Trail Homes with Shady Cove School Middle school

Welcome to Trail, Oregon – a hidden gem nestled in the heart of Jackson County. This picturesque community is surrounded by the stunning natural beauty of the Cascade Mountains and the serene waters of the Rogue River, making it a perfect retreat for nature lovers and outdoor enthusiasts alike. Trail offers a tranquil atmosphere, while still being conveniently located near larger towns, ensuring that residents can enjoy both the peace of rural living and the amenities of urban life.

One of the standout features of Trail is its close-knit community feel, where neighbors become friends and local events foster a sense of belonging. The area is not only rich in outdoor adventures, from hiking and fishing to camping, but it also boasts a strong commitment to education. Families seeking a nurturing environment for their children will be pleased to know that homes in Trail are served by the Shady Cove School District, which includes the well-regarded Shady Cove Middle School. This institution is dedicated to providing quality education and fostering a supportive learning environment, ensuring that students thrive academically and socially.

Real estate in Trail offers a variety of options, from charming single-family homes to spacious properties with ample land, perfect for those looking to escape the hustle and bustle of city life. Whether you’re a first-time homebuyer or searching for your forever home, Trail has something to offer everyone. Embrace the beauty, community spirit, and educational opportunities that Trail, Oregon has to offer – your dream home awaits!

Newest Trail Homes with Shady Cove School Middle school

$475,000

3 Beds ⋅ 3 Baths ⋅ 220224437 MLS

Nestled on 6.1 wooded acres, this charming chalet-style retreat offers a blend of privacy, character, & functionality. Abundant natural light, & large windows that showcase the surrounding natural beauty. Architectural details include a spiral staircase leading to a loft and additional bedroom + bath, stained glass accents, honed granite countertops, & a warm, inviting atmosphere throughout. Recent updates include newer decks, windows, & durable metal roofs. Stay cozy year-round w/ a certified wood stove. The detached 2-car garage includes versatile flex space w/ a bathroom, perfect for a home office. Detached outbuilding w/ electricity. Ample room for equipment, recreational vehicles, and outdoor toys, this property is perfect for those seeking space and adventure. Conveniently located near BLM land, river access, and Shady Cove amenities, this tranquil property captures the best of Southern Oregon living.

238 Citadel Road, Trail

$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

$919,000

3 Beds ⋅ 3 Baths ⋅ 220219182 MLS

Nest with the Eagles on nearly 11 acres overlooking the mighty Rogue River! This stunning 3BR/4BA retreat sits atop a treed knoll with breathtaking river and mountain views from every angle. Watch the salmon spawn from your back deck, unwind in the hot tub with a cool breeze, and enjoy end-of-road privacy that makes this property truly one of a kind. Soak in the scenery from multiple private decks and balconies, or cool off in the solar-heated in-ground pool. The main level features soaring open ceilings, a wood-burning fireplace, and a galley kitchen, while the upper level offers two master suites plus a third bedroom. The finished daylight basement is perfect for a game room or guest quarters, and a private pool house with full bath sits just steps away. All of this within moments of world-class boating, recreation, and trails. Nearly 11 fenced and gated acres of peace and tranquility, yet just minutes from town. This is Southern Oregon living at its finest!

7201 Crowfoot Road, Trail

$245,000

1 Beds ⋅ 1 Baths ⋅ 220218910 MLS

Private 10.3-acre setting with usable land and strong potential. The property previously received county approval for a replacement homesite--buyers to verify current status with Jackson County--offering an opportunity to rebuild while having a functional setup already in place. A finished shop with studio-style living area provides space for use as primary residence, guest use, or living and workspace during construction. Backs to 41 acres of BLM for added privacy and direct access to recreation. Generator and Greenhouse on site supports homestead or self-sufficient living. Located about 7 minutes to Shady Cove and 15 minutes to Lost Creek Lake. Owner is in the process of obtaining permits and DEQ approval for a new septic system. Due to condition, conventional financing may be limited--buyer to perform due diligence. Altered aerial photos are for illustrative purposes only. Actual design and footprint of homesite will vary, if any homesite is available.

164 Busch Road, Trail

$265,000

220218243 MLS

Owner carry available to qualified buyer! Tucked at the end of a private road, this peaceful 10-acre retreat offers sweeping valley and mountain views with a soulful, off-grid feel. A 4,000-watt solar array with twelve 6V batteries supports true self-sufficiency, complemented by a strong well with solar pump, installed septic, approved homesite, and passive geothermal ducting already in place. The land carries a quiet sense of history with signs of Native American presence, adding depth and connection to the setting. Enjoy full sun exposure, exceptional privacy, and 400 acres of timberland to the west with expansive BLM beyond. Parcel is hidden from the road and accessed by its own private drive. Minutes to the Rogue River and Shady Cove. Photos don't do it justice. This is a must-tour property!

300 Citadel Road, Trail

$549,999

5 Beds ⋅ 3 Baths ⋅ 220216407 MLS

Stills Family Estate | 5.55 Acres | Two Homes | Southern Oregon Country Living This rare multigenerational property offers the kind of space, privacy, and freedom that you have been searching for. Close enough to share life's moments, far enough apart for everyone to have their own. Two fully independent homes on 5.55 acres of Southern Oregon countryside -- each with its own septic and electric meter. Gather the generations, bring the animals, and plant something that lasts. A 3-bay garage, 2-car garage, upper-level studio with expansion potential, and a high-producing filtered well round out this legacy property. Minutes to Shady Cove, the Rogue River, and everything Southern Oregon is known for. Properties like this don't come twice.

778 Ragsdale Road, 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: