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425 W Nevada Street, Ashland
$839,000
5 Beds ⋅ 3 Baths ⋅ 220229842 MLS
Beautiful 2018 Craftsman home in Ashland's Billings Ranch neighborhood with 5 bedrooms and 2.5 baths, backing to open space with Cascade mountain and valley views. A covered porch opens to a bright foyer and main-level office or fifth bedroom behind French doors. The vaulted great room has view windows and stacked-stone fireplace, open to dining and a kitchen with white shaker cabinetry, pantry, breakfast bar, and smart convection gas double oven plus a third oven. The main-level primary suite has patio access, dual copper sinks, soaking tub, walk-in shower, and walk-in closet. Upstairs: second living room with built-in desk, a bedroom with a second walk-in closet, additional bedrooms, and a full bath. Washer and dryer stay. Outside: xeriscaped front, fenced backyard with firewise patio, fruit trees, grape vines, raised beds, garden shed, and 4-zone smart drip/sprinkler irrigation. Extra-deep 2-car garage with storage and workbench. Nearby wetland offers great bird watching!

425 W Nevada Street, Ashland

1650 Neil Creek Road, Ashland
$1,175,000
5 Beds ⋅ 4 Baths ⋅ 220229364 MLS
OWNER CARRY AVAILABLE! GOURMET KITCHEN. EMIGRANT LAKE VIEWS. 22 ACRES OF PRIVACY. This updated 5-bedroom, 3.5-bath home offers 3,270 sq ft on 22.05 acres. The gourmet kitchen features granite countertops and a stunning oversized island with 360-degree access for cooking and entertaining. Guest quarters and two separate laundry rooms provide flexibility. Updates include all-new doors and windows, a new roof, and new stucco with an imperfect smooth finish and upgraded cloth underneath designed to help reduce temperatures. A large garage with generous shop space accommodates vehicles, tools, and hobbies. The engineered greenhouse includes a concrete perimeter and separate power meter, with potential for shop conversion, subject to buyer due diligence. Level areas offer possibilities for future projects; buyers to verify permitted uses and development options. Enjoy beautiful lake views, exceptional privacy, and versatile spaces--with owner financing available to bring your vision to life!

1650 Neil Creek Road, Ashland

1395 Woodland Drive, Ashland
$899,000
4 Beds ⋅ 3 Baths ⋅ 220229360 MLS
There's something special about a home that gives you room to live a little bigger. Your mornings can start with coffee on the large porch with unobstructed views of Grizzly Peak, while evenings offer the same backdrop from the large sitting room on the main level. Built in 1932 and offering 3,127 SF on a .30-acre lot, this is a home with history, personality, and plenty of room for what comes next. The main house has 3 bedrooms and 1.5 baths, while a permitted 1/1 ADU on the lower level creates a separate space for guests, family, or rental income. Beyond the house, the oversized heated two-story garage and shop is a major part of what makes this property unique. There's room for serious projects, hobbies, gear, storage, and vehicles, plus dedicated off-street RV parking. Inside, the home hasn't been updated to look like every other house on the market--and that's part of the opportunity.

1395 Woodland Drive, Ashland

100 Belle Fiore Lane, Ashland
$14,000,000
3 Beds ⋅ 2 Baths ⋅ 220228854 MLS
Offered for sale for the first time ever, Belle Fiore Estate Winery is Oregon's most significant vineyard estate and event destination situated on 51+ acres, including 37+ irrigated acres and an established vineyard with 14 grape varieties. Encompassing more than 27,000 sqft, the winery features multiple tasting rooms, an elegant ballroom, a restaurant, expansive terraces, and outdoor dining areas overlooking the vineyard and valley. The production facility is designed for commercial-scale operations with 8 barrel-storage bays, refrigerated wine storage, soaring ceilings, and extensive infrastructure. Hosting more than 50,000 visitors annually, Belle Fiore is a recognized destination for wine tourism, weddings, and private events. A 13.17 acre RR-5 zoned parcel with legal homesite is included in acreage. Business assets and inventory available, subject to applicable licensing and regulatory requirements. Property may be purchased together with 200 Belle Fiore Lane, Ashland, OR 97520.

100 Belle Fiore Lane, Ashland

161 Fourth Street, Ashland
$649,900
4 Beds ⋅ 2 Baths ⋅ 220228571 MLS
Two single-level homes on a spacious 0.16-acre lot with alley access in the heart of Ashland's Railroad District. Charming historic front home with covered porch, double-paned vinyl windows, original fir floors, high ceilings, picture rail moldings, dining with cast-iron gas stove, kitchen with glass-fronted display cabinets and butcher block counters, mudroom pantry with washer and dryer, primary bedroom with large walk-in closet, full bathroom with clawfoot tub shower, and guest bedroom with closet. Fully permitted second dwelling built in 1999 with front deck and covered entry, operable casement windows, oak hardwood flooring, spacious dining area and kitchen with wood cabinets, laundry closet, two bedrooms with closets, full bath with shower, and attached garage with second bay converted to workshop studio. New roofs, ductless mini-splits, and fully fenced private yards. Excellent investment opportunity and potential for short-term travelers' accommodations. Inquire for details!

161 Fourth Street, Ashland

145 Normal Avenue, Ashland
$1,035,000
3 Beds ⋅ 3 Baths ⋅ 220228353 MLS
Tucked at the end of a cul-de-sac, this distinctive single-level home offers the rare feeling of country living right in Ashland. Set on a private, fenced and irrigated acre, it was thoughtfully built with Logix ICF insulated walls, owned solar, radiant-heated floors and energy-efficient windows. Inside, warm wood ceilings, a dramatic skylit cupola, walls of windows and a large fireplace give the home character, while the spacious kitchen features abundant cabinetry and a generous granite island. A large studio/game room adds wonderful flexibility. Outdoors, expansive Trex decking connects to a screened gazebo, pergola and covered patio overlooking mature landscaping, a pond and waterfall, raised garden beds and fruit trees, with mountain and valley views beyond. Oversized 2-car garage, workshop/storage and RV/boat parking. Near the bike path, schools and Hunter Park--peaceful, private and wonderfully connected to town.

145 Normal Avenue, Ashland

5831 Old Highway 99 S, Ashland
$950,000
3 Beds ⋅ 4 Baths ⋅ 220228020 MLS
Set on more than 37 private acres in the Siskiyou Mountains, this property offers space, privacy minutes from Ashland and the Rogue Valley. Mt. Ashland Ski Area, Emigrant Lake and the Pacific Crest Trail are nearby, putting Southern Oregon recreation close at hand. The main residence features soaring wood-clad ceilings, exposed beams, expansive windows and a stone fireplace. The open great room flows into a gourmet kitchen with cabinetry, full-size refrigerator and freezer, double ovens and island. A media room, geothermal heating and cooling, and hard-wired generator add comfort and peace of mind. A detached four-car garage provides spaces, while the auxiliary building offers an open area, kitchen, full bath and three-car garage--ideal for a studio, workshop, recreation or guest space. A loft studio, greenhouse, gardens, water storage, creek, rock outcroppings and wildlife complete this Southern Oregon retreat.

5831 Old Highway 99 S, Ashland

2590 Siskiyou Highway, Ashland
$635,000
4 Beds ⋅ 2 Baths ⋅ 220227582 MLS
This beautiful recently renovated ranch is home located just 15 minutes from Ashland. Step inside to hickory hardwood floors, an open floor plan and unobstructed million-dollar panoramic views of Emigrant Lake, Pompadour Bluff, Grizzly Peak and the Siskiyou Mountains. Several french doors offer an immersive indoor-outdoor living concept with an ample patio perfect for dining and BBQing. The fourth extra large bedroom is adjacent to a solarium that would make a fantastic hot tub space. This 7+ acre mini-ranch is fully fenced and gated, with an interior dog fence line that is approximately two acres. Irrigated with water rights from a spring source, the ample lawn space is a dream come true. This versatile property features offer multiple workshops, a greenhouse, a paved basketball court, two carports, plenty of parking for RVs, boats, trailers and so much more. This one wont last long!

2590 Siskiyou Highway, Ashland

5597 Highway 66, Ashland
$875,000
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

400 Allison Street, Ashland
$1,100,000
2 Beds ⋅ 3 Baths ⋅ 220225582 MLS
Experience refined living just one block from downtown Ashland in this custom, open concept, built 2012 luxury home, designed for comfort and ease. An elevator to take you to all levels makes stair use unnecessary and 36 inch doorways provide seamless accessibility throughout. Rich oak and red oak floors and cabinetry pair beautifully with custom metalwork and soaring wood-paneled ceilings throughout the home. The chef's kitchen features a 6 burner Wolf cooktop, wall ovens, Sub Zero refrigerator, exposed edge granite countertops and custom pot racks. Spa inspired bathrooms include heated tile floors, dual vanities, tiled showers and abundant natural light, one with a soaking tub. The private flagstone courtyard with gas BBQ and pergola is perfect for relaxing and outdoor entertaining with lovely, low maintenance landscaping. The oversized, finished, two + car garage with sealed floors offers space for a workshop, gym and storage with an additional washer & dryer, sink and gas heater.

400 Allison Street, Ashland

1700 Tyler Creek Road, Ashland
$725,000
2 Beds ⋅ 1 Baths ⋅ 220224351 MLS
OWNER CARRY AVAILABLE.Experience the Southern Oregon lifestyle on 7.34 acres of mostly level, park-like land bordering BLM. This custom passive solar home features hardwood floors, an open floor plan, a finished basement ideal for guests or a studio, and a unique third-floor office with elevated views. Built in 2016, the insulated 3,400 sq ft shop features Hardie siding, 220 power, a 10-ft roll-up door, 1,000 sq ft loft, ductless mini-split heating and cooling upstairs, custom trim, tongue-and-groove ceilings, and a wraparound driveway. A detached cabin with power has a remodeled Hardie exterior. Extensive fire mitigation creates a beautiful park-like setting with defensible space, complemented by 6,000 gallons of water storage. Just 10 minutes to Emigrant Lake and 20 minutes to downtown Ashland. See attached upgrades list.

1700 Tyler Creek Road, Ashland

590 Taylor Street, Ashland
$695,000
2 Beds ⋅ 3 Baths ⋅ 220223937 MLS
Beautifully Maintained Custom Ashland View Home! This property offers a blend of distinctive architecture and serene privacy with custom windows and natural beauty throughout. Step-down living room with gas fireplace, dining room has built-in shelving; house has engineered hardwood flooring and carpeted bedrooms; kitchen has newer 36'' gas range and built-in desk. Spacious ground-floor master bedroom, separate office that could be used as a guest bedroom, second upstairs bedroom, plus upstairs laundry room. View decks for indoor-outdoor living, mature landscaping and peaceful setting that includes patio, firepit, walking paths and fully fenced backyard. Quality upgrades include Karastan wool carpeting, newer roof, high-efficiency 2-stage HVAC, fresh interior paint, oversized garage with workshop/bonus area, central vac, 220v for EV charging and great storage throughout. Lovely hillside home on a quiet cul-de-sac just minutes from downtown with EZ access to Ashland's trail system.

590 Taylor Street, Ashland

100 Belle Fiore Lane, Ashland
$14,000,000
220223436 MLS
Offered for sale for the first time ever, Belle Fiore Estate Winery is Oregon's most significant vineyard estate and event destination situated on 51+ acres, including 37+ irrigated acres and an established vineyard with 14 grape varieties. The estate encompasses more than 27,000 sqft and features multiple tasting rooms, a ceremonial barrel room, elegant ballroom, full-service restaurant, expansive terraces, and outdoor dining areas overlooking the vineyard and valley. The production facility is designed for commercial-scale operations with 8 barrel-storage bays, refrigerated wine storage, soaring ceilings, and extensive infrastructure. Hosting more than 50,000 visitors annually, Belle Fiore is a recognized destination for wine tourism, weddings, corporate retreats, and private events. This combined with significant growth potential make this a rare opportunity to own a premier winery. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

100 Belle Fiore Lane, Ashland

200 Belle Fiore Lane, Ashland
$12,000,000
7 Beds ⋅ 19 Baths ⋅ 220223437 MLS
Chateau at Belle Fiore is one of Oregon's most extraordinary estates. Spanning over 17,400 sqft across 4 levels, this French-inspired masterpiece offers 7 bedrooms, 19 bathrooms, and exceptional craftsmanship throughout. An elevator services all floors, including an 8,000 sqft lower level with a wine room, game room, gentleman's lounge, multiple wine bars, and expansive entertaining spaces. Premium finishes include custom cumaru flooring, granite surfaces, and intricate architectural detailing. Set on 17+ acres, including 12+ irrigated acres and a producing vineyard, the estate is ideal for private enjoyment, weddings, retreats, and special events. Exterior features include hand-chiseled golden granite, a hand-cut slate roof, custom copper gutters, dormers, and downspouts. A 2,500+ sqft carriage house, 4-car garage, prep kitchen, and grand gathering spaces complete this iconic estate. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

500 Mt Ashland Ski Road, Ashland
$825,000
3 Beds ⋅ 3 Baths ⋅ 220223070 MLS
Priced to sell & Owner will carry! Tranquil mountain oasis on 121+ acres featuring a campground, marketable timber, greenhouse, stream with waterfall, natural springs, and breathtaking views of Mt. Shasta and Pilot Rock. The 2,145-SQ-FT main home offers a tiled entry, stained glass, 3 bedrooms, 2.5 baths, open-beam vaulted ceilings, and a great room with a striking stone staircase. The kitchen includes granite counters and tile floors, opening to the dining area and loft. Two primary suites overlook the deck and creek; one opens to a large covered deck. Includes a detached 2-car garage, woodshed with Japanese-inspired details, and on-site fire suppression. A secluded off-grid cabin sits near the waterfall and campground. Adjacent to forestland with private hiking trails, wildlife, berries, and mushroom hunting. Enjoy stargazing, snowshoeing, sledding, and more--just 20 minutes from downtown Ashland. Last house before the lodge & the Pacific Crest Trail is right outside your door!

500 Mt Ashland Ski Road, Ashland

575 Dogwood Way, Ashland
$769,000
4 Beds ⋅ 3 Baths ⋅ 220220097 MLS
It's the home you've dreamed of with astounding views of the valley and mountains from living and dining rooms and all four bedrooms! Designed by Jerry Toney it's been well cared for and improved over time with meaningful updates including terraced lawn with sundeck, two kitchen sinks, 16 (owned) solar panels and more! A large room on the first floor with built-in shelves is suitable for use as media, gym, or library. Garage has storage room plus workbench and sink. On the main level, vaulted ceilings and oversized windows running the length of the home create a spacious feeling that invites the valley below indoors. The primary suite boasts a walk-in closet/dressing area and a tiled bathroom complete with two-person soaking jacuzzi. The kitchen opens onto the main outside deck facilitating meals outside or barbecuing meals for inside. Throughout the home, custom western maple cabinetry and quality woodwork add warmth and character. Call your Realtor for a private showing today!

575 Dogwood Way, Ashland

128 S Mountain Avenue, 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

8612 OR-66, Ashland
$999,999
3 Beds ⋅ 4 Baths ⋅ 220217132 MLS
Stunning new contemporary home with mountain views on 20+ private acres! Interior highlights include natural hickory and maple hardwood floors and steps; porcelain tile in kitchen, bathrooms and great room, granite counter tops, washer and dryer in upstairs primary bedroom closet and connections for a second set up downstairs, windows wired for electric blinds or shades, beautiful stone fireplace all the way to the ceiling, all Dacor appliances. The exterior has stucco siding, and a metal roof on both the main house and detached garage. The oversized garage has enough space for 2 cars plus a shop area with ample lighting, EV charging outlet, and a heated full bathroom. The garage also has an attached 2 car carport. The covered patio boasts an outdoor fireplace and the upstairs balcony off of the primary bedroom is a perfect place to accommodate a hot tub and enjoy the views.

8612 OR-66, Ashland

15922 Green Springs  66 Highway, Ashland
$735,000
3 Beds ⋅ 3 Baths ⋅ 220215130 MLS
Modern Airstrip Estate in Oregon's Green Springs Wilderness Usable land adjacent to BLM forest offers endless recreation--horseback riding, hiking, swimming, and paddleboarding. Enjoy rural privacy without sacrificing modern comfort or convenience: cable internet, reliable utilities, and strong cell service year-round--the perfect blend for today's lifestyle. Nestled along the scenic Green Springs Highway, this standout property includes deeded private access to Pinehurst Airstrip, ideal for aviation enthusiasts. Approx. 1,500 sq ft upstairs is perfect for a home office or creative studio. Shop 2,500.sq ft 347,500 estimate at 139.00 sq ft ,install/permit, 220 amp, box, 220 wiring foundation engineered, 12x 12 rolling door, 14 ft ceilings metal snap lock roof. Property sits on13.63 acres of usable land. Open Meadows, mature timber, large pond, with direct context inside the Cascade Siskiyou National Monument area. Seller finance, 3,488 sq ft Airstrip Estate, investment opportunity.

15922 Green Springs 66 Highway, 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:

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