Jacksonville Homes with Territorial View

Welcome to Jacksonville, Oregon – a charming town steeped in history and surrounded by breathtaking natural beauty. Nestled in Jackson County, this picturesque city is known for its vibrant arts scene, rich cultural heritage, and stunning landscapes that captivate residents and visitors alike. With its roots dating back to the gold rush of the 1850s, Jacksonville boasts a well-preserved historic district that features quaint shops, delightful eateries, and unique galleries, all set against a backdrop of the stunning Siskiyou Mountains.

One of the most alluring features of Jacksonville is its diverse real estate market, particularly homes with territorial views. Imagine waking up each morning to panoramic vistas that stretch across lush valleys and rolling hills. These homes provide not only a serene living environment but also a connection to the breathtaking Oregon landscape that surrounds you. Each property offers a unique perspective, whether it's the tranquility of the countryside or the vibrant colors of the changing seasons.

Living in Jacksonville means embracing an outdoor lifestyle, with ample opportunities for hiking, biking, and exploring the nearby Applegate Valley and Rogue River. The community is also known for its local wineries and breweries, making it a haven for those who appreciate fine food and drink.

Whether you’re seeking a charming historic home or a modern retreat with territorial views, Jacksonville, Oregon, offers a delightful blend of history, community, and natural beauty that’s perfect for anyone looking to call this enchanting town home. Come discover the magic of Jacksonville, where every day feels like a getaway!

Newest Jacksonville Homes with Territorial View

$1,090,000

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 with natural light, the open great room design features soaring ceilings and a stunning chef's kitchen with premium appliances, custom cabinetry, and quality finishes. The thoughtfully designed floor plan offers 3 bedrooms, an office/bedroom, loft, & spacious laundry room. Over the past few years, nearly every aspect of the home has been upgraded, including the kitchen, bathrooms, flooring, lighting, HVAC systems, on demand hot water heater, electrical panel, whole-house generator, Trex decking, & more. Outside, your private retreat features a completely renovated in-ground pool with waterfall, new concrete decking, energy-efficient equipment, solar heating, hot tub, and beautifully landscaped grounds--creating an exceptional indoor-outdoor lifestyle just moments from Jacksonville's dining, shopping, and Woodland Trails.

120 Ponderosa Way, 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

$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

$482,000

220225558 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 Street, Jacksonville

$482,000

2 Beds ⋅ 1 Baths ⋅ 220225555 MLS

700 N 5th, 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

$99,900

220224961 MLS

Rare opportunity just outside historic Jacksonville, Oregon! This gently sloped, easy approach from Hwy 238, this 3/4-acre lot sits about 4.5 miles from town. Power is easily accessible near the property line, making it build-ready. Bring your own builder and floor plan or choose from ours. Buildable lots this close to Jacksonville rarely come available. Buyer to verify all details and complete their own due diligence.

OR-238, 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

$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. A conventional (home saver) rehab loan could be financing possibility . 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

$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

$1,585,000

220224077 MLS

A rare and enchanting commercial opportunity in the heart of Jacksonville, Oregon, Tiger Lily Inn & Venue Center is more than a property -- it is a destination. Steps from downtown shops, restaurants, wine country experiences, Britt Festival and the Historic Core, this curated venue blends storybook character, established event appeal, lodging potential and flexible commercial use. Known and loved as a boutique wedding and special-event venue, the property offers an intimate garden setting for weddings, reunions, retreats, private celebrations and unforgettable gatherings, with lush grounds, outdoor areas, guest accommodations and a bridal/flex studio. Historic Core commercial zoning may invite future possibilities such as boutique hospitality, wine tasting, culinary, wellness, private club, creative office/event use or additional improvements, subject to City approval and buyer due diligence. A distinctive Southern Oregon opportunity with beauty, brand identity and room for vision.

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

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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: