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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

Courtesy of John L Scott Ashland

12800 Dead Indian Memorial Road, Ashland
$1,458,000
220230264 MLS
Discover a unique retreat center nestled in the forested mountains of Southern Oregon, just 20 minutes above Ashland in Jackson County. Located at 12800 Dead Indian Memorial Road, this expansive 40-acre property offers mountain views, wooded landscapes, open meadows, abundant wildlife, and spectacular sunrises and sunsets. The 15,000-square-foot retreat center features a Great Room for gatherings, dormitory-style accommodations, a commercial kitchen, multi-use office space, a swimming pool, and beautiful grounds to explore year-round. Multiple water storage features and a spring house add value to this exceptional property. An existing conditional use permit may offer opportunities for buyers whose intended use aligns with current approvals. Currently operating as a meditation retreat center, this property offers tremendous potential for retreats, organizational gatherings, group activities, and other retreat-style experiences.

12800 Dead Indian Memorial Road, Ashland

Courtesy of John L. Scott Medford

1120 S Mountain Avenue, Ashland
$1,400,000
4 Beds ⋅ 4 Baths ⋅ 220229911 MLS
Rare Opportunity: Custom Ashland Estate with Panoramic Views! First time on the market! This unique, one-owner 4-bedroom (plus bonus room/den) and 3.5-bath home spans 5,192 sq. ft. on a .43-acre lot at the top of coveted South Mountain Avenue. Designed to capture breathtaking valley and Cascade Mountain views, the home features a massive wrap-around deck perfect for outdoor living and entertaining. Inside, you'll find unmatched potential and grand living spaces. Currently undergoing updates, this property offers a rare chance for a buyer to step in and customize the final finishes to their exact taste. (Note: Listing details and finished items are subject to change as renovations progress.) Unbeatable location, incredible footprint, and views that will take your breath away--don't miss one of Ashland's most unique properties!

1120 S Mountain Avenue, Ashland

Courtesy of eXp Realty, LLC

1200 Buckhorn Springs Road, Ashland
$2,999,000
4 Beds ⋅ 2 Baths ⋅ 220229566 MLS
Buckhorn Springs Ranch is a legacy landholding in Southern Oregon, just 15 minutes from downtown Ashland. The 1,674 acres in the Cascade foothills backs to BLM land and offers an extraordinary blend of privacy, natural beauty, and scale. Rolling hills and year-round creek provide important winter range for elk and deer. The property's expansive acreage and diverse terrain create a remarkable setting for recreation, conservation, ranching, or simply creating a private retreat. This is a once-in-a-generation opportunity to shape a historic property around your own vision. Seller is willing to carry the loan for a qualified buyer.

1200 Buckhorn Springs Road, Ashland

Courtesy of Windermere Van Vleet & Associates

380 E Butler Lane, Ashland
$3,900,000
3 Beds ⋅ 3 Baths ⋅ 220229525 MLS
Turnkey cannabis production and processing facility in Ashland, OR, offered with real estate, business assets, and an adjacent 4.97-acre buildable parcel featuring homesite approval. The property includes a 5,000 SF (50' x 100') red iron building complete with office space, break room, bathroom, climate-controlled dry room, vegetative room, trim area, storage mezzanine, dedicated ice-water extraction wash room, and packaging area. Cultivation infrastructure is anchored by two 40' x 120' GrowSpan internal-deprivation mix-light greenhouses, with power supplied by two separate 800-amp single-phase electrical services (~1,400 amps dedicated to the commercial facility and ~200 amps to the residence). The existing improvements sit on a 4.97-acre parcel, combining with the neighboring lot for nearly 10 acres total with expansion potential. Included in the sale is an established brand with active Oregon-wide distribution and a proven history of indoor flower and solventless production.

380 E Butler Lane, Ashland

Courtesy of Keller Williams Realty Southern Oregon

210 Alicia Street, Ashland
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 220229442 MLS
Enjoy the relaxed Ashland lifestyle just minutes from downtown, parks, and trails. Tucked into a peaceful setting with lovely East Hills views, this light-filled home is the final new build in a four-lot subdivision. Spacious rooms and an open layout are designed for comfortable living and entertaining. The custom island kitchen features a butler's pantry and flows effortlessly into the dramatic vaulted great room with a striking fireplace. The primary suite offers a spa-like retreat with walk-in shower, dual vanities, and generous walk-in closet. Abundant storage throughout adds everyday convenience. Living spaces extend outdoors to a covered patio, perfect for dining and enjoying the views. Thoughtful finishes, natural light, and a welcoming floor plan make this new Ashland home something special.

210 Alicia Street, Ashland

Courtesy of John L Scott Ashland

1650 Neil Creek Road, Ashland
$1,175,000
5 Beds ⋅ 4 Baths ⋅ 220229364 MLS
OWNER CARRY AVAILABLE! GOURMET KITCHEN. EMIGRANT LAKE VIEWS. 22 ACRES OF PRIVACY. This updated 5-bedroom, 3.5-bath home offers 3,270 sq ft on 22.05 acres. The gourmet kitchen features granite countertops and a stunning oversized island with 360-degree access for cooking and entertaining. Guest quarters and two separate laundry rooms provide flexibility. Updates include all-new doors and windows, a new roof, and new stucco with an imperfect smooth finish and upgraded cloth underneath designed to help reduce temperatures. A large garage with generous shop space accommodates vehicles, tools, and hobbies. The engineered greenhouse includes a concrete perimeter and separate power meter, with potential for shop conversion, subject to buyer due diligence. Level areas offer possibilities for future projects; buyers to verify permitted uses and development options. Enjoy beautiful lake views, exceptional privacy, and versatile spaces--with owner financing available to bring your vision to life!

1650 Neil Creek Road, Ashland

Courtesy of eXp Realty, LLC

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

Courtesy of RE/MAX Integrity Grants Pass

164 5th Street, Ashland
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 220229137 MLS
An amazing opportunity in an unbeatable location! Three separate living spaces surround gorgeous lush gardens in the heart of the Railroad District. The main home (164 5th) dates to the late 1800s and offers 3+ bedrooms, 2 baths and approximately 2,071 SF, with many improvements including a new foundation, electrical, plumbing, and HVAC ducting in '94. A detached 1 bed/1 bath apartment above the workshop provides vaulted ceilings, abundant natural light, and a private deck overlooking the gardens, plus bonus space below. A separate cottage-style home (162 5th), circa 1945, offers 2 bedrooms, 1 bath and its own private outdoor space. All three living spaces have separate meters for electric and gas. The main house and cottage also have separate water and sewer. Enjoy a greenhouse and outdoor storage bins for gardening. Lovingly cared for by the same owners for over 45 years, this special property shows true pride of ownership!

164 5th Street, Ashland

Courtesy of Ashland Homes Real Estate Inc.

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

Courtesy of RE/MAX Platinum

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

Courtesy of Cascade Hasson Sotheby's International Realty

119 Pine Street, Ashland
$1,350,000
3 Beds ⋅ 4 Baths ⋅ 220228838 MLS
Build your dream home with luxury builder Suncrest Homes in idyllic downtown Ashland--just one block from Lithia Park and a couple blocks from the Plaza and OSF. This Earth Advantage certified home design offers a thoughtful layout with main level living, vaulted ceilings, and expansive picture windows. Take in the mountain views from the deck between the living space and the kitchen/dining area. Spacious primary suite on the main level with walk-in closet and luxurious ensuite bath. Daylight basement has 2 bedrooms with walk-in closets & full bathroom. Premium finishes included: simulated wood flooring, tiled baths & laundry, quartz counters, electric fire feature, Moen fixtures, and generous allowances for appliances & lighting. Energy-smart features include ductless heating & cooling system, solar PV readiness, EV-charger wiring, and more. Detached two-car garage. Customize the floor plan and finishes to fit your lifestyle and preferences. Possible to upgrade lot size & sqft.

119 Pine Street, Ashland

Courtesy of John L. Scott Ashland

145 Normal Avenue, Ashland
$1,035,000
3 Beds ⋅ 3 Baths ⋅ 220228353 MLS
Tucked at the end of a cul-de-sac, this distinctive single-level home offers the rare feeling of country living right in Ashland. Set on a private, fenced and irrigated acre, it was thoughtfully built with Logix ICF insulated walls, owned solar, radiant-heated floors and energy-efficient windows. Inside, warm wood ceilings, a dramatic skylit cupola, walls of windows and a large fireplace give the home character, while the spacious kitchen features abundant cabinetry and a generous granite island. A large studio/game room adds wonderful flexibility. Outdoors, expansive Trex decking connects to a screened gazebo, pergola and covered patio overlooking mature landscaping, a pond and waterfall, raised garden beds and fruit trees, with mountain and valley views beyond. Oversized 2-car garage, workshop/storage and RV/boat parking. Near the bike path, schools and Hunter Park--peaceful, private and wonderfully connected to town.

145 Normal Avenue, Ashland

Courtesy of Millen Property Group

1661 Highway 99 N, Ashland
$1,700,000
220226828 MLS
• 6,448 SF ground floor condominium suite available for a medical user. The space includes 11 exams rooms, 2 procedure rooms, 1 X-Ray room, and a reception area along with other private offices. • Functional medical office layout previously occupied by Providence Health & Services and Davita Dialysis. • Well maintained medical office building developed in 2008 that is professionally managed. • Ashland currently boasts a medical office vacancy rate of 0% with no new medical properties recently delivered. • Located on Ashland's main thoroughfare Highway 99 (17,467 VPD) and less than one mile from the I-5 freeway.

1661 Highway 99 N, Ashland

Courtesy of VI Commercial Real Estate LLC

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

Courtesy of John L. Scott Ashland

312 Sky Ridge Road, Ashland
$2,400,000
3 Beds ⋅ 2 Baths ⋅ 220225850 MLS
One of the Rogue Valley's premier estate settings, this extraordinary 164-acre Ashland offering is paired with a proposed luxury residence by Asher Homes. The single-level design offers 2,778 sq ft with 3 bedrooms, 2 baths, a 912 sq ft 3-car garage, and walls of glass framing mountain and valley views. Refined finishes include large-plank hardwood, custom built-ins, a stone fireplace, metal roofing, and covered outdoor living with built-in BBQ and fireplace. Designed to Earth Advantage Platinum standards, the home features high-efficiency HVAC, solar-ready infrastructure, EV charging, generator tie-in, and wildfire-conscious materials. The build package includes vertical construction and an infrastructure allowance for driveway, septic, well systems, power, propane, water storage, trenching, and utility connections. Land offers 2,220 feet of Cove Creek frontage, a 48 GPM well, and paved access. Plans and pricing subject to site conditions, permitting, selections, and builder approval.

312 Sky Ridge Road, Ashland

Courtesy of John L. Scott Medford

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

Courtesy of Gateway Real Estate

400 Allison Street, Ashland
$1,100,000
2 Beds ⋅ 3 Baths ⋅ 220225582 MLS
Experience refined living just one block from downtown Ashland in this custom, open concept, built 2012 luxury home, designed for comfort and ease. An elevator to take you to all levels makes stair use unnecessary and 36 inch doorways provide seamless accessibility throughout. Rich oak and red oak floors and cabinetry pair beautifully with custom metalwork and soaring wood-paneled ceilings throughout the home. The chef's kitchen features a 6 burner Wolf cooktop, wall ovens, Sub Zero refrigerator, exposed edge granite countertops and custom pot racks. Spa inspired bathrooms include heated tile floors, dual vanities, tiled showers and abundant natural light, one with a soaking tub. The private flagstone courtyard with gas BBQ and pergola is perfect for relaxing and outdoor entertaining with lovely, low maintenance landscaping. The oversized, finished, two + car garage with sealed floors offers space for a workshop, gym and storage with an additional washer & dryer, sink and gas heater.

400 Allison Street, Ashland

Courtesy of Full Circle Real Estate

Hungry Ridge, Ashland
$3,995,000
2 Beds ⋅ 1 Baths ⋅ 220225545 MLS
The Four Corners Ranch offers 897.32 acres of productive timberland on the south side of Mount Ashland, near the California border. This is a rare legacy holding that pairs a strong timber inventory with live water, recreation, and several structural improvements. Elevations range from 3,600 to 4,900 feet across varied topography, supporting consistent, reliable timber growth. Current stocking is estimated at 7.7 MMBF Douglas fir, 4 MMBF white fir, 5.9 MMBF pine, and just under 1 MMBF cedar. Located in the Rogue hunting unit, an area known to produce quality black-tailed deer, the ranch is ideal for hunting and outdoor recreation. Live water, diverse terrain, and direct access to vast public lands add to its appeal. Whether acquired for merchantable timber value or held as a generational asset, the Four Corners Ranch is a genuine opportunity to own a productive expanse of land in Southern Oregon. Additional documentation available upon request.

Hungry Ridge, Ashland

Courtesy of John L. Scott Medford

40 Ashland Acres Road, Ashland
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 220225369 MLS
First time on the market for this one-of-a-kind custom ICF-built home with breathtaking panoramic views! This 4 bed, 3.5 bath, 4,972 sqft home offers a main-level office, multiple large storage rooms, and plenty of space for entertaining. The upper level features a spacious primary suite with a private balcony, plus (2) additional bedrooms and a bonus loft (not included in storage). The lower level is ideal for multigenerational living with a large entertainment area, wet bar, bedroom, bathroom, and bonus office/storage space. Situated on 14.78 acres, (house on 1 acre), 13.8 acres currently in hay production, with rare dedicated unlimited TID irrigation. Propane has been plumbed both interior and exterior to add a fireplace or connect your BBQ if desired. Also includes an approx. 1,500 sqft detached shop, barn with (6) 12x12 stalls, riding arena, plus (2) full RV hookups and 50-amp available at the barn, and endless opportunities for horses, livestock, or hobby farming.

40 Ashland Acres Road, Ashland

Courtesy of Windermere Van Vleet & Assoc.

40 Ashland Acres Road, Ashland
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 220225368 MLS
Welcome to this one-of-a-kind custom ICF-built home with breathtaking panoramic views just minutes from downtown Ashland! This 4 bed, 3.5 bath, 4,972 sqft home offers a main-level office, multiple large storage rooms, and plenty of space for entertaining. The upper level features a spacious primary suite with a private balcony, plus (2) additional bedrooms and a bonus loft (not included in storage). The lower level is ideal for multigenerational living with a large entertainment area, wet bar, bedroom, bathroom, and bonus office/storage space. Situated on 14.78 acres, (house on 1 acre), 13.8 acres currently in hay production, with rare dedicated unlimited TID irrigation. Propane has been plumbed both interior and exterior to add a fireplace or connect your BBQ if desired. Also includes an approx. 1,500 sqft detached shop with 3-phase electrical, barn with (6) 12x12 stalls, riding arena, plus (2) full RV hookups and 50-amp also available at the barn. A must-see incredible property!

40 Ashland Acres Road, Ashland

Courtesy of Windermere Van Vleet & Assoc.

1169 Iowa Street, Ashland
$1,150,000
220224634 MLS
Rare Ashland investment opportunity, three modern townhomes built in 2016, each on its own separate tax lot, offered together as a package. Every unit is a spacious 3-bedroom, 2-full-bath, a hard-to-find configuration in the local rental market. Unit 1173 offers 1,280 sf and a two-car garage, while 1169 and 1171 each offer 1,188 sf and a one-car garage. Turnkey interiors feature stainless steel appliances, warm shaker cabinetry, and 100% solid surface flooring, no carpet anywhere. Current rents total $6,605/month with near-zero vacancy since construction, a track record of dependable income that speaks for itself. Individual tax lots offer long-term flexibility that is rarely found in multi-unit properties. Ideal for the investor seeking newer, low-maintenance construction, or an owner-occupant living in one unit while the other two help pay the mortgage. Close to SOU, downtown, and everyday amenities. Not to be sold separately.

1169 Iowa Street, Ashland

Courtesy of Gateway Real Estate

4567 Old Highway 99 S, Ashland
$1,175,000
5 Beds ⋅ 3 Baths ⋅ 220224554 MLS
One of a kind Southern Oregon retreat just 15 minutes from downtown Ashland, offering privacy, exceptional craftsmanship, sweeping views & proven income in a peaceful park like setting. A true money maker, the fully permitted first floor 2 bedroom/ 1 bath ADU currently operates as a successful Airbnb, generating approximately $25,000 a year in net income, per seller. The custom one owner main home features soaring ceilings, walls of windows framing Emigrant Lake and Grizzly Peak, a dramatic curved staircase, custom pine log accents, hardwood floors, granite and travertine finishes, floor to ceiling fireplace, kitchen with breakfast nook, third floor bonus wing & over 1,900 sq. ft. of wraparound cedar decking. Also includes workshop, playhouse and covered carport. The Airbnb has its own private driveway and entrance, ADA access, kitchenette with granite counters and a custom bath, ideal for rental income, guests or multigenerational living.

4567 Old Highway 99 S, Ashland

Courtesy of John L. Scott Medford

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

Courtesy of Cascade Hasson Sotheby's International Realty

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

Courtesy of Cascade Hasson Sotheby's International Realty

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

Courtesy of Cascade Hasson Sotheby's International Realty

22494 Jefferson Road, Ashland
$2,140,000
5 Beds ⋅ 5 Baths ⋅ 220223401 MLS
Rare 203-acre Ashland estate with sweeping south-facing views offers a resort setting tucked away at the end of a mountain road. Completed in 2015, the 7,468 sq ft Craftsman residence was designed for beauty and function. The main level showcases two primary suites, two additional oversized bedrooms, expansive living and family rooms, and a gourmet kitchen. One walnut staircase leads to a private loft while a second stairway leads to a spacious upper level bonus room. The partially finished daylight basement has exterior and patio access. The original 1,812 sq ft home is now an amazing fully finished flex space, ideal for guests, office, studio, or recreation. Surrounded on three sides by the Siskiyou Cascade National Monument for vast recreational opportunities. The property offers pasture, wooded terrain, and creek frontage. This rare legacy estate delivers self sufficiency, seclusion, and unparalleled outdoor access while remaining within reach of Ashland's renowned amenities.

22494 Jefferson Road, Ashland

Courtesy of John L. Scott Medford

120 E Main Street, Ashland
$1,000,000
220222324 MLS
Unique opportunity in downtown Ashland. This commercial property offers two legal spaces with strong flexibility. 120 E Main features 1,520 sq ft plus an expansive deck--ideal for retail, office, hospitality, or possible restaurant use. 130 E Main adds 369 sq ft, well-suited for a boutique, studio, or office. Zoned C-1-D, allowing a variety of uses. Built in 1938, the building blends character and functionality with tile and hardwood floors and a convenient single-level layout. Alley access and designated parking add ease and functionality. Ideal for an owner-occupant--occupy both spaces, use one and lease the other, or maximize income by renting both. Prime location with strong visibility, steady foot traffic, and close proximity to downtown shops, dining, and everyday amenities.

120 E Main Street, Ashland

Courtesy of John L Scott Ashland

1969 Colestin Road, Ashland
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 220222210 MLS
Rare opportunity to own 160 private acres on the outskirts of Ashland, offering extreme end-of-the-road seclusion, breathtaking panoramic views, and endless potential for recreation, hunting, and homesteading. Surrounded by nature and abundant wildlife, this remarkable mountain retreat delivers the peace and privacy that are increasingly difficult to find. Located just 30 minutes from Mt. Ashland and approximately 45 minutes to downtown Ashland, the property offers the perfect balance of remote living and convenient access to dining, culture, and outdoor adventure. The custom-built home features a stunning great room that truly must be experienced in person, with soaring ceilings, warm finishes, and walls of windows framing the surrounding landscape. A spacious primary suite, inviting guest accommodations, large barn, and substantial shop space make this property ideal as a full-time residence, legacy ranch, or unforgettable weekend mountain escape.

1969 Colestin Road, Ashland

Courtesy of Cascade Hasson Sotheby's International Realty

165 Water Street, Ashland
$4,000,000
220222181 MLS
A landmark downtown Ashland land offering. Just one block from Ashland's Plaza, this rare 1.18-acre commercial development site represents one of the last opportunities of its scale & prominence in the downtown corridor. Located within the Employment Zoning District, the property offers exceptional potential for hotel, conference center, mixed-use, luxury residential, retail, offices, or destination development. Extensive prior approvals include architectural, engineering, landscaping, utility, and entitlement plans for an 8-building mixed-use project with ground-level commercial spaces and luxury residences above. Current approvals expire Summer 2026 and may be eligible for renewal. With virtually no remaining undeveloped commercial land of this size in downtown Ashland, this offering combines exceptional visibility, strong street presence, & outstanding walkability to the Plaza, acclaimed restaurants, theaters, galleries, and Lithia Park. Rare scale. Rare location. Rare opportunity.

165 Water Street, Ashland

Courtesy of Millen Property Group

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