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$1,350,000
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, 3 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

$548,000
3 Beds 2 Baths 220223843 MLS
Charming Ashland home tucked behind a solar-powered privacy gate + fully fenced front & back yard. Solar panels, double paned windows, zoned AC, hardwired internet, analog electric meter & new water heater. Stunning hardwood floors in the living room, highlighted by a beautiful brick mantle that adds character to the space. The galley-style kitchen features a gas range, tile backsplash, tile flooring, reverse osmosis system at the sink, & located adjacent to the dining area w/ a cozy wood stove. Primary suite w/ heated floor in the ensuite bath + a tile shower. Oversized covered back deck overlooking the backyard & bonus guest quarters/office space. Additional features include mature landscaping, well (buyer to do their own due diligence), organic garden, oversized 2-car garage w/ workshop space +220 voltage, and a large driveway with abundant parking, including room for an RV. This is a property you truly must see to appreciate, ideally situated in a prime close to downtown location.

1423 E Main Street, Ashland

$799,000
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

$14,000,000
220223436 MLS
Offered for sale for the first time ever, Belle Fiore Estate Winery is a premier Southern Oregon winery 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 square feet 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 eight 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. The combination of established vineyard production, hospitality operations, event revenue, and significant growth potential creates a rare opportunity to acquire Oregon's most significant vineyard esta

100 Belle Fiore Lane, Ashland

$12,000,000
7 Beds 19 Baths 220223437 MLS
Offered for sale for the first time ever, Chateau at Belle Fiore Estate Winery is one of Oregon's most extraordinary residential estates. Spanning over 17,400 sqft across four 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 over 17 acres, including 12.1 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, four-car garage, prep kitchen, and grand gathering spaces complete this iconic Southern Oregon estate.

200 Belle Fiore Lane, Ashland

$26,000,000
220223435 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is being offered for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,800 sqft; it has four levels, 5 bedrooms, 19 bathrooms, elevator service, a vineyard, a 2 bedroom 2500+ sqft carriage house, four-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 featuring 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, a priceless feature of this one of one opportunity to own Oregon's most significant vineyard estate.

100 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 being offered 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, elevator service, a vineyard, a 2 bedroom 2500+ sqft carriage house, four-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 featuring 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, a priceless feature of this one of one opportunity to own Oregon's most significant vineyard estate.

200 Belle Fiore Lane, Ashland

$1,140,000
3 Beds 3 Baths 220222186 MLS
Set privately back on 5+ acres in the Sunny Oaks community, this custom 3 bed + office, 2.5 bath, 2644 sq ft home pairs open mountain views with easy access to town -- 15 min from Downtown Ashland and near Emigrant Lake. The groundwork for comfortable rural living is in place: a dedicated 1-gigabit fiber line, 300 amp electrical, whole-home water filtration, 2021 Lennox HVAC, irrigation rights, a large cedar-fenced area, and a roof under six years old. Inside, natural light fills an updated kitchen with quartz counters and hardwood floors, opening to a great room, with a separate family room, office, and laundry on the main level. Upstairs, the primary suite offers vaulted ceilings and a balcony framing the same sweeping mountain views as the wraparound deck below, plus two more bedrooms and a full bath. Outside, a gravel RV pad offers water, power, and internet, and a barn with corrals stands ready for horses. With over $200K in updates, the property is move-in ready.

7130 Highway 66, Ashland

$1,149,808
3 Beds 3 Baths 220221584 MLS
Country living close to Downtown Ashland. 3209 sq ft w/3.68 irrigated acres, gated paved entry, beautiful landscape fenced yards w/garden beds, greenhouse, large pasture for animals, motorhome garage, heated large shop rm, potting shed. Peaceful spring fed waterfall to a KOI fishpond. This Asher Homes remodel includes a beautiful kitchen w/nice appliances; dbl convection ovens, large island w/ sitting area & lots of storage. Lg windows taking in the natural light & beautiful views of the mountains, breakfast room off kitchen, formal dining w/bay window & window seat, living room overlooking covered front porch. Downstairs bedrm & full bathrm or office/library w/built-in bookcases. 2 large primary suites upstairs w/sitting areas, vaulted ceilings, lg windows w/views, both bathrooms w/new updates, great walk in closet w/built-ins & a bonus room that could be a great studio/office/media room or hobby room. Back deck overlooking the perfect manicured mature landscaping w/hot tub

39 E Valley View Road, 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

$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

$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

$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

$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

$1,250,000
5 Beds 5 Baths 220210091 MLS
Incredibly desirable Ashland setting--private, quiet & close to town yet distinctly rural. On 5.09 acres with panoramic views of Mt. Ashland & the city, this 3566 sq ft 1985 home offers 5 bedrooms, 4.5 baths & two full primary suites, including a main-level retreat. The main floor features two sitting rooms with wood-burning fireplaces, a living room bar & a 2019 kitchen remodel with quartz leather-finish counters & painted cabinetry. Upstairs features two bedrooms with walk-in closets, a large bath & separate HVAC, plus a guest suite with a loft & window seat. Outdoor amenities: pool with Trex decking, gazebo, apple & plum trees, Gearky Creek, Talent Irrigation water & two workshops (50'x50' & 42'x36'). Other highlights: 2-car garage with workbench, wine cellar, auto generators, water softener, security system & abundant storage. Updates: roof, exterior paint, trellis, decking, railings, pool/spa (2018); HVAC (2019); blinds (2019); electrical/lighting (2018).

500 Pompadour Drive, 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

$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: