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$1,350,000
5 Beds ⋅ 6 Baths ⋅ 220225703 MLS
Live the Southern Oregon Dream! Welcome to an extraordinary Ashland estate where breathtaking views of Mount Ashland, the Cascades, downtown Ashland, and surrounding vineyards create a spectacular backdrop. Nestled behind a private gated entrance on 5 acres, 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 ⋅ 220225368 MLS
Welcome to this one-of-a-kind custom ICF-built home with breathtaking panoramic views just minutes from downtown Ashland! This 4 bed, 3.5 bath, 4,972 sqft home offers a main-level office, multiple large storage rooms, and plenty of space for entertaining. The upper level features a spacious primary suite with a private balcony, plus (2) additional bedrooms and a bonus loft (not included in storage). The lower level is ideal for multigenerational living with a large entertainment area, wet bar, bedroom, bathroom, and bonus office/storage space. Situated on 14.78 acres, (house on 1 acre), 13.8 acres currently in hay production, with rare dedicated unlimited TID irrigation. Propane has been plumbed both interior and exterior to add a fireplace or connect your BBQ if desired. Also includes an approx. 1,500 sqft detached shop, 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
$749,000
3 Beds ⋅ 2 Baths ⋅ 220223795 MLS
Vintage Craftsman with an exceptional location, just five easy blocks from the Ashland Plaza and Lithia Park. Welcoming covered front porch entry is just an example of the many period details of the original portion of the home. The living and dining area includes many light capturing windows, beautiful wide moldings, vintage tile surround gas fireplace, solid wood flooring, antique light fixtures and a wall of built-ins that encase a lovely stained-glass window and built-in hutch. Cheerful kitchen has black and white tiled flooring and a cozy breakfast nook. Current owners added a spacious ''lock off'' primary suite that was perfectly integrated to fit the overall feel of the home. R-2 zoning has allowed for a live/ work use and provides so much versatility depending on one's needs. Lovely, paved patio and mature landscaping compliment the overall picture. Plenty of storage between the basement and detached single car garage. This is a great opportunity for the next owner to enjoy.

307 N Main Street, Ashland
$845,000
3 Beds ⋅ 3 Baths ⋅ 220219802 MLS
Stunning Chalet Retreat with Breathtaking Mt. Ashland Views! Nestled on 7.51 private acres, this gorgeous 2,306-sq-ft chalet offers unparalleled views of the Colestin Valley and Mt. Ashland. The thoughtfully designed interior features 3 spacious bedrooms, 3 full baths, and a versatile bonus room. Uniquely permitted for short-term rentals, this property is a proven income-producer and an ideal part-time residence or year-round sanctuary. Located just 15 minutes from the culture of downtown Ashland and minutes from world-class skiing, it perfectly balances seclusion with convenience. High-quality infrastructure includes a robust 16 GPM well and a state-of-the-art Advantex septic system. Whether you are seeking a mountain getaway, a savvy investment, or a private estate, this home delivers the best of Southern Oregon living. Experience ultimate privacy without sacrificing proximity to the city. A rare find in an iconic setting--this mountain masterpiece is ready for its next owner!

12673 Highway 99 S, Ashland
The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

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. Listing content is copyright © 2018 SOMLS, Medford, Oregon. Last updated: