Applegate Homes with Two Stories

Welcome to Applegate, Oregon—a hidden gem nestled in the picturesque Jackson County. Known for its breathtaking landscapes, this charming community offers a delightful blend of rural tranquility and outdoor adventure. With the majestic Applegate River winding through the area and the stunning backdrop of the Siskiyou Mountains, residents enjoy a lifestyle that embraces nature and serenity. Whether you're hiking through lush forests, fishing in crystal-clear waters, or simply soaking in the stunning views, Applegate is a haven for nature enthusiasts and those seeking a peaceful retreat.

In Applegate, you’ll find an array of beautiful homes, including the coveted two-story residences that provide ample space and versatility for families and individuals alike. These homes often feature spacious layouts, allowing for comfortable living and entertaining. Imagine hosting gatherings in your open-concept living area that flows seamlessly into a gourmet kitchen, or enjoying quiet evenings on a private deck with panoramic views of the rolling hills.

The two-story homes in Applegate are designed to maximize both functionality and aesthetics. With multiple bedrooms and bathrooms, they cater to the needs of growing families or those who desire extra space for guests or a home office. Many of these residences are set on generous lots, providing plenty of outdoor space for gardening, play, or simply enjoying the serene surroundings.

If you’re searching for a place that combines the beauty of nature with the comforts of home, Applegate, Oregon, and its stunning two-story residences may just be the perfect fit for you. Come explore this enchanting community and discover the home of your dreams!

Newest Applegate Homes with Two Stories

$460,000

2 Beds ⋅ 1 Baths ⋅ 220225722 MLS

Charming newly constructed 2020 home nestled among the pines in the heart of the Applegate Valley. This two-story 576 sq ft retreat features newer appliances, spacious layout, amazing views, and a full bathroom. An additional full 576 square feet of garage, or potential space, is not included in the listed sq footage. There are multiple entrances to property for easy parking of equipment, RVs, or vehicles. Large parking area and a new extra-large greenhouse ready for your all-season gardening visions. As a bonus, the property has been equipped with both an RV and a generator outlet. This thoughtfully constructed property sits minutes away from the Applegate river, lavender farms, and award-winning restaurants and wineries. Whether you're looking for your first home, downsizing, or an investment property, this spacious property combines character, functionality, and easy access to some of Southern Oregon's finest outdoor experiences.

4218 Thompson Creek Road, Applegate

$620,000

2 Beds ⋅ 1 Baths ⋅ 220224593 MLS

*Motivated Seller*. Historic farm land in the heart of wine country! situated next to Troon and other notable wineries, this farm land was established in 1860! High producing wells and EFU zoning give this property so much potential! features a main home, two additional guest structures, multiple established greenhouses and storage buildings - lots to see! Additional highlights: 2 barns, RV parking, irrigation system, former farm stand with walk-in cooler, and powered outbuildings. Call for more info!

13990 N Applegate Road, Applegate

$1,995,000

7 Beds ⋅ 5 Baths ⋅ 220218653 MLS

Don't miss this once-in-a-generation opportunity to own Applegate River Retreat, a true Southern Oregon legacy estate. This extraordinary riverfront sanctuary spans nearly 20 private acres with 420' of Applegate River frontage in the heart of the Applegate Valley wine country. Thoughtfully transformed, the property features 3 beautifully finished homes accommodating 21+ guests, 2 RV sites, an authentic Finnish sauna, game room, fitness/yoga studio, reclaimed pastures, forest trails, private swimming holes, and multiple river access points. Perfect for creating lifelong memories with family and friends, hosting unforgettable gatherings, or simply escaping to nature's beauty. Steps from Red Lily Vineyards and Devitt Winery, and just minutes from historic Jacksonville and the renowned Britt Music & Arts Festival. Swim, fish, kayak, hike, relax beneath towering trees, and experience one of Southern Oregon's most remarkable private retreats. Start your legacy today. Truly one of a kind!!!!

11677 Highway 238, Applegate

$430,000

2 Beds ⋅ 1 Baths ⋅ 220204243 MLS

Private & Charming Mini-Farm on Humbug Creek in the Applegate Valley. Cross a creek through the forest up to your own private little hobby farm homestead on 11.2 acres backed by 4,900 acres BLM. Unique, cozy custom built cedar sided home with dramatic architectural angles, custom details & rustic charm. Central wood stove, vaulted ceilings, stone & bamboo flooring throughout. Detached laundry room with additional storage & covered firewood area. Turn-key fenced & terraced garden area sports 3 automated greenhouses (one solar), mature fruit trees, blueberries, animal corrals & a chicken coop. Spacious workshop w/ vaulted ceiling is set up for wood stove, a previously certified kitchen & view into the attached hothouse. Hike up the hill to gorgeous views. A dreamy must see!

2231 Humbug Creek Road, Applegate

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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: