luxury houses for sale Ashland, United States

Beautifully maintained 5-bedroom, 3-bathroom home offering the convenience of mostly single-level living in a desirable Ashland location less than one mile from downtown, Lithia Park, and the Oregon Shakespeare Festival. The thoughtfully designed floor plan features a spacious main-level primary suite and a private upper-level en suite bedroom with views, perfect for guests, multigenerational living, or a home office. The heart of the home is an incredible chef's kitchen with Brazilian cherry hardwood floors, leathered granite countertops, an oversized island with stylish pendant lighting above, double ovens, and wine refrigerator. Open-concept living spaces are filled with natural light and connect seamlessly to the partially covered patio and large, fully fenced backyard. Additional highlights include wide doorways, a dedicated laundry room, whole-house water filtration, generous storage, and a large walk-in closet. Call for a tour today!

Located in one of Ashland's most sought-after neighborhoods less than a mile from downtown, this beautifully updated single-level home offers 3 bedrooms, 2 full bathrooms, and nearly 1,700 square feet of thoughtfully designed living space on a .17-acre corner lot. A studs-out remodel completed in 2018 brought modern style and quality updates throughout. Oak hardwood flooring extends through the main living areas, while both bathrooms feature tile flooring and contemporary finishes. The primary suite includes an ensuite bath with a tiled walk-in shower. Expansive living room windows frame Cascade Mountain views. Enjoy the scenery from the view deck or relax among meticulously maintained grounds with a tranquil water feature. Owned solar adds efficiency and value. Move-in ready and ideally located near downtown Ashland, parks, dining, and shopping. Tour today!

Located in the heart of downtown Ashland, just two blocks from the plaza, this idyllic, recently renovated Victorian home offers classic Victorian curb appeal with modern upgrades throughout the home. A brand-new remodeled kitchen is finished with quartz countertops, solid wood cabinets, and stainless-steel appliances. An open-concept floor plan and an ample family room provide endless potential for families and entertaining. Step outside to the elegant hardscape patio with a covered gazebo, granite countertop, and outdoor cooking area, complete with an outdoor beverage refrigerator, designed for an immersive outdoor living experience. Upstairs, the ample master bedroom with wall-to-wall closet space is adjacent to a second den/reading nook. Step outside onto the spacious rooftop sun porch with views of Mt Ashland and the gorgeous mature landscaping below. The property also includes a detached finished shop/studio space with a sleeping loft, alley access and private parking.

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.

Rare opportunity to own 160 private acres on the outskirts of Ashland, offering extreme end-of-the-road seclusion, breathtaking panoramic views, and endless potential for recreation, hunting, and homesteading. Surrounded by nature and abundant wildlife, this remarkable mountain retreat delivers the peace and privacy that are increasingly difficult to find. Located just 30 minutes from Mt. Ashland and approximately 45 minutes to downtown Ashland, the property offers the perfect balance of remote living and convenient access to dining, culture, and outdoor adventure. The custom-built home features a stunning great room that truly must be experienced in person, with soaring ceilings, warm finishes, and walls of windows framing the surrounding landscape. A spacious primary suite, inviting guest accommodations, large barn, and substantial shop space make this property ideal as a full-time residence, legacy ranch, or unforgettable weekend mountain escape.

Gorgeous craftsman multi-generational living opportunity in one of Ashland's most desirableneighborhoods, just steps from parks, hiking trails, and hundreds of acres of public land. Immaculate landscaping and curb appeal create a striking first impression. A classic covered porch overlooks the front yard and a private park across the street. Step inside to vaulted ceilings and an open floor plan. Pristine oak flooring is complemented by modern cabinetry and a spacious kitchen island with quartz countertops, ideal for chefs and entertaining. Floor-to-ceiling sliding glass doors offer seamless indoor-outdoor living. Enjoy an expansive deck overlooking a serene backyard with pocket views of Grizzly Peak. The 350 Sq ft guest house is thoughtfully designed for convenient access while maintaining privacy with a dedicated fence, creating ideal separation between living spaces.

Located above the Boulevard in one of Ashland's most sought-after neighborhoods, this 5-bedroom, 3-bath home offers the perfect blend of convenience and opportunity. Just minutes from downtown, local shops, restaurants, and hiking trails, the location is hard to beat. Inside, you'll find a functional layout with a cozy fireplace anchoring the main living space as well as original hardwood flooring. Updated solid wood interior doors throughout the home offer a touch of modern sophistication, while multiple sky lights allow for plenty of natural light. Outside, the lot provides plenty of room to garden, or reimagine the space to fit your vision. Whether you're looking for a solid investment property or a place to create your dream home, this one is full of potential.

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 recreationhiking, horseback riding, ATV adventures, and fishingthis 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.

Private Ashland Mountain RetreatTucked away at the end of a quiet mountain road, 22494 Jefferson Road offers a rare opportunity to own one of Southern Oregon's most private and dramatic retreat properties. Set on 203.56 acres adjoining public lands, this extraordinary Ashland estate combines resort-like views, exceptional seclusion, substantial living space, and direct access to some of the region's most iconic outdoor setting is immediately memorable. With no visible neighboring homes, the property feels worlds away, yet remains connected to the natural beauty, lifestyle, and cultural appeal that make the Ashland area so desirable. Sweeping south-facing views stretch across rugged mountains, rolling forestland, wide valleys, and into Northern California, creating a dramatic backdrop in every -Like Views and SettingThe seller's vision for the property is clear: this is not simply acreage with a large home, but a private mountain sanctuary with the feel of a personal resort. The combination of scale, privacy, views, and surrounding protected lands creates an atmosphere that is increasingly difficult to sunrise over the mountains to quiet evenings overlooking the valley, the land offers a sense of peace and grandeur that is hard to capture in words. Whether used as a full-time residence, legacy family retreat, corporate getaway, private recreational basecamp, or personal mountain resort, the setting is the defining property's south-facing orientation helps capture natural light and expansive views, while the topography, wooded terrain, pasture areas, and creek frontage add depth, beauty, and usable variety across the Craftsman ResidenceCompleted in 2015, the main residence is an impressive 7,468 square foot Craftsman-style home designed with flexibility, gathering, and privacy in mind. The home offers 5 bedrooms and 4.5 bathrooms, with a multi-level layout that can accommodate a wide range of living main level includes two primary bedrooms, multiple living areas, a family room, breakfast nook, mud room, vaulted ceilings, bamboo and tile flooring, and built-ins. This layout provides practical day-to-day functionality while also creating space for extended family, guests, or multi-generational main living area opens to a deck that takes advantage of the surrounding views and natural setting. With the landscape unfolding beyond the home, the interior and exterior spaces work together to create a strong sense of -Level Flexibility and StorageTwo separate upper-level areas add useful versatility to the residence. One area includes a walnut staircase leading to a loft above one of the primary suites, creating a private and inviting space that could function as a reading area, office, studio, or retreat within the finished upper room provides additional flexibility and could serve as a bedroom, hobby space, creative studio, media room, or overflow guest area. A large unfinished attic connects the upper areas and offers substantial storage or future potential, depending on the needs of the next Basement and Additional Living PotentialThe partially finished daylight basement adds another layer of utility to the home. With flex space and patio access, this area provides room for recreation, storage, projects, guest overflow, or future customization. For a property of this scale and setting, the added space enhances the overall functionality and long-term usability of the Finished Original Home Flex SpaceIn addition to the main residence, the original 1,812 square foot home has been transformed into an amazing fully finished flex space. This adds significant lifestyle value and creates opportunities that are difficult to on the needs of the next owner, this space could be used for guests, a private office, studio, recreation area, game room, retreat space, meeting space, creative workspace, or additional gathering area. For those envisioning a family compound, legacy property, or corporate retreat, the original home greatly expands the practical use of the property beyond the main residence -Grid Living and Owned SolarThe property offers a unique private off-grid setting with owned solar, supporting a lifestyle centered around independence, privacy, and connection to the land. For buyers seeking a retreat-style property, the solar component is an important part of the overall property offers infrastructure and scale that support a substantial private estate. The owned solar system enhances the self-sufficient nature of the property and pairs well with the surrounding acreage, natural setting, and retreat-style , Pasture, Creek, and Natural BeautyThe 203.56 acres include a diverse mix of pasture, wooded terrain, and creek frontage. This variety gives the property a layered and dynamic feel, offering open areas, forested privacy, wildlife habitat, and natural water acreage provides space to explore, relax, ride, hike, gather, and enjoy the outdoors without leaving home. For those who value privacy, recreation, and stewardship of a special landscape, the land itself is one of the property's most compelling by Public LandsOne of the most extraordinary features of the Jefferson Road Estate is its relationship to the surrounding public lands. The property is surrounded on three sides by public lands, including the renowned Cascade-Siskiyou National creates a level of privacy and permanence that is increasingly rare. With protected lands surrounding the area and no visible neighboring homes, the property offers a peaceful sanctuary where nature takes center buyers concerned about long-term privacy, neighboring development, or maintaining a true retreat atmosphere, this public land adjacency is a major -Siskiyou National MonumentThe Cascade-Siskiyou National Monument is one of Southern Oregon's most significant natural landscapes, known for its biodiversity, rugged beauty, and recreational appeal. Having this protected landscape as part of the broader setting gives the property a sense of scale and distinction that few private holdings can monument landscape contributes directly to the property's identity. It frames the views, enhances the privacy, supports wildlife, and provides a deep connection to the natural world. For those drawn to conservation, recreation, photography, hunting, horseback riding, hiking, or simply quiet immersion in nature, the location is Crest Trail and Outdoor RecreationOutdoor adventure begins right at the doorstep. The Pacific Crest Trail passes just north of the property, offering access to miles of hiking and horseback riding opportunities. The nearby landscape also includes access to iconic regional destinations such as Pilot Rock and the broader Cascade-Siskiyou hiking and horseback riding to wildlife viewing, photography, hunting, and exploring the monument landscape, the recreational possibilities are extensive. The property is ideally suited for an owner who wants direct connection to the outdoors without sacrificing the comfort and scale of a substantial private residence.A Legacy Property With Multiple Possibilities22494 Jefferson Road is the kind of property that invites a larger vision. It could serve beautifully as a private family compound, a legacy retreat, a corporate getaway, a personal mountain resort, or a nature-centered combination of a large Craftsman residence, fully finished original home flex space, owned solar, creek frontage, pasture, wooded acreage, public land adjacency, and sweeping resort-like views creates a rare and compelling offering in the Ashland buyers seeking privacy, scale, beauty, and recreational access, this property represents far more than a home. It is a private retreat surrounded by protected lands, built for gathering, solitude, exploration, and long-term enjoyment.