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$515,000
5 Beds 3 Baths 220227392 MLS
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.

728 W Valley View, 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

$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

$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

$630,000
3 Beds 3 Baths 220224225 MLS
Charming custom home with panoramic mountain views on a spacious and private 0.29-acre flag lot located above the boulevard within six minutes of Ashland's downtown plaza. All new low-pile berber wool carpets and fresh interior paint in 2026, new central AC system in 2019, and new roof c. 2016. Main level with solid oak hardwood floors, living room with bay window and gas fireplace, formal dining with French door to concrete paver patio with fire pit, kitchen with tiled counters and backsplash, powder room, laundry closet, and two-car garage with extensive built-in storage cabinets. Versatile upper level with two guest bedrooms, a very spacious primary suite with private office or nursery, two full ensuite bathrooms, and three sets of French doors to the backyard. Abundant natural light with Eastern exposure - dormer windows throughout. Established trees and hedges, mature plantings, and grass lawns with automated drip and sprinkler irrigation. Inquire for details!

430 Wiley Street, Ashland

$799,000
5 Beds 2 Baths 220223588 MLS
Offered for the first time in generations, this extraordinary fourth-generation Ashland treasure presents a rare opportunity. Own a piece of local history just steps away from world-renowned Lithia Park. This timeless two-story residence sits on beautifully landscaped .32 acre lot. It offers 5 bedrooms, 2 bathrooms, and a character that cannot be replicated. This home is rich in charm and architectural detail. It showcases the craftsmanship of a bygone era, while providing ample space for modern living. Enjoy peaceful mornings on the porch, stroll through Lithia Park, and easy access to downtown Ashland's theaters, galleries, restaurants, and cultural attractions. Homes of this caliber, location, and historical significance seldom become available. This is a once-in-a-generation opportunity to continue the legacy of one of Ashland's cherished homes.

143 Granite Street, Ashland

$759,000
5 Beds 6 Baths 220221349 MLS
71, 73 and 75 Wimer. Gorgeous updated including plumbing and electric vintage home w/charm remaining a few blocks to downtown Ashland. The main home has 3 bedrooms (2 with ensuite baths) the 3rd bedroom has an ensuite 1/2 bath. Formal living and dining and eat in large kitchen w/breakfast bar & nook. Granite countertops. Wood floors on main level & carpet on stairs & bdrms. The woodwork door trim is beautiful & probably original. Newer deck & A/C unit. Detached building (71 and 73 Wimer) are one level studio units with kitchens & baths. 73 Wimer has private deck. Main house is rented for $2375.00 p/month & tenant pays utilities except water. Studios have been rented for $1250.00 & $1350.00 per month with utilities included & they have a separate shared laundry facility. Unique property for owner occupied or income producing. Circular driveway for main home & 2 parking spaces in front for studios. Has been traveler accomodations in the past. Buyer to do own due diligence on u

75 Wimer Street, Ashland

$525,000
4 Beds 2 Baths 220221283 MLS
Charming historic home with 29+ years of improvements and stewardship. Updated electrical, HVAC, plumbing, sewer line, new roof, solar tubes, skylights, wood-wrapped casement windows, and decks. Wood flooring, vintage fixtures and hardware, period lighting, leaded-glass windows, and picture rail moldings. Spacious open living and dining area with wood stove and door to covered side-porch, kitchen with wood and glass-fronted display cabinets, laundry closet, two bedrooms, and full bathroom. Vaulted upper-level landing, wood-paneled bedroom with panoramic mountain views, full bathroom, and fourth bedroom with closet. Terraced grounds with mature trees, ornamental plantings, paver patio, meandering pathways, sunny fenced gardening areas, rustic garden shed, and renovated detached garage workshop. Property backs to 1.43-acre natural greenspace owned by the City of Ashland near Hald-Straberry Park; conveniently located within a half-mile of downtown. Inquire for details!

71 Scenic Drive, Ashland

$715,000
3 Beds 3 Baths 220221008 MLS
Back on the market through no fault of the property! Custom-built home on a private .69-acre lot in Ashland with breathtaking valley and mountain views. This versatile property offers a primary bedroom on the main level, vaulted ceilings, fireplace, built-ins, and spacious living areas designed for comfort and entertaining. Large kitchen with breakfast nook and abundant storage throughout. The primary suite features double sinks, separate shower, and a jetted soaking tub with its own hot water system. Downstairs includes a finished daylight basement with separate entrance and plumbing in place ideal for guest quarters, multi-generational living, or future mother-in-law suite potential. Enjoy the fenced garden with raised beds, TID irrigation water, oversized 2-car garage, easy-care landscaping, and a new roof installed in 2023. Rare blend of privacy, flexibility, and stunning views.

1020 Walker Avenue, Ashland

$950,000
5 Beds 3 Baths 220220148 MLS
Enchanting oasis property,½ acre of lush landscaping, abundant flora waterfalls and swimming pond with its own filtration system. Main house with large wrap around deck to take in the wonderful, secluded backyard and mountain views. Lots of skylights and space with high ceilings welcomes you to your relaxing living room with custom exotic wood built-in and rock fireplace. Large primary bedroom with views via 20 windows. Primary bathrooms includes steam shower. Just outside primary bedroom you can retreat onto a private covered deck with 1 yr old spa. 2 more bedrooms on main floor then journey downstairs to 2 very large additional bonus rooms. Solar system provide total electricity for entire main house. Also, a 3-car garage. A separate addressed 915 sq ft ADU with 2 bedrooms, 2 parking spots, fireplace, vaulted knotty pine ceilings, Corian countertops in bath and kitchen, tile & oak flooring with mahogany trim wood and its own private deck that is included for family or rental options.

610 Orchard Street, Ashland

$575,000
5 Beds 3 Baths 220219281 MLS
NEW PRICE! Seller is offering $10k towards repairs or buy downs! Located above the Boulevard in one of Ashland's most sought-after neighborhoods, this 5-bedroom, 3-bath home offers the perfect blend of convenience and opportunity. Just minutes from downtown, local shops, restaurants, and hiking trails, the location is hard to beat. Inside, you'll find a functional layout with a cozy fireplace anchoring the main living space as well as original hardwood flooring. Updated solid wood interior doors throughout the home offer a touch of modern sophistication, while multiple sky lights allow for plenty of natural light. Outside, the lot provides plenty of room to garden, or reimagine the space to fit your vision. Whether you're looking for a solid investment property or a place to create your dream home, this one is full of potential.

430 Ashland Street, Ashland

$744,000
4 Beds 3 Baths 220218224 MLS
Welcome to Billings Ranch, one of Ashland's most desirable communities. This stylish 3,184 sq ft, 4 bed, 3 bath home blends comfort and functionality with standout spaces for spring and summer entertaining. Upon entry you are greeted with a sweeping spiral staircase and 20-ft vaulted ceilings that create a grand open atmosphere. The main level offers a spacious living room, a dedicated dining area, and a beautifully appointed kitchen with two gas stoves, granite countertops, and ample prep space making it perfect for gatherings. Enjoy warm-weather living on the private back patio with a built-in gas firepit and grapevine-covered pergola, ideal for outdoor dining, relaxing evenings, and hosting year-round. A main-level bedroom, full bath and den complete the comfort of the downstairs. Upstairs, are three additional bedrooms, including a luxurious primary suite with its own gas fireplace, a spa-like ensuite bathroom with a jetted tub and a generous walk-in closet.

692 Vansant Street, 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

$500,000
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 and multiple outbuildings. A rare opportunity in a prime Ashland location--contact today for more information!

220 Nutley Street, Ashland

$379,000
2 Beds 2 Baths 220214714 MLS
Thoughtfully updated Glenn Vista Estates end-unit townhome offering comfort, privacy, and flexibility. The floor plan includes a bedroom and full bath on the main level, plus an additional bedroom and bath upstairs. The kitchen and bathrooms have been tastefully updated, with a skylight that fills the space with natural light. Other recent improvements include windows, roof, siding, and a newer HVAC system. The living room features a wood-burning fireplace, currently used with an electric insert, and opens to a front deck through a large sliding door, creating a seamless indoor-outdoor feel. The downstairs bedroom opens to a private, walled-in patio. As an end unit, the home enjoys added privacy and light, along with extra storage space in the garage. Community amenities include a pool and spa, all just minutes from downtown Ashland, as well as shopping, dining, and the Oregon Shakespeare Festival.

372 Glenn Street, 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: