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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.

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

$669,000

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!

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

$1,299,000

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.

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

$799,000

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.

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

$725,000

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

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

$725,000

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.

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

$1,499,000

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.

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

$1,145,000

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.

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

$1,585,000

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.

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

$799,000

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.

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

$899,000

One of the oldest Victorians in Southern Oregon, eligible for the historic register, the Henry Klippel House has been home to only four families in its 160 years. Built for one of three prospectors credited with the 1853 discovery of Crater Lake, the main house offers 4 spacious bedrooms (incl. ground floor primary suite) and 3.5 baths, with another bedroom and half bath in its guesthouse. Restored by contractor Roger Whipple in the 1990s, with a new shake roof in 2025 and master bath remodel in 2026, the house retains its original hardwood floors, paned windows, brass gasolier fixtures, and brick fireplace. Airy 10' ceilings, covered porches, and custom woodwork showcase the home's craftsmanship. Set on a .27-acre corner lot blocks from shops and restaurants, the property also includes a detached 2-car garage with workroom, and a two-story ADU with full kitchen, half bath, private entrance and parking. A once-in-a-generation chance to steward one of Jacksonville's historic treasures

4 Beds ⋅ 4 Baths ⋅ 220217989 MLS

One of the oldest Victorians in Southern Oregon, eligible for the historic register, the Henry Klippel House has been home to only four families in its 160 years. Built for one of three prospectors credited with the 1853 discovery of Crater Lake, the main house offers 4 spacious bedrooms (incl. ground floor primary suite) and 3.5 baths, with another bedroom and half bath in its guesthouse. Restored by contractor Roger Whipple in the 1990s, with a new shake roof in 2025 and master bath remodel in 2026, the house retains its original hardwood floors, paned windows, brass gasolier fixtures, and brick fireplace. Airy 10' ceilings, covered porches, and custom woodwork showcase the home's craftsmanship. Set on a .27-acre corner lot blocks from shops and restaurants, the property also includes a detached 2-car garage with workroom, and a two-story ADU with full kitchen, half bath, private entrance and parking. A once-in-a-generation chance to steward one of Jacksonville's historic treasures

220 8th Street, Jacksonville

$8,500,000

Welcome to Red Lily, one of the most acclaimed vineyards in the Applegate Valley. This 255-acre property boasts strong water rights, breathtaking river frontage, a state-of-the-art winery, vineyard, and expanses of quality irrigated land for agricultural expansion, plus an iconic and well-trafficked wine-tasting venue. With its well-established reputation and a wealth of infrastructure, Red Lily provides an excellent canvas for developing a hospitality focus with events such as destination weddings, as well as on-site accommodations like bed and breakfast and cabin rentals. This rare gem offers an unparalleled setting with 4,000 feet of Applegate River frontage and convenient access to incredible outdoor activities. Nestled atop a secluded knoll is the main residence—a quintessential American cedar shingle-style home boasting over 4,000 SF of living space. The second home is a delightful farmhouse that has been thoughtfully updated. Owner terms may be available, call for details.

4 Beds ⋅ 3 Baths ⋅ 220180676 MLS

Welcome to Red Lily, one of the most acclaimed vineyards in the Applegate Valley. This 255-acre property boasts strong water rights, breathtaking river frontage, a state-of-the-art winery, vineyard, and expanses of quality irrigated land for agricultural expansion, plus an iconic and well-trafficked wine-tasting venue. With its well-established reputation and a wealth of infrastructure, Red Lily provides an excellent canvas for developing a hospitality focus with events such as destination weddings, as well as on-site accommodations like bed and breakfast and cabin rentals. This rare gem offers an unparalleled setting with 4,000 feet of Applegate River frontage and convenient access to incredible outdoor activities. Nestled atop a secluded knoll is the main residence—a quintessential American cedar shingle-style home boasting over 4,000 SF of living space. The second home is a delightful farmhouse that has been thoughtfully updated. Owner terms may be available, call for details.

11777 Highway 238, Jacksonville

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