Trail Homes with Three Or More Stories

Welcome to Trail, Oregon—a hidden gem nestled in the heart of Jackson County, where natural beauty meets a tight-knit community. This charming town is surrounded by stunning landscapes, including the majestic Cascade Mountains and the serene waters of the Rogue River, making it an ideal destination for outdoor enthusiasts and nature lovers alike. With a population that values community spirit and a rich history, Trail offers a unique blend of small-town charm and breathtaking scenery.

One of the standout features of this picturesque area is its diverse real estate market, particularly the availability of homes with three or more stories. These spacious residences provide ample room for families to grow and create lasting memories. Imagine waking up to panoramic views of the surrounding mountains or enjoying a sunset from your private balcony—homes in Trail are designed to embrace the beauty of the outdoors while offering modern comforts.

Whether you’re seeking a cozy retreat or a grand family home, the three-story properties in Trail often come equipped with expansive living spaces, multiple bedrooms, and versatile layouts that can accommodate various lifestyles. Many of these homes also feature beautifully landscaped yards perfect for entertaining or simply enjoying a peaceful evening under the stars.

In addition to the stunning homes, Trail boasts a welcoming community spirit with local events, parks, and recreational activities that foster connections among residents. With its breathtaking landscapes and vibrant community, Trail, Oregon, is not just a place to live; it’s a place to thrive. Come discover your dream home in this enchanting town, where adventure awaits at every corner!

Newest Trail Homes with Three Or More Stories

$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

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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: