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$855,000
220217221 MLS
Prime Investment & Development Opportunity in Ashland. Well-maintained duplex located close to downtown offering immediate cash flow and long-term upside potential. Both units are rented at $1,450 per month ($2,900 total), with tenants paying all utilities, keeping operating expenses low. Property has an excellent rental history and is professionally managed. Capital improvements include newer roof, vinyl windows, stainless appliances, gas log fireplace (rear unit), new water heater and additional updates. Situated on a large approx. 0.27-acre R-3 high-density zoned lot, creating exceptional future redevelopment potential. The City of Ashland Planning Department indicates a 5.4 base density factor with potential for up to 20 units. (buyer due diligence required). For development details contact Aaron Anderson or Nick Schubert at City of Ashland Planning Department.

128 S Mountain Avenue, Ashland

$595,808
1 Beds 1 Baths 220215560 MLS
Rare opportunity to own 71.51 acres just right outside city limits of Ashland! LOCATION IS AMAZING!! Property consist of 2 additional tax lots. Super cute 2020 built MFG home w/vaulted ceilings & floor ceiling windows w/quartz counters & tile shower & lg wood deck. Near Emigrant Lake this property would be beautiful to build your dream home w/gated entry & gently sloping gravel road to the home w/incredible views of Cascade Mountains & Pilot rock. Creek frontage w/15 acres of water rights from Neil Creek. Trust has invested over $150,000 into the Creek management and rehab planting thousands of native plants. Gently sloping acreage w/pastures for horses or cattle or grape vines. 2 adjoining tax lots including. Priced to SELL! Buyer to do their own due diligence. Potential for maybe possibly another home site?

4201 Highway 66, Ashland

$850,000
3 Beds 4 Baths 220215378 MLS
Owner will carry! Over 3,000 sq ft of custom design and stunning curb appeal define this exceptional 3 bed, 3.5 bath multi-level home set on 1.76 usable acres just 7 minutes from downtown Ashland. Walls of windows showcase sweeping panoramic views of the Siskiyou Mountains, Pompadour Bluff, Pilot Rock, and Mount Ashland. The gorgeous updated kitchen features contemporary cabinetry, granite countertops, stainless steel appliances, cork flooring, and remarkable sightlines. A bright living room with a wood-burning fireplace offers comfort and beautiful views, while the spacious primary suite includes a spa-like bath with walk-in tile shower and jetted soaking tub. Beautiful grounds, inspiring vistas, and thoughtful craftsmanship define this standout property, offering flexible living spaces, a scenic deck, privacy, and convenient access to downtown, parks, trails, and renowned cultural attractions. Come check it out today!

157 Ashland Acres Road, Ashland

$3,250,000
4 Beds 6 Baths 220214637 MLS
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!

786 Pompadour Drive, Ashland

$399,000
1 Beds 1 Baths 220214362 MLS
Your off-grid oasis awaits. Set on 5.44 acres, this unique property offers multiple structures, including a beautifully built tiny home, tree house, deck house, cabin, and pump house, perfect for sustainable living or a private getaway. The main tiny home, built by renowned Mr. Morrison, features two loft sleeping areas, a full bathroom, a full kitchen, and plenty of storage. It truly utilizes every inch of space. The tree house features vaulted ceilings, a sleeping area, and a dry flush toilet. The deck house offers a wraparound deck, expansive windows, and an abundance of natural light. The property is powered by a 1.6 kWh solar system and includes a sand filter septic, a 6 GPM well with a 1,500-gallon holding tank, plus spring water, a creek, generators, and views of Mt. Ashland. The seller has replaced appliances and installed new AMG solar batteries. Buyer to perform due diligence regarding permits and property use.

1203 Tyler Creek Road, Ashland

$1,795,000
4 Beds 3 Baths 220213243 MLS
5 magazine quality acres, masterfully landscaped with expansive emerald, green lawns, mature trees, ponds & waterfalls create the perfect setting, built with enduring quality. The walls are solid 4x6 Canadian Western Red Cedar, offering style & durability. Large open-floor plan is perfect for gatherings. Earthy materials feature Saltillo tile flooring, rich cherry custom cabinetry, Milgard wood-cased windows, & vaulted, beamed ceilings add substance & style. Upper-level primary has a private deck overlooking the estate style grounds & mountains. Guest house features dual porches, carport, & sits beside one of five waterfalls. A 22' x 44' greenhouse with raised cedar beds. Nearly a mile of crushed granite paths wind through the landscape. 3-car garage, full RV hook-ups, & a 20'x45' shop. A true paradise. Main home is 3/2, guest home is 1/1.

4896 Highway 66, Ashland

$540,000
3 Beds 3 Baths 220212828 MLS
Versatile, spacious, and thoroughly updated home on private wooded acreage in the Cascade-Siskiyou National Monument - just 14 miles from Ashland! Main level features a new kitchen with granite counters and island, walk-in pantry, glass-fronted display cabinets, all new stainless appliances, informal and formal dining areas, double-height vaulted ceilings, living room with built-in entertainment system, wood cooking stove with soapstone surround, family room, and powder room. Upper level with three vaulted bedrooms including primary with private balcony, two powder rooms with access to soaking tub and tiled shower, plus a loft area with skylights. Lower-level workshop or office studio with French doors and utility storage room. Solid frame construction with strawbale insulated walls, radiant heated floors, energy-efficient double-paned windows, concrete stucco exterior, and metal roof. High-speed internet via Greensprings Broadband Coop. Inquire for details!

827 Tyler Creek Road, Ashland

$850,000
2 Beds 3 Baths 220211093 MLS
Imagine creating your dream farm on 28+ acres of EFU farmland, surrounded by breathtaking views of the valley and mountains! The main home boasts three levels, each with its own bathroom and a deck to take in the stunning views. The radiant floor heating throughout ensures warmth in Winter and there are washer / dryer hookups on the lower floor. The potential for each level to be a separate rental unit provides a lucrative opportunity. The impressive ag building includes a room w/roll up door, a guest room with a full bathroom, a farm office space above and a deck to take in stunning views. Both structures are powered by solar energy. A large chicken house is ready for commercial chicken production or a great multi-use structure. Property is fenced and cross-fenced, ready for your animals, and features a fenced garden area. Good well flow per seller. All this and only a 5 minute drive to amenities and 10 minutes to downtown Ashland.

3152 Siskiyou Boulevard, Ashland

$449,900
4 Beds 2 Baths 220210875 MLS
Ashland Property w/ Flexible Living & Income Potential! Conveniently located near downtown Ashland, this unique property offers versatile living options and established rental income. Officially a single-family home, it features separate living areas that can function independently or be opened to the main living space for family, guests, or extended living. The layout includes a kitchenette, second bathroom, & private rooms sharing only the laundry area. A detached garden shed converted to a small cabin near the creek offers a quiet retreat space & is currently rented. Current rents total $3,500 per month--$2,200 from Unit 3, $700 from Unit 1, & $600 from the cabin. Prior short-term rentals of Units 1 & 2 averaged about $1,800 monthly. The EFU-zoned lot includes creek frontage, irrigation rights, & a fenced yard suitable for gardening. Updates include a 2020 well pump, pressure tank, reverse osmosis system, & ceiling fans. Close to Lithia Park, Oregon Shakespeare Festival, SOU, & etc.

488 Crowson Road, Ashland

$10,775,000
12 Beds 10 Baths 220210683 MLS
New Frontier Ranch - A storied and truly one-of-a-kind legacy property encompassing 958 breathtaking acres surrounded by pristine wilderness. Steeped in rich history, this remarkable ranch includes a charming farmhouse, museum building, expansive Great Hall, and a private campground with commercial kitchen and bath facilities. Scattered across the land are three rustic cabins, multiple barns and outbuildings, two reservoirs, and irrigated meadows ideal for livestock or crops. Miles of trails wind through forests, meadows, and a preserved ghost town reminiscent of the Old West. Existing resort approvals and extensive infrastructure make it perfect for corporate retreats, events, weddings, festivals, or a destination resort. With unlimited recreation—hiking, horseback riding, ATV adventures, and fishing—this ranch offers both adventure and serenity. A rare opportunity to own a vast wilderness retreat where history, nature, and imagination unite to create something truly extraordinary.

16799 Highway 66, Ashland

$2,900,000
3 Beds 2 Baths 220209913 MLS
Premier 36-Acre Cannabis Cultivation & Distribution Property - Ashland, Oregon. Rare opportunity to own a state-of-the-art Tier II cannabis cultivation & distribution facility on 36 acres near Emigrant Lake. This turnkey operation offers both scale & efficiency, featuring: Indoor Facility: 10,000 sq.ft. hydroponic grow, fully automated fertigation system capable of watering 3,200 plants in 30 minutes. Recently upgraded with 200 new 1,000-watt LED lights. Pre-wired for 3-phase power. Outdoor Grow: 20,000 sq.ft. setup with 500-plant capacity, also fully automated and plug-and-play ready. Storage & Infrastructure: 53' refrigerated unit for fresh frozen/cold storage, 4,120 sq.ft. barn & stg-bldgs. Human-detection infrared camera & alarm system provide full security. Residence: 2021 built, the 3-bed, 2-bath, 1,458 sq.ft. home includes a steel roof w/ lifetime warranty. Water Rights: Clayton Creek, Dunn & Talent Irrigation water rights included-an invaluable asset for long-term Success

420 Reiten Drive, Ashland

$525,000
2 Beds 2 Baths 220207030 MLS
A perfect blend of rural serenity & functional living awaits on this 6.65-acre property just minutes from the heart of Ashland, Oregon. Surrounded by majestic madrone and fir trees, this private retreat offers natural beauty, privacy, and remarkable versatility. The main 2-bedroom, 2-bath home features a thoughtful layout w/an art room, attached garage, and expansive windows that bring the outdoors in. Just steps away, a beautifully finished Accessory Residential Unit (ARU) with a full kitchen is perfect for guests, extended family, or rental income. A unique workshop crafted from 2 shipping containers features hydraulic doors, a professional-grade engine hoist, abundant storage, & an adjacent large covered outbuilding—ideal for makers, mechanics, or outdoor enthusiasts. Whether you're enjoying peaceful mornings under the trees, tackling your next project, or exploring Ashland's renowned theaters, restaurants, and trails, this property offers the freedom to live, create, and thrive!

5010 Old Hwy 99 S, Ashland

$4,100,000
5 Beds 5 Baths 220206087 MLS
A private retreat setting where nature meets luxurious living. The 5BR/5BA Contemporary home captures the Siskiyou mtn range at every turn. The main level offers floor to ceiling windows, hardwood floors, living & dining room & Chef's kitchen appointed w/ island, wet bar, pantry, double ovens, wolf stove & more! Upstairs the main bedroom suite is an oasis unto itself w/views, decking & spa. A second primary suite, 2 add'l bedrooms/bath & laundry room w/abundant storage are downstairs. Each room has custom finishes & exquisite views to ensure a lifestyle of privacy & relaxation. Outside you're met w/soothing soundscape of a tiered cascading creek, lagoon waterfall style pool, cabana area, outdoor kitchen & bath, for ease of entertaining. Equestrian, livestock or agricultural enthusiasts will delight w/the endless possibilities. Fruit trees, garden beds, greenhouses, chicken coop & workout room complete this singular estate. 1BD/1BA guest apartment is a bonus to this luxe property.

1440 E Nevada Street, Ashland

$850,000
3 Beds 2 Baths 220202861 MLS
GREAT OPPORTUNITY! Amazing Price. Earth Advantage certified, 2025 custom home by well-respected Suncrest Homes, a trusted builder of 450+ Rogue Valley residences. Superior efficiency, comfort, & long-term savings. Set on a private 5-acre parcel with ample parking and a paved drive, this home is designed to showcase breathtaking panoramic valley views through large picture windows & sliding French doors in the vaulted great room, anchored by a cozy electric fire feature. The stylish kitchen offers a generous island, walk-in pantry, textured quartz countertops, and artisan tile backsplash--perfect for daily living & entertaining. Durable, waterproof simulated wood flooring through, with tile in the bathrooms. Private well w/holding tank and whole-house filtration. XL 2-car garage w/workshop space. Ready for your vision of outdoor living. Close in and just 10 minutes to downtown Ashland! Sellers are VERY motivated!

3060 Ashland Mine Road, Ashland

$2,800,000
220195606 MLS
New lease-option and seller-carried financing terms available! 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 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 system, irrigated acreage with southern exposure, 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 for turn-key operations. Inquire for additional documentation and details!

1320 N Mountain Avenue, Ashland

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: