Jackson Co: Ashland Homes with Second Garage Exterior features

Welcome to Ashland, Oregon – a picturesque gem nestled in the heart of Jackson County. Known for its stunning natural landscapes and vibrant arts scene, Ashland is a haven for outdoor enthusiasts and culture lovers alike. With the majestic Siskiyou Mountains as your backdrop, this charming city boasts an array of recreational activities, from hiking and biking to world-class skiing in the winter months. Home to the renowned Oregon Shakespeare Festival, Ashland offers a unique blend of artistic flair and small-town warmth, making it an ideal place to call home.

In this enchanting region, you’ll discover homes that not only provide comfort and style but also cater to your lifestyle needs. One standout feature of many properties in Ashland is the second garage. Whether you’re a car enthusiast, need extra storage space, or require a workshop for your hobbies, these homes with second garages offer versatility that enhances your living experience. Imagine having a dedicated space for your outdoor gear, crafting projects, or even a cozy retreat away from the hustle and bustle of everyday life.

The exterior features of these homes are just as captivating, often showcasing beautiful landscaping, inviting patios, and outdoor entertainment areas that seamlessly blend with the natural beauty surrounding them. In Ashland, you can enjoy the perfect balance of tranquility and community, with easy access to local shops, restaurants, and parks. If you’re searching for a place that embodies both charm and functionality, Ashland is the perfect destination to find your dream home with that coveted second garage. Embrace the lifestyle you’ve always wanted in this vibrant and welcoming city!

Newest Jackson Co: Ashland Homes with Second Garage Exterior features

$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

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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: