O'Brien Homes with Two Stories

Welcome to O'Brien, Oregon – a hidden gem nestled in the heart of Josephine County. This charming community is surrounded by breathtaking natural beauty, making it an ideal place for those seeking a tranquil lifestyle while remaining connected to the wonders of the great outdoors. With its lush forests, rolling hills, and proximity to the stunning Rogue River, O'Brien offers residents a picturesque backdrop for their everyday lives.

In O'Brien, you’ll find a delightful array of homes, including spacious two-story residences that cater to families and individuals alike. These homes are designed to maximize space and comfort, providing ample room for gatherings, hobbies, or simply enjoying a quiet evening at home. The two-story layout not only enhances the living experience but also allows for stunning views of the surrounding landscape from upper-level windows and balconies.

Living in O'Brien means embracing a lifestyle that balances serenity with adventure. The nearby Siskiyou National Forest offers endless opportunities for hiking, fishing, and exploring the rich biodiversity of the region. Additionally, the community is known for its friendly atmosphere, where neighbors become friends and local events bring everyone together.

Whether you’re looking for a cozy retreat or a family-friendly environment, O'Brien’s two-story homes provide the perfect canvas for creating lasting memories. Experience the charm of this unique community and discover why O'Brien, Oregon, is the ideal place to call home. Come explore the possibilities that await you in this enchanting part of the Pacific Northwest!

Newest O'Brien Homes with Two Stories

$130,000

220223853 MLS

Opportunity awaits at 33105 Redwood Highway in O'Brien, Oregon. This flat 2.84-acre Commercial/Rural zoned property offers excellent visibility along a well-traveled route between Southern Oregon and the coast. Newly fenced and featuring a brand-new well, plus a second well for irrigation, this property is ready for someone with vision. The existing teardown structure helps preserve a potential homesite, creating the possibility for a commercial use with residential living on-site. Located next door to a popular restaurant and across from a gas station, the property benefits from steady everyday traffic and convenient surrounding businesses. With its usable acreage and zoning, this could be an ideal location for a food stand, mini farm, bakery, roadside market, or other creative commercial venture. Bring your ideas and explore the potential this unique investment property has to offer. Schedule your showing today!

33105 Redwood Highway, O'Brien

$335,000

1 Beds ⋅ 2 Baths ⋅ 220221104 MLS

Built by hand, with love, over years -- and it shows. This thoughtfully crafted home on Arrowhead Drive sits beneath a cathedral of tall timber on land that has been carefully cleared and kept beautiful. Wood finishes, skylights, a loft, a wood stove, and a master suite that sits just apart from the main house (easily connected with a simple alteration). A separate ~600 sq ft building serves as studio, ADU, office, or creative space -- your call. Covered carport, woodshed, garden shed, and a genuine sauna round out a property that feels rare because it is. This is a home built with intention, and it carries that feeling in every room.

555 Arrowhead Drive, O'Brien

$249,999

3 Beds ⋅ 1 Baths ⋅ 220219139 MLS

Needs remodel

1005 Naue Way, O'Brien

$235,000

3 Beds ⋅ 1 Baths ⋅ 220217244 MLS

Private and peaceful 20-acre property tucked behind a gated entrance and bordering BLM land. Where nature takes center stage, this is a place to truly unplug- a deeply restorative setting and your own private wilderness sanctuary. The 1,300+ sq ft cabin is solid and well-insulated with tongue-and-groove pine walls, a handcrafted hearth, and a flexible 7-room layout. The main level offers multiple living spaces with potential for bedrooms, while the upper level includes additional rooms, a loft, and storage. Newer metal roof. Off-grid setup with solar and generator power. The well produces approximately 14 GPM and feeds a holding tank with gravity flow to the cabin. Natural spring on the property. The land features a mix of mature trees, usable terrain, fenced garden area, greenhouse, mini barn, and an orchard with apple, pear, plum, fig, and persimmon trees. Additional features include a porch, sauna, outhouse, and outdoor bathing area with hot water. Ideal for a homestead or getaway!

1259 Waldo Road, O'Brien

$995,000

2 Beds ⋅ 3 Baths ⋅ 220214505 MLS

Nestled on 80 private acres along the scenic Redwood Highway, this unique 2-bedroom, 2.5-bath property offers privacy, space, and rustic charm. The home features a cozy cabin-style feel with a distinctive artistic design, open living areas, and a loft that provides flexible space for guests, an office, or hobbies. Fully off-grid, this property is ideal for those seeking a self-sufficient lifestyle. Enjoy peaceful mornings overlooking your private pond, surrounded by beautiful forested landscapes, three forest views, and expansive territorial scenery. A detached 2-car garage and covered RV parking provide plenty of room for vehicles, equipment, and recreational toys. The tractor and all attachments are included, adding value and convenience for maintaining the acreage. With abundant wildlife, open skies, and endless opportunities to explore or relax, this one-of-a-kind Southern Oregon retreat is perfect as a full-time residence, recreational property, or private getaway.

37010 Redwood Highway, O'Brien

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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: