Refine Search
Sort by
$699,000
220223307 MLS
Check out this Chalet-style triplex with R-2 zoning offering both short- and long-term rental possibilities just minutes from downtown Ashland. Units 1 & 3 are one-bedroom, unit 2 is 2 bedroom, all units have tile flooring, a kitchen with granite countertops and breakfast bar, a full bathroom with tile shower, and generous living area. Private decks provide outdoor living space, while the upper unit enjoys spectacular views. The property includes off-street parking, one space per unit, plus basement with shared laundry facilities and additional storage. Two units are currently vacant, creating flexibility for an owner-occupant, investor, or those seeking a combination. Updates completed in 2016 include ductless heating and cooling system, electrical improvements, and interior finishes. The metal roof has been recently painted, decks have been updated and water heaters were new in '23. This is a rare opportunity to own a versatile income-producing property in a desirable location.

326 N Main Street, Ashland

$800,000
4 Beds 4 Baths 220223301 MLS
Custom view home with charming detached guest cottage located just above downtown between Lithia Park and the Ashland Public Library. Main level great room with vaulted double-height ceiling, walls of windows, reclaimed clear-grain fir trim, solid-core doors, refinished oak floors, kitchen with composite dining bar, tile counters and backsplash, cabinets with solid wood interiors and custom pull-outs, dining room with glass door to view deck with gas BBQ hookup, bedroom with closet and full ensuite bath, and pantry with washer and dryer. Upper level primary with skylights, hanging closet, French doors to private balcony, and full ensuite bath with jetted tub. Versatile lower guest suite or family room with French doors to paver patio, full bathroom with oversized shower, storage cellar with stainless utility sink, and one-car garage. Detached cottage with permitted kitchen, living area, full bathroom, loft bedroom, and private gated entrance from Terrace Street. Inquire for details!

307 Hillcrest Street, Ashland

$315,000
2 Beds 2 Baths 220222924 MLS
Welcome home to this light-filled & beautifully maintained 2-bedroom, 2-bath condo in a desirable Ashland location near the YMCA! Perched on the second floor, this inviting home boasts what may be the best Grizzly Peak views in the entire complex, enjoyed from your private balcony. The open living space features durable Pergo waterproof, scratch-resistant laminate flooring throughout most of the home, while a mini-split system provides efficient heating & cooling. Bedrooms are equipped with their own heat & air conditioning window units for personalized comfort. The kitchen shines with stainless steel appliances & opens to a laundry room with shelving that doubles as valuable pantry storage. A single-car garage plus an additional parking space offer convenience, while the shared courtyard with patio furniture creates a welcoming outdoor gathering space for the adjoining four condos. Move-in ready, thoughtfully updated, & perfectly positioned to enjoy all that Ashland has to offer!

2244 McCall Drive, Ashland

$419,000
2 Beds 1 Baths 220222831 MLS
Charming 2 bdrm, 1 bath home with large great room. Original hard wood floors. Gas brick fireplace and brand new appliances. Large windows & skylights throughout make this a light filled home. Kitchen remodeled in 2010 with handcrafted cabinetry, soft close drawers & granite counter tops. Custom tile & river rock in bathroom shower. Mini duct heating & air. Great room features 3 sliding glass doors, 3 skylights. Enter the backyard & find an urban homestead environment with fruit trees and a pond. Also in the garden, an insulated 8x10 room that could be used for an office, a magical 2 story playhouse with large windows, is insulated & has electricity. Playground w/swing set & monkey bars. Storage shed with covered deck and separate tool shed. Fully fenced. New roof in 2017. Lots of storage & parking space. R-2 zoning. Conveniently located with Southern Oregon University, public pool, Garfield Park, tennis courts, middle school & elementary schools within blocks.

1312 Iowa Street, Ashland

$400,000
2 Beds 1 Baths 220222433 MLS
Charming historic fixer-upper on a private 0.26-acre lot with mature trees and incredible pollinator garden featuring 70+ plant species, lovingly cultivated over 30 years. New roof in 2019, new fencing in 2012, and new central ducting with gas furnace in 2006. Living and dining with solid oak floors and glass door to front office. Kitchen with antique gas stove, butcher block and tile counters, operable casement bay windows, wood and glass display cabinets, double sink with updated hardware, under-sink water filtration, and new dishwasher in 2023. Spacious main-level bedroom with closet, full bathroom with clawfoot tub shower, and sitting room with stairs to vaulted upper bedroom with closet. Backyard with deck and hot tub, raised beds, perennials, detached garage shop with alley access, and excellent potential for ADU or second dwelling. Centrally located above the boulevard in the desirable Siskiyou-Hargadine District near Triangle Park. Bring your ideas and inquire for details!

324 Liberty Street, Ashland

$419,000
3 Beds 3 Baths 220222380 MLS
Exceptional end-unit townhome less than 1 mile from Southern Oregon University! Originally built as the developer's personal residence, this thoughtfully designed home offers approximately 30% more living space than other units in the community. Inside, you'll find rich Brazilian cherry hardwood floors, elegant Italian mosaic tile accents, new interior paint, and stainless-steel kitchen appliances. The spacious kitchen features granite countertops, abundant cabinetry, and a walk-in pantry, opening to a comfortable living area with a gas stove. The main level also includes a half bath, laundry area, and access to a private fenced patio with additional storage. Upstairs, the generous primary suite captures beautiful mountain views and offers a spa-inspired bath with dual sinks, soaking tub, walk-in shower, and two closets. A detached garage, deeded parking space, community pool, exterior maintenance, and landscaped common areas complete this outstanding property.

820 Park Street, Ashland

$679,900
3 Beds 3 Baths 220222330 MLS
Lovely Ashland View Home above the boulevard, ideally situated close to downtown, the Oregon Shakespeare Festival and Lithia Park. This beautifully maintained 2,043 square foot stand-alone home offers a great floor plan, 3 bedrooms, 2.5 baths, hardwood and tile flooring throughout the main living spaces, all complemented by a cozy gas fireplace and abundant natural light. The kitchen and baths feature granite tile counters, nice cabinetry and quality finishes, along with custom window coverings throughout. The upper-level primary suite is quite spacious with vaulted ceilings, walk-in closet, private view deck, and an ensuite bath with a relaxing jetted tub. Enjoy the covered front porch and a charming back deck overlooking the private fenced backyard with a slate patio, mountain views, crawling vines, and mature plantings--perfect for low-maintenance outdoor living. Single garage, small monthly HOA fee. This is a wonderful spot to call HOME.

472 Scenic Drive, Ashland

$1,000,000
220222324 MLS
Unique opportunity in downtown Ashland. This commercial property offers two legal spaces with strong flexibility. 120 E Main features 1,889 sq ft plus an expansive 1,700 sq ft deck--ideal for retail, office, hospitality, or possible restaurant use. 130 E Main adds 369 sq ft, well-suited for a boutique, studio, or office. Zoned C-1-D, allowing a variety of uses. Built in 1938, the building blends character and functionality with tile and hardwood floors and a convenient single-level layout. Alley access and designated parking add ease and functionality. Ideal for an owner-occupant--occupy both spaces, use one and lease the other, or maximize income by renting both. Prime location with strong visibility, steady foot traffic, and close proximity to downtown shops, dining, and everyday amenities.

120 E Main Street, Ashland

$4,000,000
220222181 MLS
A landmark downtown Ashland land offering. Just one block from Ashland's Plaza, this rare 1.18-acre commercial development site represents one of the last opportunities of its scale & prominence in the downtown corridor. Located within the Employment Zoning District, the property offers exceptional potential for hotel, conference center, mixed-use, luxury residential, retail, offices, or destination development. Extensive prior approvals include architectural, engineering, landscaping, utility, and entitlement plans for an 8-building mixed-use project with ground-level commercial spaces and luxury residences above. Current approvals expire Summer 2026 and may be eligible for renewal. With virtually no remaining undeveloped commercial land of this size in downtown Ashland, this offering combines exceptional visibility, strong street presence, & outstanding walkability to the Plaza, acclaimed restaurants, theaters, galleries, and Lithia Park. Rare scale. Rare location. Rare opportunity.

165 Water Street, Ashland

$965,000
7 Beds 5 Baths 220222015 MLS
Rare opportunity to own 2 residences plus a studio on one tax lot. Offers exceptional flexibility for multigenerational living, rental income, live-work, or guest accommodations. The 1,720 SF main residence was fully renovated in 2018, including a new poured foundation, and has 4 bedrooms, 2 baths, open living spaces, a kitchen with crisp white cabinets, subway tile backsplash & a main level bedroom. The main residence includes a double garage with a 480 SF upper-level studio with a full bath. A separate second 1,070 SF residence, built in 2018, offers stylish & charming single-level living with high ceilings, 2 bedrooms, 2 baths, & contemporary finishes. Situated in an established historic neighborhood with mature trees, the property has off-street parking, modern systems, and is close to Ashland's downtown. This R-2-zoned property features separate addresses & meters & allows for 2 Airbnb units with owner occupancy on premises. Request property offering details.

563 Rock Street, Ashland

$284,000
2 Beds 2 Baths 220221539 MLS
Welcome to 818 Pavilion at the highly sought-after Mountain Meadows senior community in Ashland! This beautifully updated condo is truly better than new, offering a perfect blend of comfort, style, and low-maintenance living. Step inside to discover gorgeous LVP flooring, updated lighting, and tasteful designer touches throughout that create a warm, modern feel. The light-filled interior offers and inviting layout ideal for both everyday living and entertaining. Enjoy a thoughtfully refreshed kitchen, spacious living areas, and a charming front patio perfect for relaxing with your morning coffee or unwinding in the peaceful surroundings. Mountain Meadows offers an exceptional lifestyle with access to wonderful amenities, dining, social activities, walking paths, and a vibrant community atmosphere. Conveniently located near Ashland's renowned theaters, restaurants, and outdoor recreation.

818 Pavilion Place, Ashland

$375,000
3 Beds 2 Baths 220221263 MLS
Charming, fully remodeled home in the heart of Ashland! This beautifully updated 3-bedroom, 2-bath residence offers 1,291 sq ft of comfortable living space on a spacious .28-acre lot. Enjoy peace of mind with a newer roof (approximately 3-4 years old) and updated ducting. The interior features fresh paint throughout, brand-new carpet, and stylish tile flooring in the kitchen and bathrooms. The modern kitchen shines with quartz countertops and stainless steel appliances, perfect for everyday living and entertaining. With ample outdoor space for gardening, relaxing, or potential expansion, this move-in-ready home combines quality upgrades with a desirable location. Don't miss this exceptional Ashland property!

540 Oak Knoll Drive, Ashland

$794,000
5 Beds 6 Baths 220221349 MLS
71, 73 and 75 Wimer. Gorgeous updated including plumbing and electric vintage home w/charm remaining a few blocks to downtown Ashland. The main home has 3 bedrooms (2 with ensuite baths) the 3rd bedroom has an ensuite 1/2 bath. Formal living and dining and eat in large kitchen w/breakfast bar & nook. Granite countertops. Wood floors on main level & carpet on stairs & bdrms. The woodwork door trim is beautiful & probably original. Newer deck & A/C unit. Detached building (71 and 73 Wimer) are one level studio units with kitchens & baths. 73 Wimer has private deck. Main house is rented for $2375.00 p/month & tenant pays utilities except water. Studios have been rented for $1250.00 & $1350.00 per month with utilities included & they have a separate shared laundry facility. Unique property for owner occupied or income producing. Circular driveway for main home & 2 parking spaces in front for studios. Has been traveler accomodations in the past. Buyer to do own due diligence on u

75 Wimer Street, Ashland

$550,000
4 Beds 2 Baths 220221283 MLS
Charming historic home with 29+ years of improvements and stewardship. Updated electrical, HVAC, plumbing, sewer line, new roof, solar tubes, skylights, wood-wrapped casement windows, and decks. Wood flooring, vintage fixtures and hardware, period lighting, leaded-glass windows, and picture rail moldings. Spacious open living and dining area with wood stove and door to covered side-porch, kitchen with wood and glass-fronted display cabinets, laundry closet, two bedrooms, and full bathroom. Vaulted upper-level landing, wood-paneled bedroom with panoramic mountain views, full bathroom, and fourth bedroom with closet. Terraced grounds with mature trees, ornamental plantings, paver patio, meandering pathways, sunny fenced gardening areas, rustic garden shed, and renovated detached garage workshop. Property backs to 1.43-acre natural greenspace owned by the City of Ashland near Hald-Straberry Park; conveniently located within a half-mile of downtown. Inquire for details!

71 Scenic Drive, Ashland

$799,200
3 Beds 3 Baths 220221136 MLS
Enjoy this practically new, sophisticated, energy-efficient home just one mile from downtown Ashland. Thoughtfully designed for main-level living, it features a primary suite with walk-in closet, tile shower, dual sinks, and tile flooring, plus an office, half bath, laundry, kitchen with walk in pantry and extended storage/coffee bar, dining area, vaulted living room with gas fireplace with access to the back patio. Upstairs offers a spacious landing/bonus area, two bedrooms, one with walk-in closet, and a large bathroom with dual sinks and tub/tiled shower combo. Quartz countertops, custom cabinetry, and window shutters are found throughout. Engineered hardwood spans the main living areas, with carpet in bedrooms and stairs. The fenced, landscaped backyard includes covered patio, a paver courtyard, retractable awning, and drip irrigation. Owned solar and EV charger complete this exceptional home. Check it out today!

396 Randy Street, Ashland

$393,000
3 Beds 3 Baths 220220980 MLS
Stylish turn-key condominium with an excellent central location in beautiful Ashland, OR. Welcoming entryway sets the tone for a calming vibe from the moment you enter. The main living and dining areas have bamboo flooring. The kitchen has stainless steel appliances and granite countertops including a large center island with breakfast bar. There is a cozy gas fireplace with tile surround and large bay window with views out to the private, fenced patio area. Upstairs there are three bedrooms including a spacious primary bedroom suite with balcony, walk-in closet and tastefully updated bathroom. The two additional bedrooms share a bathroom. Laundry is also on this level. HOA fees cover all exterior maintenance as well as exterior insurance. Location is ideal with proximity to schools, parks, the bike path and a relatively level and short distance to everything downtown Ashland has to offer.

62 N Mountain Avenue, Ashland

$245,000
2 Beds 2 Baths 220220712 MLS
If you are looking for the best views in Ashland's Tudor Heights, this is it. Positioned as the premier front unit, this condo offers a perspective no other home in the complex can match. Stay comfortable year-round with the rare addition of efficient ductless mini-splits for heating and cooling--a significant upgrade over the standard baseboard heat found in most units. The main level offers a seamless open layout that flows to your outdoor patio. Upstairs, both bedrooms provide unobstructed mountain views to the north and east, including a private balcony off the main suite--perfect for watching the sunrise. Whether you're walking to the Downtown Plaza for dinner or hiking through Lithia Park, everything is within reach. Enjoy the security and ease of a comprehensive HOA that handles exterior upkeep, allowing you to simply relax and enjoy the Southern Oregon scenery.

495 Chestnut Street 1 Unit 1, Ashland

$950,000
3 Beds 3 Baths 220220668 MLS
Quality custom view home in a private natural setting above the boulevard, just six minutes to Ashland's downtown plaza. Abundant natural light and airflow with operable wood-wrapped casement windows, high vaulted ceilings, solid core doors, and unique architectural view corridors throughout. Great room with solid Brazilian cherry flooring, gas fireplace, formal dining with built-in buffet, French doors to wrap-around view deck, kitchen with granite dining counter and stainless appliances, open family and informal dining room, powder room, laundry with utility sink, and two-car garage. Step-down primary suite with French doors to private balcony, walk-in closet, full ensuite bathroom with travertine double vanity, jetted tub, shower, and water closet. Upper loft with mountain views and stairwell skylights. Two lower-level guest bedrooms, full bath with tub shower, den, and French doors to pebbled concrete patio and organic garden. Newer HVAC and exterior paint. Inquire for details!

602 Ashland Street, Ashland

$2,250,000
220220428 MLS
Rare 10-unit investment opportunity in Ashland's Hillview Condominiums -- close to Scenic Park, Asante Ashland Community Hospital, downtown dining and entertainment. Three-year seller-carried financing available at 3.75% rate with interest-only payments and balloon at maturity. Each unit ranges from 1,034 to 1,174 SqFt with two bedrooms, one full bath, open living and dining space, high ceilings, in-unit laundry, kitchen with granite counters and all appliances included, dedicated parking, storage, and access to landscaped common areas. Ground-level units with fully fenced private backyards and poured concrete patios. Portfolio includes stable tenancy, average occupancy of 4.2 years, room for rent growth, and association-maintained exterior building components including roofs, siding, paint, and landscaping. Complete investment analysis and user guide, rent roll, association documents, title information, and additional due diligence materials available upon request.

230 Grant Street, Ashland

$995,000
3 Beds 4 Baths 220220180 MLS
Built in 2016, this custom Ashland home offers refined single-level living with vaulted ceilings, expansive windows, and sweeping Cascade Mountain views. The light-filled great room features a large gas fireplace and an open layout ideal for entertaining. Multiple outdoor seating areas overlook beautifully maintained gardens, creating seamless indoor-outdoor living. The versatile floor plan includes a spacious primary suite with spa-like bath, a vaulted second bedroom with ensuite, a guest bedroom, office, plus a bonus room in the basement with half bath--perfect for guests or hobbies. An oversized 2-car garage with EV charger, along with a tool shed, wood shop, and abundant dry storage, provides exceptional functionality. Located just minutes from downtown Ashland, world-class theater, Lithia Park, and scenic hiking and biking trails, this home blends comfort, quality, and convenience in a prime setting. Schedule your private tour today!

417 Tucker Street, Ashland

$828,000
4 Beds 3 Baths 220220097 MLS
It's the home you've dreamed of with astounding views of the valley and mountains from living and dining rooms and all four bedrooms! Designed by Jerry Toney it's been well cared for and improved over time with meaningful updates including terraced lawn with sundeck, two kitchen sinks, 16 (owned) solar panels and more! A large room on the first floor with built-in shelves is suitable for use as media, gym, or library. Garage has storage room plus workbench and sink. On the main level, vaulted ceilings and oversized windows running the length of the home create a spacious feeling that invites the valley below indoors. The primary suite boasts a walk-in closet/dressing area and a tiled bathroom complete with two-person soaking jacuzzi. The kitchen opens onto the main outside deck facilitating meals outside or barbecuing meals for inside. Throughout the home, custom western maple cabinetry and quality woodwork add warmth and character. Call your Realtor for a private showing today!

575 Dogwood Way, Ashland

$375,000
2 Beds 1 Baths 220219842 MLS
Charming single-level cottage in one of Ashland's most desirable locations, with stunning views of Grizzly Peak. This clean, well-maintained home features new flooring throughout and an inviting, light-filled interior, with two bedrooms plus a detached bonus room (not included in sq. footage), perfect for home office or studio. Additional storage can be found in the spacious basement. Large undeveloped adjoining lot (not included in the sale) gives the property a feeling of openness and privacy. Among the cherry and apple trees, grapevines and herb garden, enjoy peaceful mornings on the porch, a perfect spot for coffee while taking in the quiet neighborhood. Ideally located close to downtown Ashland, Lithia Park, the Oregon Shakespeare Festival, Southern Oregon University, dining, and nearby hiking and biking trails.

480 Harrison Street, Ashland

$140,000
1 Beds 1 Baths 220219091 MLS
Step into a bright, beautifully cared-for top-floor condominium featuring a vaulted living room ceiling, expansive windows, and a seamless flow that makes the space feel both open and inviting. The well-appointed kitchen offers generous counter space, ample cabinetry, and a cozy dining area. Step outside onto your private balcony--perfect for relaxing evenings and fresh air. The spacious bedroom connects easily to a well-designed bathroom with a low-step shower and built-in linen storage, while a full-size washer and dryer add everyday convenience. Located just moments from the clubhouse and fitness center, with easy elevator access to parking and storage, this home blends accessibility with comfort. Enjoy a vibrant, amenity-rich lifestyle with beautifully maintained grounds, walking paths, gardens, an indoor pool, fitness center, and a welcoming calendar of social events, gatherings, and activities.

943 Mountain Meadows Circle, Ashland

$1,466,000
2 Beds 4 Baths 220218853 MLS
You'll be in a prime spot right in Ashland's Railroad District/Spur Rail Subdivision, a super desirable area! Just hop on the elevator to the top! This place has a fantastic modern design, with 770 square feet of first-floor commercial space and a luxurious 2-story home on the 2nd and 3rd floors. You'll find premium finishes everywhere, a huge rear patio, vaulted ceilings, big windows, an open floor plan, and materials that are easy to take care of, so they last. Plus, the property is set up to get the most out of solar panels. You'll have amazing views of Grizzly Peak to the north and Mt. Ashland to the south--it's truly a dream location. The property is zoned E1 commercial (Ashland Employment District with Residential Overlay). There's a single-car garage, EV charging, and the square footage has grown. The windows have also been upgraded to Milgard Fiberglas;, each parcel comes with a 1/6th interest in the parking lot next door.

138 Clear Creek Drive, 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: