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$1,450,000
220225791 MLS
One block from the Oregon Shakespeare Festival and downtown Ashland's restaurants, galleries, and cultural amenities, the McCall House B&B is a beautifully restored 1883 Italianate home offered for sale as a private residence. Currently operating as a boutique hotel, the property features ten historic guest rooms, including two detached private Carriage House suites, and may continue as a licensed hospitality business for a buyer who wishes to carry on that tradition. The C-1 zoning also opens the door to a variety of commercial uses, including a restaurant, office suites, or other business opportunities. Ten on-site parking spaces are included, a welcome convenience this close to the Ashland Plaza. This is a rare opportunity to own one of the city's most celebrated historic addresses. Due to the C-1 zoning, conventional 30-year financing is unavailable, and non-cash buyers are encouraged to confirm lending options before requesting an appointment. Please do not disturb guests.

153 Oak Street, Ashland

$1,450,000
10 Beds 12 Baths 220225786 MLS
One block from the Oregon Shakespeare Festival and downtown Ashland's restaurants, galleries, and cultural amenities, the McCall House B&B is a beautifully restored 1883 Italianate home offered for sale as a private residence. Currently operating as a boutique hotel, the property features ten historic guest rooms, including two detached private Carriage House suites, and may continue as a licensed hospitality business for a buyer who wishes to carry on that tradition. The C-1 zoning also opens the door to a variety of commercial uses, including a restaurant, office suites, or other business opportunities. Ten on-site parking spaces are included, a welcome convenience this close to the Ashland Plaza. This is a rare opportunity to own one of the city's most celebrated historic addresses. Due to the C-1 zoning, conventional 30-year financing is unavailable, and non-cash buyers are encouraged to confirm lending options before requesting an appointment. Please do not disturb guests.

153 Oak Street, Ashland

$564,900
3 Beds 2 Baths 220225550 MLS
'One Property. Four Possibilities. Less than a mile from downtown Ashland, this classic Victorian offers exceptional flexibility with versatile zoning and mountain views. Enjoy it as a spacious 3-bedroom, 2-bath home, a duplex with two long-term rental units, a residence with a currently licensed short-term rental, or a live/work property with a private entrance ideal for an attorney, counselor, massage therapist, or other home-based business. Features include a spacious upstairs primary suite with full bath, basement storage, dry sauna, washer, dryer, refrigerator, an inviting patio, and three deeded off-street parking spaces. Historic charm meets modern opportunity in this truly one-of-a-kind Ashland property.'

508 N Main Street, Ashland

$493,000
3 Beds 3 Baths 220225503 MLS
Spectacular Ashland Views from this lovely townhome. Turn-key home with wonderful valley and mountain views near Kestrel Park. Living room has an open-concept design and an abundance of natural light, gas fireplace and 2 remote controlled awnings- 1 for the covered patio and 1 for the dining room window. Kitchen has lovely granite counter tops, tiled backsplash, cabinets with custom pull-outs, granite dining island, stainless sink. Spacious main-level primary suite with ceiling fan, gracious tiled bath, walk-in shower and double vanities. Main level also features a 1/2 bath. Upstairs offers two bedrooms, a full bath, extra storage space, and an office alcove. Lower level has an expansive two-car garage and large storage closets. Elevator-ready floor plan would make all floors accessible. Very low HOA fees, washer & dryer, and amazing views. This is Ashland living at its best!

965 Camelot Drive, Ashland

$440,000
3 Beds 3 Baths 220225375 MLS
Tastefully updated home located less than a mile from Lithia Park. The inviting interior features new engineered hardwood flooring throughout, a spacious living area, and abundant storage. The remodeled kitchen offers newer appliances, quartz countertops, and freshly painted cabinetry, creating a clean and modern feel. Enjoy peace of mind with a new roof and a top-of-the-line HVAC system professionally installed by Janke. HOA dues provide exceptional value by covering all utilities and exterior maintenance, as well as access to the community's solar-heated outdoor pool. Move-in ready and ideally situated near Ashland's parks, dining, shopping, and cultural attractions, this home is ready to welcome its next owners.

426 Chestnut Street, Ashland

$459,000
3 Beds 2 Baths 220225105 MLS
Welcome to one of Ashland's most desirable neighborhoods - Ridgeview Place! This beautiful 3 bedroom, 2 bathroom townhouse offers 1,331 sq.ft. of thoughtfully designed living space and an attached garage. Inside you will find laminate flooring throughout the main living areas and carpet in the bedrooms. The main level features one bedroom and a full bathroom, ideal for guests or a home office. The inviting living room features soaring vaulted ceilings, creating an open feel, while the elegant staircase leads to two additional bedrooms, a split bathroom, and a spacious laundry room. The kitchen offers abundant cabinetry, a pantry, breakfast bar, and stainless steel appliances. Conveniently located just minutes from downtown shopping, Southern Oregon's finest restaurants and entertainment, SOU, and parks. HOA covers landscaping, common area maintenance, and garbage service for easy, low-maintenance living.

37 N Mountain Avenue, Ashland

$310,000
2 Beds 1 Baths 220224865 MLS
Beautiful, move in ready 2-bed / 1 bath condo, within a short walk to downtown Ashland, coffee shops , restaurants , shopping, & Southern Oregon University . Nice and bright natural light throughout with skylights in the living area. The kitchen has granite counters with stainless-steel appliances. Open floor plan flows into a spacious great room with 9ft ceilings and plenty of windows to take in the surrounding mountain views including Grizzly peak. Natural Fir doors and trim throughout. Ductless heating and air. Don't be fooled by the sq ft, this condo has a feel that it is much bigger. A modern and aesthetically pleasing living space in a small association. Don't miss out on this rare opportunity to own a low maintenance home in Ashland. The unit is upstairs. HOA includes, fencing, exterior siding gutters, down spouts and roof.

1249 Iowa, 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

$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

$215,000
2 Beds 2 Baths 220219913 MLS
Charming Ashland Condo in Prime Location! Conveniently situated near restaurants, shopping, medical facilities, & scenic hiking trails in beautiful Lithia Park, this inviting 2-bedroom, 1.5-bathroom condo offers both comfort & accessibility. Tucked toward the back of the desirable Tudor Heights Complex, updated w/ newer carpet, LVP flooring & exterior paint. The main level features a kitchen w/ refrigerator, range/oven, & microwave, plus a convenient half-bathroom. Living room opens to a covered back patio, perfect for enjoying your morning coffee. Upstairs, you'll find 2 bedrooms--one w/ a private balcony ideal for relaxation, the other w/ a walk-in closet & easterly mountain views. Full bathroom w/ a dual sink vanity & tub/shower combination. The HOA provides many amenities, including a covered assigned parking space w/ storage closet, water, sewer, garbage, roof maintenance, exterior upkeep, & common areas. Don't miss your opportunity to start enjoying the Southern Oregon Lifestyle!

495 Chestnut Street 19 Unit 19, 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

$230,000
2 Beds 2 Baths 220218166 MLS
Back on market due to buyer financing/economic changes. Home is priced aggressively for a quick sale. Rare opportunity for affordable, low-maintenance living near the heart of Ashland. This charming two-bedroom townhouse is the perfect fit for those seeking an uncluttered lifestyle, as the HOA handles all groundskeeping and full exterior maintenance. Ideally situated in a quiet neighborhood, you are just a short distance from Ashland's vibrant downtown. Inside, the home is equipped with high-efficiency mini-splits for year-round climate control and comfort. The thoughtful layout includes one bedroom featuring a beautiful view of the mountains, and the second with a private balcony. Off the living area is a private fenced covered patio, providing intimate spaces for outdoor relaxation. Added conveniences include dedicated covered parking and private storage. Combining price, position, and ease of ownership, this home is a standout offering.

495 Chestnut Street 23 Unit 23, Ashland

$239,900
2 Beds 1 Baths 220204025 MLS
BEAUTIFUL LIGHT AND BRIGHT END UNIT with views of the golf course. Don't miss this opportunity! This 2-bedroom, 1-bath condo is located in the Oak Knolls neighborhood of Ashland. The kitchen is bright with plenty of cabinet space, a garden window and a pass-through to the dining room. The living room and primary bedroom open up onto a spacious, covered private outdoor patio. This unit boasts upgraded flooring with newer kitchen and laundry appliances. The bathroom features a large step-in shower and a bidet. This unit has a lot of storage space with 3 hall closets, a storage closet on the balcony and in the covered parking area, as well as large bedroom closets. You can enjoy the tranquil views of the community garden & backyard, and the beautiful Ashland hills from your living room or primary bedroom. The unit has updated plumbing, fresh paint inside & out and a newly repaved parking lot with carport! One Seller has active Real Estate License in the State of Oregon

854 Twin Pines Circle 7 Unit 7, Ashland

$1,050,000
220191240 MLS
Hard to find Commercial investment property in Ashland right across from SOU college! Located on the main road through town Siskiyou Blvd. This great business opportunity consists of 5 updated units. These units are updated and clean and would be great for many types of business. Units 1-2 1483 sqft have been made into 1 business rents for $2,188. As you enter it has a great inviting reception area, private rooms and is light and bright and has great flow. Unit 3 just went through a major remodel and has a great reception area and private rooms and is very inviting and rents for $1,620. Unit 4 1080 Sqft offers 5 private offices with a reception area and break counter area and rents for $1,626. Unit 5 is a quaint quiet spot with approx 700 sqft, would make a good rental or for your business and is vacant. A large parking lot allows for ample parking for all units.

993 Siskiyou Boulevard, 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: