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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

472 Waterline Road, Ashland
$600,000
4 Beds ⋅ 3 Baths ⋅ 220229914 MLS
Spacious home with stunning panoramic views in an established neighborhood above the boulevard near hiking and biking trails in Ashland's Lower Watershed. Vaulted great room with walls of windows and sliding glass doors to wrap-around deck, gas fireplace with river rock surround, wet bar, formal and informal dining areas with solid oak flooring, kitchen with tiled dining counter, walk-in pantry, electric cooktop and stainless appliances, main-level bedroom with walk-in closet and ensuite access to full bathroom with tiled vanity and tub shower. Lower level includes an expansive primary bedroom with wood-burning fireplace, full ensuite bath with radiant-heated tile floor, two separate vanities, tiled shower, jetted tub, and two mirrored walk-in closets; third and fourth bedrooms with deck access and walk-in closets, full guest bath with tiled tub shower, storage room, and laundry room with washer and dryer. Home is priced for ''As-Is'' sale. Inquire for details!

472 Waterline Road, Ashland

479 Russell Street 202 Unit 202, Ashland
$265,000
1 Beds ⋅ 1 Baths ⋅ 220229841 MLS
Escape to the great town of Ashland. Easy access to College, Bus line, shopping, eateries and theater. The location is so close to Downtown and the sought after Railroad District of Ashland. Urban living with views from this end unit condo with balcony; Motivated Seller! This would be Super for second home, or easy affordable living. Elevator and small storage area are great for those who don't take stairs. Storage will hold bikes and other recreational items etc. Open floor plan with high ceilings lots of natural light, end unit with private balcony, up/down blinds, ceaser stone counters. Stainless appliances, interior ceiling fire sprinklers, and stackable washer and dryer are included. This condo is located on a private street with off-street parking for guests and residents. HOA is building up funds which cover all exterior matinence, landscaping, sewer, water garbage and roof.

479 Russell Street 202 Unit 202, 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

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

10001 Dead Indian Memorial Road, Ashland
$285,000
220227276 MLS
Escape to your own private forest retreat on 20 beautiful acres at 10001 Dead Indian Memorial Road in Ashland, Oregon. Surrounded by natural beauty and offering stunning, expansive views, views of Mt Ashland, this property is ready for your vision. Quonset hut on heavy duty cement slab. Older cabin and storage out buildings. Recent improvements include a new power pole, a new driveway and new well, plus two RV spots, making it an excellent option for a recreational getaway, base camp, or future homesite. The property also offers timber value, adding to its versatility and investment potential. Enjoy the peace, privacy, and wide-open feel of your own Southern Oregon forest escape--all while being approximately 20 minutes from I-5 and 25 minutes to downtown Ashland.

10001 Dead Indian Memorial Road, Ashland

1249 N Valley View Road, Ashland
$799,000
1 Beds ⋅ 2 Baths ⋅ 220224982 MLS
It's all about the beautiful 13.39 contiguous acres with 12.6 acres of TID irrigation, panoramic views and just minutes to downtown Ashland. Family owned since 1964, the original home was built in 1915. There are 3 separate tax lots, one with the original home,8-stall horse barn and workshop (5.81 acres), one that has a non-expiring homesite (confirm with county) with fantastic panoramic views (4.53 acres) and the third with a large barn (3.05 acres) and separate access. All 3 may be sold separately (check with Jackson County Planning). Tax lot #700 has a small home, large shop, a 8-stall barn, tack room and small living quarters in the back. There is a 2-story barn on tax lot #300. The portion of the property growing grass and clover for hay produces approximately 400-600 bales and has wheel line irrigation. There are many other potentials for this EFU property.

1249 N Valley View Road, 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

8351 Dead Indian Memorial Road, Ashland
$749,000
2 Beds ⋅ 2 Baths ⋅ 220221177 MLS
This sophisticated home combines high-end finishes & top-of-the-line infrastructure w/ stunning sunset views, a strong producing well w/ water rights, & a professional-scale solar array designed for complete self-sufficiency. Enjoy a grand layout featuring vaulted ceilings, wide plank engineered white oak floors, two wood stoves, and Knotty Alder solid core doors. Sliders lead to a brand new two-tiered deck, while the primary offers a free standing tub, marble shower, & a view balcony. This smart home provides seamless control over lighting, media, HVAC, etc via a central wireless hub. The firewise exterior includes a metal roof and fiber cement siding. A 28 solar panel array with 22,000KW storage is backed by two generators integrated for automatic operation. There's a heated barn with drive-through doors, two climate-controlled 40' shipping containers, & a storage shed. Newly completed in 2024 & 15min to town, this property is one of a kind. Inquire for a full features list.

8351 Dead Indian Memorial Road, Ashland

461 Waterline Road, Ashland
$766,000
4 Beds ⋅ 4 Baths ⋅ 220211772 MLS
Tucked away on a quiet, tree-lined street, this beautiful home strikes the perfect balance of space, comfort, and mountain charm. Boasting 3,404 square feet, 4 bedrooms (plus an office) and 3 bathrooms, it offers plenty of room for both relaxation and entertaining. The open main level flows easily from the spacious living and dining areas to a warm, inviting kitchen with rich wood cabinetry, generous counter space, and windows that frame peaceful forest views. New front and rear cedar decks (2022) extend your living space outdoors, perfect for morning coffee or evening gatherings. The lower level hosts the primary suite and three additional bedrooms, three with private deck access and peaceful vistas. A large basement provides easy access to nearby trails and could be finished for extra living space, while also offering convenient access to the home's major systems. With a clean pre-listing inspection and thoughtful updates throughout, this home truly embodies refined mountain living.

461 Waterline Road, 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

1249 N Valley View Road, Ashland
$799,000
1 Beds ⋅ 2 Baths ⋅ 220200581 MLS
It's all about the beautiful 13.39 contiguous acres with 12.6 acres of TID irrigation, panoramic views and just minutes to downtown Ashland. Family owned since 1964, the original home was built in 1915. There are 3 separate tax lots, one with the original home,8-stall horse barn and workshop (5.81 acres), one that has a non-expiring homesite (confirm with county) with fantastic panoramic views (4.53 acres) and the third with a large barn (3.05 acres) and separate access. All 3 may be sold separately (check with Jackson County Planning). Tax lot #700 has a small home, large shop, a 8-stall barn, tack room and small living quarters in the back. There is a 2-story barn on tax lot #300. The portion of the property growing grass and clover for hay produces approximately 600 bales and has wheel line irrigation. There are many other potentials for this EFU property.

1249 N Valley View Road, 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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