Trail Real Estate

Welcome to Trail, Oregon – a hidden gem nestled in the picturesque landscapes of Jackson County. With a population of just over 300 residents, this charming small town offers a sense of community that is hard to find in larger cities. Surrounded by the stunning beauty of the Cascade Mountains, Trail is perfect for those who appreciate the great outdoors and a slower pace of life.

The town is situated along the banks of the scenic Rogue River, providing residents and visitors with ample opportunities for fishing, rafting, and hiking. The nearby Siskiyou National Forest is a playground for nature enthusiasts, offering miles of trails, breathtaking vistas, and a chance to immerse yourself in Oregon's diverse wildlife. Whether you’re an avid hiker or simply love to enjoy a quiet afternoon in nature, Trail has something for everyone.

Trail's community spirit shines through in its local events and gatherings, where neighbors come together to celebrate the town’s rich history and natural beauty. The historic downtown area features quaint shops and eateries, providing a cozy atmosphere for residents and visitors alike.

For families, Trail offers a welcoming environment with excellent schools and recreational facilities, making it an ideal place to raise children. The town is also conveniently located just a short drive from the larger city of Medford, where you can access a wider range of amenities and services.

If you're seeking a tranquil lifestyle surrounded by nature, Trail, Oregon, is a perfect choice. Discover the charm of this enchanting town and envision your future in this beautiful corner of the Pacific Northwest.

Newest Listings in Trail

$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

$795,000

220223365 MLS

This property is a wonderful find! It is a riverfront property with a convenience store, one pump gas station, manager's home, cabin, vacation rental, and river rafting rentals, all rolled into one! Cash and credit both. The original structure was built in 1928, and the present owners have been operating ''Sunset on the Rogue'' for the past 33 years. It is a wonderful spot to rent raft, picnic, have a hamburger from the market, or stay in a vacation rental. It is close to Lost Creek Lake, on the way to Crater Lake, and has world-class fishing right off the bank. The convenience store is adjacent to the main manager/owner's home. It has been updated and is very comfortable with hardwood floors, and an open floorplan. One of a kind riverfront property on a desirable steelhead fishing location. Your chance to own a special Southern Oregon riverfront retreat.

26876 OR-62, Trail

$420,000

3 Beds ⋅ 2 Baths ⋅ 220222703 MLS

Amazing hilltop property with views! This 3-bedroom, 2-bathroom home offers 1,188-SF of comfortable living space on 5.14-acres backing directly to nearly 500-acres of BLM land. Enjoy unmatched privacy, abundant wildlife, hiking trails, and endless outdoor exploration right out your back door. The property features two separate driveway entrances--one leading to the home and another providing easy access to a flat meadow area ideal for gardening, animals, equipment, or future projects. The home includes a roof that's only 5-years old, new paint inside and out, plus a new well with a 2,000-gallon holding tank for added peace of mind. A huge shop offers incredible flexibility with a car lift, ample workspace/storage, and additional living quarters complete with a full bathroom. A rare combination of seclusion, functionality, and outdoor living!

235 Citadel Road, Trail

$559,000

3 Beds ⋅ 3 Baths ⋅ 220221847 MLS

Escape to your private 10+ acre wilderness sanctuary! This grand log home perfectly blends rustic luxury with ultimate functionality. The property backs up to BLM land for unmatched privacy & boasts spectacular, views of the Cascade Mtns. Inside find breathtaking, open-beam vaulted ceilings and a warm, inviting living space centered around a brick-surrounded pellet stove. The highly versatile floor plan offers 2 spacious main-level bdrms. Upstairs, discover a privately tucked-away primary suite complete with an en-suite bath and flexible loft area. Large, functional kitchen features abundant storage, walk-in pantry, and an adjacent dedicated laundry room. The exterior features an oversized garage with built-in shop area, plus dedicated RV parking. Embrace outdoor living on the massive, 932 sq ft covered porch, perfect for morning coffee or sunset views. A dream property for hobbyists, outdoor enthusiasts and travelers alike!

275 Citadel Road, Trail

$335,000

220221427 MLS

Beautiful mountain land bordering USA land, giving you a larger backyard for hunting, hiking and nice buffer from anyone else. Just minutes to Shady Cove which has your shopping, medical, dentist, library and all things needed for comfort. Also, at the gateway to all things recreational. This 20+- homesite has electric, well with abundant water and septic all ready for you. Enjoy the quiet seclusion and whispering pines of the great North West. Just minutes to the Rogue River and Lost Creek Lake for fishing, rafting, hiking and on the way to Crater Lake' you couldn't ask for a nicer place to live. Final lot size will be provided in legal lot survey prior to close of escrow. Additional lots contiguous to this if you want family nearby or community type living, private access to property.

3860 Highway 227, 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

$499,000

4 Beds ⋅ 2 Baths ⋅ 220219353 MLS

Beautifully updated 4-bedroom, 2-bath home offering 2,025 sqft on 3.92 private acres in a peaceful forest setting with fruit trees, gated entry, RV parking, and a circular (roundabout) driveway. Nearly every major component has been upgraded--new roof, siding, paint, windows, decks, gutters, and exterior lighting with security cameras. Enjoy peace of mind with a new breaker box, power drop, meter base, well pump, pressure tank, and 2,500-gallon water storage system. Inside features modern comfort with PEX plumbing, remodeled bathrooms, fresh interior paint, new flooring (carpet & LVP), updated lighting, new kitchen cabinets, appliances, and added laundry. Detached double-wide carport included. Seller willing to sell mostly furnished (minus a few items). A rare turnkey property combining privacy, space, and extensive upgrades--move-in ready!

6481 Highway 227, 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

$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: