Ashland Homes with Log Style

Welcome to Ashland, Oregon – a charming gem nestled in the heart of Jackson County. Known for its vibrant arts scene, stunning natural landscapes, and a welcoming community, Ashland is a place where culture and nature harmoniously intertwine. With its picturesque setting at the base of the Siskiyou Mountains, residents enjoy breathtaking views and an abundance of outdoor activities, from hiking and biking to skiing in the winter months.

One of the most enchanting aspects of Ashland’s real estate market is its selection of log-style homes. These unique properties exude rustic charm and warmth, making them a perfect fit for those who appreciate the beauty of natural materials and craftsmanship. Log homes in Ashland often feature open floor plans, soaring ceilings, and expansive windows that invite the stunning Oregon landscape indoors. Imagine cozy evenings by the fireplace, surrounded by the rich textures of wood, while the sounds of nature create a serene backdrop.

Living in a log-style home in Ashland not only connects you with the beauty of the outdoors but also places you within reach of the city’s renowned attractions. From the Tony Award-winning Oregon Shakespeare Festival to the local wineries and artisan shops, there’s always something to explore. Whether you’re seeking a peaceful retreat or an active lifestyle, Ashland offers a vibrant community that embraces both.

Discover the allure of log-style homes in Ashland, where every day feels like a retreat into nature, and the spirit of community thrives. Your dream home awaits in this enchanting corner of Oregon!

Newest Ashland Homes with Log Style

$900,000

5 Beds ⋅ 4 Baths ⋅ 220221548 MLS

2 HOMES AND A GUEST STUDIO/COTTAGE!!! Just 3 miles from town, this exceptional 11-acre property sits on a sunny south-facing hillside with breathtaking views and endless possibilities. Ideal for a multi-generational family compound, rental income opportunity, homestead, or private retreat, this unique property offers an incredible combination of living space, infrastructure, and outdoor amenities. The 2,200 sq. ft. log home is filled with warmth and rustic charm, while the 1,800 sq. ft. second home includes a full basement for additional living or storage space. A separate 1,200 sq. ft. fenced studio/cottage provides excellent flexibility for guests, a home office, or a creative space. Additional improvements include two large septic systems, RV hookups with water and electricity, a separate laundry room, two tiny cabins, multiple storage buildings, root cellar with shop above, and a barn-style structure on the lower portion of the property with a newer roof. Must see to appreciate!

2909 Dead Indian Memorial Road, Ashland

$1,795,000

4 Beds ⋅ 3 Baths ⋅ 220213243 MLS

5 magazine quality acres, masterfully landscaped with expansive emerald, green lawns, mature trees, ponds & waterfalls create the perfect setting, built with enduring quality. The walls are solid 4x6 Canadian Western Red Cedar, offering style & durability. Large open-floor plan is perfect for gatherings. Earthy materials feature Saltillo tile flooring, rich cherry custom cabinetry, Milgard wood-cased windows, & vaulted, beamed ceilings add substance & style. Upper-level primary has a private deck overlooking the estate style grounds & mountains. Guest house features dual porches, carport, & sits beside one of five waterfalls. A 22' x 44' greenhouse with raised cedar beds. Nearly a mile of crushed granite paths wind through the landscape. 3-car garage, full RV hook-ups, & a 20'x45' shop. A true paradise. Main home is 3/2, guest home is 1/1.

4896 Highway 66, Ashland

$10,775,000

12 Beds ⋅ 10 Baths ⋅ 220210683 MLS

New Frontier Ranch - A storied and truly one-of-a-kind legacy property encompassing 958 breathtaking acres surrounded by pristine wilderness. Steeped in rich history, this remarkable ranch includes a charming farmhouse, museum building, expansive Great Hall, and a private campground with commercial kitchen and bath facilities. Scattered across the land are three rustic cabins, multiple barns and outbuildings, two reservoirs, and irrigated meadows ideal for livestock or crops. Miles of trails wind through forests, meadows, and a preserved ghost town reminiscent of the Old West. Existing resort approvals and extensive infrastructure make it perfect for corporate retreats, events, weddings, festivals, or a destination resort. With unlimited recreation—hiking, horseback riding, ATV adventures, and fishing—this ranch offers both adventure and serenity. A rare opportunity to own a vast wilderness retreat where history, nature, and imagination unite to create something truly extraordinary.

16799 Highway 66, Ashland

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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: