Jacksonville Homes with Check With District Middle school

Welcome to Jacksonville, Oregon – a charming town steeped in history, nestled in the picturesque Rogue Valley. Known for its rich heritage and vibrant community, Jacksonville offers a unique blend of small-town charm and modern conveniences. With its roots dating back to the gold rush of the 1850s, this delightful city boasts beautifully preserved buildings, quaint shops, and a range of cultural attractions that make it a wonderful place to call home.

One of the standout features of Jacksonville is its commitment to education. Families will be pleased to know that homes in this area are serviced by the Check With District Middle School, ensuring that children have access to quality education right in their own backyard. The close-knit community fosters a supportive environment where students can thrive academically and socially.

As you explore the real estate options in Jacksonville, you’ll discover a variety of homes that cater to different lifestyles and budgets. From charming historic houses with character to modern family homes, there’s something for everyone. The scenic surroundings, including stunning views of the Siskiyou Mountains and the nearby Applegate Valley, provide a perfect backdrop for outdoor enthusiasts. Residents can enjoy hiking, biking, and exploring the many parks and natural wonders this region has to offer.

With its rich historical tapestry, strong community spirit, and excellent educational opportunities, Jacksonville, Oregon, is not just a place to live – it’s a place to thrive. Come discover the magic of Jacksonville and find your dream home in this enchanting town!

Newest Jacksonville Homes with Check With District Middle school

$1,275,000

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

$1,500,000

3 Beds ⋅ 3 Baths ⋅ 220225350 MLS

Discover unmatched privacy on this spectacular 200-acre Southern Oregon retreat just 30 minutes from downtown Medford. This custom 2,400 sq. ft. home is thoughtfully built above an impressive 2,400 sq. ft. shop and showcases breathtaking panoramic views from nearly every room and the expansive elevated deck. The home features 3 bedrooms, 3 bathrooms, and a chef's kitchen designed for entertaining. The massive shop offers soaring ceilings, in-floor radiant heat, and abundant space for RVs, equipment, vehicles, or hobbies. A 24kW solar system provides exceptional energy efficiency and peace of mind. Surrounded by abundant wildlife and endless outdoor recreation, this rare property is ideal as a full-time residence, hunting retreat, or luxury Oregon getaway. Towering trees, open meadows, and rolling terrain create an unforgettable setting with exceptional privacy, incredible star-filled nights, and room to explore, hike, ride, or simply enjoy the beauty of Southern Oregon.

7036 Griffin Lane, Jacksonville

$779,000

5 Beds ⋅ 5 Baths ⋅ 220224622 MLS

Stunning Jacksonville property offering flexibility, income potential, and exceptional upgrades. The completely remodeled kitchen features high-end appliances, granite countertops with waterfall edges, and an open layout designed for entertaining. The home can function as a two-family setup and was previously licensed as a rental, creating excellent potential for supplemental income or multigenerational living. Outdoor living has been expanded with new decks and an enclosed patio (not included in sq ft), providing additional space to relax and enjoy the surrounding setting. A standout feature is the impressive 36x36 shop with RV garage and unfinished space above, ideal for a future guest suite, office, studio, or hobby space. Beautiful gardens and chicken coops add to the property's charm and self-sufficient lifestyle appeal. Conveniently located near Jacksonville's renowned wineries, dining, and outdoor recreation. Schedule a showing today!

101 Rocky Knoll Lane, Jacksonville

$1,150,000

3 Beds ⋅ 3 Baths ⋅ 220224571 MLS

This beautifully remodeled home sits on 9.47 acres (6.4 irrigated from the river) with sweeping views overlooking the Applegate River. The exterior features batten board siding milled from trees on the property. Inside, reclaimed barn wood from Prineville's Livery Stable adds warmth, complemented by hand scraped hickory floors in the main living areas, slate floors in the kitchen and entry, and striking zinc countertops. The gourmet island kitchen includes a downdraft cooktop, while hand-blown lighting graces the home throughout. The primary suite offers cork flooring and a spacious walk-in shower. An enclosed patio provides peaceful river views. Additionally, there's a fully remodeled 2-bedroom, 1-bath ADU overlooking the river, a barn, and 5 separate pastures. Both homes have backup generators and on-demand propane water heaters. Zoned RR-5 on two tax lots, with potential for another home. Ideal for a serene, riverfront lifestyle with modern comforts and abundant outdoor space.

9662 Upper Applegate Road, Jacksonville

$850,000

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

$349,900

2 Beds ⋅ 2 Baths ⋅ 220222612 MLS

Handyman Special! Discover the charm and potential of this peaceful 4.77-acre property, featuring two taxlots, a cozy ranch-style home with expansive views of farmland and mountains. This 2 bed, 2 bath home offers privacy, space, and endless possibilities. Inside, you'll find a kitchen with ample storage and a dining area highlighted by a bay window that captures the scenic surroundings. The sunlit living room features a rustic wood-burning fireplace, perfect for cozy evenings. Both bedrooms are generously sized with oversized closets, and the primary suite includes a double vanity and a soaking tub--ideal for relaxation. A large yard offers room for gardening, pets, or hobby farming. Whether you're dreaming of a quiet retreat, a mini-homestead, or an investment property, this home delivers a solid foundation for your vision. This home will be sold AS IS.

3361 Little Applegate 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

$2,500,000

220220892 MLS

Rare opportunity to own 3 adjoining parcels being sold together within the city limits of Jacksonville! This high-potential property offers a combined 19.23 acres across three separate tax lots, creating endless possibilities for future development, investment, or estate living. Parcel #1 (10002611) consists of 4.86 acres, Parcel #2 (10982036) offers 10 acres, and Parcel #3 (10994694) includes 4.37 acres. With a prime location inside Jacksonville city limits, this unique offering combines space, privacy, and convenience while being just minutes from downtown, dining, shopping, and local amenities. Properties with this much acreage, multiple parcels, and potential within city limits are increasingly hard to find. Buyer to complete their own due diligence regarding land use, development potential, utilities, and approved uses. Exceptional opportunity to secure a large acreage holding in a highly desirable Southern Oregon location.

Applegate Street, 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

$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

$624,900

4 Beds ⋅ 4 Baths ⋅ 220218223 MLS

This updated 4-bed, 4 -bath home offers 2,907 sqft of living space on a peaceful 6-acre lot. Including a huge barn with an additional office space on the second level. Fresh paint and new laminate flooring on the main level create a crisp, modern feel. Vaulted ceilings and large windows fill the space with natural light and showcase stunning mountain views. The open layout is ideal for both relaxing and entertaining. Privately tucked away yet close to town, this property offers the best of both worlds. Highlights include a 1,000-sqft barn with a second-level office--great for storage, hobbies, or creative work. A 3-car garage provides ample room for vehicles, and a charming greenhouse supports year-round gardening. The abundant water supply is ideal for lush landscaping or agriculture. This home has incredible views of the valley and mountains - Don't miss out! Priced to sell!

3375 Little Applegate Road, Jacksonville

$549,000

3 Beds ⋅ 2 Baths ⋅ 220217326 MLS

Completely remodeled home in the heart of desirable Applegate Valley! With a new roof, new windows throughout, exterior & interior paint, HVAC, flooring, and lighting fixtures throughout, this home is truly move in ready and worry-free. Step inside the front door and you will be greeted with an open floor plan and abundant natural light. The kitchen is a culinary dream with quartz counters, custom cabinets, and top-notch stainless steel appliances - including a range / oven and microwave w/convection oven. The spacious primary bedroom offers a new vanity in the bathroom and the laundry room and guest bath feature custom cabinets. With wooded views out every window, you'll be surrounded by the beauty of nature. The wood stove with stone surround brings a cozy vibe and the Trex deck is the perfect spot to enjoy your morning coffee. Only 1 mile to gorgeous Cantrall Buckley Park and the Applegate River and a 30 minute drive to Medford make this location ideal.

1100 Cantrall Road, Jacksonville

Start Your Search

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: