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$12,000,000
7 Beds 19 Baths 220223437 MLS 19,908 SqFt. 773,190 Sqft. Lot 17.75 Acres
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
7 Beds 19 Baths 220223434 MLS 19,908 SqFt. 3,030,469 Sqft. Lot 69.57 Acres
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

$2,140,000
5 Beds 5 Baths 220223401 MLS 7,468 SqFt. 8,867,073 Sqft. Lot 203.56 Acres
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

$900,000
5 Beds 4 Baths 220221548 MLS 5,200 SqFt. 477,417 Sqft. Lot 10.96 Acres
2 HOMES AND A GUEST STUDIO/COTTAGE!!! Just 3 miles from town, this exceptional 11-acre property sits on a sunny south-facing hillside with breathtaking views and endless possibilities. Ideal for a multi-generational family compound, rental income opportunity, homestead, or private retreat, this unique property offers an incredible combination of living space, infrastructure, and outdoor amenities. The 2,200 sq. ft. log home is filled with warmth and rustic charm, while the 1,800 sq. ft. second home includes a full basement for additional living or storage space. A separate 1,200 sq. ft. fenced studio/cottage provides excellent flexibility for guests, a home office, or a creative space. Additional improvements include two large septic systems, RV hookups with water and electricity, a separate laundry room, two tiny cabins, multiple storage buildings, root cellar with shop above, and a barn-style structure on the lower portion of the property with a newer roof. Must see to appreciate!

2909 Dead Indian Memorial Road, Ashland

$2,500,000
5 Beds 7 Baths 220220624 MLS 6,033 SqFt. 87,120 Sqft. Lot 2 Acres
Discover this extraordinary Southern Oregon Luxury 2 acre estate perched above downtown Ashland w/views & incredible privacy. This custom built Pagnini home 5313 SQ FT, 5 bdrms, 5.5 bthms, 5 Car Garage + an additional 720 sq ft detached guest quarters. Grand entry, stunning wood floors, soaring ceilings, multiple fireplaces & walls of windows to take in the incredible views & abundant natural light. Gourmet kitchen w/quartz countertops, skylights & SS appliances w/double ovens. Main level primary suite w/ terrace access offers a soaking tub & steam shower. 2 upstairs guest suites both come complete w/private balcony & breakfast bar. Additionally this incredible home features a slate roof, sauna, elevator, a spacious office w/ en-suite + so much more. European-style terrace w/big natural boulders, fruit trees, a dog run, greenhouse, and manicured gardens along w/ abundant wildlife- no expense was spared on this remarkable Ashland retreat & it truly shows

500 Ashland Loop Road, Ashland

$4,500,000
5 Beds 6 Baths 220220674 MLS 6,396 SqFt. 151,588 Sqft. Lot 3.48 Acres
Set on 3.48 private acres just 500 ft from Lithia Park and within a 1/2 mile of downtown Ashland, 237 Granite is a rare, legacy estate inspired by the timeless design principles of Greene & Greene Architects. Showcasing over 5,700 sq ft of refined living, this 5-bedroom, 5.5-bath residence embodies the essence of The Arts and Crafts Movement with exceptional craftsmanship, rich walnut flooring throughout, and a seamless connection to its natural surroundings. The grounds are a destination unto themselves--featuring a solar-heated pool, tranquil Japanese gardens with tea house, two waterfalls, a koi pond, and direct access to nearby hiking trails. Main level living w/ 871 sq ft primary wing, private caretaker quarters, and a separate 676 sq ft guest cottage with 1 bed, 1 bath, 2-car garage--offering flexibility for guests or extended living. ''The Gamble House'' of Ashland, this is the largest private estate of its kind in such close proximity to the cultural and natural heart of Ashland.

237 Granite Street, Ashland

$3,250,000
4 Beds 6 Baths 220214637 MLS 5,233 SqFt. 295,336 Sqft. Lot 6.78 Acres
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

$1,650,000
5 Beds 5 Baths 220214060 MLS 6,332 SqFt. 258,746 Sqft. Lot 5.94 Acres
Known as 309 and 311 Granite Street, this exceptional estate overlooks Lithia Park on nearly six private acres, blending European elegance with a tranquil forest setting. Mature trees, stone paths, patios, and water features create rare seclusion just minutes from downtown Ashland, the Oregon Shakespeare Festival, and the historic Plaza. Vaulted ceilings, fine woodwork, stained glass, and expansive windows fill the interiors with warm, old-world character and natural light. The main home centers on an open great room with a dramatic rock fireplace, flowing to an informal dining area and oversized kitchen, with additional living spaces for entertaining or everyday life. The primary residence offers 4,479 sq ft plus 2,364 sq ft of flexible ground-level space. A second residence adds 844 sq ft, a 1,153 sq ft multi-purpose room, and carport-about 8,840 sq ft total. Near Mt. Ashland, Crater Lake, Britt Festival, and Rogue Valley wineries, this is a rare architectural retreat of tranquility

309 Granite Street, Ashland

$10,775,000
12 Beds 10 Baths 220210683 MLS 11,456 SqFt. 41,760,972 Sqft. Lot 958.7 Acres
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

$4,100,000
5 Beds 5 Baths 220206087 MLS 5,002 SqFt. 1,912,719 Sqft. Lot 43.91 Acres
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

$1,440,000
4 Beds 4 Baths 220200154 MLS 5,186 SqFt. 253,083 Sqft. Lot 5.8100000000000005 Acres
.Experience a place that transcends the ordinary, where nature's rhythms become part of your daily life. This exceptional property offers breathtaking views, magnificent craftsmanship, privacy, and multiple spaces that beckon you to pause and savor life's moments. Meticulously designed, the home blends indoors and outdoors with expansive windows framing the surrounding beauty. Multiple decks provide outdoor options for views, shade, or sun, depending on the weather, and your mood. Outside, a saltwater pool with beach entry invites relaxation. The year-round private pond is fed by a natural spring. Outbuildings include a 4-stall barn, multiple garages, and a playhouse with electricity. Yet, this home's essence lies not just in its features, but in the feelings it evokes. Here, connections deepen, stress decreases, & time slows, allowing you to embrace life's simple pleasures. More than a residence, this is a true sanctuary—a place that encourages slowing down and taking deep breaths.

1495 Tolman Creek Road, Ashland

$1,675,000
6 Beds 7 Baths 220195209 MLS 5,757 SqFt. 40,946 Sqft. Lot 0.9400000000000001 Acres
This is truly a one-of-a-kind property on.94 acre above SOU in Ashland. There are five bedrooms, six bathrooms, beautiful hardwood floors, a gourmet kitchen with Aga range, an expansive deck and a fabulous pool. The main floor has a great room, dining room, music room, and a grand staircase going up to the second floor. The architectural details in this unique home are elegant with arched doorways, large windows, and lovely natural light on each floor. It is a wonderful home for entertaining, with an upper deck and a lower deck. The guest house is beautifully designed with skylights, kitchenette and full bathroom. There is also a convenient glass elevator to access the second floor that flows with the floorplan. There is a 500 sq.ft. bonus room (daylight basement), above the garage office and a workshop off the garage. There are three separate tax lots for this property, fully fenced, with beautiful views, and mature trees. It is your own private sanctuary in town. A must tour home!

735 S Mountain Avenue, Ashland

$1,489,000
5 Beds 4 Baths 220168074 MLS 5,340 SqFt. 43,124 Sqft. Lot 0.99 Acres
Premier Ashland Property, nestled in the hills of Southern Oregon, minutes from Southern Oregon University, 5340 Sq Ft, executive home on .99 acres with stunning views of Grizzly Peak,1 mile from downtown. Gated drive with two entrances. The home boasts 3 stories & 4 fireplaces, plumbed for gas. Main floors feature Brazilian Cherry Flooring, spacious dining and living rooms, a luxurious master suite with attached office, limestone floors w/radiant heat, glass tile steam shower and soaking tub, 4 additional bedrooms, 3.5 baths. Potential for 2 family set-up. Library, commercial grade bar, chef's kitchen with 6 burner stove, double ovens, subzero frig and wired for sound throughout the home. Enjoy the inground pool/ hot tub, meticulous landscaping and renovated outdoor spaces. 30 foot waterfall, 1/2 basketball court, a 3 car garage and access to miles of hiking /biking trails from the property. Plenty of extra parking for RV, boat and toys.

615 Taylor Street, Ashland

$1,300,000
5 Beds 4 Baths 220174206 MLS 5,111 SqFt. 21,780 Sqft. Lot 0.5 Acres
A distinctive craftsman-style residence, meticulously built with a grand front porch. Take in captivating views of Grizzly Peak. The home is adorned with artistic accents: church pew railings, stained glass windows, acorn wood accents and wainscotting throughout. The main dwelling boasts 5 beds and 3 baths and hardwood floors. There is a main level library, formal living room w/ fireplace and a dining room off the kitchen. The gourmet kitchen has stone counters and fir cabinets. The primary suite offers a balcony with panoramic views. It has a high coffered ceiling, heated tile bathroom with a walk-in tub, and 2 headed shower. The finished basement could be an ideal game room along with ample storage. A .5-acre terraced backyard boasts a viewing patio and is made for entertaining. There is TID irrigation. Additional living space above the garage enhances the home's versatility. This property is a harmonious blend of craftmanship and functionality.

1655 Peachey Road, Ashland

$1,490,000
4 Beds 5 Baths 220167226 MLS 6,331 SqFt. 15,246 Sqft. Lot 0.35000000000000003 Acres
This historic Italianate home, originally designed for Domingo Perrozi in 1902, has undergone $550,000 in recent improvements, seamlessly blending the style of that historic era w/modern luxury. Located in the Heart of Ashland, adjacent to the downtown plaza, Lithia Park, restaurants & trails, it offers a stunning & serene setting. Upon entering, you are greeted by original period details, including a grand staircase, rounded arches, solid wood flooring, stained glass, bay windows & intricate moldings. The island kitchen features a sub-zero refrigerator, butler's pantry & breakfast room. W/4 bedrooms, 3 ensuite, the expansive primary bedroom has beautiful natural light from large windows overlooking lush gardens & a relaxing saline pool w/waterfalls. The property is accessible via an elevator that connects the main floor areas to the recently expanded 4-car garage & ground level. The lower level includes a spacious living/bonus/recreation area, a sauna & direct access to the garden.

88 Granite Street, Ashland

$1,900,000
4 Beds 6 Baths 220141818 MLS 6,331 SqFt. 910,404 Sqft. Lot 20.9 Acres
French country home with amazing views of the lake, mountains & sunsets. Close to downtown Ashland. Reclaimed wood beams, solid wood doors, trim and baseboards throughout. 20+ acres including its own small vineyard providing outstanding Tempranillo wine. Large island in the gourmet kitchen with Viking appliances. Including double convection oven, 6 burner gas cooktop, built in wine refrigerator, granite countertops, hardwood floors, and large butler pantry. 6 fireplaces and a 5-car garage. Beautiful library/office with fireplace, large windows and ceilings to take in the forever views. Large covered/uncovered patio areas with fireplace and built in BBQ, and living area. Tranquil courtyard with separate studio that has vaulted ceilings, formal living & dinning room, plus bonus room. This house has it all, approximately 6331 SQFT. This is country living at its finest and just outside of Ashland.

133 Meadow Oaks Drive, Ashland

$1,850,000
4 Beds 8 Baths 220178756 MLS 6,084 SqFt. 273,121 Sqft. Lot 6.27 Acres
Custom built, one owner home located in a highly sought after rural neighborhood. Incredible attention to detail, including extensive built-ins, prime window placements to take in the surrounding mountain views, formal & informal dining with easy access to the outdoors. The kitchen is a chef's dream w/ stunning granite counters, six burner Wolf range, double ovens, warming drawer, steamer, two sinks & a walk-in pantry. Primary suite w/ dual sinks, soaking tub & walk-in shower. The media room/library offers a gas fireplace & built in bookshelves. Upstairs has another primary suite w/ deck access. Follow the enclosed breezeway to another fully functioning wing w/ a primary bedroom on the main level & 2 bedrooms upstairs. Detached work shop w/ an office & ½ bath plus another two-car garage. 6+ irrigated acres, raised garden beds, producing vineyard, fruit trees, chicken coop & green house. The grounds are breathtaking w/ paver patios, covered porches & decks.

708 Pompadour Drive, Ashland

$3,100,000
4 Beds 5 Baths 220180611 MLS 5,139 SqFt. 1,703,196 Sqft. Lot 39.1 Acres
Stunning mountain modern home with panoramic views of the Siskiyous and surrounding Rogue Valley. Located in the beautiful hamlet of Ashland with world-class theater, dining, fly-fishing, skiing, and just 20 minutes to Medford Intl Airport, this home will satisfy the most discerning buyer. Completed in 2023 by Asher Homes, the open floor plan is an entertainer's dream. The kitchen island is a wonderful gathering place, and the Wolf and Sub-Zero appliances are chef's quality. The great room opens to a covered patio with a gas-fire table and an outdoor kitchen overlooking the pond. A private deck with a hot tub and outdoor shower are accessed from the spacious primary suite. Downstairs is over 1000 ft of finished basement with a full bath and plumbed for a kitchenette. Perfect for an in-law unit, workout space, home office or art studio. The irrigated property has a riding ring and space for grazing while leaving plenty of room for new ideas and projects. Live your Ashland dream.

245 Majestic Lane, Ashland

$4,500,000
2 Beds 4 Baths 220135580 MLS 11,084 SqFt. 30,840,480 Sqft. Lot 708 Acres
Centrally located between San Francisco and Portland, just minutes from I-5, 700 awe-inspiring acres of oak savannas and rolling meadows gently rise, until your view of the Siskiyou mountains feels so close, you might reach out and touch it. Sitting on a high bench, a spectacular 8,880 sq. ft home exalts the grandeur of nature that surrounds it. With its graceful, curvaceous design, myriad of windows, and unique features like rounded corners and sculptural appointments in copper, glass, stone, granite, local and exotic wood, this breathtaking home is beyond custom; it is a work of art. Every direction offers an unparalleled view. This astonishing property enjoys a pool, an outdoor entertainment space, an off-grid cabin, and features a 3000 sq. ft. basement level ready to be transformed by your imagination. Offering magnificent sanctuary and adventure, as well as convenience, the surrounding region of Southern Oregon is known for wine and phenomenal outdoor recreation opportunities.

2700 N Valley View Road, Ashland

$975,000
3 Beds 3 Baths 220174701 MLS 5,772 SqFt. 710,463 Sqft. Lot 16.31 Acres
Unobstructed views of Emigrant Lake from this custom home on 16.31 ac. of Ashland farm land. Easy access to the lake for all your water activities. Enjoy country living with the luxury of Ashland amenities. The home was blt to take in the lake views from the living room & kitchen. Vaulted living rm w/ cozy wood stove. Kitchen has a spacious island for entertaining. The main level primary suite includes separate office, double vanity, glass block shower enclosure & a walk-in closet. Venture out onto the deck to take in the stunning lake & mountain views. High end 2009 Triple Wide MH sits below, used as a Hardship Residence, with own deck and lake views. Pastures for horses & four-stall barn w/ tack room, fenced and cross-fenced. Room to store your RV. For energy efficiency there's a 26-panel solar array grid-tied system. Plenty of garden space for the green thumb w/ already established table grapes & fruit trees. Lake recedes in late summer but still remains a beautiful setting.

375 Old Greensprings Highway, Ashland

$1,075,000
4 Beds 3 Baths 220167995 MLS 5,842 SqFt. 405,979 Sqft. Lot 9.32 Acres
RARE OPPORTUNITY, 9.3 acres with full-irrigation next to the city limits. 100 yards from the driveway entrance located in the city limits, you will find a serene and peaceful country property. It's filled with bright sunshine and a night sky so dark you'll see millions of stars. There is a barn and sheds. You can enjoy living with horses, goats, growing grapes or just relaxing with the beautiful view of mountains and pasture. 3,882 SqFt, spacious single-level home with 4 bedrooms and 3 bathrooms. Many vaulted ceilings add more openness. 1,960 SqFt, extensive daylight basement is ready for versatile use. The house is well maintained and move-in ready. There are 2 tax lots allows another house to be built. Buyer to do due-diligence for the second house.

1390 Tolman Creek Road, Ashland

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. Last updated: