Ashland Real Estate

Ashland Real Estate

Welcome to Ashland, Oregon, a charming city nestled in the picturesque Rogue Valley of Jackson County. Known for its vibrant arts scene and stunning natural beauty, Ashland offers a unique blend of cultural richness and outdoor adventure, making it a sought-after destination for residents and visitors alike.

Home to the renowned Oregon Shakespeare Festival, Ashland boasts a lively cultural calendar filled with theater, music, and art events. The festival attracts theater enthusiasts from all over the country, creating a dynamic atmosphere that infuses the city with creativity and inspiration. In addition to the performing arts, Ashland is also home to numerous galleries and studios, showcasing the work of local artists and craftspeople.

Nature lovers will find themselves in paradise here, with the breathtaking landscapes of the surrounding Siskiyou Mountains and the lush greenery of Lithia Park. The park, a local treasure, offers serene walking trails, picnic areas, and even natural mineral springs, perfect for relaxation and rejuvenation. Outdoor activities abound, including hiking, biking, and skiing in the nearby mountains, making Ashland a year-round playground.

The city’s commitment to sustainability and community living is evident in its farmers' markets, local eateries, and eco-friendly initiatives. With a welcoming atmosphere and a strong sense of community, Ashland is not just a place to live; it’s a lifestyle.

Whether you’re drawn to the arts, the outdoors, or the friendly community vibe, Ashland, Oregon, offers a unique and fulfilling place to call home. Come explore all that this enchanting city has to offer!

Newest Listings in Ashland

$735,000
3 Beds ⋅ 3 Baths ⋅ 220228500 MLS
Impeccable views and quality updated home is ready to go! Step outside directly onto hiking trails and return to this tranquil turn-key home on the end of a dead end street! Ample parking and covered space for storage of all ski gear and all your toys, make this home a year round gem to come home to after a long day of adventure! Only 30 mins from Mt Ashland from the front door! Fully updated bathrooms, kitchen and backyard make this home completely turn-key! The expansive primary suite features a sauna, walk-in closet and private wrap-around deck. Impeccable views with an open floorplan provide ample opportunities for hosting. This rare gem of views, storage and quality upgrades is one you won't want to miss!

1750 Crestview Drive, Ashland

Listing courtesy of John L. Scott Medford.

$350,000
3 Beds ⋅ 2 Baths ⋅ 220228497 MLS
Charming 1910-built home offering 3 bedrooms on a spacious .32-acre lot in desirable Tolman Creek. This property presents a wonderful opportunity to enjoy the character and appeal of an older home while taking advantage of a generous lot with plenty of space and potential. Conveniently located in a sought-after area, this is a rare opportunity to own a piece of local history with room to make it your own.

795 Tolman Creek Road, Ashland

Listing courtesy of John L. Scott Medford.

$1,000,000
3 Beds ⋅ 4 Baths ⋅ 220228495 MLS
Live the best of Ashland in this iconic re-built Victorian, blending timeless charm with tasteful modern updates. Just steps from restaurants, cafés, Cabaret Theatre, and a couple blocks from OSF, it feels private while offering true downtown living. Stone-surround wood-burning fireplace with redwood mantel and beautiful fir floors welcome you in. Formal dining and covered screened patio feature mountain views. Kitchen boasts Neolith quartz counters, copper farmhouse sink, induction cooktop, smart refrigerator, double ovens, skylight, and breakfast peninsula. 2 primary suites--one on each level--offer tiled baths, glass-enclosed showers, quartz vanities, and soaking tub upstairs. Terraced low-maintenance landscaping, automated irrigation, private patios, ample off-street parking, and a backup generator add convenience. Ally access to detached 2-car garage and studio apartment above with full kitchen, bath, and large balcony--perfect for guests, rental income, or flexible living.

364 Hargadine Street, Ashland

Listing courtesy of John L. Scott Ashland.

$874,000
3 Beds ⋅ 2 Baths ⋅ 220228466 MLS
Under construction for mid-December 2026 completion, this architecturally inspired midcentury home sits off-street on a private flag lot in an established neighborhood with mature trees. Vertical-grain cedar and stucco meet clean lines and covered porches. This 3-bed, 2-bath home is light and bright with clerestory windows, 8 ft doors, and vaulted ceilings. The kitchen's large island with eating bar opens to the great room, where a fireplace with a built-in bench-and-mantel sits by a wall of windows. The primary suite offers a roll-in shower, double vanity, and walk-in closet. A rare pass-through garage links the driveway and rear alley; drive straight through in either direction. No HOA. Built by Suncrest Homes, an Ashland builder with 35+ years of experience, this Earth Advantage home is energy-efficient and exceeds code. Ask about a promo 5.125% rate with the builder's lender. Listing broker is related to the owners of Suncrest Homes, one of whom is a licensed OR real estate broker.

901 Hillview Drive, Ashland

Listing courtesy of Gateway Real Estate.

$625,000
4 Beds ⋅ 2 Baths ⋅ 220228422 MLS
Perched above downtown Ashland on a quiet street, this spacious 4-bedroom, 2-bath home offers privacy, proximity to town, and commands beautiful valley and mountain views. The open, light-filled floor plan centers around a vaulted great room and offers 2,176 square feet of flexible living space, including additional office and family rooms easily convertible to sleeping space on both levels. Step onto the expansive deck to dine outdoors, entertain, or simply enjoy the ever-changing scenery. A sauna provides a relaxing retreat, while ample storage and an attached garage add everyday convenience. Set on nearly a quarter-acre with mature fruit trees and room to garden, the property is just blocks from Lithia Park, the Ashland Plaza, dining, shopping, and the Oregon Shakespeare Festival. This is an exceptional opportunity to enjoy space, scenery, and an enviable location close to the heart of Ashland.

264 Alta Avenue, Ashland

Listing courtesy of Millen Property Group.

$642,000
2 Beds ⋅ 1 Baths ⋅ 220228381 MLS
The Hamaker-Taylor House, thoughtfully reimagined for modern living while preserving its Historic charm. Designed by notable architect Carlos Delgado, this 1889 cottage features a brand-new luxury kitchen with a beautiful sunroom/breakfast nook, new bathroom, updated windows, HVAC, plumbing, electrical, and roof (2026). Professionally landscaped and hardscaped front and back yards create inviting spaces for outdoor entertaining. An expansive covered front porch welcomes you home, while two bright bedrooms and beautiful Pergo flooring add warmth throughout. The full basement offers a unique art studio with lighting, hot/cold running water, and raised storage areas. Just three doors from Lithia Park, enjoy the sounds of the bandshell from your own porch. Minutes to OSF, the Plaza, and downtown Ashland. A rare opportunity to own a piece of Ashland history with modern luxury.

63 Nutley Street, Ashland

Listing courtesy of Windermere Van Vleet & Assoc..

$799,000
3 Beds ⋅ 3 Baths ⋅ 220228361 MLS
Rare, period Craftsman in Ashland's Railroad District, extensively remodeled while retaining wonderful original character. The 1,492 sq ft single-level main home features a deep covered front porch, built-in cabinetry, box beam ceilings and a river rock fireplace. Bright office with glass doors can also serve as a 3rd bedroom. The updated light-filled kitchen features all new appliances, induction cooking and abundant storage. The primary suite is an oasis with a beautifully updated bathroom featuring soaking tub, walk-in shower and heated floors. Private landscaped yard with mature trees, a water feature and wonderful outdoor living spaces. A detached 480 sq ft building offers additional flex space with bathroom, kitchenette and storage, plus alley access. 1,972 sq ft between the two buildings, just blocks to downtown, restaurants and bike path, this is the quintessential Ashland dream!

762 B Street, Ashland

Listing courtesy of Full Circle Real Estate.

$1,035,000
3 Beds ⋅ 3 Baths ⋅ 220228353 MLS
Tucked at the end of a cul-de-sac, this distinctive single-level home offers the rare feeling of country living right in Ashland. Set on a private, fenced and irrigated acre, it was thoughtfully built with Logix ICF insulated walls, owned solar, radiant-heated floors and energy-efficient windows. Inside, warm wood ceilings, a dramatic skylit cupola, walls of windows and a large fireplace give the home character, while the spacious kitchen features abundant cabinetry and a generous granite island. A large studio/game room adds wonderful flexibility. Outdoors, expansive Trex decking connects to a screened gazebo, pergola and covered patio overlooking mature landscaping, a pond and waterfall, raised garden beds and fruit trees, with mountain and valley views beyond. Oversized 2-car garage, workshop/storage and RV/boat parking. Near the bike path, schools and Hunter Park--peaceful, private and wonderfully connected to town.

145 Normal Avenue, Ashland

Listing courtesy of Millen Property Group.

$1,950,000
3 Beds ⋅ 3 Baths ⋅ 220228333 MLS
Welcome to Red's Cabin, an original homestead on Howard Prairie Lake, never before offered for sale. Held by the family since 1889, this 9.12-acre lakefront estate spans five generations. Built in 2008 to honor that legacy, the 2,907 SF, 3 bed, 3 bath home showcases custom juniper woodwork, exposed timber, vaulted ceilings, a dramatic stone fireplace and an upstairs loft/game room. Offered fully furnished, the home is on-grid with security panels for all main-level windows. A balcony off the bunk room overlooks an impressive permitted pond fed by a year-round spring-fed stream you can hear from the house. A covered outdoor fireplace sits streamside, joined by a bocce court and detached garage. The estate includes 4.1 acres of water rights, adding to its rare combination of water, recreation and mountain setting. Gated with direct access to public lands, Howard Prairie Lake and the shoreline trail, this is a rare opportunity to own a generational Southern Oregon legacy property.

3665 Hyatt Prairie Road, Ashland

Listing courtesy of John L. Scott Medford.

$399,000
2 Beds ⋅ 2 Baths ⋅ 220228254 MLS
Peaceful country living opportunity on 6.65 acres nestled amongst the madrones, not far from downtown Ashland! The custom primary residence offers 2 beds/2 baths with a stonework entryway, pine paneling and cabinetry in the kitchen, a cozy wood stove, large windows, a metal roof, and an attached garage. A versatile bonus room adapts to a creative workshop, office, or extra bedroom. Outside, a spacious deck and flat yard lead to an impressive shop built from steel shipping containers, offering a large open workspace with a professional-grade engine hoist, ample storage, and hydraulic hangar-style doors. Down the hill, a quaint cabin in the woods offers multigenerational living, income potential, or home office space, with a full kitchen, bath, and sleeping loft. Outdoor lovers will appreciate the unbeatable access to Mt. Ashland and the Pacific Crest Trail.

5010 Old Highway 99 S, Ashland

Listing courtesy of John L. Scott Ashland.

$99,000
220228238 MLS
SELLER WILL CARRY. Discover the perfect blend of privacy and potential on this beautiful 5-acre forested parcel. Gently sloped and surrounded by mature trees, this property offers a serene natural setting with filtered views and a homesite. The varied terrain provides character and opportunity for a custom home designed to complement the landscape. Enjoy peaceful seclusion while still being within a short drive of Ashland. A rare opportunity to own acreage with privacy, beauty, and endless possibilities.

Tyler Creek Road, Ashland

Listing courtesy of Windermere Van Vleet & Associates.

$1,000
220228218 MLS
End of Irrigation Ditch. Neither the brokers, brokerage, or Jackson County warrants, nor can verify property condition, description, fixtures, permits, hazardous substances, zoning, history of illegal activity, or tax history. No guarantee of access, no sign. ''As Is'' sale. Listing brokerage does not accept bids or offers on Jackson County Taxation's behalf for these properties. There will be one public, in-person, oral auction per year held at the County Courthouse, 10 S Oakdale Ave, Medford, OR 97501, in the Auditorium, located on the first floor of the main building. Auction date is: OCTOBER 12, 2026 @ 10 AM. Brokers and brokerage do not represent the date or process, Buyer to verify process and date for accuracy.

Tolman Cr Road, Ashland

Listing courtesy of Coldwell Banker Professional Group.

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