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$410,000
2 Beds 2 Baths 220227463 MLS
This inviting, move-in-ready home is filled with natural light and offers a functional, comfortable layout with fresh interior paint and upgraded blinds throughout. The living room features a cozy gas fireplace and flows seamlessly into the kitchen and dining area. Brand-new, high-end stainless appliances, a stylish backsplash behind the range, and a dedicated eating area complete the kitchen. The spacious primary suite offers a generous closet and ensuite bath with a walk-in shower. A second bedroom, additional full bathroom with a tub/shower combination, and conveniently located hall laundry closet add to the thoughtful layout. Step outside to a fully fenced, low-maintenance backyard featuring a concrete patio, southwest-facing exposure, and mature trees that provide beautiful filtered light and welcome shade. A beautifully landscaped front yard with a drip irrigation system and an attached two-car garage complete this truly charming home!

2140 Birchwood Lane, Ashland

Listing courtesy of John L. Scott Ashland.

$585,000
3 Beds 3 Baths 220227338 MLS
Once-in-a-generation opportunity to own an exceptional home on one of the best lots in Ashland, and in the coveted Green Meadows neighborhood. This 3-bed 2.5-bath single-level home features spacious bedrooms, beautiful laminate wood flooring, and the wood stove adds warmth and character to the spacious living room. The lush, gently sloping .43-acre lot offers mature landscaping and direct backyard access to the trails at Oredson-Todd park, along with TID irrigation rights plumbed to both the front and back yards. Enjoy unobstructed views, the secluded back patio with room to garden, an oversized two-car garage, and a RV pad on the side of the home for any large storage needs (or to provide access for the potential of a lot division, buyer to do own diligence). Above the boulevard and tucked into a friendly, walkable neighborhood, this rare property offers single-level living, privacy, generous outdoor space, and sweeping views in one of Ashland's most desirable settings.

2354 Green Meadows Way, Ashland

Listing courtesy of Cascade Hasson Sotheby's International Realty.

$1,375,000
4 Beds 4 Baths 220227401 MLS
Stunning, one-of-a-kind modern Craftsman just two blocks from downtown Ashland. An inviting open floor plan features hickory hardwood floors, a chef's kitchen with leathered granite, Italian tile, and expansive floor-to-ceiling bi-fold doors framing panoramic Siskiyou Mountain views. Upstairs, vaulted ceilings, exposed beams, skylights with automatic blinds, and beautifully appointed bedrooms create exceptional character and natural light. The finished daylight basement, currently an artist studio, offers separate exterior access, a home gym, and two bonus storage rooms--ideal for a second living space or potential ADU. The multiple levels of this versatile spacious home amount to an accumulative 3,589 Sq ft of sleek, inspiring living space. Outside, enjoy immaculate low-maintenance landscaping and a dog run. R-2 zoning and alley access add exciting development and short-term rental potential. Buyer to perform own due diligence.

533 Fairview Street, Ashland

Listing courtesy of Cascade Hasson Sotheby's International Realty.

$499,000
5 Beds 3 Baths 220227392 MLS
Income property! Tucked away at the end of a private country lane, this unique Ashland property offers privacy, flexibility and a peaceful rural setting. The 1,412 sq. ft. main home features 3 bedrooms, 1½ baths and a beautifully remodeled kitchen with newer cabinetry, wood-grain tile flooring and an indoor BBQ. Recent improvements include a new roof, HVAC system, well pump and pressure tank, plus UV water filtration. The well last tested at 8 GPM. Starlink provides internet, and gutter guards add convenience. A separate 1996 manufactured home offers county-approved living area for 2 bedrooms, a bath and utility area, with its own electric meter. RV hookups and generous parking add flexibility. Enjoy established fruit trees, grapes, raised garden beds, greenhouse and chicken coop. A rare opportunity for comfortable country living with an Ashland address. Additional income may be available with signage on the land. Buyer to do their own due diligence.

728 W Valley View, Ashland

Listing courtesy of Expert Properties Inc..

$1,625,000
5 Beds 4 Baths 220227302 MLS
This 4-bedroom home, plus a separate 1-bedroom accessory unit, is a standout on almost any block, thanks to its amazing use of space and unique contemporary design. The pitched metal roof, clean lines, and mix of materials really catch the eye. Inside, the main-floor primary bedroom suite boasts high windows in the dual-primary bath, while the expansive living/dining area off the kitchen is filled with built-ins that flow into the foyer-adjacent front office. The private, ''open horseshoe'' courtyard design brings natural light into the living room, dining room, kitchen, and primary bedroom. Plus, there's a fully self-contained private accessory residential unit with a full kitchen, one bedroom, and its own entrance.

619 Elkader Street, Ashland

Listing courtesy of Millen Property Group.

$439,920
2 Beds 3 Baths 220227296 MLS
Move-in ready and beautifully updated! The main level features new vinyl flooring (2025), LED lighting, and an electric fireplace for added ambiance. The kitchen offers an eating bar, dining area, and new dishwasher (2025). A half bath with pedestal sink and attached one-car garage complete the main level. Upstairs are 2 bedrooms, 2 full baths, new carpet (2026), a spacious landing ideal for an office or flex space, and a view deck with retractable awning. The primary suite includes a walk-in closet and ensuite bath with shower. Laundry closet includes washer & dryer. Major updates include new roof (2025), heating & A/C (2024), water heater (2024), exterior paint (2026), and new smoke/CO detectors (2026). Enjoy a private fenced backyard with patio, garden beds, views, and refreshed low-maintenance landscaping. Extensive updates and a functional floor plan make this home ready to enjoy!

2234 Dollarhide Way, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

$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

Listing courtesy of John L. Scott Ashland.

$645,000
5 Beds 4 Baths 220227203 MLS
Over 1/2 Acre lot near historic Ashland Plaza! This 5 bedroom 4 bath home offers 2,487 sqft of living space set in a highly sought after neighborhood just minutes from shopping, dining and entertainment such as the Oregon Shakespeare Festival. 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

Listing courtesy of RE/MAX Integrity.

$965,000
220227186 MLS
Ten, six, or four-unit investment opportunity in Ashland's Hillview Condominiums near Scenic Park and Asante Ashland. Seller-carried financing available at ~3.99% AFR with 50% down, interest-only payments, with balloon due in three years. Each unit ranges from 1,034 to 1,174 SqFt with two bedrooms, one full bath, open living and dining space, high ceilings, in-unit laundry, kitchen with granite counters and all appliances included, dedicated parking, storage, and access to landscaped common areas. Ground-level units with fully fenced private backyards and poured concrete patios. Current gross monthly income is $15,730 across all ten units following rent increases effective August 1st, 2026. Stable tenancy averaging four-plus years, room for further rent growth, and association-maintained exterior building components including roofs, siding, paint, and landscaping. Complete investment analysis, rent roll, association documents, and due diligence materials available upon request.

240 Grant Street, Ashland

Listing courtesy of John L. Scott Ashland.

$1,395,000
220227184 MLS
Ten, six, or four-unit investment opportunity in Ashland's Hillview Condominiums near Scenic Park and Asante Ashland. Seller-carried financing available at ~3.99% AFR with 50% down, interest-only payments, with balloon due in three years. Each unit ranges from 1,034 to 1,174 SqFt with two bedrooms, one full bath, open living and dining space, high ceilings, in-unit laundry, kitchen with granite counters and all appliances included, dedicated parking, storage, and access to landscaped common areas. Ground-level units with fully fenced private backyards and poured concrete patios. Current gross monthly income is $15,730 across all ten units following rent increases effective August 1st, 2026. Stable tenancy averaging four-plus years, room for further rent growth, and association-maintained exterior building components including roofs, siding, paint, and landscaping. Complete investment analysis, rent roll, association documents, and due diligence materials available upon request.

254 Grant Street, Ashland

Listing courtesy of John L. Scott 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

Listing courtesy of RE/MAX Platinum.

$850,000
220226802 MLS
Calling all investors and developers - rare 1.5 acre opportunity in the heart of Ashland. This expansive parcel presents exceptional potential for subdivision and redevelopment, with possibilities similar to the nearby Clear Creek Subdivision. Ideally situated in a highly desirable location, this property offers convenient access to local amenities, schools, parks and downtown Ashland. The site is well situated for those looking to capitalize on Ashland's strong housing demand and limited land availability. Buyers are advised to perform their own due diligence with the City of Ashland regarding zoning, land use,utility availability and development requirements to fully realize the property's potential. Existing structures are considered uninhabitable and are expected to be removed following approval of a redevelopment plan, providing a blank slate for your vision. Land Use Report available for interested parties.

219 N Mountain Avenue, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

$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

Listing courtesy of Morninglight Properties.

$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

Listing courtesy of John L. Scott Medford.

$725,000
1 Beds 2 Baths 220226541 MLS
A second story corner residence in the A LEED-certified Plaza West Building with a flowing, light-filled floorplan. Hardwood floors, a stone-framed gas fireplace, and high ceilings set a calm, refined tone throughout. Oversized windows frame views of the Ashland hills and watershed from the spacious primary suite.The en suite bath offers marble-style tile, a double vanity, separate water closet, and a generous walk-in closet. The kitchen is finished with stone counters, stainless appliances, and solid wood cabinetry with soft-close drawers. A media room with pocket doors serves easily as a private office or guest space, with a half bath and separate laundry nearby. Gated parking, private storage, and building surveillance offer quiet peace of mind. Just moments from Shakespeare, Lithia Park, and Ashland's finest shopping and dining.

175 Lithia Way 200 Unit 200, Ashland

Listing courtesy of John L. Scott Ashland.

$649,000
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

Listing courtesy of Full Circle Real Estate.

$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

Listing courtesy of eXp Realty, LLC.

$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

Listing courtesy of John L. Scott Ashland.

$950,000
3 Beds 2 Baths 220226122 MLS
Welcome to 501 Carter Lane, a fully flat, usable property offering the ultimate blend of agricultural potential and incredible income generation! This upgraded 2,680 sqft. house is surrounded by amazing mountain views and features an 800 sq. ft. barn home, cottage, cabin, and a tiny home. The estate boasts tons of Airbnb rental income opportunity, with a 9-year 5-star Superhost history generating up to $100k+ annually. Built for growth, this farm features OMMP/ODA licensed gardens, greenhouses, and fertile soil. You'll find amazing, crystal-clear water with an endless well, irrigation ponds, and a 1-million-gallon TID water allocation. With upgraded electrical throughout and tons of equipment for farming included, it's a turnkey operation ready for your crops. Whether you want to farm, host guests, or move the whole family into this unique dream property, your endless possibilities await!

501 Carter Lane, Ashland

Listing courtesy of Real Broker.

$739,000
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

Listing courtesy of John L. Scott 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

Listing courtesy of RE/MAX Platinum.

$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

Listing courtesy of Gateway Real Estate.

$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

Listing courtesy of Gateway Real Estate.

$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

Listing courtesy of John L. Scott Medford.

$900,000
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

Listing courtesy of John L. Scott Ashland.

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