Ashland Homes with Two Stories

Welcome to Ashland, Oregon – a picturesque gem nestled in the heart of Jackson County. Renowned for its vibrant arts scene, lush landscapes, and a rich cultural heritage, Ashland is a place where charm meets community. With its stunning views of the surrounding mountains and proximity to the renowned Oregon Shakespeare Festival, residents enjoy a unique blend of outdoor adventure and artistic inspiration. Whether you're hiking the scenic trails of the nearby Cascade-Siskiyou National Monument or indulging in the local culinary delights, Ashland offers a lifestyle that is as enriching as it is enjoyable.

For those seeking to call this enchanting city home, Ashland boasts a variety of real estate options, including beautiful two-story homes that perfectly complement the area's character. These spacious residences often feature open floor plans, allowing for seamless entertaining and family gatherings. With ample room for personalization, two-story homes in Ashland provide the ideal backdrop for creating lasting memories. Many of these homes are designed with large windows that invite natural light and showcase the breathtaking views of the surrounding landscape, making every day feel like a retreat.

Living in Ashland means being part of a close-knit community that values creativity and connection. As you explore the diverse neighborhoods, you'll find that each two-story home is not just a place to live, but a canvas for your dreams and aspirations. Embrace the opportunity to immerse yourself in the beauty and culture of Ashland, where your perfect two-story home awaits!

Newest Ashland Homes with Two Stories

$739,000

4 Beds ⋅ 3 Baths ⋅ 220225931 MLS

Located just minutes from downtown, this impressive 2,596 sq. ft., 4-bedroom, 3-bathroom home features striking curb appeal and breathtaking views of Grizzly Peak. The bright interior boasts hardwood floors, formal and informal dining, and a spacious kitchen with solid-surface counters. Soaring ceilings frame the great room, which opens to an expansive deck overlooking a tiered backyard complete with garden boxes, a potting shed, and storage shed. Highlights include a main-level vaulted primary suite with a jetted tub and walk-in closet, a flexible upper-level bonus room with skylights, and carpeted guest bedrooms. Modern upgrades feature a new heat pump with advanced UV filtration, an electric vehicle charger, and an oversized attached garage with workshop space plus dedicated RV parking.

960 Oak Street, Ashland

$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

153 Oak Street, Ashland

$739,000

4 Beds ⋅ 2 Baths ⋅ 220225773 MLS

Experience contemporary Northwest living in this one-of-a-kind 4 bed, 2 bath w/elevated views & beautiful natural surroundings. Adventure awaits just outside your door w/convenient access to miles of hiking & biking trails. Thoughtfully designed w/versatile living & dining areas to accommodate every occasion. Vaulted great room featuring a gas fireplace w/tile surround & a wall of windows. Well-appointed kitchen showcasing white painted cabinetry, leathered granite countertops, tile backsplash & large pantry. The primary suite is a true private retreat w/direct access to a secluded deck w/hot tub, luxurious ensuite & oversized dual closets. Enjoy year-round outdoor living from the expansive terrace w/both covered and open-air spaces. The perfect setting to relax or entertain while taking in the stunning mountain views. Mature, landscaped grounds w/raised garden beds plus a 2-car garage complemented by an adjacent covered area. Ideal for additional parking or versatile storage!

1000 Ivy Lane, Ashland

$950,000

3 Beds ⋅ 3 Baths ⋅ 220225745 MLS

Tremendous 360 view on 5.75 flat white fenced acres & walking distance to Emigrant Lake. You have 3 acres of water rights on open EFU land, a 36'x36' barn with loft, a 14' RV bay door, workshop & attached office. Behind the barn is a single horse stall. To the side is a gazebo to enjoy those wonderful summer outside nights. This home is greeted by a paved & gated 800' driveway leading to a drive-through that takes you to the front entrance. Brand new wrap around porch greets you so you can sit in awe at the beauty of your surroundings or sit under your backyard gazebo and say, ''Do I really live here''? Perched on a small knoll, this 2,934 sq ft 4/3 home, has 2 bonus rooms, with open floor plan, large entertaining living room with woodstove insert fireplace & kitchen with abundant cabinets & island. Ten-foot ceilings provide ample sunlight for all occasions. The upstairs primary suite has a fireplace, en-suite bathroom with soaking tub & walk-in closet. Country comfort at its best.

5597 Highway 66, Ashland

$359,000

3 Beds ⋅ 2 Baths ⋅ 220225712 MLS

Charming, move-in ready Ashland townhome priced to sell! Tucked away off the street on a quiet shared drive, this inviting 3-bedroom, 1.5-bath home has been freshly repainted and features updated kitchen cabinets with modern hardware, a brand-new refrigerator, and a bright, clean interior. The modified single-car garage provides storage access from the driveway and a spacious interior laundry/bonus room for added functionality. The private, fully fenced backyard, features a peaceful water feature and plenty of space for gardening and relaxing. Conveniently located within walking distance of everyday amenities, and just a five-minute drive to downtown Ashland's restaurants, shops, theaters, and community events. Rental units are permitted, offering flexibility for homeowners and investors alike.

690 Normal Avenue, Ashland

$1,350,000

5 Beds ⋅ 6 Baths ⋅ 220225703 MLS

Live the Southern Oregon Dream! Welcome to an extraordinary Ashland estate where breathtaking views of Mount Ashland, the Cascades, downtown Ashland, and surrounding vineyards create a spectacular backdrop. Nestled behind a private gated entrance on 5 acres, 3 TID irrigated, this custom-built 5 bedroom, 6 bath home offers luxury, privacy, and versatility. Whether you're seeking a peaceful retreat, a multigenerational home, or space to operate a home-based business, this property adapts to your lifestyle. The thoughtfully designed floor plan features TWO private suites with their own entrance, ideal for extended family, a professional office, or creative studio. Garden beds, fruit trees, space for horses, animals, a 28 GPM well, RV hookups w/220, abundant parking, just minutes from the Shakespeare Festival, galleries, wineries and award-winning restaurants. You'll enjoy the best of country living without sacrificing convenience. Luxury. Privacy. Self-sufficiency. Endless possibilities.

808 Pompadour Drive, Ashland

$2,275,000

220225702 MLS

Exclusively presented for sale - 710 Jefferson Avenue, a purpose-built CPG/co-packing facility in Ashland, OR (the ''Property''). Sited on a flexible, E-1 zoned parcel just 3 minutes to direct I-5 access, the Property is ideal for production, shipping, and regional distribution users. The ±14,812 SF building underwent substantial renovations and includes immense infrastructure and building systems supporting the previous CPG user. 3 production areas are laid out internally, each with efficient loading, clean rooms, and some remaining equipment. A large warehouse w/ racking leads to a cold storage room and shipping area with two dock-high doors accessed via the fenced yard. Several private offices, conference rooms, break room, lockers, and restrooms support operations and provide a well-rounded, flexible building for a large variety of industrial users. Remaining equipment and FF&E is negotiable; all appears to be in excellent condition. Much more info is available - contact brokers.

710 Jefferson Avenue, Ashland

$695,000

4 Beds ⋅ 2 Baths ⋅ 220225640 MLS

Tucked away in one of Ashland's most sought-after neighborhoods, this exceptional property offers the rare feeling of a private nature retreat while remaining just minutes from the heart of the city. Surrounded by mature trees and abundant natural beauty, the home feels like a treehouse with beautiful views of the mountains that create a peaceful backdrop throughout the seasons. With access to a beautiful trail system, including the Ashland Ditch Trail, outdoor recreation begins right outside your door. Whether you're hiking, running, or simply enjoying a quiet walk, this location provides an unmatched connection to nature. The unique setting combines privacy, serenity, and convenience--offering a secluded escape without sacrificing easy access to downtown Ashland, local dining, shopping, parks, hospitals, and cultural attractions.

279 Alta Avenue, Ashland

$3,995,000

2 Beds ⋅ 1 Baths ⋅ 220225545 MLS

The Four Corners Ranch offers 897.32 acres of productive timberland on the south side of Mount Ashland, near the California border. This is a rare legacy holding that pairs a strong timber inventory with live water, recreation, and several structural improvements. Elevations range from 3,600 to 4,900 feet across varied topography, supporting consistent, reliable timber growth. Current stocking is estimated at 7.7 MMBF Douglas fir, 4 MMBF white fir, 5.9 MMBF pine, and just under 1 MMBF cedar. Located in the Rogue hunting unit, an area known to produce quality black-tailed deer, the ranch is ideal for hunting and outdoor recreation. Live water, diverse terrain, and direct access to vast public lands add to its appeal. Whether acquired for merchantable timber value or held as a generational asset, the Four Corners Ranch is a genuine opportunity to own a productive expanse of land in Southern Oregon. Additional documentation available upon request.

Hungry Ridge, 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

$589,000

3 Beds ⋅ 3 Baths ⋅ 220225252 MLS

Welcome home to this wonderful 3 bedroom 2.5 bath property in the delightful Oak Knoll Neighborhood! Upon arrival, the beautifully landscaped front yard welcomes you in. The main level is perfect for entertaining with an updated kitchen, separate dining room and living room, cozy wood-burning fireplace and family room that looks out over the seasonal creek and oak trees. Upstairs you will find the three bedrooms including the primary suite! With abundant square footage and a large private lot, this home is sure to delight. Recent update include HVAC system in (June 2026) new roof (2025), exterior paint (2025) and Timbertech deck (2024).

775 Oak Knoll Drive, Ashland

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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: