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$649,000
3 Beds 2 Baths 220225730 MLS
Set back from the street on a flag lot, this lovely home offers a quiet and private retreat, bordering open space and Ashland Creek. Conveniently located a short distance from downtown Ashland, the trailhead to the Bear Creek Greenway and Lithia Park, the property combines a natural, scenic setting with easy access to local amenities. The main living and dining areas feature large windows that capture natural light and frame peaceful outdoor views. A sliding glass door opens to a large back deck, well-suited for enjoying the mountain views and entertaining. There is a nice separation of space with the three bedrooms sitting away from the living area. A daylight 500 sf basement (not included in square footage), with mini split heating and cooling, offers many options for overflow guests, art studio, media room or home office. With a unique balance of privacy, creek-side borders and proximity to Ashland's central attractions, this home is a fantastic opportunity.

1111 Oak Street, Ashland

$1,200,000
5 Beds 3 Baths 220224554 MLS
One-of-a-kind Southern Oregon retreat just minutes from Ashland! A remarkable property offering a rare blend of privacy, craftsmanship and income potential in a private park-like setting with mature trees. This custom-built 5 bedroom home showcases soaring ceilings, walls of windows with views of Emigrant Lake/Grizzly Peak, large breakfast nook, custom pine log features/dramatic curved staircase, hardwood floors, granite/travertine countertops, floor-to-ceiling fireplace, large 3rd floor bonus wing, 1900+ sq. ft. wraparound cedar deck, workshop, charming playhouse and covered carport. The 1st floor ADU currently operates as a successful AirBNB with 2 bedrooms, beautiful kitchenette, granite countertops, stunning tile bathroom, ADA access, private driveway and entrance, for use as continued rental income or separate multigenerational family living. A former homesite offers additional potential. Rarely does a property combine this level of quiet privacy, quality and versatility.

4567 Old Highway 99 S, Ashland

$765,000
4 Beds 4 Baths 220224216 MLS
Nestled in the highly desirable southwest hills of Ashland, Oregon. This is an incredible opportunity w/ so much potential for the next owner to enjoy and make their own. The contemporary ranch-style main home features over 2,600 sq. ft., 3 bedrooms, 3 bathrooms, soaring wood-vaulted ceilings, an open floor plan, abundant windows, skylights, and beautiful natural light. A charming 800 sq. ft. cottage-style ADU (built in 2003) includes its own address, metered separately, private patio, and garden making it ideal for guests, rental income, or multi-generational living. The detached three-car garage includes a studio space with a bathroom. Additional amenities include a screened sleeping deck, greenhouse, storage sheds, and firewood storage. There is an owned solar panel system and solar hot water heater for high efficiency and keeping low carbon print. This one-of-a-kind property is a gardener's dream and a rare opportunity to create your own private retreat.

155 Westwood Street, Ashland

$548,000
3 Beds 2 Baths 220223843 MLS
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

$545,000
2 Beds 2 Baths 220223679 MLS
$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
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

$895,000
3 Beds 3 Baths 220223186 MLS
Enjoy the serenity of the Green Springs year round. A rare opportunity to own a 70+ acre retreat in the Green Springs, just east of Ashland. Tucked among towering trees & open meadows, this property offers tranquility & endless possibilities. The 2,707 SF custom home, built in 1992, offers 3 bedrooms/2.5 baths, spacious light-filled spaces & a thoughtful blend of rural charm & modern comfort. The sunroom overlooks a blue-lined pond framed by old-growth forest, creating a peaceful connection to the natural surroundings. The property also includes a cabin dating to approx 1920, multiple barns & outbuildings + ample space for your equipment, hobbies or recreation. Easy access to Hyatt Lake, Howard Prairie & the Cascade-Siskiyou region. 0.3 miles to the Green Springs Inn. An ideal setting for a getaway or homestead, a true S. Oregon Mountain retreat awaits!

11871 Highway 66, Ashland

$525,000
3 Beds 2 Baths 220223157 MLS
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

$875,000
4 Beds 3 Baths 220220717 MLS
Idyllic Ashland rural sanctuary with stunning valley views and easy access to downtown. Enjoy main-level living, tons of natural light, laminate wood floors. Open kitchen/dining with tile floors, abundant built-ins, gas range, 2 sinks & French doors. Wrap-around deck & backyard oasis with cascading water feature into creek meandering between pathways and mature landscaping to pond. Remodeled primary suite features tongue-and-groove pine ceilings, tiled shower, skylight, deck access & walk-in closet. Lower-level suite has exterior entry, living area, bedroom, bathroom, kitchenette & covered patio. Talent Irrigation canal runs through the property and irrigates pasture which includes a barn with stalls & hay storage and new perimeter fencing+hot wire. 2 large gardening areas with beds & drip irrigation. 2-car garage + 40'x24' shop/garage. Perfect for 4H, farming, gardening, livestock, horses, multi-generational living, entertaining or anyone seeking privacy & views without freeway noise.

2140 N Valley View Road, Ashland

$855,000
220217221 MLS
Prime Investment & Development Opportunity in Ashland. Well-maintained duplex located close to downtown offering immediate cash flow and long-term upside potential. Both units are rented at $1,450 per month ($2,900 total), with tenants paying all utilities, keeping operating expenses low. Property has an excellent rental history and is professionally managed. Capital improvements include newer roof, vinyl windows, stainless appliances, gas log fireplace (rear unit), new water heater and additional updates. Situated on a large approx. 0.27-acre R-3 high-density zoned lot, creating exceptional future redevelopment potential. The City of Ashland Planning Department indicates a 5.4 base density factor with potential for up to 20 units. (buyer due diligence required). For development details contact Aaron Anderson or Nick Schubert at City of Ashland Planning Department.

128 S Mountain Avenue, Ashland

$735,000
3 Beds 3 Baths 220215130 MLS
Built - 2007 Craftsman Ranch -Style Home 3,488 sq ft that sits on level 13.63 acres useable beautiful land with (2,500 sq ft shop w/12x12 rolling doors ,14ft ceilings.3/4 plywood sheeting, 220 wired throughout, #3 rebar spaced throughout a concrete foundation w/ Green snap lock roof uniformed to match Home. Property features open meadows, mature timber, and a large, serene pond -- ideal for horses and outdoor living. Includes deeded access to Pinehurst Airstrip, enhancing equity and uniqueness. Located within the Cascade-Siskiyou National Monument, just 8 miles from Hyatt Lake and near Pinehurst School, this one-of-a-kind investment and lifestyle property is poised to gain equity and never lose it -- truly exceptional in Southern Oregon's most desirable areas that sits 24 miles on the outskirts of Ashland that takes only 38 min drive time to Ashland. Perfect location! Beautiful lifestyle.

15922 Green Springs 66 Highway, Ashland

$590,000
3 Beds 2 Baths 220213353 MLS
OPEN HOUSE THIS SATURDAY THE 25TH, 12-2! Nicely updated and beautifully maintained, this single-level home tucked away on a quiet cul-de-sac with several recent upgrades, including updated kitchen and bathrooms, solar panels & new windows for bright, energy-efficient living. The spacious kitchen features generous counter space, abundant cabinetry, pantry, quartz countertops & new tile backsplash. The kitchen flows into the dining area and family room, where you'll find new gas logs & built-in shelving, a warm & inviting space for everyday living. Bamboo flooring throughout with new LVP flooring in the bedrooms. The primary suite includes a beautifully updated ensuite bath with a custom tile shower. Slider to the lovely backyard complete with a covered patio and soothing water feature. The low-maintenance landscaping offers both drip irrigation and sprinklers with TID. It's the perfect setting for entertaining or simply relaxing. Ideally located close to shopping, downtown, and I-5.

780 Oakway Circle, Ashland

$564,000
3 Beds 2 Baths 220210421 MLS
Gracious, single-level 3 bed, 2 bath home located in the charming and peaceful Oak Knoll Subdivision. Updates and features throughout including hardwood floors in the main living areas, multiple spaces for living and dining, a full wall of built-in storage cabinetry, dedicated laundry/mud room plus a generous enclosed sunroom ideal for a home office, craft space or multipurpose room. Convenient kitchen equipped with leathered granite countertops and updated appliances. The cozy family room features a gas fireplace framed by brick surround and a seating ledge. Spacious primary suite with a walk-in closet, private deck access and ensuite boasting a dual-sink vanity, tile shower & flooring. Corner lot with a variety of outdoor living spaces including a deck, covered porch and secluded courtyard, perfect for entertaining or relaxing. 2-car garage, storage shed and low maintenance landscaping. Don't miss this fantastic property!

938 Cypress Point Loop, Ashland

$449,900
4 Beds 2 Baths 220210875 MLS
Ashland Property w/ Flexible Living & Income Potential! Conveniently located near downtown Ashland, this unique property offers versatile living options and established rental income. Officially a single-family home, it features separate living areas that can function independently or be opened to the main living space for family, guests, or extended living. The layout includes a kitchenette, second bathroom, & private rooms sharing only the laundry area. A detached garden shed converted to a small cabin near the creek offers a quiet retreat space & is currently rented. Current rents total $3,500 per month--$2,200 from Unit 3, $700 from Unit 1, & $600 from the cabin. Prior short-term rentals of Units 1 & 2 averaged about $1,800 monthly. The EFU-zoned lot includes creek frontage, irrigation rights, & a fenced yard suitable for gardening. Updates include a 2020 well pump, pressure tank, reverse osmosis system, & ceiling fans. Close to Lithia Park, Oregon Shakespeare Festival, SOU, & etc.

488 Crowson Road, Ashland

$1,250,000
5 Beds 5 Baths 220210091 MLS
Incredibly desirable Ashland setting--private, quiet & close to town yet distinctly rural. On 5.09 acres with panoramic views of Mt. Ashland & the city, this 3566 sq ft 1985 home offers 5 bedrooms, 4.5 baths & two full primary suites, including a main-level retreat. The main floor features two sitting rooms with wood-burning fireplaces, a living room bar & a 2019 kitchen remodel with quartz leather-finish counters & painted cabinetry. Upstairs features two bedrooms with walk-in closets, a large bath & separate HVAC, plus a guest suite with a loft & window seat. Outdoor amenities: pool with Trex decking, gazebo, apple & plum trees, Gearky Creek, Talent Irrigation water & two workshops (50'x50' & 42'x36'). Other highlights: 2-car garage with workbench, wine cellar, auto generators, water softener, security system & abundant storage. Updates: roof, exterior paint, trellis, decking, railings, pool/spa (2018); HVAC (2019); blinds (2019); electrical/lighting (2018).

500 Pompadour 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

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: