Ashland Homes under $400,000

Welcome to Ashland, Oregon – a picturesque gem nestled in the heart of Jackson County. Known for its vibrant arts scene, stunning natural beauty, and a rich cultural heritage, Ashland offers a unique blend of small-town charm and urban sophistication. Home to the renowned Oregon Shakespeare Festival, this enchanting city attracts visitors and residents alike with its lively atmosphere and engaging community events.

Ashland is not just a haven for the arts; it also boasts breathtaking landscapes, from the majestic peaks of the Siskiyou Mountains to the serene waters of Ashland Creek. Outdoor enthusiasts will revel in the abundance of recreational activities available, including hiking, biking, and skiing in the nearby mountains. With a mild climate, residents can enjoy the great outdoors year-round.

For those looking to make Ashland their home, the real estate market has some fantastic opportunities, especially for homes under $400,000. Whether you’re a first-time buyer or seeking a cozy retreat, Ashland offers a variety of charming residences that fit within your budget. From quaint bungalows to modern townhomes, the housing options cater to diverse tastes and lifestyles.

Living in Ashland means being part of a close-knit community that values sustainability, creativity, and connection. With excellent schools, local farmers' markets, and a plethora of dining options, you’ll find everything you need right at your doorstep. Embrace the Ashland lifestyle and discover your dream home in this beautiful Oregon city today!

Newest Ashland Homes under $400,000

$345,000

2 Beds ⋅ 2 Baths ⋅ 220229497 MLS

Contemporary, south-facing, single-level condo with natural light, privacy, and views of the Siskiyous and Mt. Ashland. This beautifully maintained two-bedroom, two-bathroom home features quality finishes and a thoughtful layout. Built-in bookshelves and a gas fireplace bring warmth to the living room. The kitchen offers granite countertops, solid beech wood cabinetry, and stainless steel appliances. The spacious primary bedroom includes an en suite bath and large walk-in closet. A sunny patio off the living room is ideal for morning coffee or outdoor dining. A dedicated underground garage parking space and elevator access add everyday convenience. Located near North Mountain Park and just minutes from downtown Ashland.

618 Fair Oaks Court, Ashland

Listing courtesy of Full Circle Real Estate.

$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..

$317,000

2 Beds ⋅ 2 Baths ⋅ 220229021 MLS

Charming 2004 built Victorian-style townhouse offering the perfect blend of classic character and modern convenience. This inviting end unit features 2 bedrooms and 1½ baths, with wood floors extending through the entry and living room. The comfortable floor plan offers a warm, welcoming living space with plenty of natural light and easy flow. Step outside to the back deck, ideal for relaxing, enjoying your morning coffee, or entertaining friends. As an end unit, this home offers added privacy and a desirable setting. Conveniently located near schools, shopping, dining, and everyday amenities, this delightful townhouse is a wonderful opportunity for comfortable, low-maintenance living with plenty of charm. Note, all tenant possessions have been removed from all photos.

49 California Street, Ashland

Listing courtesy of Millen Property Group.

$312,000

2 Beds ⋅ 2 Baths ⋅ 220228812 MLS

Nature meets urban convenience in this ideal Ashland home! Experience treetop living in this meticulously maintained, second story, one level condo. Enjoy an abundance of natural light in this open-concept home with bright, large kitchen and a living room with direct views of Grizzly Peak. The spacious private deck provides outdoor enjoyment. The two large bedrooms offer large closets and mountain views. Both full bathrooms have shower-tub combos and plenty of cabinet space. Updates include a new HVAC system (2025) and new fire-resistant hardi-plank siding (2024). Washer, dryer, and appliances are included. There is one dedicated carport space and the newly resurfaced drive and parking areas provide guest parking. Close to restaurants, shopping, and the YMCA. Easy freeway and school access, as well.

295 Tolman Creek Road 7 Unit 7, Ashland

Listing courtesy of Windermere Van Vleet & Associates.

$190,000

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.

$339,000

3 Beds ⋅ 2 Baths ⋅ 220228753 MLS

Tucked away in a unique and private setting just off Park Street, this charming end unit condominium offers comfort, convenience, and a little extra privacy. The home has been refreshed with new interior paint, new carpet, and an updated HVAC in 2018. The living area is clean and inviting ready for you to personalize as your own. Just off the family room is an open concept dining nook and kitchen. 3 spacious bedrooms make up the upstairs with a full bathroom for convenience. Enjoy your own private fenced yard along with a one car attached garage. This is a desirable location with upgrades that provide a modern aesthetic, while providing a move in ready home.

669 Park Street, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

$325,000

3 Beds ⋅ 2 Baths ⋅ 220228497 MLS

Charming 1910-built home offering 3 bedrooms on a spacious .32-acre lot in desirable Tolman Creek. This property presents a wonderful opportunity to enjoy the character and appeal of an older home while taking advantage of a generous lot with plenty of space and potential. Conveniently located in a sought-after area, this is a rare opportunity to own a piece of local history with room to make it your own.

795 Tolman Creek Road, Ashland

Listing courtesy of John L. Scott Medford.

$399,000

2 Beds ⋅ 2 Baths ⋅ 220228254 MLS

Peaceful country living opportunity on 6.65 acres nestled amongst the madrones, not far from downtown Ashland! The custom primary residence offers 2 beds/2 baths with a stonework entryway, pine paneling and cabinetry in the kitchen, a cozy wood stove, large windows, a metal roof, and an attached garage. A versatile bonus room adapts to a creative workshop, office, or extra bedroom. Outside, a spacious deck and flat yard lead to an impressive shop built from steel shipping containers, offering a large open workspace with a professional-grade engine hoist, ample storage, and hydraulic hangar-style doors. Down the hill, a quaint cabin in the woods offers multigenerational living, income potential, or home office space, with a full kitchen, bath, and sleeping loft. Outdoor lovers will appreciate the unbeatable access to Mt. Ashland and the Pacific Crest Trail.

5010 Old Highway 99 S, Ashland

Listing courtesy of John L. Scott Ashland.

$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.

$375,000

2 Beds ⋅ 1 Baths ⋅ 220227291 MLS

Just minutes from downtown Ashland, this light-filled single-level home offers comfort, convenience, and room to grow. The living and dining areas feel unexpectedly spacious thanks to the natural light, while laminate flooring and ductless heating and air add everyday ease. Two large bedrooms and a framed-in porch create flexible living and storage options. The refreshed kitchen makes cooking simple, and the generous yard, parking space, and detached shed support all your outdoor hobbies. Development potential, buyers to verify options with the city.

1342 E Main Street, Ashland

Listing courtesy of John L. Scott Ashland.

$400,000

2 Beds ⋅ 1 Baths ⋅ 220227289 MLS

Charming cottage just minutes from downtown Ashland, filled with great natural light. This two-bedroom, one-bath home features updated vinyl flooring and windows throughout. The oversized kitchen offers white cabinetry, an electric range/oven, and abundant storage. Enjoy surrounding mountain views from the front deck, or relax in the large fenced backyard with garden space and a concrete patio ideal for outdoor entertaining. Development potential--buyers to perform their own due diligence with the city regarding options.

1340 E Main Street, Ashland

Listing courtesy of John L. Scott Ashland.

$379,900

2 Beds ⋅ 1 Baths ⋅ 220227252 MLS

Built in 2022 with an emphasis on efficiency, simplicity, and modern design, this Earth Advantage-certified cottage offers an easy, comfortable way to live. The bright, open interior features vaulted ceilings, abundant natural light, and contemporary finishes throughout. The kitchen pairs quartz countertops with stainless steel appliances and a convenient breakfast bar, creating a stylish and functional heart of the home. Outside, the fully fenced yard is an exceptional extension of the living space, with a private patio and room for gardening, dining, or simply enjoying the mountain views. As part of a shared solar community, the home is designed with energy efficiency and lower operating costs in mind. With its manageable size, low-maintenance design, outdoor space, and modern construction, this two-bedroom, one-bath home is a smart opportunity for anyone looking for a newer home without the upkeep of a larger property.

583 Coffee Lane, Ashland

Listing courtesy of Millen Property Group.

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