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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
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 220225369 MLS ⋅ 4,979 SqFt. ⋅ 643,816 Sqft. Lot ⋅ 14.78 Acres
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
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 220225368 MLS ⋅ 4,979 SqFt. ⋅ 643,816 Sqft. Lot ⋅ 14.78 Acres
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, 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
$1,480,000
4 Beds ⋅ 5 Baths ⋅ 220225327 MLS ⋅ 4,039 SqFt. ⋅ 39,204 Sqft. Lot ⋅ 0.9 Acres
Modern Mediterranean style custom-built home on nearly 1 acre, just minutes from downtown Ashland Plaza. This exceptional home offers a grand double-door entry, arched doorways, soaring ceilings, 4 beds/4.5 baths, 4000+ sq.ft, a spacious kitchen/dining/great room floor plan with vaulted glass ceiling, dry bar/wine fridge, wood-burning fireplace, and built-in window seating. The stunning chef's kitchen has just been extensively remodeled with exquisite designer finishes- including a new oversized island that showcases Brazilian leathered quartzite countertops, handmade terra cotta tile backsplash, brass hardware, and thoughtfully selected lighting throughout the home. Upstairs loft/bonus area. Master suite with 2 walk-in closets, double-sink vanity, on-demand hot water, and vaulted ceilings. Lower level offers a generous family/bonus room along with 2 private bedrooms, each with its own full bath and heated floors. Expansive decking and beautiful surroundings, 2-car garage, and solar.

167 Tessa Lane, Ashland
$1,200,000
5 Beds ⋅ 3 Baths ⋅ 220224554 MLS ⋅ 4,768 SqFt. ⋅ 219,106 Sqft. Lot ⋅ 5.03 Acres
One-of-a-kind Southern Oregon retreat just minutes from Ashland! A remarkable property offering a rare blend of privacy, craftsmanship and income potential in a private park-like setting with mature trees. This custom-built 5 bedroom home showcases soaring ceilings, walls of windows with views of Emigrant Lake/Grizzly Peak, large breakfast nook, custom pine log features/dramatic curved staircase, hardwood floors, granite/travertine countertops, floor-to-ceiling fireplace, large 3rd floor bonus wing, 1900+ sq. ft. wraparound cedar deck, workshop, charming playhouse and covered carport. The 1st floor ADU currently operates as a successful AirBNB with 2 bedrooms, beautiful kitchenette, granite countertops, stunning tile bathroom, ADA access, private driveway and entrance, for use as continued rental income or separate multigenerational family living. A former homesite offers additional potential. Rarely does a property combine this level of quiet privacy, quality and versatility.

4567 Old Highway 99 S, Ashland
$1,700,000
4 Beds ⋅ 5 Baths ⋅ 220224430 MLS ⋅ 4,234 SqFt. ⋅ 28,749 Sqft. Lot ⋅ 0.66 Acres
Rarely does a property of this caliber come to market. Completed in 2016 by Steve Asher, this custom Earth Advantage Platinum view home offers 4 bedrooms, 4.5 baths, and 4,234 sf of total living, including a 3,537 sf main house and a detached 697 sf guest studio, half a mile from downtown Ashland. A wall of glass frames unobstructed views of Grizzly Peak. The main level is anchored by a gourmet kitchen with a Gen-Aire double oven, cooktop, and granite island, flowing into a living room with gas fireplace and bar, plus an office, half-bath, and primary suite featuring a soaking tub, spa shower, and walk-in closet. A mudroom opens onto the patio and grilling area, steps from the guest studio with its own entrance and kitchenette. Downstairs, the main house offers a second living room with wet bar, gas stove, and outdoor jacuzzi tub, two en-suite guest rooms, and a flex room (not included in sf). Direct access to the Ditch Trail and Strawberry-Hald Park rounds out this turnkey offering.

225 Grandview 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
$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
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 220222850 MLS ⋅ 4,141 SqFt. ⋅ 11,761 Sqft. Lot ⋅ 0.27 Acres
This beautifully designed and built custom Victorian by Carlos Reichenshammer sits just blocks from Lithia Park. Featuring a new roof, it blends historic charm with modern updates. Mountain views abound throughout. Up the majestic oak stairway you'll find an office/library, a guest bedroom with walk-in closet and en-suite bath, and a luxurious primary suite with fireplace, two walk-in closets, soaking tub, and shower. The spacious country French kitchen features granite countertops, two islands, a Thermador 5-burner cooktop, double Bosch ovens, and glass-paned cabinets. It opens to the family room or dining area with a fireplace and breakfast nook. Enter through the marble-floored foyer into the formal living room with vaulted ceiling, plush bench seating, and fireplace. Additional highlights include a custom 650-bottle wine cellar with travertine walls and floors, a courtyard fountain, large wrap-around front porch, and back deck. **SELLER CARRIED FINANCING AVAILABLE**

255 Scenic Drive, 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
$1,160,000
4 Beds ⋅ 4 Baths ⋅ 220221702 MLS ⋅ 4,189 SqFt. ⋅ 894,286 Sqft. Lot ⋅ 20.53 Acres
Custom-built in 1986, this meticulously maintained home blends superior craftsmanship with thoughtful design. Wrapped in clear cedar siding with a lifetime-guaranteed tile roof, it features solid cherrywood floors, cabinetry, and doors, vaulted cedar ceilings, and a two-sided granite fireplace. Abundant natural light, cross-ventilation, and expansive views flow through large windows and a 1,280 sq ft wraparound deck. The 600 sq ft primary suite offers double sinks and dual shower heads. Custom built-ins include bookcases, media center, dining storage, and a fitted office. Starlink internet ensures seamless connectivity. Dual garages—a 2-car main level and lower garage/workshop—plus a detached garage with 1,200-gallon tank. An apartment under the home includes a kitchenette. Bonus ''little house'' with utilities and deck, irrigation well and tank, dual water heaters, dual heat pumps, concrete block foundation, and oversized septic. A rare, tranquil retreat.

1999 Tolman Creek 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
$2,195,000
4 Beds ⋅ 4 Baths ⋅ 220219782 MLS ⋅ 4,977 SqFt. ⋅ 1,298,959 Sqft. Lot ⋅ 29.82 Acres
Located just outside Ashland, this property offers a rare blend of natural beauty, water, quality improvements, and convenience. The custom built home is thoughtfully positioned to capture expansive views across the surrounding valley and toward distant mountains. This elevated country estate draws from a Northwest lodge aesthetic, offering welcoming living spaces, a spacious multilevel layout and a seamless indoor outdoor connection with expansive outdoor living spaces. A picturesque stretch of Neil Creek framed by mature trees adds character and tranquility. Gently rolling topography, lush pasture, and water rights support a variety of Ag uses. A recently constructed 5,000 SF barn complements the property and offers outstanding flexibility for equipment, hobbies, or recreational use. Ideal as a homestead or simply an elegant place to enjoy connection to the outdoors, this is a property that captures the essence of Southern Oregon living while remaining just minutes from Ashland.

5293 Highway 66, Ashland
$1,410,000
3 Beds ⋅ 3 Baths ⋅ 220218218 MLS ⋅ 4,668 SqFt. ⋅ 233,046 Sqft. Lot ⋅ 5.35 Acres
Nestled on 5.35 acres, this gorgeous Tuscan-style home offers stunning scenery and peaceful living just minutes from the renowned Bella Fiore Winery. This home is the perfect blend of elegance, space and functionality. The home features a primary suite on the main level, 2 spacious bedrooms upstairs, chef's kitchen that opens into the family room complete with a woodstove and sweeping pristine views. The home is filled with natural light and the new interior paint enhances the architectural elements while making the home feel modern and fresh. The unique tower space adds character and versatility- ideal for a 4th bedroom, home office, art studio or yoga retreat. Downstairs there is a large room for entertaining and wine storage. The professionally landscaped yard features stunning color, along with a shop and creek running through the property. Enjoy the serenity of country living close to town.

988 Dead Indian Memorial Road, Ashland
$1,346,000
3 Beds ⋅ 4 Baths ⋅ 220217610 MLS ⋅ 4,558 SqFt. ⋅ 369,824 Sqft. Lot ⋅ 8.49 Acres
Comp Only - this information is for statistical purposes only.

344 E Ashland, 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
$1,035,000
3 Beds ⋅ 3 Baths ⋅ 220215933 MLS ⋅ 4,120 SqFt. ⋅ 12,196 Sqft. Lot ⋅ 0.28 Acres
Sold Only. Just four blocks from Downtown Ashland, this freshly updated 1996-built home sits above the library with fantastic mountain views. A brand-new roof, refinished hardwood floors and carpeting create an inviting and refined ambiance. Ten-foot ceilings on both levels enhance the bright and open feel. The main level features two spacious primary suites, a well-appointed living and dining area, a kitchen, a great room with an office nook, and a spacious veranda. The lower level adds great flexibility with a private 3rd bedroom and full bath, its own entrance, dedicated storage, a 3-car garage with a deep RV bay, and an oversized bonus room. The low-maintenance yard features mature landscaping and sprinklers. Detached 900 sf 2BD/1BA ADU cottage with its own entry is included in AS-IS condition. The total finished living space of the house and ADU is 4,120 sf, comprising 5 bed and 4 baths.

575 Auburn 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
$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
$885,000
4 Beds ⋅ 4 Baths ⋅ 220215066 MLS ⋅ 4,074 SqFt. ⋅ 37,897 Sqft. Lot ⋅ 0.87 Acres
Spacious and thoughtfully upgraded home with panoramic views on a large terraced flag lot above the boulevard. Replaced roof, gutters, skylights, added rooftop solar, new exterior paint, deck rails and supports, HVAC, ducting, and completely renovated lower level since 2013. Main level with double-height living room, walls of windows, French doors to wrap-around deck, river rock gas fireplace, kitchen with granite dining counter, double ovens and gas cooktop, dining area, powder room, laundry with utility sink, stacked washer dryer, and expanded two-car garage. Spacious upper-level landing with skylight, interior French doors to vaulted primary with skylight and sliding glass door to private view balcony, walk-in closet, full ensuite bath, guest bedroom with ensuite access to additional full bath, and media room or second primary with private balcony. Lower family room, full bath, and two additional bedrooms with closets. Mature plantings and fenced garden. Inquire for details!

347 Wimer Street, Ashland
$1,450,000
4 Beds ⋅ 4 Baths ⋅ 220214755 MLS ⋅ 4,382 SqFt. ⋅ 1,087,257 Sqft. Lot ⋅ 24.96 Acres
Discover refined country living on nearly 25 private, gated acres just minutes from downtown Ashland and a private airport. This 4,382 sq. ft. prairie style estate blends elegance and versatility. Vaulted ceilings, radiant canary wood floors, and expansive windows frame sweeping views of Mt. Ashland, Pilot Rock, and Pompadour Bluff. The chef's kitchen showcases Verde Marinace granite, dual Dacor ovens, a soapstone sink, and a generous island. The main level includes a tranquil primary suite with walk in shower, soaking tub, and large closet, along with two offices and seamless indoor to outdoor living. Upstairs offers a true guest suite, media room, and a deck overlooking the fenced garden. Manicured grounds, TID irrigation, an orchard, multiple patios, and a 1,400+ sq. ft. garage/workshop elevate the property. With owned solar, modern systems, and timeless design, this estate delivers exceptional privacy, beauty, and opportunity.

1475 Dead Indian Memorial Road, 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
$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
$1,250,000
5 Beds ⋅ 5 Baths ⋅ 220210091 MLS ⋅ 3,566 SqFt. ⋅ 221,720 Sqft. Lot ⋅ 5.09 Acres
Incredibly desirable Ashland setting--private, quiet & close to town yet distinctly rural. On 5.09 acres with panoramic views of Mt. Ashland & the city, this 3566 sq ft 1985 home offers 5 bedrooms, 4.5 baths & two full primary suites, including a main-level retreat. The main floor features two sitting rooms with wood-burning fireplaces, a living room bar & a 2019 kitchen remodel with quartz leather-finish counters & painted cabinetry. Upstairs features two bedrooms with walk-in closets, a large bath & separate HVAC, plus a guest suite with a loft & window seat. Outdoor amenities: pool with Trex decking, gazebo, apple & plum trees, Gearky Creek, Talent Irrigation water & two workshops (50'x50' & 42'x36'). Other highlights: 2-car garage with workbench, wine cellar, auto generators, water softener, security system & abundant storage. Updates: roof, exterior paint, trellis, decking, railings, pool/spa (2018); HVAC (2019); blinds (2019); electrical/lighting (2018).

500 Pompadour Drive, Ashland
$1,050,000
3 Beds ⋅ 4 Baths ⋅ 220208801 MLS ⋅ 4,435 SqFt. ⋅ 21,780 Sqft. Lot ⋅ 0.5 Acres
French provincial-inspired custom home located directly above Hald-Strawberry Park, just five minutes from Ashland's downtown plaza. Main level living room with integrated speakers, art lighting, gas fireplace, dining area with French doors to expansive view deck, gourmet kitchen with Electrolux Icon convection ovens and six-burner gas cooktop, powder room, media room, and office or guest bedroom with full ensuite bath. Spacious upper-level office, family room, and library with French doors to view balcony, gas fireplace, extensive custom built-in shelving. Primary bedroom with sitting area, two walk-in closets, and two full ensuite bathrooms with tiled showers, soaking tub, and sauna. Huge lower-level bonus room with washer, dryer, and utility sink. Detached three-car garage with attic storage. Landscaped grounds with mature trees, ornamental plantings, sunny gardening areas, grass lawn, stone and concrete patios. Inquire for details!

551 Strawberry Lane, Ashland

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