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$350,000
2 Beds ⋅ 2 Baths ⋅ 220225960 MLS
Upgraded and move-in-ready single-level end-unit townhome located near the Ashland Family YMCA and future site of 5.52-acre East Main Park! Fresh interior paint, all-new low-pile berber wool carpets, and new roof to be installed early August 2026. Entry with skylight and hall coat closet, bamboo flooring, kitchen with custom maple cabinets, granite counters, solar tube, and stainless appliances including Fisher & Paykel refrigerator. Open dining area and vaulted living room with sliding glass door to covered patio and fully-fenced private backyard with composite deck. Primary with dual closets and full ensuite bathroom with solid surface vanity, maple cabinets, solar tube, and tub shower. Full guest bath with matching amenities, guest bedroom with closet, laundry area with Speed Queen washer and dryer, and one-car garage. Association dues of $265 per month cover all exterior maintenance - including roof, siding, paint, front landscaping, and common areas. Inquire for details!

241 Clay Street, Ashland
$540,000
3 Beds ⋅ 2 Baths ⋅ 220225859 MLS
Enjoy 18+ acres of privacy with a gated entry and set back entrace with valley views! This 2,668 sqft, 3 bedroom, 2 bath home features a large 2 story rock fireplace and vaulted cedar ceilings in both the large formal living room and family room. Additional log studio/office. The land has been cleared and leveled and now very usable. Room for shop, gardens.

19001 Dead Indian Memorial Road, 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
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 220225369 MLS
First time on the market for this one-of-a-kind custom ICF-built home with breathtaking panoramic views! 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, barn with (6) 12x12 stalls, riding arena, plus (2) full RV hookups and 50-amp available at the barn, and endless opportunities for horses, livestock, or hobby farming.

40 Ashland Acres Road, Ashland
$1,300,000
3 Beds ⋅ 3 Baths ⋅ 220223946 MLS
An Ashland jewel, this architecturally designed & built home enjoys an exceptional setting above Lithia Park with stunning views and timeless craftsmanship. Intentionally designed, with high-performance systems throughout, showcasing exceptional interior and exterior finishes. Main level has 3 bedrooms, 2 full baths, open floor plan, den, and dedicated office space; all designed to capture abundant natural light and beautiful views. The gourmet island kitchen flows seamlessly into the living and dining areas, creating an inviting space for entertaining. Enjoy the private deck, perfect for morning coffee or twilight dining. A fully furnished 1-bedroom ADU provides flexibility for guests, extended living, or income potential, while the finished shop is ideal for a studio, workshop, or hobbies. A rare opportunity to own one of Ashland's most distinctive and notable properties.

5 Scenic Drive, Ashland
$600,000
3 Beds ⋅ 3 Baths ⋅ 220224168 MLS
Welcome to this unique 1993-built contemporary home on a private .29-acre wooded lot featuring beautiful mountain views. Dramatic floor-to-ceiling windows flood the home with natural light and frame the stunning scenery. The versatile layout features 3 bedrooms plus a main-level office, 2.5 baths, a cozy den, a sunroom, and a flexible lower-level craft room/office. The eat-in kitchen offers plentiful storage in a serene setting. Enjoy a highly private primary suite tucked away from the main living spaces. Outside, the terraced backyard, deck, and patio with mature plantings offer a quiet, relaxing sanctuary. Complete with an attached 2-car garage + extra storage. Minutes from hiking trails and shopping!

1536 Pinecrest Terrace, Ashland
$800,000
4 Beds ⋅ 4 Baths ⋅ 220223301 MLS
Custom view home with charming detached guest cottage located just above downtown between Lithia Park and the Ashland Public Library. Main level great room with vaulted double-height ceiling, walls of windows, reclaimed clear-grain fir trim, solid-core doors, refinished oak floors, kitchen with composite dining bar, tile counters and backsplash, cabinets with solid wood interiors and custom pull-outs, dining room with glass door to view deck with gas BBQ hookup, bedroom with closet and full ensuite bath, and pantry with washer and dryer. Upper level primary with skylights, hanging closet, French doors to private balcony, and full ensuite bath with jetted tub. Versatile lower guest suite or family room with French doors to paver patio, full bathroom with oversized shower, storage cellar with stainless utility sink, and one-car garage. Detached cottage with permitted kitchen, living area, full bathroom, loft bedroom, and private gated entrance from Terrace Street. Inquire for details!

307 Hillcrest Street, Ashland
$1,049,900
3 Beds ⋅ 3 Baths ⋅ 220223070 MLS
Tranquil & pristine Mountain oasis on over 121 acres with a campground, marketable timber, Greenhouse, stream w/waterfall, springs and amazing scenic views of Mt Shasta & Pilot Rock. Amazing main home w/tile entry & stained-glass w/3 bedrooms, 2.5 baths, 2145 SQ FT with open beam vaulted ceilings in the great rm w/ huge stone staircase. Kitchen w/granite counters, tile floors opens to dining & great rm loft area. 2 primary suites overlooking the deck and creek. The other primary suite has a door to lg covered deck. Detached 2 car garage. Off grid secluded unpermitted cabin by waterfall and campground. Woodshed w/Japanese architectural elements, on-site fire suppression. Next to Forest Lands w/private hiking trails; Pacific Trail, wildlife, berries and mushroom hunting. Enjoy unobstructed star gazing, snow shoeing, sledding and more just 20 minutes from downtown Ashland. Owner will carry with $500,000 Down, 6.5% for 3-5 years w/Sellers' approval of Buyer. Last house before the Lodge.

500 Mt Ashland Ski Road, Ashland
$1,140,000
3 Beds ⋅ 3 Baths ⋅ 220222186 MLS
Set privately back on 5+ acres in the Sunny Oaks community, this custom 3 bed + office, 2.5 bath, 2644 sq ft home pairs open mountain views with easy access to town -- 15 min from Downtown Ashland and near Emigrant Lake. The groundwork for comfortable rural living is in place: a dedicated 1-gigabit fiber line, 300 amp electrical, whole-home water filtration, 2021 Lennox HVAC, irrigation rights, a large cedar-fenced area, and a roof under six years old. Inside, natural light fills an updated kitchen with quartz counters and hardwood floors, opening to a great room, with a separate family room, office, and laundry on the main level. Upstairs, the primary suite offers vaulted ceilings and a balcony framing the same sweeping mountain views as the wraparound deck below, plus two more bedrooms and a full bath. Outside, a gravel RV pad offers water, power, and internet, and a barn with corrals stands ready for horses. With over $200K in updates, the property is move-in ready.

7130 Highway 66, Ashland
$1,149,808
3 Beds ⋅ 3 Baths ⋅ 220221584 MLS
Country living close to Downtown Ashland. 3209 sq ft w/3.68 irrigated acres, gated paved entry, beautiful landscape fenced yards w/garden beds, greenhouse, large pasture for animals, motorhome garage, heated large shop rm, potting shed. Peaceful spring fed waterfall to a KOI fishpond. This Asher Homes remodel includes a beautiful kitchen w/nice appliances; dbl convection ovens, large island w/ sitting area & lots of storage. Lg windows taking in the natural light & beautiful views of the mountains, breakfast room off kitchen, formal dining w/bay window & window seat, living room overlooking covered front porch. Downstairs bedrm & full bathrm or office/library w/built-in bookcases. 2 large primary suites upstairs w/sitting areas, vaulted ceilings, lg windows w/views, both bathrooms w/new updates, great walk in closet w/built-ins & a bonus room that could be a great studio/office/media room or hobby room. Back deck overlooking the perfect manicured mature landscaping w/hot tub

39 E Valley View Road, Ashland
$850,000
3 Beds ⋅ 3 Baths ⋅ 220221511 MLS
Refined country view home on serene private acreage just 10 minutes from downtown Ashland. Recent upgrades include all new cement board lap siding, updated HVAC, and architectural shingle roof with solar array. Main level with 2,375 SqFt of living area, solid oak hardwood flooring, vaulted wood-paneled ceilings, three sets of sliding glass doors to redwood deck with infrared sauna and hot tub, great room with propane fireplace, formal dining, kitchen with leathered granite and quartz counters, stainless appliances including double ovens and induction cooktop, spacious primary with walk-in closet and full ensuite bath, two guest bedrooms, full guest bath, laundry room, and two-car garage. Upper-level office or fourth bedroom. Paved driveway, ample parking, mature plantings, grass lawns, full metal fencing around home, lower view deck with pergola, stone pathways, patio, and pond. Forest management by Lomakatsi. Access via Frank Hill Road or McKenzie Canyon Rd. Inquire for details!

1601 Frank Hill Road, Ashland
$2,500,000
5 Beds ⋅ 7 Baths ⋅ 220220624 MLS
Discover this extraordinary Southern Oregon Luxury 2 acre estate perched above downtown Ashland w/views & incredible privacy. This custom built Pagnini home 5313 SQ FT, 5 bdrms, 5.5 bthms, 5 Car Garage + an additional 720 sq ft detached guest quarters. Grand entry, stunning wood floors, soaring ceilings, multiple fireplaces & walls of windows to take in the incredible views & abundant natural light. Gourmet kitchen w/quartz countertops, skylights & SS appliances w/double ovens. Main level primary suite w/ terrace access offers a soaking tub & steam shower. 2 upstairs guest suites both come complete w/private balcony & breakfast bar. Additionally this incredible home features a slate roof, sauna, elevator, a spacious office w/ en-suite + so much more. European-style terrace w/big natural boulders, fruit trees, a dog run, greenhouse, and manicured gardens along w/ abundant wildlife- no expense was spared on this remarkable Ashland retreat & it truly shows

500 Ashland Loop Road, Ashland
$245,000
2 Beds ⋅ 2 Baths ⋅ 220220712 MLS
If you are looking for the best views in Ashland's Tudor Heights, this is it. Positioned as the premier front unit, this condo offers a perspective no other home in the complex can match. Stay comfortable year-round with the rare addition of efficient ductless mini-splits for heating and cooling--a significant upgrade over the standard baseboard heat found in most units. The main level offers a seamless open layout that flows to your outdoor patio. Upstairs, both bedrooms provide unobstructed mountain views to the north and east, including a private balcony off the main suite--perfect for watching the sunrise. Whether you're walking to the Downtown Plaza for dinner or hiking through Lithia Park, everything is within reach. Enjoy the security and ease of a comprehensive HOA that handles exterior upkeep, allowing you to simply relax and enjoy the Southern Oregon scenery.

495 Chestnut Street 1 Unit 1, Ashland
$950,000
3 Beds ⋅ 3 Baths ⋅ 220220668 MLS
Quality custom view home in a private natural setting above the boulevard, just six minutes to Ashland's downtown plaza. Abundant natural light and airflow with operable wood-wrapped casement windows, high vaulted ceilings, solid core doors, and unique architectural view corridors throughout. Great room with solid Brazilian cherry flooring, gas fireplace, formal dining with built-in buffet, French doors to wrap-around view deck, kitchen with granite dining counter and stainless appliances, open family and informal dining room, powder room, laundry with utility sink, and two-car garage. Step-down primary suite with French doors to private balcony, walk-in closet, full ensuite bathroom with travertine double vanity, jetted tub, shower, and water closet. Upper loft with mountain views and stairwell skylights. Two lower-level guest bedrooms, full bath with tub shower, den, and French doors to pebbled concrete patio and organic garden. Newer HVAC and exterior paint. Inquire for details!

602 Ashland Street, Ashland
$2,250,000
220220428 MLS
Rare 10-unit investment opportunity in Ashland's Hillview Condominiums -- close to Scenic Park, Asante Ashland Community Hospital, downtown dining and entertainment. Three-year seller-carried financing available at 3.75% rate with interest-only payments and balloon at maturity. 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. Portfolio includes stable tenancy, average occupancy of 4.2 years, room for rent growth, and association-maintained exterior building components including roofs, siding, paint, and landscaping. Complete investment analysis and user guide, rent roll, association documents, title information, and additional due diligence materials available upon request.

230 Grant Street, Ashland
$2,195,000
4 Beds ⋅ 4 Baths ⋅ 220219782 MLS
Located just outside Ashland, this property offers a rare blend of natural beauty, water, quality improvements, and convenience. The custom built home is thoughtfully positioned to capture expansive views across the surrounding valley and toward distant mountains. This elevated country estate draws from a Northwest lodge aesthetic, offering welcoming living spaces, a spacious multilevel layout and a seamless indoor outdoor connection with expansive outdoor living spaces. A picturesque stretch of Neil Creek framed by mature trees adds character and tranquility. Gently rolling topography, lush pasture, and water rights support a variety of Ag uses. A recently constructed 5,000 SF barn complements the property and offers outstanding flexibility for equipment, hobbies, or recreational use. Ideal as a homestead or simply an elegant place to enjoy connection to the outdoors, this is a property that captures the essence of Southern Oregon living while remaining just minutes from Ashland.

5293 Highway 66, Ashland
$735,000
3 Beds ⋅ 3 Baths ⋅ 220218220 MLS
Fully renovated home by Coleman Creek Construction with detached studio and garage on rare E-1 zoned acreage with development potential in city limits! Charming front porch and covered wrap-around patio, open-concept living area with double-height vaulted ceiling, kitchen with quartz dining counter, designer lighting, and stainless appliances including gas range oven. Main-level primary suite with skylights, glass door to back patio with retractable awning, and full ensuite bathroom with quartz vanity, deep soaking tub, and oversized shower with seamless glass and tile surround. Additional main-level bedroom and full guest bathroom with quartz vanity, stacked washer dryer, and tiled shower. Vaulted upper-level media room, office, or third bedroom. Detached studio with quartz dining counter, stainless appliances including electric range oven, full bathroom with quartz vanity, tub shower, washer dryer, plus two-car garage. Ample off-street boat or RV parking. Inquire for details!

593 Crowson Road, Ashland
$995,000
5 Beds ⋅ 4 Baths ⋅ 220216782 MLS
Available for the first time, 2004-built custom home in Ashland's Strawberry Meadows. This 3,105 sq. ft. 5 bed/4 bath house sits on a private .46-acre lot bordering an oak-lined creek open space. Main level includes double-height entry with skylights, living room with wood-fire insert, dining room, well-planned kitchen with large pantry, and a primary suite with deck. Upper level offers four bedrooms, 3 with walk-in closets, and large family room with balcony overlooking the creek. Versatile layout accommodates expansive family life and home office space. Additional features include a 2-car garage, robust storage, an approx 200 sq ft finished bonus room not included in the square footage, and a generous patio off the dining/kitchen area with perennial gardens enclosed in a custom deer fence. Situated in a Firewise-certified neighborhood near Lithia Park with access to local hiking trails. This private and quiet property offers a rare opportunity for a special home in a coveted setting.

523 Strawberry Lane, Ashland
$595,808
1 Beds ⋅ 1 Baths ⋅ 220215560 MLS
Rare opportunity to own 71.51 acres just right outside city limits of Ashland! LOCATION IS AMAZING!! Property consist of 2 additional tax lots. Super cute 2020 built MFG home w/vaulted ceilings & floor ceiling windows w/quartz counters & tile shower & lg wood deck. Near Emigrant Lake this property would be beautiful to build your dream home w/gated entry & gently sloping gravel road to the home w/incredible views of Cascade Mountains & Pilot rock. Creek frontage w/15 acres of water rights from Neil Creek. Trust has invested over $150,000 into the Creek management and rehab planting thousands of native plants. Gently sloping acreage w/pastures for horses or cattle or grape vines. 2 adjoining tax lots including. Priced to SELL! Buyer to do their own due diligence. Potential for maybe possibly another home site?

4201 Highway 66, Ashland
$515,000
2 Beds ⋅ 2 Baths ⋅ 220215328 MLS
Stunning 2022 transformation of a classic 1920s single-level cottage situated on a spacious third-acre parcel, ideally located between Lithia Park and Hald-Strawberry Park and only moments from downtown Ashland. Comprehensive updates include new roof, foundation, windows, waterproof LVP flooring, full electrical rewire, modern plumbing, and new sewer line. The open kitchen showcases vaulted ceilings, butcher-block island, granite sink, marble backsplash, and a copper-accented range hood. Primary suite offers private deck access, designer lighting, and a spa-like bath with clawfoot tub. Vaulted living room flows to an expansive deck with mountain views. Versatile second bedroom/office, efficient mudroom laundry, and full guest bath complete the interior. Outside enjoy terraced landscaping, TID irrigation, fresh paving, multiple outbuildings, and a fully self-contained 2016 tiny home with utility hookups. A rare opportunity in a prime Ashland location—contact today for more information!

220 Nutley Street, Ashland
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 220209743 MLS
Private tranquility in the treetops 4 min. to downtown Ashland. Views of Lithia Park w/soothing sounds of Ashland Creek flowing. Style meets sophistication on this beautiful architecturally designed home w/over ½ acre. $400K in new updates in the last 2 years. Private gated courtyard entry. Hardwood floors throughout, tile bathrooms floors, over 100 windows to bring in abundant light & cement balconies w/copper railings w/unobstructed views. Many trails close by. New massive artisan river rock wood burning fireplace in great rm. Chef's kitchen w/built in refrigerator, 6 burner gas cook top, dbl ovens, wine refrigerator, granite counters w/lg island. Formal dining & breakfast rm. 3 bdrms + lg office/meditation rm; 2 bdrm en-suites; Primary w/2 walk in closets, quartz counters, glass sinks, steam shower, air jetted tub, water closet & private balcony. 4 car garage, 2nd courtyard patio off entry. Home allows for an abundance of natural light w/vaulted ceilings & skylights.

545 Ashland Creek Drive, Ashland
$525,000
2 Beds ⋅ 2 Baths ⋅ 220207030 MLS
A perfect blend of rural serenity & functional living awaits on this 6.65-acre property just minutes from the heart of Ashland, Oregon. Surrounded by majestic madrone and fir trees, this private retreat offers natural beauty, privacy, and remarkable versatility. The main 2-bedroom, 2-bath home features a thoughtful layout w/an art room, attached garage, and expansive windows that bring the outdoors in. Just steps away, a beautifully finished Accessory Residential Unit (ARU) with a full kitchen is perfect for guests, extended family, or rental income. A unique workshop crafted from 2 shipping containers features hydraulic doors, a professional-grade engine hoist, abundant storage, & an adjacent large covered outbuilding—ideal for makers, mechanics, or outdoor enthusiasts. Whether you're enjoying peaceful mornings under the trees, tackling your next project, or exploring Ashland's renowned theaters, restaurants, and trails, this property offers the freedom to live, create, and thrive!

5010 Old Hwy 99 S, Ashland
$950,000
3 Beds ⋅ 3 Baths ⋅ 220200953 MLS
Discover unparalleled privacy and the captivating beauty of the Cascade-Siskiyou region in this custom-built Cedar home. Thoughtfully designed to frame the surrounding natural beauty through every window, the home's interior features Maple hardwood floors, 20-ft vaulted ceilings, and a stunning stone fireplace, creating an authentic Oregon lodge ambiance. Effortless single-level living is complemented by a versatile loft w/ custom railings. Outside, multiple Redwood decks offer the perfect spot for al fresco dining or enjoying the wildlife. A substantial barn/shop, crafted from local Blue Pine, offers endless storage possibilities. Benefit from a newly drilled well providing 15 GPM of soft water. The natural landscaping effortlessly blends with the environment, enhanced by recent fire mitigation efforts. Enjoy a seasonal creek and picturesque meadows, finding your own private sanctuary minutes from the vibrant town of Ashland, skiing, lakes and trails. Seller and Broker related.

545 Conifer Way, 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: