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786 Pompadour Drive, Ashland
$3,250,000
4 Beds ⋅ 6 Baths ⋅ 220230483 MLS
Seller financing now available! Paradox Vineyard Estate is uniquely defined by elements of air, water, and natural light. Senses are captivated by a soaring skylight galleria spanning through the home, open-air water courts with columnar basalt fountains, and stunning panoramic mountain views. Award-winning architecture and landscape design, exceptional workmanship, and material selections demonstrate a commitment to environmental stewardship. Tranquil outdoor spaces with mature ornamental trees, 64-foot infinity-edge lap pool and spa, berry and rose garden, block barn, 96-panel solar system, four private wells with water delivery rebuilt in 2022, expansive paver motor court, and secure gated entry. Professionally managed vineyard producing CCOF-certified organic Syrah and Chenin Blanc acclaimed by local and regional winemakers. Close-in rural community of high-end estates, just five miles from downtown Ashland. Inquire for details!

786 Pompadour Drive, Ashland

2200 Lupine Drive, Ashland
$1,395,000
4 Beds ⋅ 5 Baths ⋅ 220229205 MLS
Some homes are addresses. This one was a destination. Set high in the Ashland hills, this connected double geodesic dome was the longtime home of internationally influential author Jean Houston. Inside, faceted ceilings soar overhead, pierced by triangular skylights that move light through the day. Fresh paint, restored floors, and a bold gold hearth in the great room. Below, a self-contained multi-generational suite with its own entrance, plus a 2,000 sq ft finished bonus room, once a private library. Working elevator, ramps, and accessible design throughout. Outside, a wraparound deck opens to nearly twelve acres: orchard, gardens, and matured vines on the property's own well. New septic, upgraded electrical, and completed wildfire mitigation. Bordered by BLM and protected city land, the valley views stay private and pristine. A home with a soul, ready for its next chapter.

2200 Lupine Drive, Ashland

1068 E Main Street, Ashland
$1,250,000
5 Beds ⋅ 3 Baths ⋅ 220228921 MLS
Own a piece of Ashland's history with this incredible historical home, cherished by the same family for 100 years. Built in 1900, this 3,092 sq.ft. home offers 5 bedrooms and 3 full bathrooms and has been beautifully renovated for modern living while preserving its historic elegance. Original details include beautiful woodwork throughout, formal living and dining rooms, inglenook seating, wood flooring, original entry stairwell, and an original fireplace updated with a gas insert. The updated kitchen features custom cabinetry, granite countertops, a large island, and skylights. Updated bathrooms retain their vintage charm with claw-foot soaking tubs and gorgeous custom shower tile-work. The fully fenced property features gated entry, mature landscaping, and a large 2-car garage. Ideally located in the heart of Ashland, just minutes from downtown shopping, dining, entertainment, and nearby parks, making it easy to enjoy everything Ashland has to offer.

1068 E Main Street, Ashland

100 Belle Fiore Lane, Ashland
$14,000,000
3 Beds ⋅ 2 Baths ⋅ 220228854 MLS
Offered for sale for the first time ever, Belle Fiore Estate Winery is Oregon's most significant vineyard estate and event destination situated on 51+ acres, including 37+ irrigated acres and an established vineyard with 14 grape varieties. Encompassing more than 27,000 sqft, the winery features multiple tasting rooms, an elegant ballroom, a restaurant, expansive terraces, and outdoor dining areas overlooking the vineyard and valley. The production facility is designed for commercial-scale operations with 8 barrel-storage bays, refrigerated wine storage, soaring ceilings, and extensive infrastructure. Hosting more than 50,000 visitors annually, Belle Fiore is a recognized destination for wine tourism, weddings, and private events. A 13.17 acre RR-5 zoned parcel with legal homesite is included in acreage. Business assets and inventory available, subject to applicable licensing and regulatory requirements. Property may be purchased together with 200 Belle Fiore Lane, Ashland, OR 97520.

100 Belle Fiore Lane, Ashland

5831 Old Highway 99 S, Ashland
$950,000
3 Beds ⋅ 4 Baths ⋅ 220228020 MLS
Set on more than 37 private acres in the Siskiyou Mountains, this property offers space, privacy minutes from Ashland and the Rogue Valley. Mt. Ashland Ski Area, Emigrant Lake and the Pacific Crest Trail are nearby, putting Southern Oregon recreation close at hand. The main residence features soaring wood-clad ceilings, exposed beams, expansive windows and a stone fireplace. The open great room flows into a gourmet kitchen with cabinetry, full-size refrigerator and freezer, double ovens and island. A media room, geothermal heating and cooling, and hard-wired generator add comfort and peace of mind. A detached four-car garage provides spaces, while the auxiliary building offers an open area, kitchen, full bath and three-car garage--ideal for a studio, workshop, recreation or guest space. A loft studio, greenhouse, gardens, water storage, creek, rock outcroppings and wildlife complete this Southern Oregon retreat.

5831 Old Highway 99 S, Ashland

2590 Siskiyou Highway, Ashland
$635,000
4 Beds ⋅ 2 Baths ⋅ 220227582 MLS
This beautiful recently renovated ranch is home located just 15 minutes from Ashland. Step inside to hickory hardwood floors, an open floor plan and unobstructed million-dollar panoramic views of Emigrant Lake, Pompadour Bluff, Grizzly Peak and the Siskiyou Mountains. Several french doors offer an immersive indoor-outdoor living concept with an ample patio perfect for dining and BBQing. The fourth extra large bedroom is adjacent to a solarium that would make a fantastic hot tub space. This 7+ acre mini-ranch is fully fenced and gated, with an interior dog fence line that is approximately two acres. Irrigated with water rights from a spring source, the ample lawn space is a dream come true. This versatile property features offer multiple workshops, a greenhouse, a paved basketball court, two carports, plenty of parking for RVs, boats, trailers and so much more. This one wont last long!

2590 Siskiyou Highway, Ashland

175 Lithia Way 200 Unit 200, Ashland
$710,000
1 Beds ⋅ 2 Baths ⋅ 220226541 MLS
A second story corner residence in the A LEED-certified Plaza West Building with a flowing, light-filled floorplan. Hardwood floors, a stone-framed gas fireplace, and high ceilings set a calm, refined tone throughout. Oversized windows frame views of the Ashland hills and watershed from the spacious primary suite.The en suite bath offers marble-style tile, a double vanity, separate water closet, and a generous walk-in closet. The kitchen is finished with stone counters, stainless appliances, and solid wood cabinetry with soft-close drawers. A media room with pocket doors serves easily as a private office or guest space, with a half bath and separate laundry nearby. Gated parking, private storage, and building surveillance offer quiet peace of mind. Just moments from Shakespeare, Lithia Park, and Ashland's finest shopping and dining.

175 Lithia Way 200 Unit 200, Ashland

1320 N Mountain Avenue, Ashland
$2,800,000
3 Beds ⋅ 6 Baths ⋅ 220226424 MLS
Dana Campbell Vineyards is a legacy wine business offering multiple avenues for growth with unparalleled proximity to Ashland's renowned cultural amenities. Seller-carried financing available. Elegantly remodeled tasting room residence with three guest suites ideal for boutique hospitality, panoramic valley views, great room with service bar and gas fireplace, catering kitchen, break room, ADA-compliant bathrooms. 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 for additional details of untapped revenue streams!

1320 N Mountain Avenue, Ashland

4712 Old Highway 99 S, Ashland
$384,900
1 Beds ⋅ 1 Baths ⋅ 220226151 MLS
GREAT opportunity to own 2.14 acres and finish building a newer, 688-sqft tiny home nestled on private acreage, just 15 mins from downtown Ashland. This existing permitted general purpose building, is ready to be converted into a 1-bed, 1-bath layout. Property features outdoor sauna, small seasonal pond, & high-producing well (11 GPM w/ pump, 41 GPM raw). Built in 2014, the existing permitted structure currently includes an unfinished kitchen & dining room. Purchase property as-is w/ cash (see MLS listing # 220226037) for $249,900 or finance the construction using a rehab loan w/ this listing. List price is an estimate on the the total costs including the land purchase & the amount needed to finish it, based on estimate by our contractor ($129,000). Buyer to due their own due-diligence. Buyer to enter into a separate building contract with suggested contractor or contractor of their choice outside of escrow. Final price to be determined at a later date when Rehab package is finalized.

4712 Old Highway 99 S, Ashland

501 Carter Lane, Ashland
$950,000
3 Beds ⋅ 2 Baths ⋅ 220226122 MLS
Welcome to 501 Carter Lane, a fully flat, usable property offering the ultimate blend of agricultural potential and incredible income generation! This upgraded 2,680 sqft. house is surrounded by amazing mountain views and features an 800 sq. ft. barn home, cottage, cabin, and a tiny home. The estate boasts tons of Airbnb rental income opportunity, with a 9-year 5-star Superhost history generating up to $100k+ annually. Built for growth, this farm features OMMP/ODA licensed gardens, greenhouses, and fertile soil. You'll find amazing, crystal-clear water with an endless well, irrigation ponds, and a 1-million-gallon TID water allocation. With upgraded electrical throughout and tons of equipment for farming included, it's a turnkey operation ready for your crops. Whether you want to farm, host guests, or move the whole family into this unique dream property, your endless possibilities await!

501 Carter Lane, Ashland

197 Timberlake Drive, Ashland
$725,000
4 Beds ⋅ 4 Baths ⋅ 220226035 MLS
Private 5.5-acre mountain retreat with stunning views, gated entry, asphalt drive, and expansive paved parking, only 5 minutes to town! Perched above Emigrant Lake, this impeccably maintained 2,700 sq ft home offers flexible living: two inviting living areas (one with a cozy fireplace, the other with a wet bar and patio access), a sunlit kitchen with tile floors, granite counters & backsplash, and all appliances included. Main level features formal dining, a bedroom and 1.5 baths; upstairs the spacious primary suite with walk-in closet plus two more bedrooms, 2 full baths and larger storage room. Huge attached workshop with shelving, workbenches and 220/240A service (could be converted to ADU), plus an attached 2-car garage. Entertain or unwind on the deck with pergola and hot tub, enjoy outdoor/indoor living and private hiking trails right on the property.

197 Timberlake Drive, Ashland

808 Pompadour Drive, Ashland
$1,299,000
5 Beds ⋅ 6 Baths ⋅ 220225703 MLS
Live the Southern Oregon Dream! Welcome to an extraordinary Ashland estate where breathtaking views of Mount Ashland, the Cascades, downtown Ashland, and surrounding vineyards create a spectacular backdrop. Nestled behind a private gated entrance on 5 acres, 1.6 TID irrigated, this custom-built 5 bedroom, 6 bath home offers luxury, privacy, and versatility. Whether you're seeking a peaceful retreat, a multigenerational home, or space to operate a home-based business, this property adapts to your lifestyle. The thoughtfully designed floor plan features TWO private suites with their own entrance, ideal for extended family, a professional office, or creative studio. Garden beds, fruit trees, space for horses, animals, a 28 GPM well, RV hookups w/220, abundant parking, just minutes from the Shakespeare Festival, galleries, wineries and award-winning restaurants. You'll enjoy the best of country living without sacrificing convenience. Luxury. Privacy. Self-sufficiency. Endless possibilities

808 Pompadour Drive, Ashland

143 Granite Street, Ashland
$789,000
5 Beds ⋅ 2 Baths ⋅ 220223588 MLS
Offered for the first time in generations, this extraordinary fourth-generation Ashland treasure presents a rare opportunity. Own a piece of local history just steps away from world-renowned Lithia Park. This timeless two-story residence sits on beautifully landscaped .32 acre lot. It offers 5 bedrooms, 2 bathrooms, and a character that cannot be replicated. This home is rich in charm and architectural detail. It showcases the craftsmanship of a bygone era, while providing ample space for modern living. Enjoy peaceful mornings on the porch, stroll through Lithia Park, and easy access to downtown Ashland's theaters, galleries, restaurants, and cultural attractions. Homes of this caliber, location, and historical significance seldom become available. This is a once-in-a-generation opportunity to continue the legacy of one of Ashland's cherished homes.

143 Granite Street, Ashland

100 Belle Fiore Lane, Ashland
$14,000,000
220223436 MLS
Offered for sale for the first time ever, Belle Fiore Estate Winery is Oregon's most significant vineyard estate and event destination situated on 51+ acres, including 37+ irrigated acres and an established vineyard with 14 grape varieties. The estate encompasses more than 27,000 sqft and features multiple tasting rooms, a ceremonial barrel room, elegant ballroom, full-service restaurant, expansive terraces, and outdoor dining areas overlooking the vineyard and valley. The production facility is designed for commercial-scale operations with 8 barrel-storage bays, refrigerated wine storage, soaring ceilings, and extensive infrastructure. Hosting more than 50,000 visitors annually, Belle Fiore is a recognized destination for wine tourism, weddings, corporate retreats, and private events. This combined with significant growth potential make this a rare opportunity to own a premier winery. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

100 Belle Fiore Lane, Ashland

200 Belle Fiore Lane, Ashland
$12,000,000
7 Beds ⋅ 19 Baths ⋅ 220223437 MLS
Chateau at Belle Fiore is one of Oregon's most extraordinary estates. Spanning over 17,400 sqft across 4 levels, this French-inspired masterpiece offers 7 bedrooms, 19 bathrooms, and exceptional craftsmanship throughout. An elevator services all floors, including an 8,000 sqft lower level with a wine room, game room, gentleman's lounge, multiple wine bars, and expansive entertaining spaces. Premium finishes include custom cumaru flooring, granite surfaces, and intricate architectural detailing. Set on 17+ acres, including 12+ irrigated acres and a producing vineyard, the estate is ideal for private enjoyment, weddings, retreats, and special events. Exterior features include hand-chiseled golden granite, a hand-cut slate roof, custom copper gutters, dormers, and downspouts. A 2,500+ sqft carriage house, 4-car garage, prep kitchen, and grand gathering spaces complete this iconic estate. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

200 Belle Fiore Lane, Ashland
$26,000,000
7 Beds ⋅ 19 Baths ⋅ 220223434 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is for sale for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,400+ sqft; it has four levels, 5 bedrooms, 19 bathrooms, a 4-stop elevator, vineyard, 2 bedroom 2500+ sqft carriage house, 4-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard with 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

5293 Highway 66, Ashland
$2,195,000
4 Beds ⋅ 4 Baths ⋅ 220219782 MLS
Located just outside Ashland, this property offers a rare blend of natural beauty, water, quality improvements, and convenience. The custom built home is thoughtfully positioned to capture expansive views across the surrounding valley and toward distant mountains. This elevated country estate draws from a Northwest lodge aesthetic, offering welcoming living spaces, a spacious multilevel layout and a seamless indoor outdoor connection with expansive outdoor living spaces. A picturesque stretch of Neil Creek framed by mature trees adds character and tranquility. Gently rolling topography, lush pasture, and water rights support a variety of Ag uses. A recently constructed 5,000 SF barn complements the property and offers outstanding flexibility for equipment, hobbies, or recreational use. Ideal as a homestead or simply an elegant place to enjoy connection to the outdoors, this is a property that captures the essence of Southern Oregon living while remaining just minutes from Ashland.

5293 Highway 66, Ashland

16799 Highway 66, 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

1440 E Nevada Street, Ashland
$3,750,000
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

1320 N Mountain Avenue, Ashland
$2,800,000
220195606 MLS
Dana Campbell Vineyards is a legacy wine business offering multiple avenues for growth with unparalleled proximity to Ashland's renowned cultural amenities. Seller-carried financing available. Elegantly remodeled tasting room residence with three guest suites ideal for boutique hospitality, panoramic valley views, great room with service bar and gas fireplace, catering kitchen, break room, ADA-compliant bathrooms. 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 for additional details of untapped revenue streams!

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:

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