Ashland Real Estate

Welcome to Ashland, Oregon – a charming gem nestled in the heart of Jackson County. Renowned for its vibrant arts scene and stunning natural beauty, Ashland offers a unique blend of culture and outdoor adventure that captivates both residents and visitors alike.

Home to the prestigious Oregon Shakespeare Festival, Ashland is a haven for theatre enthusiasts. The festival draws thousands each year, showcasing world-class performances that celebrate the timeless works of Shakespeare as well as contemporary plays. Beyond the stage, the city boasts a thriving arts community, with galleries, studios, and local craft shops lining its picturesque streets.

Nature lovers will find themselves in paradise here. Ashland is surrounded by the breathtaking landscapes of the Siskiyou Mountains and the stunning Ashland Creek, offering endless opportunities for hiking, biking, and exploring. The nearby Lithia Park, with its lush gardens, tranquil ponds, and scenic trails, serves as a perfect escape for relaxation and recreation.

Culinary enthusiasts will delight in Ashland's diverse dining scene, featuring farm-to-table restaurants, cozy cafes, and local wineries that showcase the region's rich agricultural heritage. Whether you're savoring a gourmet meal or enjoying a glass of local Pinot Noir, the flavors of Ashland are sure to impress.

With its friendly community, excellent schools, and a plethora of outdoor activities, Ashland is not just a destination; it’s a place to call home. Experience the warmth and charm of Ashland, where culture and nature intertwine seamlessly, making it an ideal location for those seeking a vibrant lifestyle in Southern Oregon.

Newest Listings in Ashland

$535,000

5 Beds ⋅ 3 Baths ⋅ 220226295 MLS

Escape to a private retreat on five level, wooded acres in the heart of the Highway 66 recreation corridor, just minutes from Howard Prairie, Hyatt Lake, and Lake of the Woods. This beautifully maintained, recently updated split-level home seamlessly blends comfort, privacy, and year-round adventure. A slate entry opens into a spacious living room featuring a bay window and a wood-burning stove insert. The home offers five bedrooms, three full baths, a formal dining area, and flexible living and family rooms--each with its own fireplace--plus a dedicated office or hobby space. The kitchen is equipped with granite countertops and tile flooring, ideal for casual meals or hosting guests. Set in a peaceful forest environment close to fishing, boating, hiking, mountain biking, and snowmobiling, this property is perfect as a primary residence, seasonal getaway, or investment property. Experience the quintessential Southern Oregon lifestyle in a serene, nature-filled setting.

12300 Oregon 66, Ashland

Listing courtesy of eXp Realty, LLC.

$635,000

3 Beds ⋅ 2 Baths ⋅ 220226260 MLS

Beautifully maintained and thoughtfully updated, this home offers main-level living with an inviting open floor plan, 10-foot ceilings, a cozy gas fireplace, a remodeled bathroom, a thoughtfully designed kitchen with granite countertops, and new flooring throughout. Large picture windows and a private deck capture expansive views of Oak Knoll Golf Course, Grizzly Peak, and the surrounding mountains. The finished basement features flexible space ideal for a guest suite or fourth bedroom, hobby room, or additional living area, along with abundant storage. An oversized two-car garage offers generous room for vehicles. Located in a well-maintained neighborhood with miles of nearby trails, the low-maintenance front yard features a drip irrigation system, allowing you to spend more time enjoying the exceptional setting.

900 Cypress Point Loop, Ashland

Listing courtesy of John L. Scott Ashland.

$399,000

2 Beds ⋅ 2 Baths ⋅ 220226205 MLS

Welcome to your dream sanctuary! Perched high in an exclusive residential community, this extraordinary second-floor condominium seamlessly combines modern luxury with natural tranquility. Step inside to discover a bright, open-concept living space framed by multiple windows which capture the views over a quaint green park. At the heart of the living room there is a cozy gas fireplace, creating an inviting ambience for relaxing or entertaining. Culinary lovers will adore the gourmet kitchen, fully equipped with stainless steel style appliances. Dual private balconies extend your living area outdoors, offering perfect vantage points to the scenic vistas. Both full bathrooms showcase exquisite custom stone tile work, transforming daily routines into a spa-like experience. For ultimate ease, an elevator ascends smoothly from the secure underground garage straight to your second-floor retreat.

624 Fair Oaks Court, Ashland

Listing courtesy of Gateway Real Estate.

$1,695,000

3 Beds ⋅ 4 Baths ⋅ 220224372 MLS

Exclusive equestrian property just outside Ashland! This 8+ acre unique estate has it all, from the beautiful single level updated home with stunning views of Grizzly Peak, to the well-equipped horse facilities & fully irrigated pastures. Horse boarder's dream w/ 8+ paddocks, 7 cross-fenced pastures w/ more stables, 9000+ sf sand-filled covered arena w/ lighting for night riding, hay barn, & water access to Tolman Creek. Gorgeous 3 bed, 4 bath 3765 sf custom home surrounded by lush landscaping, welcomes w/ beautiful hardwood floors, vaulted ceilings, exquisite kitchen, closed in patio, custom built-ins, & topped off w/ a 1000 bottle wine cellar. Light & bright primary suite features magnificent windows & a spa-like bathroom w/ jetted soaking tub, custom slate tile shower, heated floor & dual sinks. Step from the open concept living to a refreshing oasis boasting of a solar-heated pool, hot tub, peaceful water feature, & a tranquil pond full of bass and blue gill that beckons to stay.

550 Crowson Road, Ashland

Listing courtesy of John L. Scott Ashland.

$399,000

1 Beds ⋅ 1 Baths ⋅ 220226151 MLS

Affordable opportunity to own 2.14 acres and finish building a newer, 688-sqft tiny home nestled on private acreage, just 15 minutes from downtown Ashland. This existing permitted general purpose building, is ready to be converted into a 1-bedroom, 1-bathroom layout. Property features outdoor sauna, small seasonal pond, and high-producing well (11 GPM with pump, 41 GPM raw). Built in 2014, the existing permitted structure currently includes an unfinished kitchen & dining room. Purchase property as-is with cash (see MLS listing # 220226037) for $275,000 or finance the construction using a rehab loan with this listing. List price is an estimate on the the total costs including the land purchase and the amount needed to finish it, based on estimate by contractor ($129,000). Buyer to due their own due-diligence. Buyer to enter into a separate building contract with contractor of their choice outside of escrow. Final price to be determined at a later date when Rehab package is finalized.

4712 Old Highway 99 S, Ashland

Listing courtesy of John L. Scott Ashland.

$550,000

220226144 MLS

Excellent duplex opportunity near Ashland Hospital, with easy access to I-5 and downtown. Located just 1 mile from Lithia Park and the Ashland Plaza, each unit offers 3 bedrooms, 1.5 bathrooms, its own garage, and a private backyard with beautiful views of Grizzly Peak and the surrounding mountains. Recent updates include new mini-split heating and cooling systems and fresh interior paint. The property is currently vacant, providing flexibility to establish new rental agreements. Situated on a desirable corner lot, this property offers a versatile opportunity for long-term rental income, owner-occupancy, or a combination of both, all in a highly convenient location.

Ashland

Listing courtesy of John L. Scott Medford.

$999,999

3 Beds ⋅ 2 Baths ⋅ 220226122 MLS

Welcome to 501 Carter Lane, a fully flat, usable property offering the ultimate blend of agricultural potential and incredible income generation! This upgraded 2,680 sqft. house is surrounded by amazing mountain views and features an 800 sq. ft. barn home, cottage, cabin, and a tiny home. The estate boasts tons of Airbnb rental income opportunity, with a 9-year 5-star Superhost history generating up to $100k+ annually. Built for growth, this farm features OMMP/ODA licensed gardens, greenhouses, and fertile soil. You'll find amazing, crystal-clear water with an endless well, irrigation ponds, and a 1-million-gallon TID water allocation. With upgraded electrical throughout and tons of equipment for farming included, it's a turnkey operation ready for your crops. Whether you want to farm, host guests, or move the whole family into this unique dream property, your endless possibilities await!

501 Carter Lane, Ashland

Listing courtesy of Real Broker.

$449,000

3 Beds ⋅ 2 Baths ⋅ 220225551 MLS

Spacious 3 bedroom townhome in the heart of Ashland with easy access to the bike path, close to downtown, SOU and the Oregon Shakespeare Festival. This ideal end-unit home has an open floor plan that welcomes you with gas fireplace in the living room, dining area with patio access, breakfast bar and beautiful solid wood kitchen cabinets. Easy living with attached single car garage and a main level bedroom and full bathroom. Upstairs you'll find two more bedrooms with mountain views and a full bathroom, as well as a landing loft area perfect for a reading, craft nook or office. Seller will pay 13-month Enhanced CRES home warranty. Association covers all exterior maintenance, trash, sewer, and landscaping. Beautiful, turn-key, Ashland living at it's finest!

39 N Mountain Avenue, Ashland

Listing courtesy of Gateway Real Estate.

$275,000

220226037 MLS

Affordable opportunity to own 2.14 acres and finish building a newer, 688-sqft tiny home nestled on private acreage, just 18 minutes from downtown Ashland. Currently sold as land with a permitted general purpose building, this ready-to-go property features premium outdoor sauna, small irrigation pond, and high-producing well (11 GPM with pump, 41 GPM raw). Built in 2014, the existing structure currently includes an unfinished kitchen & dining room. Attached garage space is ready to be converted into a 1-bedroom, 1-bathroom layout. Purchase this property as-is or finance the construction using a 203k rehab loan. Electricity is available at the property line. A comprehensive estimate of $129,000 can be provided upon request, which includes finishing with high-end finishes, new septic system, electrical, plumbing and labor. Buyer to conduct independent due diligence regarding cost and financing.

4712 Old Highway 99 S, Ashland

Listing courtesy of John L. Scott Ashland.

$798,500

4 Beds ⋅ 4 Baths ⋅ 220226035 MLS

Private 5.5-acre mountain retreat with stunning views, gated entry, asphalt drive, and expansive paved parking, only 5 minutes to town! Perched above Emigrant Lake, this impeccably maintained 2,700 sq ft home offers flexible living: two inviting living areas (one with a cozy fireplace, the other with a wet bar and patio access), a sunlit kitchen with tile floors, granite counters & backsplash, and all appliances included. Main level features formal dining, a bedroom and 1.5 baths; upstairs the spacious primary suite with walk-in closet plus two more bedrooms, 2 full baths and larger storage room. Huge attached workshop with shelving, workbenches and 220/240A service (could be converted to ADU), plus an attached 2-car garage. Entertain or unwind on the deck with pergola and hot tub, enjoy outdoor/indoor living and private hiking trails right on the property.

197 Timberlake Drive, Ashland

Listing courtesy of John L. Scott Ashland.

$535,000

3 Beds ⋅ 2 Baths ⋅ 220225426 MLS

Overlooking a protected wetlands corridor with panoramic views of the Southern Cascades and Grizzly Peak, this beautifully updated mid-century Ashland home offers exceptional privacy in a peaceful natural setting. An expansive picture window fills the living room with natural light while framing the ever-changing landscape. Hardwood floors and a cozy wood-burning stove create a warm, inviting space, while the updated kitchen and well-maintained bathrooms provide comfortable everyday living. Outside, enjoy a spacious deck, spa, mature oak tree, and lush gardens--perfect for relaxing or entertaining. Located on a quiet, low-traffic street just minutes from downtown Ashland, the home is within walking distance of North Mountain Park Nature Center, the Bear Creek Greenway, scenic trails, and bike paths. A rare blend of privacy, nature, and convenience in one of Ashland's most desirable neighborhoods.

304 Clinton Street, Ashland

Listing courtesy of eXp Realty, LLC.

$350,000

2 Beds ⋅ 2 Baths ⋅ 220225960 MLS

Upgraded and move-in-ready single-level end-unit townhome located near the Ashland Family YMCA and future site of 5.52-acre East Main Park! Fresh interior paint, all-new low-pile berber wool carpets, and new roof to be installed early August 2026. Entry with skylight and hall coat closet, bamboo flooring, kitchen with custom maple cabinets, granite counters, solar tube, and stainless appliances including Fisher & Paykel refrigerator. Open dining area and vaulted living room with sliding glass door to covered patio and fully-fenced private backyard with composite deck. Primary with dual closets and full ensuite bathroom with solid surface vanity, maple cabinets, solar tube, and tub shower. Full guest bath with matching amenities, guest bedroom with closet, laundry area with Speed Queen washer and dryer, and one-car garage. Association dues of $265 per month cover all exterior maintenance - including roof, siding, paint, front landscaping, and common areas. Inquire for details!

241 Clay Street, Ashland

Listing courtesy of John L. Scott Ashland.

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