Jackson Co: Jacksonville Area Homes with Outbuilding Exterior features

Welcome to the enchanting Jacksonville area in Jackson County, Oregon, where history meets natural beauty in a charming small-town setting. Nestled at the foot of the majestic Siskiyou Mountains, Jacksonville is renowned for its rich heritage, vibrant arts scene, and welcoming community spirit. This picturesque town boasts beautifully preserved 19th-century architecture, making it a delightful destination for history buffs and nature lovers alike.

One of the standout features of Jacksonville is its diverse real estate market, particularly homes with outbuildings. These properties offer a unique blend of functionality and charm, perfect for those seeking extra space for hobbies, workshops, or even guest accommodations. Imagine having a rustic barn or a cozy studio just steps from your back door, providing endless possibilities for creativity or relaxation.

The exterior features of these homes often reflect the region's stunning natural surroundings, with lush gardens, mature trees, and picturesque views that invite you to unwind and soak in the beauty of the area. Whether you're drawn to the warmth of a craftsman-style home or the elegance of a Victorian, Jacksonville offers a variety of architectural styles to suit your taste.

Beyond the homes, the Jacksonville area is a haven for outdoor enthusiasts. With nearby hiking trails, vineyards, and the scenic Applegate Valley, adventure awaits at every turn. Enjoy the local farmer's market, quaint shops, and community events that make Jacksonville a truly special place to call home. Embrace the charm of Jacksonville, where your dream home with an outbuilding is waiting for you!

Newest Jackson Co: Jacksonville Area Homes with Outbuilding 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

$485,000

3 Beds ⋅ 2 Baths ⋅ 195284107 MLS

Head to the hills! Bucolic 2.48 acres, bordering BLM land and Poorman's Creek, part of the old Pearce Placer Goldmining Claim in George Black Gulch.Remodeled throughout with vaulted and beamed ceilings, second kitchen, open floor plan. RV parking with water, power and septic hook-up. Workshop, garage and cabin.

4539 HWY 238, 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: