Jacksonville Homes with Second Residence Exterior features

Welcome to Jacksonville, Oregon—a charming town steeped in history and surrounded by breathtaking natural beauty. Nestled in Jackson County, this picturesque community is renowned for its well-preserved 19th-century architecture and vibrant arts scene. With a population of just over 2,800 residents, Jacksonville offers a close-knit atmosphere where neighbors become friends, and local businesses thrive.

One of the standout features of Jacksonville is its unique blend of small-town charm and modern convenience. Residents enjoy access to a variety of amenities, including boutique shops, delightful restaurants, and cultural attractions such as the historic Jacksonville Museum and the annual Britt Music & Arts Festival. Nature enthusiasts will appreciate the town's proximity to the stunning Rogue River and the scenic trails of the nearby Cascade Mountains, perfect for hiking, biking, and exploring.

For those seeking a home with a second residence, Jacksonville has a selection of properties that cater to this desire. Many homes boast spacious exterior features, including expansive yards, beautifully landscaped gardens, and outdoor living spaces perfect for entertaining or simply enjoying the serene surroundings. Imagine sipping your morning coffee on the patio of your second residence, surrounded by the lush greenery that defines this enchanting area.

Whether you're looking for a primary residence or an investment opportunity, Jacksonville offers a unique lifestyle that harmonizes the comforts of home with the beauty of nature. Come discover the charm of Jacksonville, where history meets modern living, and find your perfect home today!

Newest Jacksonville Homes with Second Residence Exterior features

$1,585,000

3 Beds ⋅ 2 Baths ⋅ 667754935 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 ST, Jacksonville

$8,500,000

4 Beds ⋅ 3 Baths ⋅ 23696912 MLS

Welcome to Red Lily Vineyards, one of the most acclaimed vineyards in the esteemed Applegate Valley of Southern Oregon. Renowned for its exceptional wines and captivating scenery, Red Lily Vineyards presents an alluring mix of established wine and agri-business with great opportunities for event and hospitality expansion. It's not just a business; it's a gateway to an extraordinary experience and a haven for those seeking a rare and sought-after investment and lifestyle opportunity. This 255-acre ranch and estate boasts strong water rights, breathtaking river frontage, a state-of-the-art winery, mature vineyards, and an expanses of quality irrigated land for vineyard and agricultural expansion plus perhaps the most iconic and well-trafficked wine tasting experience in Southern Oregon. Nestled atop a secluded knoll, commanding picturesque views of the Applegate Valley, is the main residence, a quintessential American cedar shingle-style home boasting over 4,000 square feet of living space. The second home, known as the winemaker's house, is a delightful farmhouse that has been thoughtfully updated. With its well-established reputation and a wealth of infrastructure, Red Lily provides an excellent platform for business expansion. This includes options for expanding vineyard and agri-business operations, developing a hospitality business with a focus on events such as destination weddings, as well as on-site accommodations like bed and breakfast and cabin rentals. An additional estate dwelling and farm-to-consumer sales are also relevant opportunities. This rare gem offers an unparalleled setting with 3,300 feet of Applegate River frontage and convenient access to incredible outdoor activities. The phenomenal location is a short commute from all the conveniences of Jacksonville and Medford and is centrally located within Southern Oregon. The offering is a hybrid sale that includes the business, brand, and real estate. Owner terms may be available. Thank you!

11777 Highway 238, 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: