Trail Homes for Sale

Welcome to Trail, Oregon – a hidden gem nestled in the scenic beauty of Jackson County! This charming community offers a unique blend of small-town warmth and breathtaking natural surroundings, making it an ideal destination for those seeking a peaceful lifestyle amidst nature's splendor.

Trail is surrounded by the majestic Cascade Mountains and is just a stone's throw away from the stunning Rogue River. Whether you're an outdoor enthusiast or simply looking to escape the hustle and bustle of city life, Trail provides endless opportunities for adventure. Hiking, fishing, and camping are just a few of the activities that await you in this picturesque locale.

As you explore the homes for sale in Trail, you'll discover a variety of options suited to different tastes and budgets. From cozy cabins perfect for weekend getaways to spacious family homes with stunning views, there’s something for everyone. Many properties boast expansive yards, allowing you to soak in the serene atmosphere and enjoy the fresh mountain air. The real estate market here is both inviting and competitive, making it an opportune time to invest in your dream home.

Trail's close-knit community is another highlight, where neighbors become friends and local events foster a sense of belonging. With its rich history, vibrant culture, and stunning landscapes, Trail is not just a place to live; it's a place to thrive. Come and discover the charm of Trail, Oregon, and find your perfect home in this enchanting corner of the world!

Newest Trail Homes for Sale

$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

$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

$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

$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

$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

$725,000

2 Beds ⋅ 3 Baths ⋅ 220214205 MLS

Gorgeous 2512 sf home w/ 156.04-acres of recreational property offering privacy, abundant wildlife, and sweeping 360-degree mountain views. Located near Rogue River trophy fishing waters and minutes from Lost Creek Lake, this property provides exceptional access to fishing, boating, hunting, and outdoor adventure. The 2,512 sq ft home is designed for multi-generational living, featuring a main-floor private suite with full bath and French doors, an open-concept living area with high ceilings, wood-burning fireplace, and a kitchen with eat-bar seating, stainless appliances, and tile backsplash. A dedicated office and guest half bath add flexibility. Upstairs, a loft-style living space opens to a view deck and a private primary suite with walk-in shower, soaking tub, double vanity, and walk-in closet. The land includes open and wooded terrain, greenhouse, woodshed, fenced paddocks, a cleared shooting range area, and fully owned solar--ideal for outdoor enthusiasts.

12594 McNeil Creek Road, Trail

$519,900

3 Beds ⋅ 2 Baths ⋅ 220211814 MLS

Freshly remodeled 3-bedroom, 2-bath home featuring 1,911-sq. ft. of spacious, open living filled with natural light! Enjoy breathtaking mountain views and abundant wildlife from every room. The home offers a new kitchen with butcher block counters, freshly updated bathrooms, laminate flooring throughout, wood-burning fireplace, expansive decking, durable metal roof, and new mini splits for year-round comfort. Plenty of room for all your toys, projects, and hobbies on 21.51-private acres. The property backs up to over 2,500-acres of public lands, providing endless opportunities for hunting, trail riding, hiking, and outdoor recreation in every season. Just 7 minutes from Shady Cove, this home combines privacy, comfort, and adventure, making it a true nature lover's paradise where every day feels like a getaway.

5015 Highway 227, 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: