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$899,000
220221479 MLS 7,143,840 Sqft. Lot 164 Acres
312 Sky Ridge Road offers 164 acres in the hills above Ashland, combining privacy, natural beauty, and usable land in a premier Southern Oregon setting. Zoned EFU, the property features a blend of moderately sloping terrain, open ground, and native landscape ideal for recreation, investment, or an exceptional estate setting. Approximately 2,220 feet of Cove Creek frontage adds scenic beauty and recreational appeal. A strong 48 GPM well, per 2018 well log, provides an excellent water source for future improvements. A fully paved drive leads to the property, with plans underway for a custom luxury entrance designed to complement the scale and quality of the setting. Elevations ranging from approximately 2,120 to 2,520 feet capture panoramic views in nearly every direction, creating a remarkable sense of space and connection to the surrounding mountains and valleys. Conveniently located near Medford, outdoor recreation, public lands, and Southern Oregon amenities.

312 Sky Ridge Road, Ashland

$749,000
2 Beds 2 Baths 220221177 MLS 2,235 SqFt. 938,282 Sqft. Lot 21.54 Acres
This sophisticated home combines high-end finishes & top-of-the-line infrastructure w/ stunning sunset views, a strong producing well w/ water rights, & a professional-scale solar array designed for complete self-sufficiency. Enjoy a grand layout featuring vaulted ceilings, wide plank engineered white oak floors, two wood stoves, and Knotty Alder solid core doors. Sliders lead to a brand new two-tiered deck, while the primary offers a free standing tub, marble shower, & a view balcony. This smart home provides seamless control over lighting, media, HVAC, etc via a central wireless hub. The firewise exterior includes a metal roof and fiber cement siding. A 28 solar panel array with 22,000KW storage is backed by two generators integrated for automatic operation. There's a heated barn with drive-through doors, two climate-controlled 40' shipping containers, & a storage shed. Newly completed in 2024 & 15min to town, this property is one of a kind. Inquire for a full features list.

8351 Dead Indian Memorial Road, Ashland

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

2042 Hyatt Prairie Road, Ashland

$159,000
220220683 MLS 10,886,079 Sqft. Lot 249.91 Acres
Own your own private Southern Oregon Retreat. With nearly 250 acres just 15 miles east of Ashland, a Homesite approval is already in place, and the property may offer marketable timber. Surrounded by mountains, trees, and abundant wildlife, this exceptional property is ideal for outdoor enthusiasts seeking privacy, recreation, or investment opportunity. Enjoy breathtaking views and year-round activities with Howard Prairie Lake and Hyatt Lake nearby for fishing, boating, kayaking, paddle boarding, camping, and hiking, hunting, snowshoeing, cross-country skiing, sledding, and snowmobiling. Wildlife sightings include deer, elk, and turkey. Whether you're looking for a secluded homesite, private hunting retreat, vacation getaway, or long-term investment, this one-of-a-kind property offers unmatched beauty and adventure. Gated access with ingress and egress easement in place. A rare opportunity to own your own slice of wilderness paradise.

Soda Mountain Road, Ashland

$975,000
4 Beds 3 Baths 220220664 MLS 3,391 SqFt. 223,898 Sqft. Lot 5.14 Acres
Perched on a hillside with sweeping valley and mountain views, this timeless, architecturally designed home blends traditional style with European flair. Built with Rastra Block construction and one-foot-thick walls, it features a 12 kW solar array and radiant heat floors on the main level, designed for natural air exchange. Offering 4 bedrooms, 3 bathrooms, and approx. 3,400 SF, plus a bonus storage room, the home includes a well-designed kitchen with ample cabinetry, granite countertops, and pantry. The dining room is filled with natural light, and the living room features a fireplace and built-in cabinetry. Main level includes a bedroom, media room, and full bath. Upstairs offers 3 bedrooms, including a spacious primary suite with dual vanities, walk-in closet, fireplace, and view balcony. Private gated drive, 5 acres total (4 of which have 8 ft fence) w/ flowers, fruit trees, strong well, and 2,000-gallon holding tank. This is a special property awaiting the next owner's enjoyment!

1678 Ashland Mine Road, Ashland

$754,808
4 Beds 3 Baths 220220182 MLS 1,872 SqFt. 1,971,090 Sqft. Lot 45.25 Acres
Privacy in Southern Oregon less than 20 minutes from downtown Ashland. Bring your horses & all the animals! Private Farm house and Ranch Buildings! Just South of Ashland in SW Oregon. Over 45 Acres. Craftsman style finishes, stained glass accent, lg enclosed in front porch w/lots of windows. Red Fir floors & staircase, wood windows, solid wood doors, 2 bdrms downstairs, 2 bdrms & bath upstairs + finished attic area that is not included in the SQ FT w/new carpet. Country style kitchen w/pantry. Laundry/mud room with laundry chute. Cement carport. Pastures used for hay & grazing. Adjoins BLM land for miles of trails. Seasonal creek, 40X48 Barn, 2nd level loft area, Workshop w/ finished rm w/power & ½ bath. The workshop area has 14' door & RV hook ups, Enjoy fruit trees & fenced garden area.

2245 Colestin Road, Ashland

$250,000
220219860 MLS 244,371 Sqft. Lot 5.61 Acres
Experience year-round beauty in the stunning Hyatt Pines subdivision, where an exceptional opportunity awaits to build your custom home. Located just 40 minutes to Ashland, this 5.61 acre parcel has a level homesite, well, septic, shed and garage already in place. Within a community of beautiful homes and cabins, this lot offers a desirable location with year-round neighbors. Tucked away at the end of a shared road, you'll appreciate snow removal services provided by the association each winter. Adjacent to vast BLM land, this peaceful woodland retreat offers a private atmosphere. Enjoy fishing, hiking, sailing, and cross-country skiing, all within easy reach of Hyatt Reservoir and Howard Prairie Lake. Immerse yourself in this remarkable opportunity to create your own sanctuary amidst breathtaking natural surroundings!

7890 Hyatt Prairie Road, Ashland

$799,900
3 Beds 3 Baths 220219802 MLS 2,306 SqFt. 327,135 Sqft. Lot 7.51 Acres
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

$695,000
220219785 MLS 3,466,940 Sqft. Lot 79.59 Acres
79.59-acre EFU property offering a rare combination of usable land, privacy, and natural beauty just 15 minutes from downtown Ashland. Approximately 50% prime pasture and 50% gently sloping forestland create a versatile setting for a variety of uses. Includes 29 acres of irrigated farmland with valuable 1888 water rights. Carter Creek, a tributary to Emigrant Creek, runs through the property, adding both character and a reliable water source. Ideal for a homesite, horse property, or recreational retreat with sweeping views of the Cascade Mountains and surrounding valleys. Just 5 minutes from Emigrant Lake with convenient backroad access to Mt. Ashland. Borders 120+ acres of BLM land with direct access to additional open space. Close to the Cascade-Siskiyou National Monument, offering miles of recreation and protected landscape. A unique opportunity to own a well-balanced Southern Oregon property with both usability and scenic appeal.

Buckhorn Road 1000 Unit 1000, Ashland

$2,195,000
4 Beds 4 Baths 220219782 MLS 4,977 SqFt. 1,298,959 Sqft. Lot 29.82 Acres
Located just outside Ashland, this property offers a rare blend of natural beauty, water, quality improvements, and convenience. The custom built home is thoughtfully positioned to capture expansive views across the surrounding valley and toward distant mountains. This elevated country estate draws from a Northwest lodge aesthetic, offering welcoming living spaces, a spacious multilevel layout and a seamless indoor outdoor connection with expansive outdoor living spaces. A picturesque stretch of Neil Creek framed by mature trees adds character and tranquility. Gently rolling topography, lush pasture, and water rights support a variety of Ag uses. A recently constructed 5,000 SF barn complements the property and offers outstanding flexibility for equipment, hobbies, or recreational use. Ideal as a homestead or simply an elegant place to enjoy connection to the outdoors, this is a property that captures the essence of Southern Oregon living while remaining just minutes from Ashland.

5293 Highway 66, Ashland

$1,200,000
4 Beds 3 Baths 220219409 MLS 3,246 SqFt. 405,543 Sqft. Lot 9.31 Acres
Incredible opportunity in Ashland -- Turnkey equestrian lifestyle estate on 9.31 acres of fully pressure-irrigated picture-perfect country living with sweeping views. Relax on the full wrap-around porch and savor sunrises and sunsets from your swinging bench seat. The 2,846 sq ft home offers 4 bedrooms, a cozy gas fireplace with ceramic logs, dual-zone heat pump, natural gas furnace, and a tastefully updated 2016 kitchen. Fully fenced and cross-fenced with electric, perfect for livestock. A 30x40 barn includes four powered stalls, tack room with bunk, hay loft and elevator; plus round arena, chicken coop and storage shed. Detached 3-car garage with 400 sqft ADU/guest house for income or multigenerational living. New 25 GPM well pump and Charter high-speed internet. Turnkey, functional, and ready to enjoy!

900 Butler Creek Road, Ashland

$1,410,000
3 Beds 3 Baths 220218218 MLS 4,668 SqFt. 233,046 Sqft. Lot 5.35 Acres
Nestled on 5.35 acres, this gorgeous Tuscan-style home offers stunning scenery and peaceful living just minutes from the renowned Bella Fiore Winery. This home is the perfect blend of elegance, space and functionality. The home features a primary suite on the main level, 2 spacious bedrooms upstairs, chef's kitchen that opens into the family room complete with a woodstove and sweeping pristine views. The home is filled with natural light and the new interior paint enhances the architectural elements while making the home feel modern and fresh. The unique tower space adds character and versatility- ideal for a 4th bedroom, home office, art studio or yoga retreat. Downstairs there is a large room for entertaining and wine storage. The professionally landscaped yard features stunning color, along with a shop and creek running through the property. Enjoy the serenity of country living close to town.

988 Dead Indian Memorial Road, Ashland

$550,000
3 Beds 3 Baths 220218174 MLS 2,639 SqFt. 223,027 Sqft. Lot 5.12 Acres
$35,000 Price Reduction!!! Peaceful mountain retreat with sweeping views and abundant natural light from expansive picture windows. This bright, open-concept home blends craftsman character--wood trim and beams--with modern industrial elements like steel beams, metal cable railing, and stylish fixtures. Soaring vaulted ceilings create an airy feel throughout. Enjoy main-level living with a spacious primary suite featuring a double vanity, walk-in closet, and access to the wrap-around deck. The kitchen offers a built-in cooktop, stainless steel appliances, solid wood cabinetry, and pantry. Upstairs includes a versatile loft and full bath. Above the 2-car garage, 672 sqft of bonus space with full bath and laminate flooring offers ADU potential (buyer to verify). Well system fully upgraded with new pump & casing, 900+ gallons of storage, and filtration. Fresh 2025 exterior paint and metal roof complete this rare rural property!

30 Steinman Drive, Ashland

$304,000
1 Beds 1 Baths 220217321 MLS 418 SqFt. 365,904 Sqft. Lot 8.4 Acres
Peaceful RETREAT? Legacy family hunting cabin? Remote OASIS? Once you get here, you'll never want to leave. Located along Jenny Creek, this 8.4 acre property overlooks the Cascade Range and is located in the protected Cascade-Siskiyou National Monument. The cozy cabin has a covered porch where you can sit outside and listen to the creek, work on your novel, or return with friends after a day of fishing. Built in 1997, the open floorplan includes a galley kitchen and full bath. The multi-story barn is ready for your animals, your boat, or ideas. Originally part of the Box R Ranch, this was used as a short term rental and visitors enjoyed the nearby Greensprings and Pinehurst Inn. Winters here are magical, with lots of time to enjoy nature and explore this beautiful area.

17637 Highway 66, Ashland

$390,000
3 Beds 2 Baths 220217447 MLS 1,536 SqFt. 731,808 Sqft. Lot 16.8 Acres
Serene, private & ready for adventure! This mountain retreat blends tranquility with endless recreation. Whether you're seeking a private getaway, a recreational basecamp, or full-time off-grid living, this property delivers it all. Situated on level acreage tucked back from a county-maintained road, the setting offers privacy among trees & open meadows-ideal for relaxing, exploring & storing all your outdoor gear. The cozy home is equipped with solar power, making off-grid living comfortable & sustainable. Even better, the property borders 1,000 acres of BLM land, giving you direct access to expansive natural surroundings right from your doorstep. Outdoor enthusiasts will love the location: Just 7 miles from the Pacific Crest Trail & a short drive to Hyatt Lake Resort, featuring a year-round bar & restaurant, a convenience store & emergency fuel. This is more than a property--it's a lifestyle. A rare opportunity to enjoy seclusion, adventure & convenience all in one incredible setting

19009 Dead Indian Memorial, Ashland

$349,000
220217224 MLS 2,566,119 Sqft. Lot 58.91 Acres
Perched above the scenic Ashland valley, this remarkable 58.91 acre property at 3727 Old Siskiyou Highway offers sweeping panoramic views across rolling hills, forested ridgelines, and nearby Emigrant Lake. The land features a beautiful mix of open grassy slopes and mature oak woodland, creating a private and peaceful setting that feels far removed while still offering convenient access to town. Zoned WR, this parcel presents outstanding potential for a rural estate, recreational retreat, or future homesite surrounded by the beauty of Southern Oregon. Septic and well are already installed, adding meaningful value for future use. Ashland is beloved for its vibrant arts scene, destination dining, boutique shopping, outdoor recreation, and small town charm, all anchored by the world renowned Oregon Shakespeare Festival and a strong sense of community. Rarely do properties of this size, privacy, natural beauty, and proximity to Ashland come available in one offering.

3727 Old Siskiyou Highway, Ashland

$1,350,000
3 Beds 4 Baths 220217132 MLS 2,451 SqFt. 902,998 Sqft. Lot 20.73 Acres
Seller will carry with acceptable terms. 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

$1,750,000
6 Beds 5 Baths 220216989 MLS 4,537 SqFt. 4,389,976 Sqft. Lot 100.78 Acres
This home is like a warm hug! The 100-acre property embraces everything! You can have it all...3025sf Main Home, 1512sf Guest House, RV barn, workshop, gardens. Main house: built by Asher Homes in 2016, expertly sited to capture optimal sun exposure, stunning views-Mt Ashland, Pilot Rock, Cascades & Siskiyous. Interior finishes in PNW style. Main level primary, custom cabinetry throughout. Even a ''secret'' room upstairs! All modern amenities you'd expect w/ sustainability at the forefront of design. Earth Adv Platinum Certification, 2 solar PV systems, water catchment, energy efficient systems. Outdoors: low-impact landscape, stone patio, fenced gardens, greenhouse, pond, fruit trees, grape vines, spring bulbs. The original home: conveniently located next door, can serve as guest quarters, office/workspace, wrap around porch, main level bdrm & full bath, 2 add'l rooms upstairs. This property has been nurtured, cultivated with love and purpose, making it a special place to call home.

1940 Soda Mountain Road, Ashland

$1,375,000
3 Beds 4 Baths 220215845 MLS 3,436 SqFt. 865,972 Sqft. Lot 19.88 Acres
This single-level retreat delivers the best of southern Oregon living...amazing views, wooded privacy and a gorgeous light filled home only 10 minutes to Ashland. A gated, paved drive leads to four fenced acres with rolling lawn, two ponds, raised garden beds and beautiful landscaping surrounding home. Stepping inside, the vaulted great room opens up with skylights, hardwood floors, and a stone fireplace that anchors the space. The kitchen means business: Sub Zero fridge, Wolf cooktop and oven, huge island and slab granite counters. A large walk-in pantry and oversized mudroom with half bath keep daily life organized. The primary suite includes a reading nook and deck overlooking the pond. Two additional bedrooms complete the split floor plan- one has its own entrance and on-suite bath, the other has a built-in murphy bed. Wrap-around decks provide multiple outdoor living spaces to enjoy the views. This is the kind of property that doesn't come along often in Ashland!

178 Meadow Oaks Drive, Ashland

$595,808
1 Beds 1 Baths 220215560 MLS 513 SqFt. 3,114,975 Sqft. Lot 71.51 Acres
Rare opportunity to own 71.51 acres just right outside city limits of Ashland! LOCATION IS AMAZING!! Property consist of 2 additional tax lots. Super cute 2020 built MFG home w/vaulted ceilings & floor ceiling windows w/quartz counters & tile shower & lg wood deck. Near Emigrant Lake this property would be beautiful to build your dream home w/gated entry & gently sloping gravel road to the home w/incredible views of Cascade Mountains & Pilot rock. Creek frontage w/15 acres of water rights from Neil Creek. Trust has invested over $150,000 into the Creek management and rehab planting thousands of native plants. Gently sloping acreage w/pastures for horses or cattle or grape vines. 2 adjoining tax lots including. Priced to SELL! Buyer to do their own due diligence. Potential for maybe possibly another home site?

4201 Highway 66, 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: