Refine Search
Sort by
$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

$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

$965,000
7 Beds 5 Baths 220222015 MLS 2,790 SqFt. 8,712 Sqft. Lot 0.2 Acres
Rare opportunity to own 2 residences plus a studio on one tax lot. Offers exceptional flexibility for multigenerational living, rental income, live-work, or guest accommodations. The 1,720 SF main residence was fully renovated in 2018, including a new poured foundation, and has 4 bedrooms, 2 baths, open living spaces, a kitchen with crisp white cabinets, subway tile backsplash & a main level bedroom. The main residence includes a double garage with a 480 SF upper-level studio with a full bath. A separate second 1,070 SF residence, built in 2018, offers stylish & charming single-level living with high ceilings, 2 bedrooms, 2 baths, & contemporary finishes. Situated in an established historic neighborhood with mature trees, the property has off-street parking, modern systems, and is close to Ashland's downtown. This R-2-zoned property features separate addresses & meters & allows for 2 Airbnb units with owner occupancy on premises. Request property offering details.

563 Rock Street, Ashland

$1,750,000
6 Beds 5 Baths 220216989 MLS 4,537 SqFt. 4,389,976 Sqft. Lot 100.78 Acres
This home is like a warm hug! The 100-acre property embraces everything! You can have it all...3025sf Main Home, 1512sf Guest House, RV barn, workshop, gardens. Main house: built by Asher Homes in 2016, expertly sited to capture optimal sun exposure, stunning views-Mt Ashland, Pilot Rock, Cascades & Siskiyous. Interior finishes in PNW style. Main level primary, custom cabinetry throughout. Even a ''secret'' room upstairs! All modern amenities you'd expect w/ sustainability at the forefront of design. Earth Adv Platinum Certification, 2 solar PV systems, water catchment, energy efficient systems. Outdoors: low-impact landscape, stone patio, fenced gardens, greenhouse, pond, fruit trees, grape vines, spring bulbs. The original home: conveniently located next door, can serve as guest quarters, office/workspace, wrap around porch, main level bdrm & full bath, 2 add'l rooms upstairs. This property has been nurtured, cultivated with love and purpose, making it a special place to call home.

1940 Soda Mountain Road, Ashland

$1,426,550
6 Beds 4 Baths 220214093 MLS 4,579 SqFt. 13,939 Sqft. Lot 0.32 Acres
Enjoy the relaxed Ashland lifestyle just minutes from downtown, parks, and trails. Tucked into a peaceful setting, this property offers privacy and lovely East Hills views—ideal for quiet mornings and easy evenings at home. Located in Ash Meadows, a new 4 lot subdivision, this light-filled 3,921 sq ft home features spacious rooms and an open layout designed for comfort and entertaining. The custom island kitchen includes a butler's pantry and effortless flow into a dramatic vaulted great room with stunning fireplace. The primary suite is a spa-like retreat with a soaking tub and walk-in shower. Living spaces extend outdoors to a covered patio, perfect for year-round dining and relaxing. The main level allows for convenient single-level living, while upstairs offers a family room and additional bedrooms. A private one-bedroom in-law suite provides flexibility for guests, extended family, or potential rental income.

218 Alicia Avenue, 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

$600,000
7 Beds 3 Baths 220210405 MLS 3,084 SqFt. 439,956 Sqft. Lot 10.1 Acres
Rare family homestead served by 400+ GPM well on EFU-zoned acreage in the foothills of Grizzly Peak near Pompadour Bluff, just six miles from downtown Ashland. Seller financing available with variable interest rates starting at 4.5% for up to five years! Main level of primary residence with covered front porch, two bedrooms with closets, full bathroom with tub shower, living room with pellet stove, dining area with bay window, kitchen with walk-in pantry, and laundry room. Upper level with three additional bedrooms and full bathroom with tub shower. Double-paned windows with vinyl frames throughout. Accessory structure with huge 1,080 SqFt workshop, 220V electrical, full bathroom with washer, dryer, and tub shower, and an additional 864 SqFt of finished area with kitchen, living room with wood stove and sliding glass door to view balcony, and three bedrooms with closets. Mature shade trees, panoramic views, and gently sloping pasture with Southern exposure. Inquire for details!

2011 Dead Indian Memorial Road, Ashland

$785,575
6 Beds 4 Baths 220202587 MLS 4,478 SqFt. 27,442 Sqft. Lot 0.63 Acres
REDUCED-$195 SF! Private & double gated .63 acre parcel for this 4478 SF home with 6 bedrooms & 4 bathrooms. Entirely rebuilt in 1996 to combine modern luxury with timeless appeal & spacious living. Multiple distinct living areas cater to both relaxation & entertainment. The main living area has warm hardwood floors & an expansive, light-filled living room with stone fireplace. The chef's kitchen is the heart of the home with large island, 4-person dining bar, open breakfast & dining area & a separate office. Additional main living includes a versatile passive solar sunroom, dual bedrooms on the main level plus a 2nd office that could easily convert to primary bathroom. Upper-level features 2 bedrooms & a bath & lower-level features 2 bedrooms, bath & very large multi-purpose room. Massive wraparound deck extends the living space outdoors & invites you to unwind & savor the remarkable setting. Detached garages, gardening beds, multiple sheds, lawn areas, blooms galore, privacy & view

1320 Prospect 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

$945,000
6 Beds 4 Baths 220186927 MLS 3,640 SqFt. 13,939 Sqft. Lot 0.32 Acres
Wonderful 2X8 frame custom home on an oversized lot that can be split with a separate sewer connection in place & TID irrigation. Located on a quiet street above SOU, this home has a wraparound porch that is both private & extends the living space. The warm & welcoming interior has an open floor plan with exposed beams & a large brick fireplace in the living room. The kitchen & dining area open to an expansive deck with incredible views, perfect for entertaining & indoor/outdoor living. The primary suite is on the main level. Upstairs has a landing family/entertainment room along with four more bedrooms. The finished daylight basement has a private entrance & is connected to the main house with a covered porch, fireplace, bedroom & office, perfect for a separate unit or two family set up. A bonus studio (432 sf) with a bathroom can be used as an art studio, workout space, home office, guest space or garage. Enjoy the mountain breeze & views just a short jaunt to SOU, shopping & trails

650 Monroe Street, Ashland

$1,060,000
6 Beds 4 Baths 220165716 MLS 4,257 SqFt. 14,374 Sqft. Lot 0.33 Acres
Gorgeous 1890 Craftsman home, steps to the Plaza, Shakespeare, Lithia Park & more. Spacious with plenty of period detail; pocket doors, built-ins & enclosed sunporch. Comfortable living room with woodstove & window seat, library & multiple bonus rooms for crafting & media. Main level primary wing has a sitting room, large walk-in closet & private bath. Many upgrades over the years including 2001 addition of primary bed & 61 Baum, 2013 kitchen remodel with custom cherry cabinets, granite counters & Heath tile surrounds. The upstairs bath was completely remodeled in 2018 with marble & tile finishes. Large .33 acre lot features mature landscaping with fruit trees, small pond, rose garden & drought tolerant pollinator garden; side deck for lounging, covered deck for BBQing and covered front porch for summer evenings. Full basement, spacious pantry, two car garage and off-street parking. 61 Baum St is a lovely second dwelling, w/ a quiet second floor location; 1 bed/1 bath, sold furnished.

55 Granite Street, 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

$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

$510,000
6 Beds 5 Baths 220168412 MLS 3,372 SqFt. 9,583 Sqft. Lot 0.22 Acres
The failure of this transaction isn't attributable to the condition of the home. Nestled near Southern Oregon University, local schools, and the bike path, this spacious single-level home spans 3,332 sq. ft. Boasting 6 bedrooms and 4.5 bathrooms, it's being sold fully furnished at no extra cost or value, ensuring a hassle-free transition. The property offers detached parking and a fenced private yard for your convenience. Meticulously maintained and updated, the home features a spacious living room and kitchen with new appliances and flooring. Large rooms with ample closet and storage space cater to your needs. Some of these rooms could easily be transformed into a home office space. With its prime location and desirable amenities, this property is ideal for residents or potential tenants.

200 Walker Avenue, 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: