Ashland Homes for Sale

Welcome to Ashland, Oregon – a picturesque gem nestled in the heart of Jackson County. Known for its vibrant arts scene, stunning natural landscapes, and a welcoming community, Ashland offers a unique blend of small-town charm and cultural richness. With the iconic Oregon Shakespeare Festival at its core, this city attracts visitors and residents alike who appreciate the performing arts, fine dining, and eclectic shopping experiences.

Surrounded by the breathtaking Cascade Mountains and lush forests, outdoor enthusiasts will find a paradise for hiking, biking, and exploring the great outdoors. The nearby Ashland Creek and Lithia Park provide serene spots for picnics and nature walks, making it easy to embrace the beauty of the region.

For those considering a move to this enchanting city, the real estate market in Ashland is thriving. Homes for sale range from charming historic properties to modern new builds, catering to diverse tastes and budgets. Whether you’re seeking a cozy bungalow, a spacious family home, or a luxurious retreat, Ashland has something for everyone. The community is known for its friendly atmosphere, excellent schools, and strong sense of belonging, making it an ideal place to raise a family or enjoy retirement.

With its stunning scenery, rich cultural offerings, and a variety of homes for sale, Ashland is not just a place to live; it’s a lifestyle waiting to be embraced. Come discover your dream home in this enchanting city where every day feels like a celebration of life!

Newest Ashland Homes for Sale

$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.

$675,000

3 Beds ⋅ 3 Baths ⋅ 220228159 MLS

HYATT PINES RETREAT! Escape to this beautiful year-round mountain sanctuary on 7.76 ac. Tranquil setting & backing to BLM land. Mostly level, nicely treed & surrounded by exceptional homes & towering pines. Across from Hyatt Lake & near Howard Prairie Lake, outdoor adventure is at your doorstep--hiking, swimming, boating, camping, fishing, skiing & more! The home features a striking metal roof, fiber-cement siding, & wood casement windows. Cozy living room w/pellet stove. Main-level primary suite offers deck access, walk-in closet, ensuite bath with walk-in shower. 2nd main-level bedroom across from guest bathroom. Upstairs includes 3rd bedroom, loft, full bath & large bonus room (~23'x16') not included in the 1,912sf. Numerous updates include roof/siding/windows, kitchen, flooring, baths, doors, furnace, water heater. Four outbuildings include two large sheds, well house & garden shed. HOA $500/yr for road maintenance/winterization. Rare blend of privacy, recreation & mountain living!

7696 Hyatt Prairie, Ashland

Listing courtesy of John L. Scott Medford.

$649,000

5 Beds ⋅ 3 Baths ⋅ 220228065 MLS

Welcome home to this spacious 5 bedroom, 3 bath multigenerational home offering approximately 3,100 square feet of comfortable living space on a roomy .23-acre lot. Thoughtfully designed with two living rooms, there's plenty of room for gathering, relaxing, or creating separate spaces for extended family. A 2-car garage provides convenient parking and storage, while the covered back deck provides space to enjoy the tranquil backyard complete with a charming fish pond; perfect for enjoying your morning coffee or unwinding at the end of the day. Located in a quiet neighborhood just minutes from everything Ashland has to offer, you're less than 10 minutes from downtown Ashland, the Oregon Shakespeare Festival, and Emigrant Lake. Come experience the space, flexibility, and peaceful setting this special home has to offer!

1058 Linda Avenue, Ashland

Listing courtesy of John L Scott Real Estate Grants Pass.

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