Jackson Co: Ashland Homes with 2 Story Style

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 welcoming community, Ashland offers a unique blend of culture and outdoor adventure. With the iconic Oregon Shakespeare Festival at its core, residents and visitors alike enjoy a rich tapestry of theatrical performances, art galleries, and local festivals that celebrate creativity and community spirit.

Ashland is also renowned for its breathtaking views of the surrounding mountains, lush parks, and the tranquil embrace of the nearby Lithia Park, which is perfect for leisurely strolls or picnics with family and friends. The region’s mild climate allows for year-round outdoor activities, from hiking and biking in the summer to skiing and snowboarding in the winter.

When it comes to real estate, Ashland boasts a variety of homes that cater to diverse lifestyles and preferences. Among the most sought-after styles are the charming two-story homes that grace the streets of this picturesque town. These residences often feature spacious layouts, inviting porches, and ample room for families to grow. With their elegant designs and thoughtful craftsmanship, two-story homes provide not just a place to live but a backdrop for creating cherished memories.

Whether you're drawn to the artistic flair of downtown Ashland or the serene beauty of its natural surroundings, this vibrant community offers the perfect setting for your next home. Explore the possibilities today and discover why Ashland, Oregon, is the ideal place to plant your roots!

Newest Jackson Co: Ashland Homes with 2 Story Style

$1,080,000

3 Beds ⋅ 2 Baths ⋅ 221762307 MLS

Set privately back on 5+ acres in the Sunny Oaks community, this custom 3 bed + office, 2.5 bath, 2644 sq ft home pairs open mountain views with easy access to town -- 15 min from Downtown Ashland and near Emigrant Lake. The groundwork for comfortable rural living is in place: a dedicated 1-gigabit fiber line, 300 amp electrical, whole-home water filtration, 2021 Lennox HVAC, irrigation rights, a large cedar-fenced area, and a roof under six years old. Inside, natural light fills an updated kitchen with quartz counters and hardwood floors, opening to a great room, with a separate family room, office, and laundry on the main level. Upstairs, the primary suite offers vaulted ceilings and a balcony framing the same sweeping mountain views as the wraparound deck below, plus two more bedrooms and a full bath. Outside, a gravel RV pad offers water, power, and internet, and a barn with corrals stands ready for horses. With over $200K in updates, the property is move-in ready.

7130 HIGHWAY 66, Ashland

$1,295,000

4 Beds ⋅ 3 Baths ⋅ 660672633 MLS

Platinum Earth Advantage home just minutes from downtown, offering 2,750 sq ft of thoughtfully designed 4BR, 3BA + office living space with stunning views of Grizzly Peak and the Cascades. This light-filled residence features 12’ ceilings, expansive windows, quartz surfaces, designer lighting, and blonde wide-plank hardwood floors. The main level features two ensuite bedrooms, highlighted by a luxurious primary suite with radiant heated floors, dual shower system, and two walk-in closets. The chef’s kitchen boasts an 11-ft island, double ovens, gas cooktop, beverage fridge, and walk-in pantry. Enjoy seamless indoor-outdoor living with an 8’ slider to a spacious view deck. Lower level offers 2 bedrooms, office, second laundry, and potential for separate living. Professionally landscaped, private setting with detached 2-car garage, EV charging, and energy-efficient 2-zone HVAC system. Home designed by Vadim Agakhanov.

852 OAK ST, Ashland

$325,000

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

Start Your Search

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.