Jacksonville Homes with Outbuilding Exterior features

Welcome to Jacksonville, Oregon, a charming town nestled in the heart of Jackson County. Renowned for its rich history and vibrant arts scene, Jacksonville is a delightful blend of small-town charm and modern conveniences. Originally a gold rush town in the 1850s, it has preserved its historic buildings and quaint streets, making it a picturesque destination for residents and visitors alike. With a backdrop of stunning mountain views and lush greenery, Jacksonville offers a serene lifestyle that is hard to resist.

As you explore the homes in Jacksonville, you'll discover a variety of properties that showcase unique exterior features, including spacious outbuildings. These versatile structures can serve multiple purposes, whether you envision a workshop, studio, or even additional storage for your outdoor gear. The presence of outbuildings enhances the functionality of your property, providing ample space for hobbies, projects, or potential rental opportunities.

The homes here often boast beautiful gardens, wrap-around porches, and ample outdoor space, perfect for enjoying the temperate climate that Oregon is famous for. Imagine sipping your morning coffee while surrounded by the natural beauty of your yard, or hosting gatherings with friends and family in your expansive outdoor setting.

With a welcoming community, excellent schools, and easy access to outdoor adventures, Jacksonville is not just a place to live; it’s a lifestyle. Explore the possibilities of finding your dream home with outbuilding features in this enchanting town, where every day feels like a retreat. Come and experience the magic of Jacksonville, Oregon, and discover a place you’ll be proud to call home.

Newest Jacksonville 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: