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$650,000
3 Beds 3 Baths 220224225 MLS
Charming custom home with panoramic mountain views on a spacious and private 0.29-acre flag lot located above the boulevard within six minutes of Ashland's downtown plaza. All new low-pile berber wool carpets and fresh interior paint in 2026, new central AC system in 2019, and new roof c. 2016. Main level with solid oak hardwood floors, living room with bay window and gas fireplace, formal dining with French door to concrete paver patio with fire pit, kitchen with tiled counters and backsplash, powder room, laundry closet, and two-car garage with extensive built-in storage cabinets. Versatile upper level with two guest bedrooms, a very spacious primary suite with private office or nursery, two full ensuite bathrooms, and three sets of French doors to the backyard. Abundant natural light with Eastern exposure - dormer windows throughout. Established trees and hedges, mature plantings, and grass lawns with automated drip and sprinkler irrigation. Inquire for details!

430 Wiley Street, Ashland

$714,900
2 Beds 3 Baths 220223937 MLS
Beautifully Maintained Custom Ashland View Home! This property offers a blend of distinctive architecture and serene privacy with custom windows and natural beauty throughout. Step-down living room with gas fireplace, dining room has built-in shelving; house has engineered hardwood flooring and carpeted bedrooms; kitchen has newer 36'' gas range and built-in desk. Spacious ground-floor master bedroom, second upstairs bedroom, separate office that could be used as a guest bedroom, plus upstairs laundry room. View decks for indoor-outdoor living, mature landscaping and peaceful setting that includes patio, firepit, walking paths and fully fenced backyard. Quality upgrades include Karastan wool carpeting, newer roof, high-efficiency 2-stage HVAC, fresh interior paint, oversized garage with workshop/bonus area, central vac, 220v for EV charging and great storage throughout. Lovely hillside home on a quiet cul-de-sac just minutes from downtown with EZ access to Ashland's trail system.

590 Taylor Street, Ashland

$565,000
5 Beds 3 Baths 220220823 MLS
Escape to your private retreat on 5 level, wooded acres in the heart of the Highway 66 recreation corridor, minutes from Howard Prairie, Hyatt Lake, and Lake of the Woods. This beautifully maintained, recently updated split-level home blends comfort, privacy, and year-round recreation. A slate entry opens to a spacious living room with bay window and wood-burning stove insert. The kitchen offers granite countertops and tile flooring, while formal and casual living areas provide flexible space for entertaining and everyday life. Features include 5 bedrooms, 3 full baths, formal dining, expansive living and family rooms, each with a fireplace, plus a dedicated office or hobby room. Enjoy a peaceful forest setting near fishing, boating, hiking, mountain biking, and snowmobiling. Ideal as a full-time home, seasonal getaway, retreat, or investment property, this exceptional property captures the best of Southern Oregon living.

12300 Highway 66, 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

$749,000
4 Beds 3 Baths 220218224 MLS
Welcome to Billings Ranch, one of Ashland's most desirable communities. This stylish 3,184 sq ft, 4 bed, 3 bath home blends comfort and functionality with standout spaces for spring and summer entertaining. Upon entry you are greeted with a sweeping spiral staircase and 20-ft vaulted ceilings that create a grand open atmosphere. The main level offers a spacious living room, a dedicated dining area, and a beautifully appointed kitchen with two gas stoves, granite countertops, and ample prep space making it perfect for gatherings. Enjoy warm-weather living on the private back patio with a built-in gas firepit and grapevine-covered pergola, ideal for outdoor dining, relaxing evenings, and hosting year-round. A main-level bedroom, full bath and den complete the comfort of the downstairs. Upstairs, are three additional bedrooms, including a luxurious primary suite with its own gas fireplace, a spa-like ensuite bathroom with a jetted tub and a generous walk-in closet.

692 Vansant Street, Ashland

$399,000
1 Beds 1 Baths 220214362 MLS
Your off-grid oasis awaits. Set on 5.44 acres, this unique property offers multiple structures, including a beautifully built tiny home, tree house, deck house, cabin, and pump house, perfect for sustainable living or a private getaway. The main tiny home, built by renowned Mr. Morrison, features two loft sleeping areas, a full bathroom, a full kitchen, and plenty of storage. It truly utilizes every inch of space. The tree house features vaulted ceilings, a sleeping area, and a dry flush toilet. The deck house offers a wraparound deck, expansive windows, and an abundance of natural light. The property is powered by a 1.6 kWh solar system and includes a sand filter septic, a 6 GPM well with a 1,500-gallon holding tank, plus spring water, a creek, generators, and views of Mt. Ashland. The seller has replaced appliances and installed new AMG solar batteries. Buyer to perform due diligence regarding permits and property use.

1203 Tyler Creek Road, Ashland

$1,795,000
4 Beds 3 Baths 220213243 MLS
5 magazine quality acres, masterfully landscaped with expansive emerald, green lawns, mature trees, ponds & waterfalls create the perfect setting, built with enduring quality. The walls are solid 4x6 Canadian Western Red Cedar, offering style & durability. Large open-floor plan is perfect for gatherings. Earthy materials feature Saltillo tile flooring, rich cherry custom cabinetry, Milgard wood-cased windows, & vaulted, beamed ceilings add substance & style. Upper-level primary has a private deck overlooking the estate style grounds & mountains. Guest house features dual porches, carport, & sits beside one of five waterfalls. A 22' x 44' greenhouse with raised cedar beds. Nearly a mile of crushed granite paths wind through the landscape. 3-car garage, full RV hook-ups, & a 20'x45' shop. A true paradise. Main home is 3/2, guest home is 1/1.

4896 Highway 66, Ashland

$4,100,000
5 Beds 5 Baths 220206087 MLS
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

$2,800,000
220195606 MLS
New lease-option and seller-carried financing terms available! Dana Campbell Vineyards is a legacy wine business offering multiple avenues for growth with unparalleled proximity to Ashland's renowned cultural amenities. Elegantly remodeled tasting room residence with panoramic valley views, great room with service bar and gas fireplace, catering kitchen, break room, ADA bathrooms, and three guest suites ideal for boutique hospitality. Landscaped grounds with expansive paver patio, outdoor speakers, gas fire pit, composite deck and pergola with retractable awning, bocce ball court, and rose garden. State-of-the-art cold storage facility or potential winery building with glycol system, irrigated acreage with southern exposure, 13,000+ established vines of eight estate-grown varietals producing 2,200 cases per year, seven additional acres ready for planting, wind turbine, frost fan, and all essential equipment for turn-key operations. Inquire for additional documentation and details!

1320 N Mountain Avenue, 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: