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$650,000
3 Beds 3 Baths 220210077 MLS 3,006 SqFt. 7,405 Sqft. Lot 0.17 Acres
Built in 1930 and brimming with warmth, this 2,300-sqft Ashland home offers 3 bedrooms, 3 full baths, and a large den that could easily become a 4th bedroom. With an attached apartment, you'll have the perfect space for family and friends - or even a short-term rental opportunity. Inside, you'll be greeted by timber floorboards, high ceilings, and rustic beamed accents that create a sense of timeless charm. The living room centers around a welcoming fireplace, while the stainless steel kitchen opens effortlessly to the dining and living areas, making entertaining both easy and inviting. An unfinished 700-square-foot basement adds even more flexibility for hobbies, fitness, or extra storage. Could your ideal retreat be a primary suite with a private bath and walk-in closet? Here, you'll find exactly that—alongside additional bedrooms, a sitting room, and a spacious family room designed for comfort and entertaining. Just 0.8 mile to Downtown Ashland! Inquire for more details!

811 Iowa Street, Ashland

$925,000
220209916 MLS 10,018 Sqft. Lot 0.23 Acres
This beautiful Ashland triplex in the heart of the Railroad District, blocks from Food Co-op, theater and downtown, has a large .23 acre lot, plenty of parking and lovely historic curb appeal with modern amenities and upgrades. Currently owner-occupied, 254 has a large living area, a 2017 kitchen remodel, 2 bedrooms each with its own bath and laundry. 256 is a one bedroom w/ full kitchen, living area, bathroom and a patio with garden boxes. 252 is upstairs and was newly built in 2017. It is a permitted vacation rental with gorgeous high ceilings, large view windows, spacious kitchen, 2 beds, 2 baths and washer/dryer. Upgrades galore- tankless water heaters, new concrete pathway and parking for 4 cars, plus 1 RV & a sundeck. Whether you seek an investment property or a primary residence w/ a multi-generational layout, this beautiful home is a must-see. Buyer to perform their own due diligence regarding permitted uses & future possibilities.

252 B Street, Ashland

$845,000
5 Beds 3 Baths 220209677 MLS 2,842 SqFt. 9,147 Sqft. Lot 0.21 Acres
In this 5 bedroom, + flex bonus room space, daylight ranch, every inch has been thoughtfully redesigned and renovated. Nestled in the trees of Roca Canyon above SOU and minutes from Downtown Ashland. Enter the main living area through the solid mahogany pivot door. The open floor plan is anchored by the restored white oak flooring, flooded with light and features a vaulted ceiling and sleek 2-sided fireplace. The designer kitchen includes a BOSCH appliance package with 36'' induction range, solid wood soft-close custom cabinetry and floating shelves and plenty of storage. The primary suite with mountain views and two guest bedrooms and an additional bathroom complete this level. Downstairs, discover a large den/theater/playroom with fireplace, stylish dry bar with beverage fridge, laundry area, and two massive bedrooms with walk-ins. Step outside to the energy efficient lagoon bottom pool. Enjoy the backyard oasis with large deck, zero-maintenance turf and full fencing for privac

704 Elkader Street, Ashland

$850,000
3 Beds 2 Baths 220209371 MLS 2,211 SqFt. 8,712 Sqft. Lot 0.2 Acres
Enter into a historic Ashland beauty where timeless charm meets modern comfort. Imagine sipping your morning coffee on the welcoming front porch while enjoying a front-row view of parades and all the vibrant downtown events just minutes away. Thoughtfully remodeled in 2001-2002, the home retains its original character while offering today's conveniences, including a spacious kitchen that opens seamlessly to a warm, inviting family room. French doors lead you into a private backyard retreat, where lush landscaping creates a peaceful escape for entertaining or simply unwinding. Inside you'll find three comfortable bedrooms and two full baths, blending history and functionality with ease. This is more than a home, it's a lifestyle in the heart of Ashland, with theater, dining, and community right outside your door.

478 Siskiyou Boulevard, Ashland

$723,500
3 Beds 2 Baths 220209453 MLS 1,221 SqFt. 6,098 Sqft. Lot 0.14 Acres
Charming and beautifully maintained, this Ashland cottage captures the essence of the Railroad District. The main home offers 1,221 SF of inviting living space, filled with natural light and designed with warmth and comfort in mind. A welcoming front porch, bright kitchen w/custom cabinetry, and spacious primary BR create the perfect blend of character and function. Tucked behind the main house is a 704 SF detached guest cottage with its own BR and BA-ideal for extended family, private office, or art studio. Together, the two dwellings provide nearly 1900 sq. ft. of versatile living. The storybook backyard is a private retreat with mature landscaping and garden spaces for outdoor enjoyment. A short stroll brings you to Ashland's restaurants, shops, theaters and Lithia Park. This is the Ashland dream-an enchanting home, magical setting and in one of the most sought-after locations.

939 B Street, Ashland

$515,000
3 Beds 2 Baths 220209169 MLS 1,776 SqFt. 7,405 Sqft. Lot 0.17 Acres
Welcome to this beautifully maintained single-level home, tucked away in a private, woodsy setting. Built in 1963 and thoughtfully updated, it offers the perfect blend of vintage charm and modern comfort. Inside, the bright kitchen features vaulted ceilings, a skylight, and stainless steel appliances. The living room is warm and inviting with a cozy fireplace, vaulted ceilings, and engineered wood floors—an ideal space to relax or gather with loved ones. The primary suite includes a convenient walk-in closet and a custom en-suite bath with a tub and shower. Outdoors, you'll appreciate the low-maintenance yard and tranquil atrium with a lovely water feature—a peaceful retreat to enjoy at any time of day. Just minutes from downtown Ashland, this charming property combines peace, convenience, and timeless style. Don't miss this opportunity to own this charming piece of Ashland!

767 Twin Pines Circle, Ashland

$615,000
220209104 MLS 6,969 Sqft. Lot 0.16 Acres
Motivated seller! Situated on a corner lot just minutes from downtown Ashland and SOU, this tastefully updated Victorian home offers two distinct living spaces and exceptional flexibility. The 1,024 sqft main level unit features , 3 bedrooms and 1 bathroom. Highlights include high ceilings, a remodeled kitchen and bathroom, luxury plank flooring, marble floors in the bathroom and laundry room, new windows, updated copper plumbing and electrical systems, and energy-efficient ductless heating and air conditioning. The 988 sqft upper-level unit offers 2 bedrooms and 1 bathroom. It includes a spacious living room with a gas heater, new luxury plank flooring in the kitchen, and bathroom. The large backyard provides space for gardening. A small shop offers additional storage or space for your creative projects. Live in one unit and rent the other, or lease both for income potential.

770 Iowa Street, Ashland

$360,000
3 Beds 2 Baths 220208797 MLS 1,268 SqFt. 30,492 Sqft. Lot 0.7000000000000001 Acres
Discover the perfect getaway with this charming 3-Bedroom, 1 1/2 bath cabin nestled along the peaceful shores of Hyatt Lake. Surrounded by tall pines and crisp mountain air, this classic cabin offers a cozy retreat with plenty of room for family and friends. Inside, you'll find a warm and inviting living space with rustic wood finishes, an open kitchen, and plenty of natural light. The upstairs adds extra sleeping space or a perfect hideaway for kids. Outside, a large Trex deck with brand-new railings provides the perfect spot for entertaining, relaxing, or simply soaking in the lake views. Step down to your own slice of lake frontage-ideal for launching a kayak, casting a line, or sipping your morning coffee in peace. If you want a year-round escape, this cabin blends comfort, character, and an unbeatable setting. Property is on leased land from Bureau of Land Management.

6000 E Hyatt Lake Road, Ashland

$750,000
3 Beds 2 Baths 220208570 MLS 2,524 SqFt. 101,494 Sqft. Lot 2.33 Acres
Check out the views in a super desirable location overlooking the rolling hills of Ashland! This beautiful estate was established in 1966 with 3 bed 2 full baths and 2524 total Sq ft!! The home is the last one on the road into a dead end so its private slice of paradise. The architecture of the home is unique as seen on the front photos. This house is move in ready and is a prestigious location in Southern Oregon. Ashland is home to Shakespeare, Independent Film Festival, and the world famous Lithia Park, Ashland's crown jewel with walking paths, duck ponds, Japanese Garden, Park Benches, Parking, Pickleball Courts, Picnic Areas, Playground, Restrooms,Volleyball and all kinds of activities during the summer! There is a work shop in the home and a office that overlooks the rolling hills around Ashland! Check out the walk thru video and Come take a tour TODAY!

55 Birnam Wood Road, Ashland

$375,000
4 Beds 1 Baths 220208511 MLS 1,380 SqFt. 7,405 Sqft. Lot 0.17 Acres
Historic home on a spacious lot with ~121 feet of alley access — centrally located across from Triangle Park! Living and formal dining with high ceilings, curved archways, built-ins, and ceiling fans. Kitchen with tiled counter and backsplash, stainless double sink, refrigerator, and gas range; adjacent informal dining or breakfast nook with built-ins. Main-level bedroom with abundant natural light and second bedroom or office with built-in cabinets and shelving. Full bathroom with pedestal sink and tiled tub shower. Enclosed back porch mudroom with washer and dryer. Two upper-level bedrooms with closets and ceiling fans. Exterior stairs to lower-level basement with poured concrete foundation. Fully fenced yard with mature trees, sunny gardening areas, gated alley access, and large parking area with space for multiple vehicles. Detached 288 SqFt garage with power, storage shelving, and poured concrete slab. Property shall be sold ''As-Is'' in present condition. Inquire for details!

753 Siskiyou Boulevard, Ashland

$1,500,000
3 Beds 3 Baths 220208104 MLS 4,024 SqFt. 12,196 Sqft. Lot 0.28 Acres
Impeccably remodeled historic home in the desirable Skidmore Academy Historic District - steps from Briscoe Park and four blocks from Ashland's downtown Plaza. Main level with bespoke powder room, expansive gourmet kitchen with new Thermador induction cooktop and ovens, Taj Mahal quartzite counters, gracious formal and informal dining areas, butler's pantry with wet bar, living room, library alcove, two guest bedrooms, renovated guest bathroom, and thoughtfully redesigned pantry laundry room. Upper-level office or potential fourth bedroom with closet; expansive primary with sitting area, skylight, private view balcony, dual walk-in closets, and luxurious full ensuite bath with soaking tub, tiled shower, water closet, and double vanity. Lower-level garage with space for three vehicles, workshop, and utility room. Landscaped grounds with mature trees, ornamental plantings, meandering pathways, patio, and pond with water feature. Inquire for details!

124 Manzanita Street, Ashland

$440,000
2 Beds 1 Baths 220208016 MLS 1,226 SqFt. 69,696 Sqft. Lot 1.6 Acres
Nature Lover's Retreat with no neighbors in sight! Located in the protected Cascade Siskiyou National Monument. This property has 1.6 acres, but it feels like a hundred. There are no other houses in sight. Mountain views with Jenny Creek running though the property giving you direct access to this year round beauty. Abundant wildlife year round. Sit on one of the 2 large decks or the covered porch and listen to nature as the birds chirp and the creek flows, you will hear none of the city noise up here! Recent updates in 2025 include a new roof, full exterior paint, complete kitchen remodel to include high end LG smart appliances and new cabinets, new wood for all decks, and LED lighting. This house is the full package; both exterior and interior. You must see it in person to feel the serenity and beauty, it's magical!

17629 Highway 66, Ashland

$489,000
3 Beds 2 Baths 220207889 MLS 1,400 SqFt. 10,454 Sqft. Lot 0.24 Acres
Located in a wonderful south Ashland neighborhood, this single-level house offers a comfortable and versatile living space. It features 3 bedrooms and 2 bathrooms, and at 1400 sq. ft., the L-shape floor plan makes it live larger. The living room is particularly inviting with its wood-clad vaulted ceiling, built-in bookcases, and a cozy fireplace, which together create a lovely blend of classic charm and modern appeal. Excellent views of the hills from the dining area and primary bedroom. A generous .24 acre lot with a welcoming entry courtyard, attached carport with storage, and a fenced backyard. The yard is truly a highlight, featuring mature fruit trees and benefiting from TID irrigation rights, which provides opportunities for gardening and development of engaging outdoor spaces. This home is an excellent value in a very sweet setting.

2321 Black Oak Way, Ashland

$710,000
2 Beds 2 Baths 220207386 MLS 1,789 SqFt. 11,325 Sqft. Lot 0.26 Acres
Rare Ashland treasure on highly desirable Nutley St, just steps from Lithia Park and all that downtown Ashland has to offer. Instantly fall in love with this home with expansive windows that fill the living space with light and frame picturesque views. The open layout offers spaciousness and at the same time a functional separation of space. Beautiful cabinetry, a dining nook and full dining area. Most of the living is on the main floor and includes a walk-in soaking tub, making it ideal for aging in place. The daylight basement is a great flex space with an updated bathroom, walk-in closet and new flooring. Outside, enjoy the oversized backyard with its gorgeous cobblestone walkway. With a second garage and additional yard space, the property may offer (per the City of Ashland) a potential for an ADU, Airbnb income, or even between 3-6 dwellings (buyer to verify). Truly a wonderful opportunity to own a lovingly maintained home in one of Ashland's most coveted locations.

64 Nutley Street, Ashland

$945,000
4 Beds 3 Baths 220206958 MLS 2,974 SqFt. 11,761 Sqft. Lot 0.27 Acres
Midcentury ranch home with detached guest apartment on a large lot with mature trees located within 500 feet of Lithia Park - just two minutes from Ashland's downtown plaza! Main level living with large picture windows, custom built-in wood cabinets and window seat, fireplace with gas starter, formal dining and kitchen with solid oak hardwood floors, granite counters, butcher block dining bar, gas range with convection oven, breakfast nook, two bedrooms with closets, full bathroom with granite vanity and tub shower surround, office nook with built-ins, plus a bonus room studio or potential fourth bedroom with track lighting and sound insulation. Spacious upper-level primary suite with custom built-in wardrobes and window seat, integrated speakers, private balcony, and full ensuite bathroom with tiled vanity and tub shower surround. Detached two-car garage with renovated upper-level guest apartment complete with kitchenette, one bedroom, and full bath. Inquire for details!

107 Granite Street, Ashland

$1,175,000
4 Beds 4 Baths 220206654 MLS 3,020 SqFt. 15,681 Sqft. Lot 0.36 Acres
Winner of the 2012 Historic Preservation Award, this beautifully renovated 2,300 sq ft. home comes with a 720 sq ft guesthouse for a total square footage of 3,020. This home is situated in a well-established Ashland neighborhood, conveniently walkable to downtown. Modern open floor plan. Main-level living boasts a gourmet kitchen, primary suite with tiled bath, 2 additional bedrooms, second full bath, plus a half-bath for guests. Expansive decks offer mountain views. Beautifully landscaped grounds with perennial gardens, fruit trees & flowering shrubs are served by a zoned irrigation system. Hardwood floors, walnut cabinetry + built-ins add warmth throughout the well-appointed living space. Upstairs is perfect for office or 4th bedroom with half-bath and private balcony. New HVAC, electrical, and plumbing systems installed during 2011 renovation. Detached guesthouse, built in 2016, is currently a 5-star VRBO rental, or use for guests, Mother-In-Law or office/studio.

111 Nursery Street, Ashland

$792,000
4 Beds 4 Baths 220206437 MLS 2,019 SqFt. 10,018 Sqft. Lot 0.23 Acres
There is so much to love about this home nestled in one of the best neighborhoods in Ashland. This 3 bed, 3 bath home features two primary bedrooms with walk-in closets and en-suite baths, as well as a detached 252 square foot guest cottage with another full bath. It boasts a huge laundry/mud room, beautiful kitchen with an oversized island, solid countertops, a bar, built-in bench seating with storage, and views of Grizzly Peak. The living room has a cozy wood-burning stove with built-in shelves. The back yard is stunning, with a huge pergola covering the back deck, a hot tub, outdoor kitchen with plumbing and electricity, garden beds on a drip system, fruit trees, thornless blackberries, raspberries, and more! Garage has EV charging and the home even has a partial, unfinished basement. Lastly, there is RV parking in the front yard with full hookups. Come see all this home has to offer, just down the hill from the Oredson-Todd woods. Listing broker is one of the owners.

1108 Park Street, Ashland

$495,000
3 Beds 1 Baths 220206432 MLS 1,250 SqFt. 9,583 Sqft. Lot 0.22 Acres
Discover the perfect blend of character, comfort, and future opportunity in this beautifully updated home, ideally located in a walkable neighborhood just steps from Sammich and other local favorites. Recent upgrades include a brand-new mini split system, water heater, and electrical—offering peace of mind and energy efficiency. Inside, you'll find updated modern light fixtures, distinctive arched walls, and a kitchen window with a view into the expansive backyard. Step outside and experience the openness of nearly a 1/4 acre, featuring a large covered deck, greenhouse, and deer-proof garden enclosure—perfect for relaxing, entertaining, and cultivating your own food. Bonus: a 500 sq/ft detached garage offers exciting potential for an ADU (Accessory Dwelling Unit)—ideal for guest space, rental income, or a home studio. This home combines important updates, unique charm, and flexible options for the future!

350 Avery Street, Ashland

$1,100,000
220206369 MLS 6,969 Sqft. Lot 0.16 Acres
Three units with median gross receipts over $100,000 per year in Ashland's Railroad District! The charming and thoroughly updated Second Street Cottages feature two furnished and permitted vacation rentals along with a spacious and comfortable owner's suite — each with full kitchen, central air conditioning, gas furnace and water heater, separate laundry facilities, double-paned windows and sliding glass doors to private fenced and gated outdoor spaces. Heritage House has four bedrooms and three full baths, large front porch, original fir floors, and operable Velux skylights. Garden Cottage has two bedrooms and two full baths, vaulted ceilings, oak floors, quartz and granite counters, and new kitchen appliances. The owner's Hideaway Suite has two separate exterior entrances, full main-level bath, office or formal dining, pantry, upper-level bedroom with full ensuite bath and ample closet storage. Accommodations featured on top booking sites in Ashland. Inquire for details!

144 N 2nd Street, Ashland

$625,000
220205786 MLS 5,662 Sqft. Lot 0.13 Acres
A rare opportunity located in Ashland's beloved Railroad District! This charming & versatile property offers 3 separate units just blocks from the Co-op, OSF, & downtown Ashland. Lovingly maintained, the property blends timeless character w/ modern functionality & includes newer sewer & water lines, electrical panel, & window coverings. The main unit offers a spacious 2-bedroom layout w/ stunning wood accents & built-ins throughout. The kitchen is conveniently located next to the dining area & has its own laundry facility. Unit #2 is a 1-bedroom apartment w/ a galley kitchen + great natural light. Unit #3 is a charming studio. Large fenced yard w/ mature landscaping, garden space, deck + 4 alley off street parking spaces. Whether you seek a primary residence with added flexibility, a multi-generational layout, or a unique investment opportunity, this one-of-a-kind property is full of potential. Buyer to perform their own due diligence regarding permitted uses and future possibilities

237 B Street, Ashland

$925,000
220205870 MLS 9,583 Sqft. Lot 0.22 Acres
971, 975, and 977 Siskiyou Blvd. Extremely hard-to-find Ashland three unit property! Unit 1) 1940 built - 1713 sf single level with 3 beds and 2 baths completely remodeled from the ground up in 2018. Units 2 & 3 - 2018 built - detached duplex with 875 sf on each side. Each unit includes 1 bedroom and 1.5 baths. The light filled duplex has vaulted ceilings, stainless steel appliances, and vinyl wood plank flooring. The upper level is entirely devoted to the owner's suite with a loft style bedroom, full bath, bonus space, and a walk-in closet. The property includes separate electrical meters for all units and a large private parking area across from Southern Oregon University. All three units are currently rented with monthly income totaling $5,350. The listing photos were taken in 2018 at the completion of the house remodel and duplex new construction.

971 Siskiyou Boulevard, Ashland

$510,000
3 Beds 2 Baths 220205795 MLS 2,139 SqFt. 12,196 Sqft. Lot 0.28 Acres
Beautiful mountain views from this hillside home. This charming 1947 home offers classic character and comfort with entry vestibule, arched doorways, large picture windows, many built-ins and a living room fireplace. Spacious living room with bamboo floors, large picture windows framing the view and a lovely dining room with built-in buffet. The kitchen is spacious with abundance of counter space, crisp white cabinets and loads of built-ins. Featuring 3 bedrooms, 2 bathrooms, all on the main level and a versatile sizable loft on upper-level. Enjoy outdoor living on the spacious relaxing deck—perfect for sunrises and taking in the view. This property is private and the lot is spacious. Sweet, small, detached studio is wonderful for private space to use as an office, for hobbies, to create or for storage. Also includes a one-car garage. Lots of parking. A wonderful opportunity to own a piece of the past with modern comfort.

681 Liberty Street, Ashland

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. Last updated: