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$900,000
4 Beds 3 Baths 220227282 MLS
Welcome to PrayerFarm, a unique oasis for multi-generational living, community, homesteading, and events, all close to town. The light-filled primary home features sustainably harvested wood floors, a high-efficiency woodstove, a masonry Tulikivi, and ample indoor/outdoor entertaining spaces. A self-contained guest cabin provides overflow living. The massive 1,700+ SF ''barn'' is an absolute powerhouse, packed with an artist studio, guest suite with composting toilet, a scenic retreat loft, and a large office. Outdoor features include a cobb fireplace kitchen, ceremonial Tipi with an earthen floor, and a soothing Koi pond. The land is fully set up for self-sufficiency with a natural spring, abundant water storage, a fenced garden, mature fruit orchards, and an animal pen/coop. Modern convenience meets rural paradise with hardwired high-speed Ethernet throughout. Lovingly maintained for decades, this rare, special sanctuary is ready for its next chapter.

2260 Old Highway 99 S, Ashland

$389,900
2 Beds 1 Baths 220227252 MLS
Built in 2022 with an emphasis on efficiency, simplicity, and modern design, this Earth Advantage-certified cottage offers an easy, comfortable way to live. The bright, open interior features vaulted ceilings, abundant natural light, and contemporary finishes throughout. The kitchen pairs quartz countertops with stainless steel appliances and a convenient breakfast bar, creating a stylish and functional heart of the home. Outside, the fully fenced yard is an exceptional extension of the living space, with a private patio and room for gardening, dining, or simply enjoying the mountain views. As part of a shared solar community, the home is designed with energy efficiency and lower operating costs in mind. With its manageable size, low-maintenance design, outdoor space, and modern construction, this two-bedroom, one-bath home is a smart opportunity for anyone looking for a newer home without the upkeep of a larger property.

583 Coffee Lane, Ashland

$695,000
5 Beds 4 Baths 220227203 MLS
Charming 5 bedroom 4 bath home offers 2,487 sqft of living space on an oversized .55 acre lot, set in a highly sought after neighborhood just minutes from shopping, dining and the historic Ashland Plaza! The spacious floor plan provides plenty of room for everyday living, hosting and creating dedicated spaces for work, hobbies or relaxation. Two fireplaces add warmth and character, while the multiple sliding doors allow natural light to flood the living areas. One bathroom features an ADA accessible shower with floor to ceiling tile and custom stone, delivering both style and functionality. Outside, the beautifully landscaped lot offers an ideal setting for gardening or entertaining while providing convenient parking for multiple RVs, campers, trailers or boats. Don't wait, your next chapter starts here!

485 Orchard Street, Ashland

$699,000
4 Beds 3 Baths 220227055 MLS
Beautiful Mountain Views on 5.4 Acres ! Enjoy stunning mountain views from the spacious front deck of this beautiful 2,989 sq. ft. home situated on 5.4 acres. The open--concept upper level features large, bright windows that fill the home with natural light, creating a warm and inviting living space . This home offers 4 bedrooms and 3 bathrooms, providing plenty of room for family, guests, or a home office. Additional features include TID irrigation, a newer roof, and a newer energy--efficient heat pump for year--round comfort. The lower level has 2 bedrooms with a full bath and side access door to enter. Whether you're relaxing on the deck, entertaining in the open living area, or enjoying the privacy of your acreage, this property offers the perfect blend of space, comfort, and scenic beauty.

3404 Siskiyou Boulevard, Ashland

$399,900
2 Beds 1 Baths 220226872 MLS
Back on market...no fault of property! A sweet place to call home! This well maintained single level home in the Millpond Subdivision is ready for it's next owner. Ample windows give this home a light filled spacious feeling. And the open floorplan living room/dinning room/ kitchen welcomes you in. The two bedrooms both have sliding glass doors leading to the private backyard. New fencing around the property a couple years ago. The backyard is quite large and flat and has mature trees including 2 different varieties of apple. The neighborhood is sweet and has a lovely pond just a short stroll away. Close to downtown Ashland, schools, shopping and bike path. This home is very clean and would make a wonderful first home for someone and also has great rental opportunity.

1302 Mill Pond Road, Ashland

$525,000
4 Beds 3 Baths 220226768 MLS
This beautiful home has an open floorplan with lots of room for entertaining. The recently remodeled kitchen will take your breath away. Custom cabinetry with under-mount lights, soft close drawers, granite counters, stainless steel appliances. The living room has a gas fireplace for cozy nights in. The downstairs also has one bedroom, half bath and office. Upstairs you will find the spacious primary suite with mountain views. The primary bath has a walk in shower, separate tub and large walk-in closet. Also upstairs are two additional bedrooms. Dual zone HVAC and new AC unit upstairs. The low maintenance backyard is like a private oasis with abundant plants, a lovely custom metal planter that runs the length of the yard, hot tub and privacy shades. The 2 car attached garage is both heated and insulated. An incredible place to call home!

986 Stoneridge Avenue, Ashland

$449,000
2 Beds 2 Baths 220226686 MLS
Well-maintained single level townhome in the desirable Birchwood at Ashland, a planned community designed for easy living. Lovely curb appeal, private entry and a user-friendly floor plan with two bedrooms and two bathrooms, approx.1359 SF of living space. Oak hardwood floors run throughout. Living room features a gas fireplace and French doors open to the professionally landscaped private backyard patio area. Lots of colorful plantings and a custom water feature. The kitchen opens to the dining area with direct patio access for indoor/ outdoor enjoyment. Attached garage includes an EV charger. The heat pump and tankless hot water heater were installed in late 2022. Private street, guest parking and common area grounds are HOA owned and beautifully maintained with mature trees, shrubs and plantings. Convenient location close to shopping, the YMCA, city services and I-5 access.

2148 Birchwood Lane, Ashland

$649,000
4 Beds 2 Baths 220226618 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 mountain views creating 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, and shopping. When driving by the property go Wimer st to Alta. Do not use Grandview.

279 Alta Street, Ashland

$325,000
2 Beds 2 Baths 220226605 MLS
''Where the living is easy'' -- and in this Ashland condo, it truly is. This modern 2-bedroom, 2-bathroom condo offers effortless main-level living just minutes from everything that makes Ashland, Ashland. Rich bamboo flooring, granite countertops, and a gas fireplace give the space warmth and polish, while a laundry room and abundant storage keep daily life simple. A new water heater and dedicated underground parking check the practical boxes, while the HOA handles all exterior maintenance -- so your weekends are yours. Location? Hard to beat. You're close to N. Mountain Park, bike paths, ball fields, scenic nature trails, top-rated schools, and everyday shopping -- plus a quick hop to the world-renowned Oregon Shakespeare Festival and the beauty of Lithia Park. Whether you're catching a matinee downtown or a sunset walk in the park, this is Ashland living at its most comfortable.

608 Fair Oaks Court, Ashland

$649,000
3 Beds 4 Baths 220226544 MLS
Built in 1996, this Ashland property features a 1,910 square foot main residence and a permitted 944 square foot attached ADU. The main home offers one bedroom, two full bathrooms, an office, vaulted ceilings, hardwood flooring, granite counters, a kitchen island, breakfast bar, generous laundry room, and two gas fireplaces in the living room and primary suite. An oversized two car garage provides additional workshop space. The primary bedroom opens to a private deck, while the bathroom includes a soaking tub and separate shower. A large view deck extends from the main living area and captures mountain and territorial views. The single level ADU includes two bedrooms, two full bathrooms, and its own two car garage. It is currently rented for $1,400 per month on a month to month basis, offering immediate income potential. Set on a landscaped 0.22 acre lot with public utilities, this versatile property offers comfortable living, rental income, and flexible long term use.

369 Alta Avenue, Ashland

$2,800,000
3 Beds 6 Baths 220226424 MLS
Dana Campbell Vineyards is a legacy wine business offering multiple avenues for growth with unparalleled proximity to Ashland's renowned cultural amenities. Seller-carried financing available. Elegantly remodeled tasting room residence with three guest suites ideal for boutique hospitality, panoramic valley views, great room with service bar and gas fireplace, catering kitchen, break room, ADA-compliant bathrooms. Expansive paver patio, outdoor speakers, gas fire pit, composite deck and pergola with retractable awning, bocce ball court, and rose garden. State-of-the-art cold storage facility or potential winery building with glycol cooling system, fully irrigated acreage with southern exposure, over 13,000 established vines of eight estate-grown varietals producing 2,200 cases per year, seven additional acres ready for planting, wind turbine, frost fan, and all essential equipment included for turnkey tasting room operations. Inquire for additional details of untapped revenue streams!

1320 N Mountain Avenue, Ashland

$674,900
3 Beds 3 Baths 220226344 MLS
Updated mid-century modern/contemporary home located just a short distance from downtown, Lithia Park, and premier hiking trails. This light-filled 3-bed+office, 2.5-bath residence offers 2,090 sq ft of well-designed living space. The open floor plan features a wood-burning fireplace and connects seamlessly to two large decks, showcasing expansive views across the valley to Grizzly Peak. The spacious master suite includes its own fireplace, a large walk-in closet, and an en suite with a deep soaking tub, rain shower, and direct deck access. Additional amenities include a private wet sauna--perfect after time spent on the nearby trails--and a large, fully fenced, low-maintenance backyard. Combining thoughtful updates with convenient proximity to Ashland's central attractions, this home provides a great balance of comfort and utility.

424 Courtney Street, Ashland

$499,900
5 Beds 3 Baths 220226295 MLS
Escape to a private retreat on five level, wooded acres in the heart of the Highway 66 recreation corridor, just minutes from Howard Prairie, Hyatt Lake, and Lake of the Woods. This beautifully maintained, recently updated split-level home seamlessly blends comfort, privacy, and year-round adventure. A slate entry opens into a spacious living room featuring a bay window and a wood-burning stove insert. The home offers five bedrooms, three full baths, a formal dining area, and flexible living and family rooms--each with its own fireplace--plus a dedicated office or hobby space. The kitchen is equipped with granite countertops and tile flooring, ideal for casual meals or hosting guests. Set in a peaceful forest environment close to fishing, boating, hiking, mountain biking, and snowmobiling, this property is perfect as a primary residence, seasonal getaway, or investment property. Experience the quintessential Southern Oregon lifestyle in a serene, nature-filled setting.

12300 Oregon 66, Ashland

$1,695,000
3 Beds 4 Baths 220224372 MLS
Exclusive equestrian property just outside Ashland! This 8+ acre unique estate has it all, from the beautiful single level updated home with stunning views of Grizzly Peak, to the well-equipped horse facilities & fully irrigated pastures. Horse boarder's dream w/ 8+ paddocks, 7 cross-fenced pastures w/ more stables, 9000+ sf sand-filled covered arena w/ lighting for night riding, hay barn, & water access to Tolman Creek. Gorgeous 3 bed, 4 bath 3765 sf custom home surrounded by lush landscaping, welcomes w/ beautiful hardwood floors, vaulted ceilings, exquisite kitchen, closed in patio, custom built-ins, & topped off w/ a 1000 bottle wine cellar. Light & bright primary suite features magnificent windows & a spa-like bathroom w/ jetted soaking tub, custom slate tile shower, heated floor & dual sinks. Step from the open concept living to a refreshing oasis boasting of a solar-heated pool, hot tub, peaceful water feature, & a tranquil pond full of bass and blue gill that beckons to stay.

550 Crowson Road, Ashland

$399,000
1 Beds 1 Baths 220226151 MLS
Affordable opportunity to own 2.14 acres and finish building a newer, 688-sqft tiny home nestled on private acreage, just 15 minutes from downtown Ashland. This existing permitted general purpose building, is ready to be converted into a 1-bedroom, 1-bathroom layout. Property features outdoor sauna, small seasonal pond, and high-producing well (11 GPM with pump, 41 GPM raw). Built in 2014, the existing permitted structure currently includes an unfinished kitchen & dining room. Purchase property as-is with cash (see MLS listing # 220226037) for $275,000 or finance the construction using a rehab loan with this listing. List price is an estimate on the the total costs including the land purchase and the amount needed to finish it, based on estimate by contractor ($129,000). Buyer to due their own due-diligence. Buyer to enter into a separate building contract with contractor of their choice outside of escrow. Final price to be determined at a later date when Rehab package is finalized.

4712 Old Highway 99 S, Ashland

$750,000
4 Beds 4 Baths 220226035 MLS
Private 5.5-acre mountain retreat with stunning views, gated entry, asphalt drive, and expansive paved parking, only 5 minutes to town! Perched above Emigrant Lake, this impeccably maintained 2,700 sq ft home offers flexible living: two inviting living areas (one with a cozy fireplace, the other with a wet bar and patio access), a sunlit kitchen with tile floors, granite counters & backsplash, and all appliances included. Main level features formal dining, a bedroom and 1.5 baths; upstairs the spacious primary suite with walk-in closet plus two more bedrooms, 2 full baths and larger storage room. Huge attached workshop with shelving, workbenches and 220/240A service (could be converted to ADU), plus an attached 2-car garage. Entertain or unwind on the deck with pergola and hot tub, enjoy outdoor/indoor living and private hiking trails right on the property.

197 Timberlake Drive, Ashland

$775,000
3 Beds 2 Baths 220225944 MLS
Welcome to this beautiful eco-frlendly home in Ashland's sought-after Beach Creek Community. This thoughtfully designed 3-bedroom, 2-bath home offers 1,538 sq. ft. of sustainable living with soaring vaulted ceilings, expansive windows providing lots of natural light wlth mountain views. Built by KDA Homes, this Earth Advantage Platinum-certified, Net Zero-rated home features owned solar panels, providing lower utility. costs. The modern open-concept floor plan features seamless lndoor--0utdoor living, granite countertops, custom tile work, quality craftsmanship throughout, and two private decks ideal for relaxing. Located in the heart of Ashland, just minutes from downtown shopping, dining, entertainment, and nearby parks, allowing you to fully enjoy everything Ashland has to offer.

1221 Kirk, Ashland

$2,400,000
3 Beds 2 Baths 220225850 MLS
One of the Rogue Valley's premier estate settings, this extraordinary 164-acre Ashland offering is paired with a proposed luxury residence by Asher Homes. The single-level design offers 2,778 sq ft with 3 bedrooms, 2 baths, a 912 sq ft 3-car garage, and walls of glass framing mountain and valley views. Refined finishes include large-plank hardwood, custom built-ins, a stone fireplace, metal roofing, and covered outdoor living with built-in BBQ and fireplace. Designed to Earth Advantage Platinum standards, the home features high-efficiency HVAC, solar-ready infrastructure, EV charging, generator tie-in, and wildfire-conscious materials. The build package includes vertical construction and an infrastructure allowance for driveway, septic, well systems, power, propane, water storage, trenching, and utility connections. Land offers 2,220 feet of Cove Creek frontage, a 48 GPM well, and paved access. Plans and pricing subject to site conditions, permitting, selections, and builder approval.

312 Sky Ridge Road, 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

$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

$999,999
3 Beds 4 Baths 220224770 MLS
Enjoy spectacular views of Emigrant Lake & the surrounding mountains from this exceptional 3,713 sf custom 3 bd 3.5 ba home on over 30 acres, just 10 min from Ashland and a short drive to Mt. Ashland. From the moment you enter through the stunning mahogany door from your wrap around deck, you are welcomed into a great room with vaulted ceilings, a floor-to-ceiling rock fireplace, & windows that fill the home with natural light. Living space blends seamlessly into your gorgeous chef's kitchen & formal dining. An office w/ custom built-ins, bonus family room, & a guest half bath round out the main living space alongside an impressive primary suite, which features a private balcony, fireplace, & newly remodeled luxurious bathroom. Downstairs, you will find a guest ensuite, another guest bedroom, full bathroom, & laundry room. A 3-car garage provides plenty of space for cars & toys. Seller has done extensive fire mitigation work & paved the driveway, making this property insurable.

3729 Old Highway 99 S, 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, 1.6 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

$650,000
2 Beds 1 Baths 220225643 MLS
Opportunity to own an historic two bedroom, one bath, 1,233 square feet, 1925 Craftsman-style home Above the Boulevard with easy access to town and all the amenities Ashland has to offer. This gracious property has been lovingly maintained by its present owner for the last thirty-four years. From the welcoming and covered front porch to the spacious, light-filled interior everything about this property harkens back to a time when life was a little slower. This single-story home with a full basement sits on a level .3 acre lot with a duplex that backs to the alley. Properties like this don't often come on the market. Home is located in ''The Siskiyou-Hargadine Historic District.'' Buyers are encouraged to do their own due diligence and check with the City Ashland regarding the legality of existing structures and possibilities for expansion.

363 Beach Street, Ashland

$1,200,000
2 Beds 3 Baths 220225582 MLS
Experience refined living just one block from downtown Ashland in this custom, open concept, built 2012 luxury home, designed for comfort and ease. An elevator to take you to all levels makes stair use unnecessary and 36 inch doorways provide seamless accessibility throughout. The oversized, finished, two + car garage with sealed floors offers space for a workshop, gym and storage with an additional washer & dryer, sink and gas heater. Rich oak and red oak floors and cabinetry pair beautifully with custom metalwork and soaring wood-paneled ceilings throughout the home. The chef's kitchen features a 6 burner Wolf cooktop, wall ovens, Sub Zero refrigerator, exposed edge granite countertops and custom pot racks. Spa inspired bathrooms include heated tile floors, dual vanities, tiled showers and abundant natural light, one with a soaking tub. The private flagstone courtyard with gas BBQ and pergola is perfect for relaxing and outdoor entertaining with lovely, low maintenance landscaping.

400 Allison 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

$1,650,000
4 Beds 4 Baths 220225368 MLS
Welcome to this one-of-a-kind custom ICF-built home with breathtaking panoramic views just minutes from downtown Ashland! This 4 bed, 3.5 bath, 4,972 sqft home offers a main-level office, multiple large storage rooms, and plenty of space for entertaining. The upper level features a spacious primary suite with a private balcony, plus (2) additional bedrooms and a bonus loft (not included in storage). The lower level is ideal for multigenerational living with a large entertainment area, wet bar, bedroom, bathroom, and bonus office/storage space. Situated on 14.78 acres, (house on 1 acre), 13.8 acres currently in hay production, with rare dedicated unlimited TID irrigation. Propane has been plumbed both interior and exterior to add a fireplace or connect your BBQ if desired. Also includes an approx. 1,500 sqft detached shop with 3-phase electrical, barn with (6) 12x12 stalls, riding arena, plus (2) full RV hookups and 50-amp also available at the barn. A must-see incredible property!

40 Ashland Acres Road, 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: