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$1,450,000
10 Beds ⋅ 12 Baths ⋅ 220225786 MLS ⋅ 4,544 SqFt. ⋅ 13,939 Sqft. Lot ⋅ 0.32 Acres
One block from the Oregon Shakespeare Festival and downtown Ashland's restaurants, galleries, and cultural amenities, the McCall House B&B is a beautifully restored 1883 Italianate home offered for sale as a private residence. Currently operating as a boutique hotel, the property features ten historic guest rooms, including two detached private Carriage House suites, and may continue as a licensed hospitality business for a buyer who wishes to carry on that tradition. The C-1 zoning also opens the door to a variety of commercial uses, including a restaurant, office suites, or other business opportunities. Ten on-site parking spaces are included, a welcome convenience this close to the Ashland Plaza. This is a rare opportunity to own one of the city's most celebrated historic addresses. Due to the C-1 zoning, conventional 30-year financing is unavailable, and non-cash buyers are encouraged to confirm lending options before requesting an appointment. Please do not disturb guests.

153 Oak Street, Ashland
$1,350,000
5 Beds ⋅ 6 Baths ⋅ 220225703 MLS ⋅ 4,935 SqFt. ⋅ 217,800 Sqft. Lot ⋅ 5 Acres
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
$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
$794,000
5 Beds ⋅ 6 Baths ⋅ 220221349 MLS ⋅ 1,616 SqFt. ⋅ 9,147 Sqft. Lot ⋅ 0.21 Acres
71, 73 and 75 Wimer. Gorgeous updated including plumbing and electric vintage home w/charm remaining a few blocks to downtown Ashland. The main home has 3 bedrooms (2 with ensuite baths) the 3rd bedroom has an ensuite 1/2 bath. Formal living and dining and eat in large kitchen w/breakfast bar & nook. Granite countertops. Wood floors on main level & carpet on stairs & bdrms. The woodwork door trim is beautiful & probably original. Newer deck & A/C unit. Detached building (71 and 73 Wimer) are one level studio units with kitchens & baths. 73 Wimer has private deck. Main house is rented for $2375.00 p/month & tenant pays utilities except water. Studios have been rented for $1250.00 & $1350.00 per month with utilities included & they have a separate shared laundry facility. Unique property for owner occupied or income producing. Circular driveway for main home & 2 parking spaces in front for studios. Has been traveler accomodations in the past. Buyer to do own due diligence on u

75 Wimer Street, 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
$2,100,000
9 Beds ⋅ 10 Baths ⋅ 220215748 MLS ⋅ 5,406 SqFt. ⋅ 49,222 Sqft. Lot ⋅ 1.13 Acres
This 1880 farmhouse was originally converted into a bed and breakfast in 1983. The Morical House Garden Inn has a rich history and now has 9 bedrooms and 10 bathrooms. The main house has original red fir floors and much of the Victorian era woodwork and other features have been maintained over the years. The carriage house was added in 1995, and the Inn created a luxurious experience for its clients for more than two decades. Although day-to-day operations ceased in 2020, the Morical stands ready to resume its role as a high-end boutique hotel or move on to its next adventure.

668 N Main 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
$1,249,000
8 Beds ⋅ 9 Baths ⋅ 220212846 MLS ⋅ 3,666 SqFt. ⋅ 13,068 Sqft. Lot ⋅ 0.30000000000000004 Acres
Just blocks from downtown, this historic gem blends charm and flexibility. Original fir floors, built-ins, high ceilings, and abundant natural light pair with modern updates. Enjoy the welcoming lawn, pollinator garden, and large covered front porch. The main level offers spacious living and dining areas, kitchen, half bath, and generous entry spaces. A 1-bedroom apartment with interior and private exterior access--includes a kitchen, laundry and full bathroom--a separate additional en-suite bedroom with exterior entry adds versatility. Upstairs are four lovely en-suite bedrooms, one with a balcony, all with updated Renewal by Andersen windows and balcony door. A detached 704 sq ft, 2 bedroom, 1.5 bath, single level cottage with its own address and electric meter provides added flexibility or income potential. With six paved off-street parking spaces, sheds, on-street parking, and alley access, this property offers exceptional possibilities for multi-generational living or investors.

451 N Main 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
$1,850,000
4 Beds ⋅ 6 Baths ⋅ 220199795 MLS ⋅ 4,584 SqFt. ⋅ 16,552 Sqft. Lot ⋅ 0.38 Acres
1910 Craftsman Style home in the Railroad District of Ashland, Oregon. This incredible property underwent an extensive renovation in 2008 by Bostwick Construction. The seamless transition from original to additional space was done in such a way as to restore the authenticity of the style, while adding amenities in a tasteful manner. Main house has approx. 4144 sf w/ 4 bedrooms and 4 1/2 bathrooms. Cherry wood floors, built-in shelving and cabinetry, lots of windows for natural light. Kitchen is a chef's dream w/ high end appliances, huge Soapstone center-island, built-in breakfast nook, pantry and office space. There is a main level bedroom suite w/ exterior access. Upstairs has additional three bedrooms, including spacious primary bedroom suite w/ two large walk-in closets. There's a detached studio space w/full bathroom and an oversized garage. The grounds are simply amazing, pool w/ spa, patio areas, garden walls, arbors, fencing and gates that create a wonderful sense of privacy.

586 B Street, 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
$1,900,000
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
$760,000
6 Beds ⋅ 6 Baths ⋅ 220178221 MLS ⋅ 2,654 SqFt. ⋅ 9,147 Sqft. Lot ⋅ 0.21 Acres
Lovely Historic Granite Street Home and Studio Across from Ashland's Lithia Park! This wonderful property in the Skidmore Academy Historic District is one of Ashland's most sought-after locations--close to downtown and everything Ashland has to offer. The home's main level features 3 bedrooms (one with French door access to a small patio), 2 beautiful new full bathrooms, 1 fully updated bath, hardwood floors and laundry/utility room with sink. The upper level offers an open living area with cozy gas fireplace, good-sized kitchen, 2 Park-View bedrooms, 2 full baths (one new and one updated) and an office that could be an extra bedroom. PLUS, there is a detached studio guest cottage with kitchenette, full bath and convenient parking. Currently used as a wonderful family vacation compound, this historic gem has potential to be traveler's accommodations, VRBO, Air BnB or multi-family living (check with City of Ashland). Great possibilities so close to Shakespeare and Ashland's Plaza.

171 Granite Street, 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
$839,000
7 Beds ⋅ 8 Baths ⋅ 220179240 MLS ⋅ 3,601 SqFt. ⋅ 10,018 Sqft. Lot ⋅ 0.23 Acres
Nestled just a block away from downtown Ashland, the timeless charm of the former Albion Inn awaits. This updated classic is primed to accommodate a variety of business ventures, thanks to its versatile R-2 zoning. Remodeled from the studs up, this property blends historic appeal with modern convenience. The main residence has four well appointed bedrooms, each featuring its own en-suite bathroom. Complementing the main house, a rear building offers two offices, a versatile multi-purpose room equipped with a sink, and a large en-suite studio upstairs. A converted carriage house presents two more independent en-suite units. Central to the property's allure is an enchanting courtyard and garden, additionally an ample laundry facility. There are seven dedicated off-street parking spots providing space for visitors. Don't miss this rare opportunity for a home for your business close to the vibrant heart of downtown Ashland.

34 Union Street, Ashland
$1,540,010
6 Beds ⋅ 6 Baths ⋅ 220165773 MLS ⋅ 7,070 SqFt. ⋅ 2,338,736 Sqft. Lot ⋅ 53.69 Acres
Multi-Family DREAM ESTATE!! 6601, 6633 & 6639 Old Hwy 99 S being sold together ** Listing reflects totals ** 3 Parcels, 2 Homes, 24'x45' Shop - 3rd parcel w Home-site Approval and installed septic. Must Tour to appreciate!! Parcel #1- MAIN HOME, 13 ac, over 5300 sf living & acc space, 1981 yr built, 3 bds+office, High-Speed Internet, 3 full baths, unique heating system- forced air & optional wood boiler! Multiple outbuildings & Builders' workshop! Parcel #2 - GUEST HOME, Contemporary design, 1765 sf, 1997 yr built, on 20 ac, 3 bd, 2.5 ba. Parcel #3 - Lush meadow w/ approved home-site, septic system on 20 ac. Marketable timber, 2 seasonal creeks, abundant wildlife.

6601 Old Hwy 99 S, 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: