Trail Homes with Craftsman Style

Nestled in the heart of Jackson County, Trail, Oregon, is a hidden gem that beautifully marries the charm of small-town living with the breathtaking landscapes of the Pacific Northwest. Known for its stunning natural scenery, Trail offers residents an abundance of outdoor activities, from hiking and fishing to exploring the nearby Rogue River. The community is characterized by its friendly atmosphere, making it a perfect place for families, retirees, and outdoor enthusiasts alike.

One of the standout features of homes in Trail is the exquisite Craftsman style architecture. These homes are a testament to timeless design, showcasing intricate woodwork, built-in cabinetry, and cozy porches that invite you to relax and enjoy the serene surroundings. The Craftsman style is not only aesthetically pleasing but also emphasizes functionality, making these homes ideal for modern living while retaining a classic appeal.

Imagine coming home to a charming Craftsman that reflects the character of Trail itself—a place where warmth and craftsmanship meet the beauty of nature. With spacious interiors and thoughtful layouts, these homes are designed to accommodate both intimate family gatherings and lively entertaining.

Living in Trail means embracing a lifestyle enriched by community spirit and natural beauty. Whether you're sipping coffee on your front porch or taking a leisurely stroll through the picturesque streets, you'll find that every day in this enchanting town feels like a breath of fresh air. Discover your dream Craftsman home in Trail, and experience the perfect blend of comfort and charm in this idyllic Oregon town.

Newest Trail Homes with Craftsman Style

$899,000

5 Beds ⋅ 3 Baths ⋅ 220222418 MLS

Introducing Wheeler Ranch & Estate - a singular Southern Oregon estate set on 5.67 private acres with seasonal creek, open pasture, & a landmark Spiral Willow gracing this land for generations. Crafted from natural stone, rough-cut wood beams, cedar shakes, & anchored by a real stone fireplace across three dramatic levels. Step inside to 18-foot soaring ceilings, rich hardwood floors, wrought-iron detail work, & lookout skylights. A spiral staircase rises to an open upper loft with whole-home audio & room-by-room controls. Stone countertops, custom range hood, & breakfast bar island. Primary suite with private patio & jet tub. The lower level is a fully independent with a private entrance, full kitchen, stone wood stove, three bedrooms, knotty pine music room, stamped concrete floors, & wine cellar. Solid construction ensures true separation. Quiet. Private. Minutes to Rogue River rafting & fishing, Lost Creek Lake, OHV & horseback trails. A legacy property built to last!

838 Ragsdale Road, Trail

$699,900

2 Beds ⋅ 2 Baths ⋅ 658767959 MLS

Fisherman's retreat on the world-famous Rogue River! This prime riverfront prop. offers a beautiful setting w/seasonal Salmon/Steelhead runs right out your back door. Enjoy rolling low-bank frontage/your own private boat launch, and concrete dock perfect for relaxing/taking in the river/forest. Home is already updated - features upgraded LVP floors/barn doors/newer roof/paint/cabinets, a newly built expansive deck w/plenty of space for entertaining, and a functional kitchen w/dining area overlooking the large yard and river. Detached 2nd bedroom/office w/half bath adds flexibility. Functional multi-space shop, w/additional carport/RV pkg/irrigation pump/fenced dog run/mature landscaping complete the package. Minutes to Shady Cove/Lost Creek Lk./hunting/hiking/rafting/vineyards/endless recreation/short jaunt Crater Lk. Natl. Park. Potential income producing short term rental. Don't miss this rare opportunity!

24990 HIGHWAY 62, Trail

$699,900

2 Beds ⋅ 3 Baths ⋅ 220216483 MLS

Fisherman's retreat or potential short term rental income on the world-famous Rogue River! This prime riverfront prop. offers a beautiful setting w/seasonal Salmon/Steelhead runs right out your back door. Rolling low-bank frontage/your own private boat launch, and concrete dock perfect for relaxing/taking in the river/forest. Home is already updated - upgraded LVP floors/barn doors/newer roof/paint/cabinets, a newly built expansive deck w/plenty of space for entertaining, and a functional kitchen w/dining area overlooking the large yard and river. Detached 2nd bedroom/office w/half bath. functional multi-space shop, w/additional carport/RV pkg/fenced dog run/mature landscaping complete the package. Minutes to Shady Cove/Lost Creek Lk./hunting/hiking/rafting/vineyards/endless recreation/short jaunt Crater Lk. Natl. Park. Might make great 2nd home, seasonal retreat, Air BNB or primary Res.

24990 Highway 62, Trail

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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: