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$535,000
3 Beds 2 Baths 220225426 MLS 1,196 SqFt. 9,583 Sqft. Lot 0.22 Acres
Overlooking a protected wetlands corridor with panoramic views of the Southern Cascades and Grizzly Peak, this beautifully updated mid-century Ashland home offers exceptional privacy in a peaceful natural setting. An expansive picture window fills the living room with natural light while framing the ever-changing landscape. Hardwood floors and a cozy wood-burning stove create a warm, inviting space, while the updated kitchen and well-maintained bathrooms provide comfortable everyday living. Outside, enjoy a spacious deck, spa, mature oak tree, and lush gardens--perfect for relaxing or entertaining. Located on a quiet, low-traffic street just minutes from downtown Ashland, the home is within walking distance of North Mountain Park Nature Center, the Bear Creek Greenway, scenic trails, and bike paths. A rare blend of privacy, nature, and convenience in one of Ashland's most desirable neighborhoods.

304 Clinton Street, Ashland

$560,000
3 Beds 2 Baths 220225903 MLS 1,406 SqFt. 8,276 Sqft. Lot 0.19 Acres
Enjoy the best of Ashland from this charming single-level 3-bedroom, 1.5-bath home, just a short stroll to coffee shops, shopping, Southern Oregon University, & the world-famous Oregon Shakespeare Festival. Built in 1965, this inviting home features hardwood floors, abundant storage, & a cozy wood-burning fireplace with a convenient pass-through from the garage for firewood. The remodeled kitchen offers granite countertops, under-cabinet lighting, & a stainless steel gas range with double ovens. Relax year-round in the bright sunroom with a ceiling fan & removable insulated skylight covers overlooking the backyard with fruit trees, sprinkler system, clothesline, & room to garden. Carport included. Major updates include a new roof & skylights in 2021 and fresh exterior paint in fall 2025. Combining timeless mid-century appeal with thoughtful updates, major improvements, and an unbeatable close-in location, this is a wonderful opportunity to enjoy the best of Ashland living!

429 Morton Street, Ashland

$564,900
3 Beds 2 Baths 220225550 MLS 1,498 SqFt. 3,484 Sqft. Lot 0.08 Acres
'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

$575,000
1 Beds 1 Baths 220225275 MLS 860 SqFt. 12,632 Sqft. Lot 0.29 Acres
Two homes on one lot. 1372 Iowa has new roof and 1364 Iowa's roof was replaced in 2014. Charming one level home with covered porch and back deck with detached cottage in central location close to downtown Ashland, schools, SOU, Scienceworks, shopping and parks. Main home (1372 Iowa) approximately 1633 square feet is a 3 bedrooms, 2 bath (one with claw foot tub) with large Living room, separate dining, nice kitchen and large laundry/mud room with access to level back yard. The detached cottage (1364 Iowa) is a one bedroom, office and 1 bath darling cottage approximately 860 square feet. Property is landscaped for privacy for both units and has mature plants and various fruit trees. Dwelling square footage is per Jackson County Assessor and buyer to verify.

1372 Iowa Street, Ashland

$545,000
3 Beds 3 Baths 220225022 MLS 1,556 SqFt. 3,484 Sqft. Lot 0.08 Acres
Welcome home to this charming, move-in ready cottage-style home with modern updates throughout! This beautifully maintained 3-bedroom, 2.5-bath home features engineered hardwood floors, a cozy living room with a built-in gas fireplace, and a flexible main-level office or bedroom with built-in shelving. The updated kitchen has fresh painted cabinets, stainless steel appliances and gas range. Upstairs, you'll find remodeled bathrooms with granite countertops and tiled showers. The primary suite includes a walk-in closet, and the bedrooms feature modern ceiling fans. Enjoy gorgeous valley views from the back deck. The freshly painted exterior, beautifully landscaped yard, fenced backyard, under-home storage, and one-car garage add both charm and functionality. Full of character with abundant built-ins, this adorable home is beautifully maintained and truly move-in ready!

955 Overlook Drive, Ashland

$535,000
3 Beds 2 Baths 220224643 MLS 1,300 SqFt. 11,761 Sqft. Lot 0.27 Acres
Tucked into a peaceful wooded setting where trees seem to embrace the home, this 3-bedroom, 2-bath retreat offers comfort & privacy. A welcoming front courtyard with deer fencing blends beautifully into the landscape, creating a warm first impression. The home features rich walnut hardwood flooring, a vaulted great room with a stunning wood-lined ceiling, skylights & a beautiful rock fireplace with a cozy gas insert. The kitchen is designed for the cook with granite countertops, a center island & an open flow to the living area. The main bath features a tiled shower, while the refurbished back deck invites entertaining or quiet times surrounded by nature. The added concrete patio is ready for a hot tub or hammock. The neighbor's side yard creates the feeling of space & privacy on the .27-acre lot. Highlights include durable concrete composition siding, a long-lasting metal roof, upgraded garage doors & a setting that feels like a private escape while being only minutes from town.

886 Palmer Road, Ashland

$600,000
3 Beds 3 Baths 220224168 MLS 2,287 SqFt. 12,632 Sqft. Lot 0.29 Acres
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

$550,000
3 Beds 2 Baths 220224331 MLS 1,418 SqFt. 6,534 Sqft. Lot 0.15 Acres
Charming and tastefully updated 1965 Ashland bungalow with exceptional curb appeal. Thoughtful improvements throughout include new flooring, fresh interior paint, and a beautifully remodeled primary suite featuring a spacious walk-in closet and updated bathroom. The inviting living room showcases a striking wood-burning ,rock fireplace creating a warm and welcoming gathering space. The kitchen has been refreshed with new hardware and charming beadboard wainscoting, blending character and functionality. Outside, the backyard is a true standout with newly terraced landscaping, retaining walls, and raised garden beds designed for both beauty and function. Enjoy relaxing or entertaining on the private patio, the perfect spot for morning coffee or an evening beverage. Conveniently located near hiking trails, a park and Ashland's outdoor recreation opportunities, this move-in ready home combines classic character with modern updates in a desirable setting.

492 Herbert Street, Ashland

$525,000
3 Beds 2 Baths 220223843 MLS 1,576 SqFt. 8,712 Sqft. Lot 0.2 Acres
Charming Ashland home tucked behind a solar-powered privacy gate + fully fenced front & back yard. Solar panels, double paned windows, zoned AC, hardwired internet, analog electric meter & new water heater. Stunning hardwood floors in the living room, highlighted by a beautiful brick mantle that adds character to the space. The galley-style kitchen features a gas range, tile backsplash, tile flooring, reverse osmosis system at the sink, & located adjacent to the dining area w/ a cozy wood stove. Primary suite w/ heated floor in the ensuite bath + a tile shower. Oversized covered back deck overlooking the backyard & bonus guest quarters/office space. Additional features include mature landscaping, well (buyer to do their own due diligence), organic garden, oversized 2-car garage w/ workshop space +220 voltage, and a large driveway with abundant parking, including room for an RV. This is a property you truly must see to appreciate, ideally situated in a prime close to downtown location.

1423 E Main Street, Ashland

$579,000
3 Beds 2 Baths 220223772 MLS 2,009 SqFt. 13,939 Sqft. Lot 0.32 Acres
Tucked in a private cul-de-sac, this thoughtful home offers character & beautiful views of the surrounding hills, on a third-acre lot near hiking trails & convenient access to town. Custom hand-crafted cherry cabinetry, bamboo and hickory hardwood floors create an inviting atmosphere. High ceilings, tall windows & fireplace anchor the spacious living room, while the split-level layout adds flexibility with a lofted reading nook, dedicated office w/ French doors, & an open kitchen. Designed for both everyday living & entertaining, the kitchen features Corian countertops, brand-new fridge, soft-close cabinetry. Primary suite opens to a private balcony. Outside, enjoy the pool, hot tub, multiple decks, and plenty of space to gather or take in the views. Well maintained w/ numerous system updates, including HVAC, furnace, service panel, and vinyl double-pane windows. Bonus attic storage room & RV parking available. A welcoming home filled with craftsmanship, comfort & space to relax.

565 Henley Way, Ashland

$545,000
2 Beds 2 Baths 220223679 MLS 1,448 SqFt. 49,658 Sqft. Lot 1.1400000000000001 Acres
$30,000 Price Improvement! Enjoy life on two parcels totaling 1.18 acres just 10 minutes from Ashland Plaza. This country property offers a rare blend of privacy, usable land, and opportunity. Enjoy peaceful, creek views, paid TID irrigation rights, mature shade trees, and a spacious detached shop with concrete floors, power, and air compressor set up; ideal for hobbyists, craftsman, or extra storage. The home features a newer wood stove, generous covered decking, hot tub area, office space, and a functional 2 bed, 2 bath floor plan ready for your personal updates and vision. Convenient access to I-5, local wineries, Oak Knoll Golf Club & more! An exceptional opportunity to build equity in a property thoughtfully priced to reflect its current condition.

624 Crowson Road, Ashland

$529,000
4 Beds 2 Baths 220222486 MLS 1,584 SqFt. 8,712 Sqft. Lot 0.2 Acres
Welcome to 351 Oxford, a rare single-level 4-bedroom home in Ashland with updates, mountain views, outdoor space, and a prime location near Helman Elementary, Ashland Ponds, parks, trails, and downtown. This nicely updated home features a stylish kitchen with stainless appliances, tile backsplash, updated baths, indoor laundry, and comfortable living spaces. The spacious backyard offers a deck, pergola, garden space, storage shed, room to play, relax, or entertain, and beautiful mountain views. Attractive low-maintenance front landscaping and a covered front porch add curb appeal. Located in the Helman Elementary attendance area with nearby access to Bear Creek Greenway, Ashland Dog Park, BMX Park, shopping, dining, and the best of Ashland living. A compelling blend of 4 bedrooms, single-level living, updates, outdoor space, views, and location at this price point.

351 Oxford Street, Ashland

$550,000
3 Beds 2 Baths 220223426 MLS 1,202 SqFt. 6,534 Sqft. Lot 0.15 Acres
Thoroughly updated midcentury bungalow with detached guest cottage on a spacious 0.15-acre lot with alley access in the heart of Ashland's historic Railroad District. Extensive recent improvements to main home include all-new cement board siding and trim, double-paned vinyl windows, interior and exterior doors, bathroom vanity and tub shower, dishwasher and butcher block counter, composite back deck and front porch, ductless mini-splits, waterproof vinyl tile flooring, refinished solid oak hardwood, poured concrete entry, and new gutters from 2025 to 2026. Separately metered guest cottage with private fenced yard, three alley parking spaces, all new carpets in 2026, full kitchen with Viking gas range oven, ductless mini-split, vaulted living and bedroom with skylight, enclosed porch, and full bathroom with shower. Detached storage shed, mature trees, grass lawn, fresh mulch, and new irrigation system for front plantings. Inquire for details!

840 B Street, Ashland

$525,000
3 Beds 2 Baths 220223157 MLS 1,741 SqFt. 6,969 Sqft. Lot 0.16 Acres
Lovely single level home within the Oak Knoll Meadows subdivision, also known as ''Ashland's Hidden Gem'' a wonderful neighborhood at the southeast end of town. Home has three bedrooms, two bathrooms with approx. 1741 SF of living space. Light filled kitchen has lots of cabinetry and surface space with a cozy breakfast nook area and window seat. Kitchen opens to the dining area and great room. There is also versatile separate space off the main living area perfect for a den or media room. Primary bedroom suite with dual vanities and walk-in closet. 2nd bedroom is close to the shared bathroom and bedroom number three is up by the entryway and could make for a nice office depending on one's needs. Great curb appeal, nicely landscaped grounds and the backyard is fenced in. Neighborhood has lots of open space, trails, a pond and streams for all to enjoy!

935 Cypress Point Loop, Ashland

$653,000
2 Beds 2 Baths 220222945 MLS 1,384 SqFt. 6,098 Sqft. Lot 0.14 Acres
This Nob Hill home sits four blocks from the Ashland plaza, with Lithia Park, dining, and shopping nearby. It's all on one level and beautifully remodeled. A custom front door opens into the great room, vaulted and beamed, with a skylight overhead and a wood-burning fireplace below. The kitchen was remodeled with quartz counters, stainless Kitchen Aid appliances, and custom light fixtures. The same care shows in the large primary suite, where a two-sided gas fireplace divides the bedroom and bath. The bath features a limestone soaking tub and a custom tiled shower with rain and wall shower heads, all under a solarium of natural light. There's a walk-in closet, plus room for a sitting area or a desk. Maple hardwood runs through the house, and the guest bedroom and bath complete the floor plan. Out back, a covered deck looks over the fenced yard, with alley access and RV parking. Laundry is in the 2-car garage. New roof in spring 2026.

120 Nob Hill Street, Ashland

$590,000
3 Beds 3 Baths 220222853 MLS 2,206 SqFt. 2,178 Sqft. Lot 0.05 Acres
Lovely & private end-unit townhome in Ashland's Highland Pines community. This move-in ready home offers 2,206 sq ft., 3 bedrooms, and 2.5 baths. The spacious primary suite features beautiful mountain views, relaxing tub, separate shower, private deck and generous walk-in closet w/a built-in floor safe. A split-level entry welcomes you into a bright interior with high ceilings, slate entry, wood flooring throughout the main level, and a cozy gas fireplace. The kitchen, dining area, and great room open to a covered patio. The two full bathrooms and laundry room have tile flooring; all bedrooms are carpeted. Additional features include a spacious one-car garage with alley access, and additional guest parking. Excellent location above downtown and Ashland's amenities make this a wonderful opportunity to enjoy low-maintenance living in one of the area's most desirable communities.

461 Holly Street, Ashland

$599,000
3 Beds 2 Baths 220222826 MLS 1,924 SqFt. 10,890 Sqft. Lot 0.25 Acres
Just minutes from downtown Ashland, this home is nestled below Holly St. on a 0.25 acre lot with tons of space to entertain! The home features a kitchen with lots of storage, gas range/oven, and lots of natural light from a skylight above. Hardwood throughout this spacious 1924 square foot house creates a warm ambiance, especially when sitting in the conversation pit style living room! With two bedrooms, full bathroom, and laundry on the main level, the entire upstairs is the primary suite with walk-in closet, full bath including a soaking tub, as well as an office with lots of windows. Outside is a spacious yard with a seasonal creek that flows through, a carport, as well as a storage room about half the size of a garage!

545 Holly Street, Ashland

$515,000
220222605 MLS
Position your business for success in this flexible commercial opportunity in the desirable hills of Ashland! Formerly operated as a fitness and wellness space, this unique property features an open gym-style floor plan with multiple private rooms ideal for offices, storage, treatment rooms, massage, counseling, personal training, studio use, or creative workspace. The current business is relocating, opening the door for a new owner or tenant to bring fresh vision and energy to the space. Take all the space as your own or divide the space into 3 units as either commercial or residential for additional income and offset of expenses! There are 3 separate entrances, 3 meters, and 3 bathrooms. Don't wait, this is the only one like this!

905 Skylark Place, Ashland

$582,500
4 Beds 3 Baths 220221710 MLS 2,051 SqFt. 3,484 Sqft. Lot 0.08 Acres
Beautifully designed home with a warm, spacious atmosphere and incredible natural light. Surrounded by trees and views, the home has a treehouse feel with scenery brought into nearly every room. Tall vaulted ceilings, skylights, gorgeous wood floors throughout, built-ins and custom finishes give the home character and comfort while remaining refined and timeless. Room to spread out with generous spaces, including a main level primary suite with beautiful views, abundant storage, and bonus 12x14 storage space downstairs with 6ft ceilings and small built in work table, perfect for wine or cold storage. The kitchen stuns with granite counters, gas range, and custom cabinetry. Enjoy indoor/outdoor living from upper and lower patio spaces surrounded by low maintenance landscaping. This is a very special home that feels beautifully put together, the kind of place you could move into and enjoy!

969 Overlook Drive, Ashland

$550,000
4 Beds 2 Baths 220221283 MLS 1,956 SqFt. 8,712 Sqft. Lot 0.2 Acres
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

$550,000
3 Beds 2 Baths 220221016 MLS 1,664 SqFt. 217,800 Sqft. Lot 5 Acres
Lake views, forest privacy, wraparound outdoor living spaces, & classic mountain character combine effortlessly to create the beauty of a true mountain setting. With its warm architectural presence, serene wooded setting, & exceptional sense of seclusion, this mountain retreat is for you. The 2-story floorplan offers flexibility & separation of space, making this home ideal for both everyday living & hosting guests. The layout provides a comfortable balance of open gathering areas & quieter private retreats. Main living spaces are designed to highlight the views& natural surroundings, while upper & lower levels create opportunities for privacy, work-from-home flexibility, guest accommodations, or multigenerational living. Every space within the home feels connected to the tranquil setting outside. The ever-changing seasonal scenery creates a living work of art, from vibrant spring greens and warm summer afternoons to colorful autumn foliage and peaceful winter landscapes.

2042 Hyatt Prairie Road, Ashland

$599,000
4 Beds 3 Baths 220220812 MLS 2,485 SqFt. 10,018 Sqft. Lot 0.23 Acres
Timeless mid-century home just a block above Lithia Park and only a short jaunt to the plaza. Sitting in a quiet location with views, this home offers serenity while still being close in. Exposed beam ceilings on the lower level offers warmth and charm. A bank of picture windows in the living room allows one to take in the mountain views as well as overlooking the backyard. The kitchen opens to the spacious back deck which is perfect for entertaining and indoor/outdoor living. An oversized mudroom/pantry as well as an office nook round out the downstairs. Upstairs sit 4 bedrooms, including a spacious primary suite that opens to a private deck with views to take in the natural beauty. One bedroom with vaulted ceiling could be used as a media room or flex space. Outside, the yard is fully fenced and has garden beds and room to play. With a solar array and backup battery, this home is well-equipped. All of this is so close to town, Lithia Park and the incredible trail network of Ashland!

34 Scenic Drive, Ashland

$584,500
2 Beds 2 Baths 220220315 MLS 1,408 SqFt. 4,356 Sqft. Lot 0.1 Acres
Welcome to 765 Creek Stone, where quiet comfort and privacy await in the heart of Mountain Meadows, a 55 + Community Living. This inviting home features a wonderful open floor plan with a cozy fireplace in the spacious living room, an elegant arched opening leading to the dining room, pass through kitchen design, plenty of storage and a versatile bonus room perfect as an office, sitting area, or third bedroom. The generous primary suite boasts a walk-in closet and beautiful windows overlooking a private, fenced backyard. Two garage spaces and end-of-road seclusion. Exit to the back deck to soak in the wildlife, enjoy the flowing creek, and take advantage of trails and a park right in your backyard. Back yard is fenced to protect your small family pets. Amazing!

765 Creek Stone Way, Ashland

The data relating to real estate for sale on this web site comes in part from the Internet Data Display (IDX) of the Southern Oregon Multiple Listing Service. Real estate listings held by brokerage firms other than our company are marked with the IDX logo and detailed information about them includes the name of the listing brokers. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information subject to change and should be independently verified. Last updated: