Jackson Homes with Barn(s) Exterior features

Welcome to Jackson County, Oregon, a picturesque region that beautifully marries the charm of rural living with the vibrancy of city life. Nestled in the heart of Southern Oregon, Jackson County is renowned for its breathtaking landscapes, including the majestic Rogue River, the stunning peaks of the Cascade Mountains, and the lush vineyards that dot the countryside. With a rich history, a thriving arts scene, and a plethora of outdoor activities, it’s no wonder that this area has become a sought-after destination for homebuyers.

One of the most enchanting features of homes in Jackson County is their captivating barn-style exteriors. Imagine stepping into your dream home, complete with rustic charm and modern comforts. These homes often boast expansive properties, perfect for those who appreciate the beauty of nature and the serenity of rural life. The barn aesthetic not only adds character but also offers functional spaces for hobbies, workshops, or even livestock.

Whether you’re looking for a cozy farmhouse with a classic red barn or a sprawling estate with modern barn-inspired architecture, Jackson County has a diverse range of properties to suit your lifestyle. Enjoy the freedom of space while being just a short drive away from the vibrant communities of Medford and Ashland, where you can indulge in fine dining, shopping, and cultural events.

In Jackson County, you’ll find not just a home, but a lifestyle—one that embraces the beauty of the great outdoors and the warmth of community. Come explore the possibilities that await you in this enchanting corner of Oregon!

Newest Jackson Homes with Barn(s) Exterior features

$1,140,000

3 Beds ⋅ 2 Baths ⋅ 221762307 MLS

Set privately back on 5+ acres in the Sunny Oaks community, this custom 3 bed + office, 2.5 bath, 2644 sq ft home pairs open mountain views with easy access to town -- 15 min from Downtown Ashland and near Emigrant Lake. The groundwork for comfortable rural living is in place: a dedicated 1-gigabit fiber line, 300 amp electrical, whole-home water filtration, 2021 Lennox HVAC, irrigation rights, a large cedar-fenced area, and a roof under six years old. Inside, natural light fills an updated kitchen with quartz counters and hardwood floors, opening to a great room, with a separate family room, office, and laundry on the main level. Upstairs, the primary suite offers vaulted ceilings and a balcony framing the same sweeping mountain views as the wraparound deck below, plus two more bedrooms and a full bath. Outside, a gravel RV pad offers water, power, and internet, and a barn with corrals stands ready for horses. With over $200K in updates, the property is move-in ready.

7130 HIGHWAY 66, Ashland

$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: