Ashland Oregon homes for sale starting at Fifty Thousand Dollars

$3,900,000 - Ashland, OR

786 Pompadour Drive Ashland, OR - Paradox Vineyard Estate is uniquely defined by elements of water, air, the natural light and beauty of the Rogue Valley, and a resounding commitment to environmental stewardship. Award-winning architecture and landscape design implemented by reputable local contractors with the highest caliber of building materials certified through LEED, Energy Star, and Green Globes. Senses are captivated by a soaring skylight galleria spanning through the home, four open-air water courts with columnar basalt fountains, and stunning panoramic mountain views. Tranquil and private outdoor spaces with mature plantings and ornamental trees encircle the home, including an in-ground spa and lap pool. Vineyard operations are professionally managed for continued turn-key production of organic grapes acclaimed by local and regional winemakers. Close-in rural community of high-end estates located within five miles of Ashland's downtown plaza. Inquire for additional details and documentation!

$3,800,000 - Ashland, OR

99 Granite Street Ashland, OR - This extraordinary Greene and Greene inspired Craftsman home will not disappoint. No expense was spared and this turn-key estate is awaiting the next steward. Inviting front porch features an impressive wood burning fireplace, overhead heaters & sound system. Two story great room exudes natural light & overlooks the park-like setting, Generous kitchen & dining rooms are ideal for entertaining: double dishwashers, stainless appliance, wet bar + food & butler's pantry & incredible storage. Incredible Owner's suite with fireplace and dual bathrooms adorned with exquisite tile and glass work. Radiant floor heat, Eucalyptus floors, vertical grain fir detailing throughout. Elevator, theatre, interior spa-room with private bathroom. Heated brick patio, concrete benches and path to the natural water pool, spa, sauna and bath house. Outdoor kitchen w/ fridge and d/w. Guitar vault, 3 car garage + fitness room/home office. Wired for sound, internet, ultimate connectivity.

$2,800,000 - Ashland, OR

1320 N Mountain Avenue Ashland, OR - Dana Campbell Vineyards is a legacy wine business offering multiple avenues for growth with unparalleled proximity to Ashland's renowned cultural amenities. Elegantly remodeled tasting room residence with panoramic valley views, great room with service bar and gas fireplace, catering kitchen, break room, ADA-compliant bathrooms, and three guest suites ideal for boutique hospitality. Landscaped grounds with expansive paver patio, outdoor speakers, gas fire pit, composite deck and pergola with retractable awning, bocce ball court, and rose garden. State-of-the-art cold storage facility or potential winery building with glycol cooling system, fully irrigated acreage with southern exposure, over 13,000 established vines of eight estate-grown varietals producing 2,200 cases per year, seven additional acres ready for planting, wind turbine, frost fan, and all essential equipment included for turnkey tasting room operations. Inquire with agents to access additional documentation and details!

$2,199,000 - Ashland, OR

3721 Old Highway 99 S Highway Ashland, OR - Discover a breathtaking haven in Ashland, OR--a 4-bed, 4.5-bath, 4,793-sqft custom villa on 80.58 lush acres, listed at $2,199,000. Just 15 minutes from town, this estate (updated in 08/09) offers serene privacy and views of Emigrant Lake, Mt. Ashland, and the valley. Inside, Black Walnut floors, soaring ceilings, and marble-clad baths exude elegance. The chef's kitchen dazzles with a Wolf 8-burner range, granite island, double ovens, and custom cabinetry, perfect for lavish gatherings. The primary suite enchants with a spa-like bath, dressing room, and sweeping vistas. Each bdrm boasts en-suite luxury and scenic views. Outside, a sparkling pool, hot tub, and outdoor kitchen craft a resort-like oasis. A small vineyard adds charm to the sprawling grounds. Host epic nights in the gameroom, ideal for sports and friends. Earning ~$125,000 yearly as an Airbnb, opportunity awaits.. A $150,000 paved driveway ensures seamless access. this estate is a rare jewel. See it, fall in love--View today

$1,900,000 - Ashland, OR

987 Dead Indian Memorial Road Ashland, OR - Rare Ashland Multifamily opportunity w/ TWO homes on two separate 5+ acre tax lots, only 2 miles up DIMR. Main house is 4,668 sq ft (3 beds/3 baths), & the guest home is 1,132 sq ft (2/1). Innovative design w/ radius walls, stucco & perfect window placement. Rustic maple hardwood cabinets, trim & flooring. Dream kitchen w/ Wolf cooktop, double ovens, full freezer/fridge combo, 2 sinks, & granite counters. Travertine, granite & marble adorn the entry. 360-degree views from the tower room, perfect for a home office/potential 4th bedroom. Main level master w/ huge closet, serene bath w/ double headed shower & corner tub. There also is a second living area on the main floor. Wine cellar, large rec room, single car garage + detached RV shop. Second home was built in 2017 and is just as stunning. Views of Mt. Ashland, Pompadour Bluff & the Ashland city lights. The landscaping is nothing short of a dream, w/ raised beds, mature trees, sitting areas + more. Don't miss the creek frontage.

$1,849,000 - Ashland, OR

211 Normal Avenue Ashland, OR - Country living on 2 acres with town amenities at your doorstep. Tastefully remodeled with every attention to detail. Sought-after single level home offers 3 bedrooms and office. Chef's dream kitchen with Wolf steam oven, warming drawer, vacuum seal drawer, and convection oven. Walnut island, beverage fridge, and walk-in pantry. Serene, spa-like primary with mountain views, beautiful curved walls, thoughtfully designed walk-in closet, private dressing room. Living is easy with heated floor in the primary bath, 3-zone HVAC, whole house vac, and ample storage. Temperature controlled 600 bottle wine room. Great room boasts wood burning fire & nano doors that open onto outdoor living space. Solar heated pool, water feature & outdoor kitchen. Extremely private w/ gated circle drive and mountain views. Oversized 2 car garage w/ EV charger. Barn offers 1/2 bath, workout room, bonus room, and space for RV + 2 more cars. Fenced organic garden & fruit trees. This is one you won't want to miss.

$1,750,000 - Ashland, OR

1495 Tolman Creek Road Ashland, OR - This isn't just a house--it's a feeling. A place where the weather becomes part of the story, where fog, rain, wind, or sun are never intrusions, but invitations to pause and take it all in. Every corner offers a space to simply be--to read, reflect, gather, or dream. Covered decks, cozy nooks, grounded stairways, and low-rise steps all speak the language of comfort. The home feels solid, like it was built to hold you through every season of life. It's handcrafted with intention--stained glass, warm wood, thoughtful finishes that echo consistency and care. Yes, there are stunning features--panoramic views, a saltwater pool, a barn, garages, chef's kitchen, theater, and more. But the real beauty is how it lives. This is where people connect, unwind, and linger longer than they meant to. It doesn't just impress--it restores. It doesn't just function--it feels like home in the truest sense.

$1,585,000 - Ashland, OR

2208 Lupine Drive Ashland, OR - Seller financing terms considered w/ 6% interest rate! Searching for a stunning estate w/ a park-like setting that's only mins away from Downtown Ashland & I5? This Earth Advantage tri-level Suncrest home features 5 bedrms, 3.5 bathrms, 3635 sq ft, 10 acres, open floor plan, chef's kitchen (large island, top end appliances, granite countertops, ample cabinetry), stunning views of the valley & Grizzly Peak, main level primary suite, detached 2 car garage, in ground hot tub, fenced garden area (fruit trees & raised garden beds), brand new wrap-around deck, & solar system! Primary suite is large w/ 2 walk-in closets, walk-in shower, dual vanities, & a luxury stand-a-lone tub. Upstairs features 2 large bedrms that share a full bathrm. Lower-level features 2 bedrms, 1 full bathrm, family rm, & finished storage rm w/ built in safe. Property borders an extensive trail network (Ordson-Todd trailhead is steps away) that leads to Mt Ashland & Lithia Park!

$1,569,225 - Ashland, OR

1620 Butler Creek Road Ashland, OR - East Ashland hills dream! This 3-bed, 2-bath home set on 62.19 acres of irrigated land is a rare find. Offering a peaceful rural feel while being just minutes from downtown Ashland. The recently repaired 13,500 sqft barn provides ample space for animals, equipment, and storage. An attached office space with its own bathroom is perfect for a home business or guest quarters. Take in the breathtaking views of the surrounding landscape and experience the beauty of country living with modern conveniences.

$1,500,000 - Ashland, OR

310 Holly Street Ashland, OR - Masterfully renovated mid-century view home with timeless quality and refined finishes by renowned craftsman Ron Albano in the hills above downtown Ashland. All new Sierra Pacific windows, wide-plank hardwood floors, solid-core doors, designer fixtures and hardware, Level 5 drywall finish, quarter-sawn vertical grain white oak cabinetry, meticulous tilework, and gourmet appliances. Vaulted primary with private view balcony and full ensuite bath with soaking tub, tiled shower, double vanity, and custom walk-in closet. Main level with two guest bedrooms and two full baths, living room, family room, and great room with formal dining area. Detached guest home with kitchenette and full bath. Upgraded electrical, plumbing, and mechanical systems throughout with new high-efficiency gas furnace, AC unit, mini-splits, ducting, and tankless water heater. Completely rebuilt in-ground pool, new flatwork, low-voltage lighting, drip irrigation, and fully fenced backyard. Inquire for details!

Ashland, Oregon listings for sale

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