248 Wimer + 369 Alta Ashland, Oregon

Tucked into the heart of Ashland, Oregon, this thoughtfully designed property offers a rare combination of comfortable living, rental income, and long-term flexibility. Built in 1996, it includes a 1,910 square foot main residence and a permitted 944 square foot attached ADU, creating an ideal setup for owner occupancy, multigenerational living, or investment use.

The main residence offers one bedroom, two full bathrooms, an office, and a spacious layout designed for everyday comfort and entertaining. An inviting foyer opens into a bright interior with vaulted ceilings, hardwood flooring, granite countertops, a kitchen island, and a breakfast bar. The living and dining areas flow together naturally, anchored by a gas fireplace that adds warmth and character.

A large view deck extends from the main living area, creating an easy indoor-outdoor connection for morning coffee, outdoor dining, or evening sunsets. Mountain and territorial views add to the setting and help distinguish the property from a typical income-producing residence.

The primary suite serves as a private retreat with its own gas fireplace and access to a separate deck. The spacious bathroom includes a soaking tub and separate shower. A generous laundry room, ample storage, and an oversized two-car garage with workshop space add valuable function to the home.

The attached 944 square foot ADU features a practical single-level layout with two bedrooms and two full bathrooms. It also includes its own two-car garage, an uncommon and desirable feature for an Ashland rental. The ADU is currently rented for $1,400 per month on a month-to-month basis, providing immediate income potential while preserving flexibility for the next owner.

Set on a landscaped 0.22 acre lot with public utilities, the property offers a versatile opportunity in one of Southern Oregon’s most desirable communities. Ashland is known for its vibrant downtown, locally owned restaurants, parks, trails, cultural attractions, and access to year-round recreation. Lithia Park, the Oregon Shakespeare Festival, Mt. Ashland, local wineries, and the broader Rogue Valley lifestyle are all within easy reach.

For buyers seeking an Ashland home with an ADU, an owner-occupied investment, or a property that combines personal living space with rental income, this is a distinctive and difficult-to-replace opportunity.

OLD: Tucked into the heart of Ashland, Oregon, this thoughtfully designed 1996-built duplex offers a rare blend of space, comfort, and flexibility in one of Southern Oregon’s most sought-after markets. With 2,831 square feet total and two 2-bedroom, 2-bathroom units, the property is ideal for a buyer looking for an owner-occupied duplex in Ashland or a long-term hold with built-in rental appeal.

The main residence lives and feels like a standalone home, starting with an inviting foyer that opens into a bright, open layout enhanced by vaulted ceilings and a warm, welcoming flow. Hardwood floors and granite countertops add a timeless finish, while the generous floorplan provides space to spread out, perfect for everyday living and easy entertaining. The great-room concept connects the living and dining areas in a way that feels natural and spacious, centered by a living room fireplace that adds character and comfort through the seasons. Step outside and you’ll find one of the home’s standout features: a large view deck off the living and dining area, creating a seamless indoor-outdoor extension for morning coffee, summer dinners, or sunset unwinding.

The primary suite is designed as a true retreat, featuring its own fireplace and access to a private deck, a quiet corner that feels removed from the day-to-day. The bathrooms are notably spacious, and the primary bath includes a soaking tub, offering that spa-like exhale at the end of the day. A dedicated laundry room, ample storage, and the convenience of a double garage round out the main unit, giving it the functionality buyers want in a full-time residence.

The second unit complements the property beautifully with a practical, efficient design that appeals to tenants and low-maintenance living. Set up all on one level, it includes two bedrooms and two full bathrooms, plus a two-car garage of its own, an increasingly rare bonus in Ashland’s rental landscape. A tenant is already in place, making this an immediate rental opportunity for buyers who value stability (buyer to verify terms). Whether your goal is to live on one side while generating rental income on the other, or to hold it as a traditional investment, this property supports multiple strategies without sacrificing livability.

Beyond the home itself, the location speaks for itself. The Rogue Valley is known for its four-season lifestyle, mountain views, wineries, outdoor recreation, and strong sense of community—an area where people come for the beauty and stay for the quality of life. Ashland is the crown jewel for many, celebrated for its vibrant downtown, locally owned restaurants, parks, trails, and the world-renowned Oregon Shakespeare Festival. From Lithia Park strolls to quick access to skiing at Mt. Ashland, rafting and fishing on the Rogue, or weekend tasting rooms throughout the valley, it’s an environment that supports both daily ease and weekend adventure.

If you’ve been searching for an Ashland duplex for sale, a Southern Oregon investment property, or a home that lets you combine personal living with rental upside, this is a standout opportunity, designed, well located, and hard to replace.