Jacksonville Homes with Check With District High school

Welcome to Jacksonville, Oregon, a charming city that beautifully blends history, community, and natural beauty. Nestled in Jackson County, Jacksonville is a hidden gem that offers a unique glimpse into the past, with its well-preserved 19th-century architecture and vibrant arts scene. As you stroll through the historic downtown, you'll find delightful boutiques, cozy cafes, and local galleries, all set against the backdrop of stunning mountain views.

For families considering a move to Jacksonville, the area is served by the highly regarded Check With District High School, ensuring that educational excellence is just around the corner. This commitment to quality education makes Jacksonville an ideal choice for families looking to plant roots in a nurturing environment.

The homes in Jacksonville are as diverse as the community itself, ranging from charming historic residences to modern family homes. Whether you’re seeking a quaint cottage with vintage character or a spacious new build with all the contemporary amenities, Jacksonville has something for everyone. The lush landscapes and proximity to outdoor activities, such as hiking, biking, and wine tasting in the nearby Applegate Valley, ensure that there’s never a dull moment.

Living in Jacksonville means embracing a lifestyle rich in culture and community spirit. With annual events, farmers' markets, and a strong sense of camaraderie among residents, you’ll quickly feel at home in this picturesque Oregon town. Come discover the allure of Jacksonville, where history meets modern living, and make it your next home sweet home!

Newest Jacksonville Homes with Check With District High school

$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

$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

$275,000

220216972 MLS

Build your dream home on this exceptional 13.24-acre residential property just outside the Jacksonville city limits. Located only five minutes from downtown Jacksonville, this rare offering combines privacy, convenience, and natural beauty in the foothills of Southern Oregon. The gently sloping terrain provides a highly usable and buildable layout with an approved homesite, making it ideal for a custom residence or private retreat. Set within a classic oak savannah, the property is dotted with mature oak trees and offers the opportunity to create a truly park-like setting. With ample space for outdoor living, recreation, and future improvements, this is a rare chance to own a large, buildable parcel so close to Jacksonville's shops, dining, and charm. A perfect canvas to bring your vision to life.

Sterling Creek Road, Jacksonville

$849,000

3 Beds ⋅ 3 Baths ⋅ 220216793 MLS

Single-level custom home on acreage showcases dramatic views and architecture. Rare privacy in the midst of nature; yet home is close to Medford and historic Jacksonville and has high-speed cable internet. 14+ acres backed by BLM land at the end of a quiet country road. High-level view overlooking the Applegate Valley and mountains beyond. Possible seller-financing at below-market rate with 50% down, or lease-option. Home's design is inspired by Frank Lloyd Wright's principles, with sleek horizontal lines and a flowing open layout with prominent use of wood, stone, concrete and glass. Spacious high-ceilinged great room with clerestory, stone-finish fireplace and wall of patio doors. Luxurious primary suite boasts its own panoramic views, patio access, dedicated office, walk-in closet, and spa-like bathroom. Fire-resistant ICF construction. Zoned radiant heated floors, extensive cherry wood cabinetry, abundant storage, quality Pella windows, oversized garage, 400-amp electrical.

615 Tumbleweed Trail, Jacksonville

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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: