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$798,500
4 Beds ⋅ 4 Baths ⋅ 220226035 MLS ⋅ 2,700 SqFt. ⋅ 239,580 Sqft. Lot ⋅ 5.5 Acres
Private 5.5-acre mountain retreat with stunning views, gated entry, asphalt drive, and expansive paved parking, only 5 minutes to town! Perched above Emigrant Lake, this impeccably maintained 2,700 sq ft home offers flexible living: two inviting living areas (one with a cozy fireplace, the other with a wet bar and patio access), a sunlit kitchen with tile floors, granite counters & backsplash, and all appliances included. Main level features formal dining, a bedroom and 1.5 baths; upstairs the spacious primary suite with walk-in closet plus two more bedrooms, 2 full baths and larger storage room. Huge attached workshop with shelving, workbenches and 220/240A service (could be converted to ADU), plus an attached 2-car garage. Entertain or unwind on the deck with pergola and hot tub, enjoy outdoor/indoor living and private hiking trails right on the property.

197 Timberlake Drive, Ashland
$540,000
3 Beds ⋅ 2 Baths ⋅ 220225859 MLS ⋅ 2,668 SqFt. ⋅ 817,185 Sqft. Lot ⋅ 18.76 Acres
Enjoy 18+ acres of privacy with a gated entry and set back entrace with valley views! This 2,668 sqft, 3 bedroom, 2 bath home features a large 2 story rock fireplace and vaulted cedar ceilings in both the large formal living room and family room. Additional log studio/office. The land has been cleared and leveled and now very usable. Room for shop, gardens.

19001 Dead Indian Memorial Road, Ashland
$2,400,000
3 Beds ⋅ 2 Baths ⋅ 220225850 MLS ⋅ 2,778 SqFt. ⋅ 7,143,840 Sqft. Lot ⋅ 164 Acres
One of the Rogue Valley's premier estate settings, this extraordinary 164-acre Ashland offering is paired with a proposed luxury residence by Asher Homes. The single-level design offers 2,778 sq ft with 3 bedrooms, 2 baths, a 912 sq ft 3-car garage, and walls of glass framing mountain and valley views. Refined finishes include large-plank hardwood, custom built-ins, a stone fireplace, metal roofing, and covered outdoor living with built-in BBQ and fireplace. Designed to Earth Advantage Platinum standards, the home features high-efficiency HVAC, solar-ready infrastructure, EV charging, generator tie-in, and wildfire-conscious materials. The build package includes vertical construction and an infrastructure allowance for driveway, septic, well systems, power, propane, water storage, trenching, and utility connections. Land offers 2,220 feet of Cove Creek frontage, a 48 GPM well, and paved access. Plans and pricing subject to site conditions, permitting, selections, and builder approval.

312 Sky Ridge Road, Ashland
$950,000
3 Beds ⋅ 3 Baths ⋅ 220225745 MLS ⋅ 2,934 SqFt. ⋅ 250,470 Sqft. Lot ⋅ 5.75 Acres
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
$1,350,000
5 Beds ⋅ 6 Baths ⋅ 220225703 MLS ⋅ 4,935 SqFt. ⋅ 217,800 Sqft. Lot ⋅ 5 Acres
Live the Southern Oregon Dream! Welcome to an extraordinary Ashland estate where breathtaking views of Mount Ashland, the Cascades, downtown Ashland, and surrounding vineyards create a spectacular backdrop. Nestled behind a private gated entrance on 5 acres, 3 TID irrigated, this custom-built 5 bedroom, 6 bath home offers luxury, privacy, and versatility. Whether you're seeking a peaceful retreat, a multigenerational home, or space to operate a home-based business, this property adapts to your lifestyle. The thoughtfully designed floor plan features TWO private suites with their own entrance, ideal for extended family, a professional office, or creative studio. Garden beds, fruit trees, space for horses, animals, a 28 GPM well, RV hookups w/220, abundant parking, just minutes from the Shakespeare Festival, galleries, wineries and award-winning restaurants. You'll enjoy the best of country living without sacrificing convenience. Luxury. Privacy. Self-sufficiency. Endless possibilities.

808 Pompadour Drive, Ashland
$3,995,000
2 Beds ⋅ 1 Baths ⋅ 220225545 MLS ⋅ 1,649 SqFt. ⋅ 39,087,259 Sqft. Lot ⋅ 897.32 Acres
The Four Corners Ranch offers 897.32 acres of productive timberland on the south side of Mount Ashland, near the California border. This is a rare legacy holding that pairs a strong timber inventory with live water, recreation, and several structural improvements. Elevations range from 3,600 to 4,900 feet across varied topography, supporting consistent, reliable timber growth. Current stocking is estimated at 7.7 MMBF Douglas fir, 4 MMBF white fir, 5.9 MMBF pine, and just under 1 MMBF cedar. Located in the Rogue hunting unit, an area known to produce quality black-tailed deer, the ranch is ideal for hunting and outdoor recreation. Live water, diverse terrain, and direct access to vast public lands add to its appeal. Whether acquired for merchantable timber value or held as a generational asset, the Four Corners Ranch is a genuine opportunity to own a productive expanse of land in Southern Oregon. Additional documentation available upon request.

Hungry Ridge, Ashland
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 220225369 MLS ⋅ 4,979 SqFt. ⋅ 643,816 Sqft. Lot ⋅ 14.78 Acres
First time on the market for this one-of-a-kind custom ICF-built home with breathtaking panoramic views! This 4 bed, 3.5 bath, 4,972 sqft home offers a main-level office, multiple large storage rooms, and plenty of space for entertaining. The upper level features a spacious primary suite with a private balcony, plus (2) additional bedrooms and a bonus loft (not included in storage). The lower level is ideal for multigenerational living with a large entertainment area, wet bar, bedroom, bathroom, and bonus office/storage space. Situated on 14.78 acres, (house on 1 acre), 13.8 acres currently in hay production, with rare dedicated unlimited TID irrigation. Propane has been plumbed both interior and exterior to add a fireplace or connect your BBQ if desired. Also includes an approx. 1,500 sqft detached shop, barn with (6) 12x12 stalls, riding arena, plus (2) full RV hookups and 50-amp available at the barn, and endless opportunities for horses, livestock, or hobby farming.

40 Ashland Acres Road, Ashland
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 220225368 MLS ⋅ 4,979 SqFt. ⋅ 643,816 Sqft. Lot ⋅ 14.78 Acres
Welcome to this one-of-a-kind custom ICF-built home with breathtaking panoramic views just minutes from downtown Ashland! This 4 bed, 3.5 bath, 4,972 sqft home offers a main-level office, multiple large storage rooms, and plenty of space for entertaining. The upper level features a spacious primary suite with a private balcony, plus (2) additional bedrooms and a bonus loft (not included in storage). The lower level is ideal for multigenerational living with a large entertainment area, wet bar, bedroom, bathroom, and bonus office/storage space. Situated on 14.78 acres, (house on 1 acre), 13.8 acres currently in hay production, with rare dedicated unlimited TID irrigation. Propane has been plumbed both interior and exterior to add a fireplace or connect your BBQ if desired. Also includes an approx. 1,500 sqft detached shop, barn with (6) 12x12 stalls, riding arena, plus (2) full RV hookups and 50-amp available at the barn, and endless opportunities for horses, livestock, or hobby farming

40 Ashland Acres Road, Ashland
$786,000
3 Beds ⋅ 2 Baths ⋅ 220225306 MLS ⋅ 2,216 SqFt. ⋅ 298,386 Sqft. Lot ⋅ 6.85 Acres
Rolling pastures, gentle hills & gorgeous Mt. Ashland views create an exceptional setting for this beautifully updated single-level home on 6.85 acres. Rebuilt from the studs in 2004, it blends timeless craftsmanship with a light-filled, open design where every room connects to the surrounding landscape. Vaulted ceilings, expansive view windows, maple hardwood floors, custom Shaker-style woodwork, fir doors, built-ins & two fireplaces add warmth and character. The spacious kitchen with sunny breakfast nook opens to wraparound decking & gardens, inviting outdoor living amid sweeping views, colorful seasonal blooms, spectacular sunsets & brilliant star-filled skies. The rebuild included updated plumbing, electrical, Milgard windows, raised ceilings, remodeled kitchen & baths, added living space, on-demand hot water & underground utilities. Outbuildings with animal shed & approx. 850-sf shop complete this peaceful, private retreat, above the fog, below the snow & just 10 minutes to town

2815 Dead Indian Memorial Road, Ashland
$685,000
3 Beds ⋅ 2 Baths ⋅ 220225001 MLS ⋅ 1,394 SqFt. ⋅ 592,416 Sqft. Lot ⋅ 13.6 Acres
End-of-the-road privacy on 13.6 acres just above Emigrant Lake, less than 4 miles to south Ashland. The 3-bedroom, 1.5-bath ranch home with a dedicated office captures incredible views of the lake and Grizzly Peak from the kitchen, eating area, and spacious view deck. An in-ground saltwater pool enjoys its own mountain backdrop, while sloping oak woodland and old-growth Manzanita shelter bluebirds, orioles, and abundant wildlife in a true Southern Oregon setting. A detached 864-SF metal shop building provides excellent workspace and storage. Buyers can move forward with confidence: fresh exterior paint, a 3-year-old roof, recent septic and furnace servicing, and a 4-hour well flow test at 9.05 GPM. Shown by appointment only.

6790 Highway 66, Ashland
$799,000
1 Beds ⋅ 2 Baths ⋅ 220224982 MLS ⋅ 1,160 SqFt. ⋅ 583,268 Sqft. Lot ⋅ 13.39 Acres
It's all about the beautiful 13.39 contiguous acres with 12.6 acres of TID irrigation, panoramic views and just minutes to downtown Ashland. Family owned since 1964, the original home was built in 1915. There are 3 separate tax lots, one with the original home,8-stall horse barn and workshop (5.81 acres), one that has a non-expiring homesite (confirm with county) with fantastic panoramic views (4.53 acres) and the third with a large barn (3.05 acres) and separate access. All 3 may be sold separately (check with Jackson County Planning). Tax lot #700 has a small home, large shop, a 8-stall barn, tack room and small living quarters in the back. There is a 2-story barn on tax lot #300. The portion of the property growing grass and clover for hay produces approximately 400-600 bales and has wheel line irrigation. There are many other potentials for this EFU property.

1249 N Valley View Road, Ashland
$1,200,000
5 Beds ⋅ 3 Baths ⋅ 220224554 MLS ⋅ 4,768 SqFt. ⋅ 219,106 Sqft. Lot ⋅ 5.03 Acres
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
$625,000
2 Beds ⋅ 2 Baths ⋅ 220224484 MLS ⋅ 1,157 SqFt. ⋅ 208,652 Sqft. Lot ⋅ 4.79 Acres
Single-level contemporary view home on very private acreage with southern exposure and seasonal creek -- just seven minutes from Ashland's downtown plaza. Custom-designed and built by Gary Dorris Construction with high vaulted ceilings, solid maple floors, designer fixtures and hardware, low-texture walls with art niches, and abundant natural light throughout. Open-concept great room with walls of windows and sliding glass doors to patio, breakfast nook, and kitchen with granite counters, clear-grain alder cabinets, and stainless appliances including electric range with convection oven. Pocket doors to primary suite with glass slider to patio, walk-in closet with skylight and washer dryer, and full ensuite bath with floating walnut vanity, stone vessel sink, soaking tub, and shower with marble surround. Guest bedroom with closet and glass slider to patio; full guest bath with floating vanity, stone vessel sink, and tub shower with marble surround. Inquire for details!

1921 Ashland Mine Road, Ashland
$300,000
220224404 MLS ⋅ 818,928 Sqft. Lot ⋅ 18.8 Acres
Your future homestead, farm, and launch pad for outdoor recreation! A well-maintained road leads to 18.8 usable acres w/panoramic backdrops. Forest & lovely pastures w/mountain views. Approved homesite in your choice of two locations. Septic system installed. 12gpm well drilled in 2013. The charming log-frame barn and paddocks are in full swing and ready for your animals! Property is partially fenced and fully surveyed, with all corners marked. Bring your plans and your joy to the getaway setting you've always wanted. Next door to adventure territory for hiking, biking, paddle-boarding and more! Near extensive BLM & just 15-20 minutes to Howard Prairie & Hyatt Lakes! Buyer to perform due diligence on all aspects of the property, its uses and development potential. One seller is a licensed Broker in the state of Oregon. Shown by appointment only--Buyer's agent must accompany.

15861 Highway 66, Ashland
$789,000
2 Beds ⋅ 1 Baths ⋅ 220224351 MLS ⋅ 1,864 SqFt. ⋅ 319,730 Sqft. Lot ⋅ 7.34 Acres
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
$129,500
220224297 MLS ⋅ 175,546 Sqft. Lot ⋅ 4.03 Acres
Priced to sell, won't last!! Picture 4.03 private acres just a 10 minute drive to downtown Ashland and right around the corner from Emigrant Lake! Neil Creek flows along the front boundary while mature pines and oaks frame the property in shade and privacy. Forest Resource zoning sets the stage, so bring your plans and build the home you have always wanted! Room to roam, a flowing creek, and the lake just minutes away. Opportunities like this in Ashland do not wait! Buyer to perform their own due diligence.

1600 Neil Creek Road, Ashland
$250,000
220223581 MLS ⋅ 1,095,969 Sqft. Lot ⋅ 25.16 Acres
This expansive 25.16-acre WR (Woodland Resource) zoned parcel is located just outside Ashland city limits, offering rare privacy, sweeping views, and abundant space in a highly desirable area of Southern Oregon. The property allows for a single-family homesite, as confirmed by Naomi at Jackson County Planning. Establishing the homesite requires a $1,650 application fee plus the standard approval process and associated costs. Zoning supports woodland resource uses while providing the opportunity to create your private retreat. With rolling terrain and natural beauty, this large acreage is ideal for a custom home, gardens, trails, or low-impact recreation, all while staying conveniently close to Ashland's theaters, restaurants, and amenities. Buyers are strongly encouraged to perform their own due diligence with Jackson County Planning to verify all details, access, and requirements. A unique opportunity to own significant acreage bordering Ashland.

Elkader Street TL 200 Unit TL 200, Ashland
$525,000
220223564 MLS ⋅ 175,982 Sqft. Lot ⋅ 4.04 Acres
This 4.04-acre parcel sits just outside Ashland city limits, offering privacy and space while remaining conveniently close to town. Residential zoning (RR-10) allows construction of a single-family home (subject to standard 50-foot setbacks from property lines and creeks) plus a maximum 900 sq. ft. Accessory Dwelling Unit (ADU). The property features a usable homesite with strong development potential. Enjoy the best of both worlds: semi-rural living with easy access to Ashland's renowned theater, dining, trails, and amenities. Buyers should perform their own due diligence with Jackson County to confirm all zoning, building, and site details. A rare opportunity for a custom home on acreage so close to Ashland.

Elkader TL 100 Street, Ashland
$198,000
2 Beds ⋅ 1 Baths ⋅ 220223509 MLS ⋅ 399 SqFt. ⋅ 1,314,640 Sqft. Lot ⋅ 30.18 Acres
Escape to the mountains just 35 minutes from downtown Ashland at The Cabins at Hyatt Lake. Surrounded by pines and just a short walk from the water, this fully furnished retreat offers the perfect balance of peaceful cabin living and successful vacation rental income. One of only 10 authorized vacation rentals in the community, it's a rare opportunity to own a turnkey four-season getaway in one of Southern Oregon's most unique recreational settings. Inside, vaulted wood ceilings and warm natural light create an inviting space to relax after days spent boating, hiking, fishing, or exploring nearby trails. The efficient layout includes a main-level bedroom and bath plus loft sleeping space above. Outside, enjoy the wraparound deck, hot tub, and quiet forest setting. Oversized shared 2-car garage included for boats, snow toys, and outdoor gear, with year-round recreation right outside your door.

7979 Hyatt Prairie Road 43 Unit 43, Ashland
$235,000
2 Beds ⋅ 1 Baths ⋅ 220223508 MLS ⋅ 640 SqFt. ⋅ 1,314,640 Sqft. Lot ⋅ 30.18 Acres
The cabin of your dreams is waiting for you just 35 minutes from downtown Ashland at The Cabins at Hyatt Lake. Tucked into the trees near the shores of the Lake, this peaceful mountain getaway offers the kind of escape people search for and rarely find. With one of the larger and more desirable layouts, the added bump-out creates extra room to relax, gather, and enjoy every season. Vaulted wood ceilings, warm natural light, and a spacious open living area create an inviting place to unwind after a day on the lake, hiking nearby trails, or winter adventures in the snow. Step outside to the wraparound deck, enjoy coffee in the crisp mountain air, soak in the hot tub, and take in the quiet forest setting. Never used as a rental, this fully furnished retreat is truly turnkey. Main-level bedroom and bath, loft sleeping space above, and an oversized shared 2-car garage for boats, gear, and toys complete the package. Just a short walk to the lake and endless outdoor recreation year-round.

7979 Hyatt Prairie Road 42 Unit 42, Ashland
$14,000,000
220223436 MLS ⋅ 2,257,279 Sqft. Lot ⋅ 51.82 Acres
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 ⋅ 19,908 SqFt. ⋅ 773,190 Sqft. Lot ⋅ 17.75 Acres
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 ⋅ 3,030,469 Sqft. Lot ⋅ 69.57 Acres
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 ⋅ 19,908 SqFt. ⋅ 3,030,469 Sqft. Lot ⋅ 69.57 Acres
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
$2,140,000
5 Beds ⋅ 5 Baths ⋅ 220223401 MLS ⋅ 7,468 SqFt. ⋅ 8,867,073 Sqft. Lot ⋅ 203.56 Acres
Rare 203-acre Ashland estate with sweeping south-facing views offers a resort setting tucked away at the end of a mountain road. Completed in 2015, the 7,468 sq ft Craftsman residence was designed for beauty and function. The main level showcases two primary suites, two additional oversized bedrooms, expansive living and family rooms, and a gourmet kitchen. One walnut staircase leads to a private loft while a second stairway leads to a spacious upper level bonus room. The partially finished daylight basement has exterior and patio access. The original 1,812 sq ft home is now an amazing fully finished flex space, ideal for guests, office, studio, or recreation. Surrounded on three sides by the Siskiyou Cascade National Monument for vast recreational opportunities. The property offers pasture, wooded terrain, and creek frontage. This rare legacy estate delivers self sufficiency, seclusion, and unparalleled outdoor access while remaining within reach of Ashland's renowned amenities.

22494 Jefferson Road, Ashland
$895,000
3 Beds ⋅ 3 Baths ⋅ 220223186 MLS ⋅ 2,707 SqFt. ⋅ 3,118,024 Sqft. Lot ⋅ 71.58 Acres
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 ⋅ 2,145 SqFt. ⋅ 5,313,448 Sqft. Lot ⋅ 121.98 Acres
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
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 220222210 MLS ⋅ 2,224 SqFt. ⋅ 6,969,600 Sqft. Lot ⋅ 160 Acres
Rare opportunity to own 160 private acres on the outskirts of Ashland, offering extreme end-of-the-road seclusion, breathtaking panoramic views, and endless potential for recreation, hunting, and homesteading. Surrounded by nature and abundant wildlife, this remarkable mountain retreat delivers the peace and privacy that are increasingly difficult to find. Located just 30 minutes from Mt. Ashland and approximately 45 minutes to downtown Ashland, the property offers the perfect balance of remote living and convenient access to dining, culture, and outdoor adventure. The custom-built home features a stunning great room that truly must be experienced in person, with soaring ceilings, warm finishes, and walls of windows framing the surrounding landscape. A spacious primary suite, inviting guest accommodations, large barn, and substantial shop space make this property ideal as a full-time residence, legacy ranch, or unforgettable weekend mountain escape.

1969 Colestin Road, Ashland
$1,080,000
3 Beds ⋅ 3 Baths ⋅ 220222186 MLS ⋅ 2,644 SqFt. ⋅ 237,402 Sqft. Lot ⋅ 5.45 Acres
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
$900,000
5 Beds ⋅ 4 Baths ⋅ 220221548 MLS ⋅ 5,200 SqFt. ⋅ 477,417 Sqft. Lot ⋅ 10.96 Acres
2 HOMES AND A GUEST STUDIO/COTTAGE!!! Just 3 miles from town, this exceptional 11-acre property sits on a sunny south-facing hillside with breathtaking views and endless possibilities. Ideal for a multi-generational family compound, rental income opportunity, homestead, or private retreat, this unique property offers an incredible combination of living space, infrastructure, and outdoor amenities. The 2,200 sq. ft. log home is filled with warmth and rustic charm, while the 1,800 sq. ft. second home includes a full basement for additional living or storage space. A separate 1,200 sq. ft. fenced studio/cottage provides excellent flexibility for guests, a home office, or a creative space. Additional improvements include two large septic systems, RV hookups with water and electricity, a separate laundry room, two tiny cabins, multiple storage buildings, root cellar with shop above, and a barn-style structure on the lower portion of the property with a newer roof. Must see to appreciate!

2909 Dead Indian Memorial Road, 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: