Ashland Homes under $300,000

Welcome to Ashland, Oregon—a charming gem nestled in the heart of Jackson County. Known for its vibrant arts scene and stunning natural landscapes, Ashland is a place where culture and community intertwine beautifully. Home to the renowned Oregon Shakespeare Festival, this picturesque town draws visitors and residents alike with its rich theatrical heritage and lively downtown filled with boutique shops, cozy cafes, and delightful eateries. With the majestic Siskiyou Mountains as a backdrop, outdoor enthusiasts can enjoy hiking, biking, and exploring the breathtaking scenery that surrounds this enchanting city.

For those looking to plant roots in Ashland, the housing market offers exciting opportunities, particularly for first-time homebuyers and those seeking affordable options. Homes priced under $300,000 can be found, providing a gateway to experience the allure of Ashland without breaking the bank. Whether you’re searching for a quaint cottage, a modern condo, or a charming bungalow, there’s something for everyone in this welcoming community.

Imagine waking up to the serene beauty of Ashland, with its vibrant seasons and friendly neighborhoods. In addition to its cultural offerings, residents enjoy a strong sense of community and access to quality schools, parks, and local events. With homes under $300,000, Ashland presents an inviting opportunity for anyone looking to embrace the charm of this unique city. Come explore Ashland, where your dream home awaits amidst the stunning backdrop of Oregon’s natural beauty and a thriving community spirit!

Newest Ashland Homes under $300,000

$175,000

3 Beds ⋅ 1 Baths ⋅ 220229064 MLS

Excellent opportunity to build your dream home! Conveniently located near the future site of East Main Park, this property offers the potential to create a custom home in an area positioned for future neighborhood amenities. Offered for sale via online auction. Opening bid meets reserve and will sell to the highest bidder. A 5% buyer's premium will be added to the winning bid. The property will be sold in its present ''AS IS, WHERE IS'' condition, with no financing or inspection contingencies. A large Fremont Cottonwood, designated as a Heritage Tree, provides shade and adds character to the property. Buyers should be aware that removal of the Cottonwood requires a Tree Removal Permit in accordance with City requirements. See Gov Deals for more information, disclosures, and auction terms and conditions.

380 Clay Street, Ashland

Listing courtesy of Bang Realty-Oregon Inc..

$195,000

1 Beds ⋅ 1 Baths ⋅ 220228771 MLS

Location, location, location! Located in the fabulous 55+ Mountain Meadows Community, this charming ground level 1 bed + office, 1 bath, 872 sq ft condo is perfect for anyone looking for a low maintenance property! Owner spared no expense over the last 2 years by replacing the HVAC system, replacing flooring throughout with new luxury vinyl plank & carpeting, & painting the entire interior. Floor plan is ADA compliant (wider doorways and open floor plan). Kitchen is spacious w/ ample cabinetry, dining space, and working appliances. Covered front porch provides shade while you gander at the mountainside. Only one neighbor above you (no neighbors on the left and right), allows enhanced privacy from the rest of the community. Dedicated parking and additional storage room are included as well! Mountain Meadows Community is absolutely lovely and includes dining, clubhouse, fitness center, pool, community events, & much more!

853 Pavilion Place, Ashland

Listing courtesy of John L. Scott Medford.

$184,600

220227685 MLS

1977 456 sq ft cottage. 40 acres wooded. Neither the brokers, brokerage, or Jackson County warrants, nor can verify property condition, description, fixtures, permits, hazardous substances, zoning, history of illegal activity, or tax history. No guarantee of access, no sign. ''As Is'' sale. Listing brokerage does not accept bids or offers on Jackson County Taxation's behalf for these properties. There will be one public, in-person, oral auction per year held at the County Courthouse, 10 S Oakdale Ave, Medford, OR 97501, in the Auditorium, located on the first floor of the main building. Auction date is: OCTOBER 12, 2026 @ 10 AM. Brokers and brokerage do not represent the date or process, Buyer to verify process and date for accuracy.

13099 Old Hwy 99 S, Ashland

Listing courtesy of Coldwell Banker Professional Group.

$279,000

2 Beds ⋅ 1 Baths ⋅ 220224865 MLS

This Beautiful, turn key ready 2-bed / 1 bath condo, within a short walk to downtown Ashland, coffee shops , restaurants , shopping, & Southern Oregon University . Nice and bright natural light throughout with skylights in the living area. The kitchen has granite counters with stainless-steel appliances. Open floor plan flows into a spacious great room with 9ft ceilings and plenty of windows to take in the surrounding mountain views including Grizzly peak. Natural Fir doors and trim throughout. Ductless heating and air. Don't be fooled by the sq ft, this condo has a feel that it is much bigger. A modern and aesthetically pleasing living space in a small association. The furniture is included in the sale. Don't miss out on this rare opportunity to own a low maintenance home in Ashland. The unit is upstairs. Sellers are open to offers.

1249 Iowa, Ashland

Listing courtesy of RE/MAX Platinum.

7979 Hyatt Prairie Road 42 Unit 42, Ashland

$235,000

2 Beds ⋅ 1 Baths ⋅ 220223508 MLS

The cabin of your dreams is waiting for you just 35 minutes from downtown Ashland at The Cabins at Hyatt Lake. Tucked into the trees near the shores of the Lake, this peaceful mountain getaway offers the kind of escape people search for and rarely find. With one of the larger and more desirable layouts, the added bump-out creates extra room to relax, gather, and enjoy every season. Vaulted wood ceilings, warm natural light, and a spacious open living area create an inviting place to unwind after a day on the lake, hiking nearby trails, or winter adventures in the snow. Step outside to the wraparound deck, enjoy coffee in the crisp mountain air, soak in the hot tub, and take in the quiet forest setting. Never used as a rental, this fully furnished retreat is truly turnkey. Main-level bedroom and bath, loft sleeping space above, and an oversized shared 2-car garage for boats, gear, and toys complete the package. Just a short walk to the lake and endless outdoor recreation year-round.

7979 Hyatt Prairie Road 42 Unit 42, Ashland

Listing courtesy of eXp Realty, LLC.

$180,000

1 Beds ⋅ 1 Baths ⋅ 220219632 MLS

Beautiful refreshed condo in the award-winning Mountain Meadows 55+ community. This ground-level home features its own private front porch and easy access from North Mountain. New vinyl plank flooring has been installed throughout and the open kitchen offers a breakfast bar that is perfect for casual dining, cooking, and conversation. An additional flex room provides great space for an office, TV room, or guest area. Light and bright throughout, including the spacious primary and main living areas, adding to the thoughtful layout and convenience this inviting home provides.

851 Pavilion Place, Ashland

Listing courtesy of RE/MAX Platinum.

$130,000

1 Beds ⋅ 1 Baths ⋅ 220219091 MLS

Step into a bright, beautifully cared-for top-floor condominium featuring a vaulted living room ceiling, expansive windows, and a seamless flow that makes the space feel both open and inviting. The well-appointed kitchen offers generous counter space, ample cabinetry, and a cozy dining area. Step outside onto your private balcony--perfect for relaxing evenings and fresh air. The spacious bedroom connects easily to a well-designed bathroom with a low-step shower and built-in linen storage, while a full-size washer and dryer add everyday convenience. Located just moments from the clubhouse and fitness center, with easy elevator access to parking and storage, this home blends accessibility with comfort. Enjoy a vibrant, amenity-rich lifestyle with beautifully maintained grounds, walking paths, gardens, an indoor pool, fitness center, and a welcoming calendar of social events, gatherings, and activities.

943 Mountain Meadows Circle, Ashland

Listing courtesy of Full Circle Real Estate.

$159,900

2 Beds ⋅ 1 Baths ⋅ 220212880 MLS

Welcome to your perfect Southern Oregon Retreat at 16170 Highway 66 in Ashland! This charming 2-bedroom, 1-bathroom single-wide home offers 840 square feet of comfortable living space on a generous .59-acre lot, providing the ideal blend of cozy functionality and outdoor potential. Whether you're seeking a peaceful vacation getaway just minutes from Ashland's renowned cultural attractions, wineries, and outdoor recreation, or looking for a smart investment property in one of Oregon's most desirable destinations, this well-proportioned home delivers exceptional value. The spacious lot offers room for gardening, outdoor entertaining, or simply enjoying the natural beauty of the Rogue Valley, while the efficient floor plan ensures easy maintenance and comfortable year-round living. Don't miss this rare opportunity to own an affordable piece of Ashland's lifestyle at an attractive price point!

Ashland

Listing courtesy of John L. Scott Medford.

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