Jackson Co: Ashland Real Estate

Welcome to Ashland, Oregon – a charming gem nestled in the heart of Jackson County. Known for its vibrant arts scene, stunning natural landscapes, and a strong sense of community, Ashland is a place where small-town charm meets cultural richness.

Ashland is perhaps best known as the home of the Oregon Shakespeare Festival, one of the oldest and most prestigious theater festivals in the United States. Each year, thousands flock to this picturesque town to enjoy world-class performances, making it a cultural hub that attracts artists, performers, and theater enthusiasts alike. Beyond the stage, the town boasts a plethora of galleries, local artisans, and live music venues that contribute to its dynamic creative atmosphere.

Nature lovers will find Ashland equally enchanting. Surrounded by the breathtaking Cascade Mountains and the stunning landscapes of the Rogue Valley, residents and visitors can explore an array of outdoor activities, from hiking and biking to skiing and river rafting. The nearby Lithia Park, with its beautiful gardens and serene ponds, offers a perfect escape for leisurely strolls and picnics.

Ashland’s community is as welcoming as its scenery. With a rich history and a commitment to sustainability, the town embraces a lifestyle that values local businesses, farmers' markets, and community events. The annual Ashland Independent Film Festival and the Ashland Culinary Festival are just a few examples of how this town celebrates creativity and connection.

Whether you’re seeking a vibrant community, cultural experiences, or outdoor adventures, Ashland, Oregon, offers a unique blend of all these elements, making it a wonderful place to call home. Come discover the magic of Ashland, where every day feels like a work of art!

Newest Listings in Jackson Co: Ashland

$325,000

1 Beds ⋅ 1 Baths ⋅ 495266734 MLS

This 1br/1bath 2nd-floor corner condo greets you w/ sunlight pouring through generous windows, illuminating the inviting finishes that give the space its timeless, easy charm. Its open floor plan unfolds naturally, with the living area flowing into the kitchen with abundant counter space, ample storage, & brand-new appliances waiting to be used for the very first time. You'll love spending your mornings on your private balcony gazing out toward the Cascade Mountains as the light shifts across the peaks. Even workdays feel lighter here, thanks to a dedicated office nook that keeps productivity close to comfort. With its own dedicated laundry area & built-in storage, even the practical parts of life feel organized & beautifully tucked away. Perfectly located minutes from downtown Ashland, the Oregon Shakespeare Festival, shopping, dining, & scenic hiking/ biking trails -- with quick access to I-5 & just 30 minutes north of the California state line -- you're moments from everything!

2205 ASHLAND ST Unit #210, Ashland

$950,000

3 Beds ⋅ 4 Baths ⋅ 786738387 MLS

Set among more than 37 private acres in the beautiful Siskiyou Mountains, this remarkable property offers space, privacy and versatility within easy reach of Ashland and the Rogue Valley. Mt. Ashland Ski Area, Emigrant Lake and the Pacific Crest Trail are all just minutes away, putting some of Southern Oregon’s best outdoor recreation close at hand.The thoughtfully designed main residence captures the warmth and character of its surroundings. Soaring wood-clad ceilings, exposed beams, expansive windows and a striking stone fireplace create a dramatic yet inviting great room filled with natural light. The open layout flows into a spacious gourmet kitchen with abundant cabinetry and prep space, full-size refrigerator and freezer, double ovens and a generous island—equally suited to everyday living or gathering with family and friends. A dedicated media room provides another comfortable place to relax, while geothermal heating and cooling and a hard-wired generator add year-round comfort and peace of mind. A detached four-car garage offers exceptional space for vehicles, storage and more.A substantial auxiliary building adds another dimension to the property, featuring a large finished open area, kitchen, full bath and three-car garage. With room for hobbies, recreation, a studio, workshop or a variety of other uses, the space provides tremendous flexibility to adapt to your needs.Additional features include a charming loft studio, greenhouse, garden areas and abundant water storage. Wooded acreage, natural rock outcroppings, a creek and abundant wildlife create a peaceful setting with room to explore, garden or simply enjoy the natural beauty that surrounds you.Thoughtfully designed, quality built and carefully maintained, this distinctive property combines the space and privacy of a rural setting with convenient access to Ashland, the Rogue Valley and all that Southern Oregon has to offer.

5831 OLD HIGHWAY 99, Ashland

$299,000

693671412 MLS

Step into a world of pristine natural beauty, remarkable solitude, and boundless potential with this extraordinary ±78-acre property, nestled in the heart of Southern Oregon’s picturesque Colestin Valley. Offering commanding panoramic views, rich ecological diversity, and a peaceful ambiance that feels worlds away from the bustle of daily life, this land is more than just real estate—it’s a legacy in the making.Bordering the western edge of the renowned Cascade-Siskiyou National Monument, this unique parcel features a stunningly varied topography that includes a prominent knoll-top view site, gently undulating hills, timbered draws, and open meadows. Whether you're drawn by the call of nature, inspired by the land’s tranquility, or envisioning a future full of off-grid potential, this property delivers on every front. Outdoor enthusiasts will relish the opportunity to hike, hunt, camp, and rockhound on their own land, all while sharing space with abundant wildlife such as deer, wild turkey, black bear, and even the occasional elk.Just minutes from the iconic Pacific Crest Trail and a short drive to some of the region’s most treasured destinations—including Pilot Rock, Mt. Ashland Ski Area, Emigrant Lake, and majestic Mt. Shasta—this property is perfectly positioned for adventure and exploration. Whether you're seeking seclusion or inspiration, you’ll find both here. Buyer to perform and satisfy all due diligence regarding the property and its permitted uses.

COLESTIN RD, Ashland

$358,000

2 Beds ⋅ 1 Baths ⋅ 22257576 MLS

Rare opportunity to own a true off-the-grid retreat that is completely surrounded by thousands of acres of BLM land! This unique offering boasts privacy and security that are often only dreamt about. Developed by the founders of Home Power magazine and designed to be a model for off-grid and self-sustainable living. Esive solar array and battery bank powers the property and is backed up with generators. The uniqueness, privacy, and ability to live sustainably make this a rare opportunity.

10000 COPCO RD, Ashland

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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:

Jackson Co: Ashland Real Estate

Newest Listings in Jackson Co: Ashland

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