
$790,000
4 Beds ⋅ 3 Baths ⋅ 220228879 MLS
Charming Victorian-style home in quiet, desirable neighborhood in Historic Jacksonville. Beautifully landscaped .19 acre, 4 bdrm, 2.5 bath, 2,259 sf home. Enjoy cooking in the large kitchen w/ island, granite counters, stainless steel Bosch appliances, soft-close cabinetry w/ lots of natural light. Kitchen is open to the family room w/ gas fireplace and sliding glass doors leading to the private, landscaped backyard w/ built-in firepit, gazebo, greenhouse and garden. Great room also has a gas fireplace and opens to a separate dining room area. Relax on the covered front porch and enjoy the manicured yard and mountain views. Awake to views from the primary bdrm w/ walk-in closet, lg vanity w/ dbl sinks, step-in shower, and enclosed toilet. Extra wide garage suitable for a sm. workshop & storage areas. Neighborhood is near walking trails, close to downtown and vineyards.

640 Carriage Lane, Jacksonville

Listing courtesy of John L Scott Ashland.

560 S Oregon Street, Jacksonville
$595,000
3 Beds ⋅ 2 Baths ⋅ 220228605 MLS
Built in 1910, this historic home of secondary significance perfectly blends timeless charm with modernized comfort, located just a short walk from vibrant downtown Jacksonville's local shops, parks, fine dining, award-winning wineries, and the renowned Britt Music & Arts Festival. Inside, the home offers 3 bedrooms, including 2 en-suite bedrooms, and 2 beautifully remodeled full bathrooms. The updated, functional kitchen flows seamlessly into the dining area, where a sliding glass door opens to a private backyard oasis with persimmon, peach, pear, apple, fig, pomegranate, table grapes and olive trees. This remarkable property has an expansive pottery shed--formerly the studio of a celebrated local artist--and a generous attic space offering endless potential for a home office, studio, or hobby room. Come experience life in Southern Oregon at its best!

560 S Oregon Street, Jacksonville

Listing courtesy of Windermere Van Vleet Jacksonville.

931 Hogan Road, Jacksonville
$1,299,000
4 Beds ⋅ 3 Baths ⋅ 220228041 MLS
Private Applegate Valley farmstead on 14.13 EFU acres with two homes, water rights and a new barn. The light-filled 2,382 sq. ft. main residence features a chef's kitchen with breakfast nook, formal dining room, living room with stone fireplace, 9-foot ceilings and a covered porch overlooking English gardens, pond and pastures. The spacious primary suite includes a walk-in closet and double shower with garden views. A separate 1,188 sq. ft. cottage offers an upstairs bedroom, covered porch and private patio--ideal for guests, multigenerational living, a studio or home office. Property features include a new 36x48 barn/shop with concrete slab, Hardie Board siding and metal roof; two historic barns; fenced pasture; two wells; two water-right certificates; Generac generator; and Starlink internet. Sweeping Applegate Valley and BLM mountain views near wineries, river recreation and trails. About 20 minutes to Jacksonville or Grants Pass and 45 minutes to the Medford airport.

931 Hogan Road, Jacksonville

Listing courtesy of Realty Net of Central Oregon.

105 W Pine Street, Jacksonville
$799,000
3 Beds ⋅ 3 Baths ⋅ 220227734 MLS
A rare offering in the heart of historic Jacksonville, this elegant, beautifully updated home blends timeless character with sophisticated modern living. Light and bright throughout, the home features hardwood and tile floors, beautifully remodeled baths, and a stunning kitchen framed by a bank of windows. The entire upper level is devoted to an open-concept primary suite with dramatic A-frame ceilings, marble countertops, a walk-through closet and abundant storage. A private ADU offers a bedroom and bath, ideal for guests or flexible living. Outdoors, an in-ground pool and expansive deck create an inviting setting for entertaining, relaxing and enjoying Southern Oregon summers. An art studio, pool-equipment storage and EV charging station add function and convenience. Set in Jacksonville's historic core, just moments from Britt Festival, charming shops, celebrated restaurants and nearby trails, this exceptional property is refined, welcoming and truly one of a kind and unforgettable.

105 W Pine Street, Jacksonville

Listing courtesy of Windermere Van Vleet & Associates.

420 S Oregon Street, Jacksonville
$725,000
3 Beds ⋅ 3 Baths ⋅ 220226553 MLS
Location, Location, Location! Opportunities like this are rare. Just two blocks from Historic Downtown Jacksonville, you'll enjoy coffee shops, restaurants, boutique shopping, the renowned Britt Music & Arts Festival, nearby Woodlands trails, and Southern Oregon wineries. Beautifully maintained inside and out, this home reflects true pride of ownership. The spacious floor plan offers 3 bedrooms plus a large bonus room, 2.5 bathrooms, a spacious living and dining room, a separate family room, and a beautifully updated cook's kitchen featuring quartz countertops and new appliances including a premium ILVE Italian range. A flexible additional dining space, currently designed as a pub, offers endless possibilities. Central heating and air, plus gas and wood-burning fireplaces, provide year-round comfort. Outside, relax on the inviting covered front porch or enjoy the park-like yard with a pergola, patio, garden area, and gated access to the attached 2 car garage with EV charger

420 S Oregon Street, Jacksonville

Listing courtesy of Murphy Real Estate Group LLC.

300 Dunlap Road, Jacksonville
$725,000
3 Beds ⋅ 3 Baths ⋅ 220226774 MLS
Nestled on 28 beautiful acres in the heart of the Applegate Valley, 300 Dunlap Road in Jacksonville, OR, offers a one-of-a-kind retreat with unmatched privacy and natural beauty. This custom-built redwood craftsman cabin spans 2,408 square feet over three stories, featuring 3 bedrooms, 2.5 bathrooms, and a warm, colorful wood interior that enhances its rustic charm. Built in 1988, the home boasts a cozy fireplace and woodstove, perfect for chilly evenings. The expansive property provides serene wooded views and direct access to Cantrall Buckley Park, offering plenty of opportunities for outdoor adventures right at your doorstep. In addition to its scenic beauty, the property also features RV parking with full hookups, making it ideal for guests or an RV getaway. With easy access to local trails, vineyards, and the historic town of Jacksonville, this rare property offers the perfect blend of seclusion and convenience. Don't miss the chance to make this extraordinary paradise your own.

300 Dunlap Road, Jacksonville

Listing courtesy of John L Scott Real Estate Grants Pass.

5361 Highway 238, Jacksonville
$899,900
4 Beds ⋅ 3 Baths ⋅ 220226224 MLS
Handcrafted Log Home with pool, bordering thousands of acres of Public Land with Development Potential. The logs for this exceptional home were harvested, hand-cut, and polished right on the very property where the home proudly stands today. Designed by an architect - no load-bearing walls! - and built by skilled local craftsmen with extraordinary attention to detail-from the antique doorknobs to the handcrafted cabinetry and staircases -this is truly a one-of-a-kind residence. Every beam and stair tread is made from solid wood, reflecting the quality and craftsmanship found throughout the home. In-floor heat, heat pump, AC, Immaculate cared for inground pool, with concrete surround, paved driveway and parking lot, 2 covered sheds with concrete floors. Up to 47 additional acres available: 4 additional permitted lots - see plat map, two homes are allowed on each lot.

5361 Highway 238, Jacksonville

Listing courtesy of Sky Lodge Investments LLC.

4218 Thompson Creek Road, Jacksonville
$445,000
2 Beds ⋅ 1 Baths ⋅ 220225722 MLS
Home in the Heart of the Applegate River Valley; situated just minutes away from the Applegate River Bridge, local lavender farms, award-winning restaurants, venues and wineries. This custom built 2020 two-story retreat features newer appliances, spacious layout, peacefull setting and amazing views. Property offers a large level area for easy parking of equipment, RVs, extra vehicles, or a potential new homesite. *Additional 600+ sq. ft. of garage/shop space (not included in listing sq footage). Grow year round with the brand new extra large greenhouse on the property. *Bonus, the property is equipped with both an RV and a generator outlet. Whether you're looking for a country home, downsizing, or an investment property, this custom home on land combines character, functionality, and easy access to Southern Oregon's finest outdoor experiences.

4218 Thompson Creek Road, Jacksonville

Listing courtesy of Kelly Right Real Estate.

120 Ponderosa Way, Jacksonville
$1,045,000
4 Beds ⋅ 3 Baths ⋅ 220225663 MLS
Resort-style living awaits in this extensively remodeled custom home on a private 1.74-acre setting just minutes from historic downtown Jacksonville. Filled w/ natural light, the open great room design features soaring ceilings & a stunning chef's kitchen w/ premium appliances, custom cabinetry, & quality finishes. The thoughtfully designed floor plan offers 3 bedrms, an office/bedrm, loft, & spacious laundry rm. Over the past few years, nearly every aspect of the home has been upgraded, including the kitchen, bathrms, flooring, lighting, HVAC systems, on demand hot water heater, electrical panel, wired for whole-house generator, Trex decking, & more. Outside, your private retreat features a completely renovated in-ground pool w/ waterfall, new concrete decking, energy-efficient equipment, solar heating, hot tub, & beautifully landscaped grounds; creating an exceptional indoor-outdoor lifestyle just moments from Jacksonville's dining, shopping, & Woodland Trails. SELLER FINANCING AVAIL

120 Ponderosa Way, Jacksonville

Listing courtesy of Windermere Van Vleet Jacksonville.

2076 Upper Applegate Road, Jacksonville
$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

Listing courtesy of Windermere Van Vleet & Assoc2.

2459 Little Applegate Road, Jacksonville
$1,229,000
3 Beds ⋅ 2 Baths ⋅ 220225637 MLS
Privacy & tranquility on a little piece of paradise. Imagine living in a beautiful custom-built single-story Pacific Northwest lodge style home w/ Little Applegate River frontage, away from noise & neighbors, yet under 20 minutes to Jacksonville. From the vaulted wood-beam ceilings, to the spacious primary suite w/ stunning views & natural light, this home has been designed for relaxation. Two natural stone fireplaces anchor the living & dining areas, & the huge chef's kitchen features granite countertops, an island, peninsula, pantry, & beverage bar. Throw a summer soiree under a canopy of oaks that shade the lighted composite deck or relax down at the river on your own riverside deck. A 4-car attached garage, shop, wine cellar & historic barn provide exceptional space for hobbies. The property features 1872 irrigation rights & fire safety features are thoughtfully included in the home design. Direct access to BLM lands bordering this private 14.53-acre paradise.

2459 Little Applegate Road, Jacksonville

Listing courtesy of Windermere Van Vleet Jacksonville.

700 N 5th, Jacksonville
$475,000
2 Beds ⋅ 1 Baths ⋅ 220225555 MLS
Built in 1912, this classic Jacksonville home reflects the character and craftsmanship of an earlier era. This 2 bedroom, 1 bath property is suited for residential, commercial, or live/work use (buyer to verify permitted uses). Positioned on Jacksonville's main thoroughfare, generous ceiling heights and abundant natural light complement a welcoming front porch, fully fenced backyard, two detached outbuildings, and the original hand dug well, a reminder of the property's long history. Equally suited as a private residence, boutique business, or short-term vacation rental, this is one of those properties that invites imagination from the moment you arrive.

700 N 5th, Jacksonville

Listing courtesy of John L. Scott Medford.

340 Miner Way, Jacksonville
$650,000
4 Beds ⋅ 2 Baths ⋅ 220225334 MLS
Discover this spacious 4-bed, 2-bath home (2,328 sq ft) on a large 8,712 sq ft lot, just a short walk to historic downtown Jacksonville and the Britt Festival. Enjoy mountain views from the expansive deck, an open floor plan, daylight basement, and a main-level master suite. Sit and watch the deer on your large, covered entry patio, overlooking the front yard. The back deck wraps around the house, offering multiple areas to enjoy the views and overlook the backyard. The sloped, fenced backyard offers is ready for your touches. A below ground workshop, daylight basement with studio and laundry room adds separate space for your hobbies. No HOA. Experience comfort, convenience, and the best of Jacksonville living.

340 Miner Way, Jacksonville

Listing courtesy of John L. Scott Medford.

7935 Upper Applegate Road, Jacksonville
$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

Listing courtesy of Windermere Van Vleet Jacksonville.

831 Juanita Way, Jacksonville
$1,145,000
4 Beds ⋅ 3 Baths ⋅ 220224700 MLS
Exceptional custom home offering flexible two-family living on 5.01 acres in desirable Jacksonville. This one-of-a-kind residence showcases European-inspired design, soaring vaulted ceilings with exposed beams, stunning custom rock walls, beautiful wood/tile flooring, and walls of windows framing breathtaking views of Mt. McLoughlin. The main level features a gourmet kitchen with a Wolf gas range, center island, spacious great room with wood-burning fireplace insert, office, laundry room, two oversized bedrooms, and a luxurious primary suite with a private deck, soaking tub, walk-in tile shower, and walk-in closet. A partially covered deck spans the length of the home, creating the perfect space for entertaining & views. new metal roof. The finished two-car garage, new garage door. The 2nd level offers a private entrance & parking, two bedrooms, a kitchen,, living room, office, laundry, full bath, and covered patio.

831 Juanita Way, Jacksonville

Listing courtesy of Expert Properties Inc..

465 Strawberry Hill Lane, Jacksonville
$799,000
3 Beds ⋅ 2 Baths ⋅ 220224388 MLS
High on a hill near Jacksonville is the 21.49 acre property with a custom built home of 2626 sq ft. Featuring 3 bedrooms and 2.5 baths with an open concept and soaring tongue and grove wood ceilings in great room and Primary suite and massive windows to take in the incredible panoramic view. This primary has an ensuite bath room with double vanity and walk in shower and walk in closet. There are two additional bedrooms that share a bath. The Trex decking runs the length of the great room and the primary with access from both and super for entertaining. There is also access to the 1/2 bath from the deck. The seller is motivated and this property needs some TLC. Attached in documents is an estimate for roof repair needed, not including the dry wall repair needed on the inside. Some of the photos have been virtually staged . All information is deemed accurate and the buyer should do own due diligence as to the uses and condition of this property.

465 Strawberry Hill Lane, Jacksonville

Listing courtesy of Windermere Van Vleet Jacksonville.

5900 Upper Applegate Road, Jacksonville
$749,000
3 Beds ⋅ 3 Baths ⋅ 220224295 MLS
Private two story custom built home on 9.42 Acres with Applegate River frontage. 12 miles from Historic Jacksonville and 5 miles from the town of Ruch and 6 miles to Applegate Lake and Squaw Lake. The beautiful home has a barn/shop and car ports attached for all your toys. This property backs up to BLM and all the trails for great horse riding. There is an above ground pool structure that needs liner and some TLC is in the process of being removed. The property is partially fenced but could work for some horses or other critters with additional fencing. Home is back from the River and the road so no Flood Insurance needed. EV charging station in the garage. There is a seating area down by the river( follow the sign )All information is believed to be accurate but buyer to do own due diligence as to the uses and condition of the property.

5900 Upper Applegate Road, Jacksonville

Listing courtesy of Windermere Van Vleet Jacksonville.

215 S 4th Street, Jacksonville
$1,585,000
3 Beds ⋅ 3 Baths ⋅ 220224076 MLS
A rare offering in the heart of Historic Jacksonville, Tiger Lily Inn blends storybook charm, refined design and flexible living/income potential just steps from shops, dining, Britt, wine tasting and Doc Griffin Park. Set on approx. .23 acre with two beautifully curated buildings, the property includes two exquisite guest suites, 3 baths, inviting living areas, designer finishes, layered textures, romantic décor, gardens, patios, event lawn and a bridal/flex studio opening to the outdoors. Every space feels thoughtfully composed, warm, elegant and memorable. Currently known as an intimate inn and special-event setting, for weddings, celebrations, gatherings & reunions it also lives beautifully as a private residence, guest retreat or multigenerational compound. Seller believes additional cottage-style improvements may be possible; Buyer to verify with City. Historic Core zoning creates added versatility; all future use subject to City. Inquire for full details.

215 S 4th Street, Jacksonville

Listing courtesy of Millen Property Group.

443 Conestoga Drive, Jacksonville
$790,000
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

Listing courtesy of John L. Scott Medford.

5758 Sterling Creek Road, Jacksonville
$825,000
3 Beds ⋅ 1 Baths ⋅ 220223445 MLS
Unique opportunity on 64+ scenic acres w/ EFU zoning, offering exceptional privacy & versatility. Bordering public lands on two sides, this remarkable property provides a peaceful setting w/ endless possibility. The 3-bedroom, 1-bath home is complemented by three separate guest sleeping buildings, creating space for visitors, hobbies, or creative pursuits. Additional features include two barns, detached greenhouse w/ a dedicated office space + a separate farm building w/ commercial kitchen potential. Two wells on the property. The basement offers extra guest quarters w/ its own private entrance, adding flexibility for an at home office. Surrounded by natural beauty & abundant wildlife, this property is ideal for those seeking room to roam, work, recreate, or simply enjoy a tranquil rural lifestyle. Fenced organic garden w/ garden beds, English walnut trees etc. makes this perfect for homesteading. A rare combination of acreage, privacy, improvements, less than 15 mins to J'ville.

5758 Sterling Creek Road, Jacksonville

Listing courtesy of John L Scott Ashland.

1528 Morton Way, 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

Listing courtesy of Redfin.

9595 Sterling Creek Road, Jacksonville
$767,000
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. Owner may carry.

9595 Sterling Creek Road, Jacksonville

Listing courtesy of Pine-Rok Realty.

2365 Eastside Road, Jacksonville
$1,149,000
4 Beds ⋅ 4 Baths ⋅ 220222432 MLS
Experience elevated mountain living on this breathtaking 9-acre estate at the base of Boaz Mountain. Designed with timeless lodge-inspired architecture, this 3,737 SF custom home captures luxury, warmth, and privacy at every turn. Towering vaulted ceilings, tile floors, handcrafted woodwork, and dramatic floor-to-ceiling windows create an unforgettable atmosphere filled with natural light and stunning views. The gourmet kitchen features quartz countertops, high-end appliances, oversized island, and walk-in pantry, opening seamlessly to expansive living and entertaining spaces. Resort-style outdoor living awaits with a heated in-ground pool with PebbleTec finish, outdoor kitchen, pool house, hot tub, 1,000+ SF deck, and beautifully curated grounds designed for unforgettable gatherings and peaceful evenings alike. Backing thousands of acres of public land, this is more than a home--it's a private Southern Oregon retreat built for luxury, adventure, and connection.

2365 Eastside Road, Jacksonville

Listing courtesy of John L. Scott Medford.

205 N Oregon Street, Jacksonville
$799,000
3 Beds ⋅ 3 Baths ⋅ 220222075 MLS
Exceptional 2026 new construction in the heart of historic Jacksonville, Or. Enjoy being just a short stroll from local favorites including the Britt Music & Arts Festival, trolley tours, wine tasting rooms, woodland trails, charming art boutiques, and fine dining. This beautifully designed home offers 3 spacious bedrooms, 2.5 bathrooms, and over 1,570 sq ft of living space filled with abundant natural light and an inviting open-concept layout. The gourmet kitchen features soft-close cabinetry, granite countertops, stainless steel appliances, and a convenient eating bar. The primary suite offers a relaxing retreat with a walk-in closet and a beautifully tiled walk-in shower. Additional highlights include luxury laminate flooring, a finished 1-car garage, an elegantly tiled guest bathroom, and a private driveway. Located within the historic district, this property also qualifies for short-term rental applications, creating a unique opportunity for both homeowners and investors.

205 N Oregon Street, Jacksonville

Listing courtesy of RE/MAX Integrity.

The content relating to real estate for sale on this website comes in part form the MLS of Central Oregon. Real Estate listings held by Brokerages other than Henselman Realty & Managment are marked with the Reciprocity/IDX logo, and detailed information about these properties includes the name of the listing Brokerage. © MLS of Central Oregon (MLSCO). This content was last updated on . Some properties which appear for sale on this website may subsequently have sold or may no longer be available. All information provided is deemed reliable but is not guaranteed and should be independently verified. All content displayed on this website is restricted to personal, non-commercial use, and only for ascertaining information regarding real property for sale. The consumer will not copy, retransmit not redistribute any of the content from this website. The consumer is reminded that all listing content provided by automatic transmission by MLSCO is © MLS of Central Oregon (MLSCO).

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