Vintage homes for sale & real estate in Ashland, OR

Vintage Home for sale in Ashland, OR:

Fully renovated historic home and detached cottage on a corner lot with alley access in the Skidmore Academy Historic District - just three blocks from Ashland's downtown plaza or one block to Briscoe Park! New foundation, roofing, sewer line, and utility services - including all electrical, gas, and plumbing. Single-level home with high ceilings, living room with crown molding, dining area with built-in china cabinet, kitchen with granite counters, stainless appliances including gas range with convection oven, two bedrooms with closet and built-in wardrobe - each with access to full ensuite bathroom with marble vanity and tiled tub shower. Charming period fixtures and vintage hardware thro

Vintage Home for sale in Ashland, OR:

Discover the rare opportunity to own a thoughtfully maintained, multi-residence property tucked in the heart of Ashland's vibrant Railroad District. One property, two homes, three distinct addresses & utilities — 134, 136, and 138 North 2nd Street — this versatile collective blends character, comfort, & possibility. Each home has been lovingly cared for, featuring updated Jen-Weld windows (2010) and a new roof (Oct 2025). The 1952 cottage (136 N Second St, facing Second St) was beautifully remodeled in 1996 by Brad Roupp. The 1998 Don Greene Classic cottage (134 & 138 N Second St) has the downstairs being run as a short-term rental approximately 40% of the year.

Vintage Home for sale in Ashland, OR:

Exceptional home in the heart of Ashland, within minutes of Shakespeare festival and downtown. This amazing abode situated on a sizeable lot demonstrates vintage appeal, extensive remodel embodies every modern amenity one could desire. Large covered front deck flows into spacious entryway, generous chefs kitchen, capacious living and dining room. The main floor is set up for easy living, with tons of room to entertain. Tall ceilings, large windows, beautiful stained glass door surrounds and more. Upstairs you will find the Primary bedroom, en suite bath and enormous closet, additional upstairs bedrooms are generous and all have large closets. Tons of storage space, custom doors, windows and

Vintage Home for sale in Ashland, OR:

A true expression of Ashland's early days, this iconic 1874 Victorian is the original home from Max Pracht's Peachblow Paradise orchard that helped put Ashland on the map with its world-class peaches. On the market for the first time in 30+ years, it sits on a private . 61-acre lot surrounded by old-growth sequoia, wisteria, and cypress trees. Lovingly restored in the 1990s, the home blends modern comforts with details that echo those early days, vaulted ceilings, fir hardwood floors, carved banisters, crown molding, and period fixtures. Double-pane windows fill the home with light. The chef's kitchen features granite counters, luxury appliances, and built-ins, flowing into the spacious liv