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$950,000
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
$1,200,000
2 Beds ⋅ 3 Baths ⋅ 220225582 MLS
Experience refined living just one block from downtown Ashland in this custom-built 2012 luxury home designed for comfort and ease. Rich oak and red oak floors and cabinetry pair beautifully with custom metalwork and soaring wood-paneled ceilings in the great room. The chef's kitchen features a 6 burner Wolf cooktop, wall oven, speed oven, 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. An elevator and 36 inch doorways provide seamless accessibility throughout. The oversized finished two car garage offers space for a workshop, gym and storage with additional laundry, sink and gas heater. The private flagstone courtyard with gas BBQ, is perfect for relaxing and outdoor entertaining with lovely, low maintenance landscaping.

400 Allison Street, Ashland
$509,000
3 Beds ⋅ 2 Baths ⋅ 220225202 MLS
Back on Market, no fault to the property! You'll experience the ease of ownership in this well-maintained, split-level home in Ashland. This 3-bedroom, 2-bathroom home has charming curb appeal with shade trees and views of the north valley. Vaulted ceilings and large windows welcome you into the great room with a cozy, stone fireplace with custom mantle. All bedrooms and bathrooms are upstairs; downstairs is a spacious 2-car garage with plenty of room for creativity in the workspace. Outside you'll find a multi-level deck space with plenty of room for entertaining and gardening. Just 1 mile to downtown Ashland for shows, shops and dining. Welcome Home!

635 Chestnut Street, Ashland
$1,700,000
4 Beds ⋅ 5 Baths ⋅ 220224430 MLS
Rarely does a property of this caliber come to market. Completed in 2016 by Steve Asher, this custom Earth Advantage Platinum view home offers 4 bedrooms, 4.5 baths, and 4,234 sf of total living, including a 3,537 sf main house and a detached 697 sf guest studio, half a mile from downtown Ashland. A wall of glass frames unobstructed views of Grizzly Peak. The main level is anchored by a gourmet kitchen with a Gen-Aire double oven, cooktop, and granite island, flowing into a living room with gas fireplace and bar, plus an office, half-bath, and primary suite featuring a soaking tub, spa shower, and walk-in closet. A mudroom opens onto the patio and grilling area, steps from the guest studio with its own entrance and kitchenette. Downstairs, the main house offers a second living room with wet bar, gas stove, and outdoor jacuzzi tub, two en-suite guest rooms, and a flex room (not included in sf). Direct access to the Ditch Trail and Strawberry-Hald Park rounds out this turnkey offering.

225 Grandview Drive, Ashland
$789,000
2 Beds ⋅ 1 Baths ⋅ 220224351 MLS
Experience the rural southern Oregon lifestyle on 7.34 acres of mostly flat, park-like property bordered by BLM. This custom built home features passive solar design, hardwood floors throughout and an open floor plan with a finished basement ideal for a guest space or studio. A unique third floor office tower provides an inspiring workspace with elevated views. The property is well-equipped for a variety of uses with a large, wood framed 3,400 square foot shop including 220 power, a 10 foot roll up door and 1,000 sq ft of loft space. Detached cabin with power has a completely remodeled exterior with Hardie board siding. Extensive tree thinning and fire prevention work has been done over the years to help provide a ''park like'' feel on the property as well as defensible space. Conveniently located just 10 minutes to Emigrant lake and 20 minutes to downtown Ashland, this property offers privacy, recreation and opportunity for a homestead or retreat. See list of upgrades attached.

1700 Tyler Creek Road, Ashland
$714,900
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, second upstairs bedroom, separate office that could be used as a guest 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
$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
$888,000
3 Beds ⋅ 2 Baths ⋅ 220223497 MLS
Tucked in the hills of Ashland, this exquisite light filled home offers a rare blend of elegance, privacy, views and natural beauty. This 3 bedroom, 2 bath house features a large open floorplan, skylights, chef's kitchen with 6 burner gas range and island, expansive great room, double paned windows, dining room, primary suite with walk in closet and so much more. This thoughtfully designed home showcases quality craftsmanship, refined finishes and allows for seamless indoor-outdoor living. The yard features fire safe landscaping, custom organic gardens, dozens of varieties of flowers and trees, Japanese maples, dogwoods, abundant wildlife and a koi pond with waterfall. Enjoy the large 3 car garage and workshop, along with an additional downstairs bonus room and multigenerational living potential. The home has been immaculately maintained, with both a newer roof and HVAC system.

1365 Ponderosa Drive, Ashland
$14,000,000
220223436 MLS
Offered for sale for the first time ever, Belle Fiore Estate Winery is a premier Southern Oregon winery 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 square feet 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 eight 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. The combination of established vineyard production, hospitality operations, event revenue, and significant growth potential creates a rare opportunity to acquire Oregon's most significant vineyard esta

100 Belle Fiore Lane, Ashland
$12,000,000
7 Beds ⋅ 19 Baths ⋅ 220223437 MLS
Offered for sale for the first time ever, Chateau at Belle Fiore Estate Winery is one of Oregon's most extraordinary residential estates. Spanning over 17,400 sqft across four 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 over 17 acres, including 12.1 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, four-car garage, prep kitchen, and grand gathering spaces complete this iconic Southern Oregon estate.

200 Belle Fiore Lane, Ashland
$26,000,000
220223435 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is being offered for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,800 sqft; it has four levels, 5 bedrooms, 19 bathrooms, elevator service, a vineyard, a 2 bedroom 2500+ sqft carriage house, four-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard featuring 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights, a priceless feature of this one of one opportunity to own Oregon's most significant vineyard estate.

100 Belle Fiore Lane, Ashland
$26,000,000
7 Beds ⋅ 19 Baths ⋅ 220223434 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is being offered for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,400+ sqft; it has four levels, 5 bedrooms, 19 bathrooms, elevator service, a vineyard, a 2 bedroom 2500+ sqft carriage house, four-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard featuring 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights, a priceless feature of this one of one opportunity to own Oregon's most significant vineyard estate.

200 Belle Fiore Lane, 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
$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
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 220222850 MLS
This beautifully designed and built custom Victorian by Carlos Reichenshammer sits just blocks from Lithia Park. Featuring a new roof, it blends historic charm with modern updates. Mountain views abound throughout. Up the majestic oak stairway you'll find an office/library, a guest bedroom with walk-in closet and en-suite bath, and a luxurious primary suite with fireplace, two walk-in closets, soaking tub, and shower. The spacious country French kitchen features granite countertops, two islands, a Thermador 5-burner cooktop, double Bosch ovens, and glass-paned cabinets. It opens to the family room or dining area with a fireplace and breakfast nook. Enter through the marble-floored foyer into the formal living room with vaulted ceiling, plush bench seating, and fireplace. Additional highlights include a custom 650-bottle wine cellar with travertine walls and floors, a courtyard fountain, large wrap-around front porch, and back deck. **SELLER CARRIED FINANCING AVAILABLE**

255 Scenic Drive, Ashland
$400,000
2 Beds ⋅ 1 Baths ⋅ 220222433 MLS
Charming historic fixer-upper on a private 0.26-acre lot with mature trees and incredible pollinator garden featuring 70+ plant species, lovingly cultivated over 30 years. New roof in 2019, new fencing in 2012, and new central ducting with gas furnace in 2006. Living and dining with solid oak floors and glass door to front office. Kitchen with antique gas stove, butcher block and tile counters, operable casement bay windows, wood and glass display cabinets, double sink with updated hardware, under-sink water filtration, and new dishwasher in 2023. Spacious main-level bedroom with closet, full bathroom with clawfoot tub shower, and sitting room with stairs to vaulted upper bedroom with closet. Backyard with deck and hot tub, raised beds, perennials, detached garage shop with alley access, and excellent potential for ADU or second dwelling. Centrally located above the boulevard in the desirable Siskiyou-Hargadine District near Triangle Park. Bring your ideas and inquire for details!

324 Liberty Street, 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
$550,000
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
$828,000
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
$845,000
3 Beds ⋅ 3 Baths ⋅ 220219802 MLS
Stunning Chalet Retreat with Breathtaking Mt. Ashland Views! Nestled on 7.51 private acres, this gorgeous 2,306-sq-ft chalet offers unparalleled views of the Colestin Valley and Mt. Ashland. The thoughtfully designed interior features 3 spacious bedrooms, 3 full baths, and a versatile bonus room. Uniquely permitted for short-term rentals, this property is a proven income-producer and an ideal part-time residence or year-round sanctuary. Located just 15 minutes from the culture of downtown Ashland and minutes from world-class skiing, it perfectly balances seclusion with convenience. High-quality infrastructure includes a robust 16 GPM well and a state-of-the-art Advantex septic system. Whether you are seeking a mountain getaway, a savvy investment, or a private estate, this home delivers the best of Southern Oregon living. Experience ultimate privacy without sacrificing proximity to the city. A rare find in an iconic setting--this mountain masterpiece is ready for its next owner!

12673 Highway 99 S, 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
$1,350,000
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. Seller carry option available with a considerable down.

8612 OR-66, Ashland
$950,000
3 Beds ⋅ 3 Baths ⋅ 220216742 MLS
This view property will not disappoint. Perfect wood window placement throughout takes in the surrounding mountain & valley views. Open floor plan w/ formal/informal dining & living, creates ample spaces for entertaining. Vaulted living room w/ slate tile flooring & a corner woodburning fireplace. Roomy kitchen w/ plenty of storage, granite counters & slider access to the large outdoor deck & integrated paneled Thermador refrigerator. Primary bedroom on the main floor is situated perfectly to take in the city views from the private deck. It also has walk-in closet, soaking tub & separate tile shower. One other bedroom & full bathroom located on the main floor. Downstairs is perfect for overflow guests, w/ its own living room, full bath, bedroom & an office space. Each level has its own 2 car attached garage. Mature, easy-care landscaping on this large lot w/ great privacy provided from the city owned lot below, which gives a rural atmosphere to the back yard while being close to town.

290 Skycrest Drive, Ashland
$850,000
3 Beds ⋅ 4 Baths ⋅ 220215378 MLS
Owner will carry! Over 3,000 sq ft of custom design and stunning curb appeal define this exceptional 3 bed, 3.5 bath multi-level home set on 1.76 usable acres just 7 minutes from downtown Ashland. Walls of windows showcase sweeping panoramic views of the Siskiyou Mountains, Pompadour Bluff, Pilot Rock, and Mount Ashland. The gorgeous updated kitchen features contemporary cabinetry, granite countertops, stainless steel appliances, cork flooring, and remarkable sightlines. A bright living room with a wood-burning fireplace offers comfort and beautiful views, while the spacious primary suite includes a spa-like bath with walk-in tile shower and jetted soaking tub. Beautiful grounds, inspiring vistas, and thoughtful craftsmanship define this standout property, offering flexible living spaces, a scenic deck, privacy, and convenient access to downtown, parks, trails, and renowned cultural attractions. Come check it out today!

157 Ashland Acres Road, 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
$3,250,000
4 Beds ⋅ 6 Baths ⋅ 220214637 MLS
Paradox Vineyard Estate is uniquely defined by elements of water, air, the natural light and beauty of the Rogue Valley, and a resounding commitment to environmental stewardship. Award-winning architecture and landscape design implemented by reputable local contractors with the highest caliber of building materials certified through LEED, Energy Star, and Green Globes. Senses are captivated by a soaring skylight galleria spanning through the home, four open-air water courts with columnar basalt fountains, and stunning panoramic mountain views. Tranquil and private outdoor spaces with mature plantings and ornamental trees encircle the home, including an in-ground spa and lap pool. Vineyard operations are professionally managed for continued turn-key production of organic grapes acclaimed by local and regional winemakers. Close-in rural community of high-end estates located within five miles of Ashland's downtown plaza. Inquire for additional details and documentation!

786 Pompadour Drive, 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: