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$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

$735,000
3 Beds 3 Baths 220215130 MLS 3,488 SqFt. 593,722 Sqft. Lot 13.63 Acres
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

$1,450,000
4 Beds 4 Baths 220214755 MLS 4,382 SqFt. 1,087,257 Sqft. Lot 24.96 Acres
Discover refined country living on nearly 25 private, gated acres just minutes from downtown Ashland and a private airport. This 4,382 sq. ft. prairie style estate blends elegance and versatility. Vaulted ceilings, radiant canary wood floors, and expansive windows frame sweeping views of Mt. Ashland, Pilot Rock, and Pompadour Bluff. The chef's kitchen showcases Verde Marinace granite, dual Dacor ovens, a soapstone sink, and a generous island. The main level includes a tranquil primary suite with walk in shower, soaking tub, and large closet, along with two offices and seamless indoor to outdoor living. Upstairs offers a true guest suite, media room, and a deck overlooking the fenced garden. Manicured grounds, TID irrigation, an orchard, multiple patios, and a 1,400+ sq. ft. garage/workshop elevate the property. With owned solar, modern systems, and timeless design, this estate delivers exceptional privacy, beauty, and opportunity.

1475 Dead Indian Memorial Road, Ashland

$3,250,000
4 Beds 6 Baths 220214637 MLS 5,233 SqFt. 295,336 Sqft. Lot 6.78 Acres
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

$815,000
4 Beds 2 Baths 220214436 MLS 2,070 SqFt. 296,643 Sqft. Lot 6.8100000000000005 Acres
Privately tucked at the end of Maywood Way, this stunning single-level contemporary home sits on 6.81 irrigated acres just minutes from downtown Ashland, the golf course, & Emigrant Lake. Surrounded by peaceful pastureland, this custom home is designed for exceptional indoor-outdoor living, featuring a light-filled great room with vaulted ceilings, lime-washed walls, hardwood floors, and a beautiful Tulikivi soapstone fireplace providing radiant heat throughout. The open kitchen includes granite countertops, a center island, and gas range. Enjoy the large enclosed tiled patio with hot tub and attached greenhouse room. The thoughtful floor plan offers 4 beds and 2 baths with radiant floor heat and tiled showers. The flat, fertile land is ideal for farming, vineyard, or equestrian use with irrigation piping, water filtration & storage, garden areas, pastures, a 1728-sq-ft farm building, and a 768-sq-ft flex space for art or office use. No drive bys. Ask your agent for an amenities list.

288 Maywood Way, Ashland

$399,000
1 Beds 1 Baths 220214362 MLS 252 SqFt. 236,966 Sqft. Lot 5.44 Acres
Your off-grid oasis awaits. Set on 5.44 acres, this unique property offers multiple structures, including a beautifully built tiny home, tree house, deck house, cabin, and pump house, perfect for sustainable living or a private getaway. The main tiny home, built by renowned Mr. Morrison, features two loft sleeping areas, a full bathroom, a full kitchen, and plenty of storage. It truly utilizes every inch of space. The tree house features vaulted ceilings, a sleeping area, and a dry flush toilet. The deck house offers a wraparound deck, expansive windows, and an abundance of natural light. The property is powered by a 1.6 kWh solar system and includes a sand filter septic, a 6 GPM well with a 1,500-gallon holding tank, plus spring water, a creek, generators, and views of Mt. Ashland. The seller has replaced appliances and installed new AMG solar batteries. Buyer to perform due diligence regarding permits and property use.

1203 Tyler Creek Road, Ashland

$1,650,000
5 Beds 5 Baths 220214060 MLS 6,332 SqFt. 258,746 Sqft. Lot 5.94 Acres
Known as 309 and 311 Granite Street, this exceptional estate overlooks Lithia Park on nearly six private acres, blending European elegance with a tranquil forest setting. Mature trees, stone paths, patios, and water features create rare seclusion just minutes from downtown Ashland, the Oregon Shakespeare Festival, and the historic Plaza. Vaulted ceilings, fine woodwork, stained glass, and expansive windows fill the interiors with warm, old-world character and natural light. The main home centers on an open great room with a dramatic rock fireplace, flowing to an informal dining area and oversized kitchen, with additional living spaces for entertaining or everyday life. The primary residence offers 4,479 sq ft plus 2,364 sq ft of flexible ground-level space. A second residence adds 844 sq ft, a 1,153 sq ft multi-purpose room, and carport-about 8,840 sq ft total. Near Mt. Ashland, Crater Lake, Britt Festival, and Rogue Valley wineries, this is a rare architectural retreat of tranquility

309 Granite Street, Ashland

$830,000
3 Beds 3 Baths 220214053 MLS 2,530 SqFt. 1,004,058 Sqft. Lot 23.05 Acres
Country living on just over 23 acres of rolling green hills & mountain views. Home w/ wide covered porch for vistas from sunrise to sunset. Beautiful hardwood floors throughout open-concept design. Vaulted great room w/ fireplace & expansive windows. Gourmet kitchen w/ granite countertops, island w/ seating, ss appliances, & flow to formal dining room w/ custom built-in cabinetry & door to patio for. Primary suite is at one end of home, w/ walk-in closet, private bath w/ double sinks & walk-in shower, door to back patio & private exercise room. 2 more bedrooms & full bath w/ jetted tub & shower are at opposite end for privacy. Office w/ custom built-ins & laundry room w/ sink. Oversized two-car garage w/ workspace & half bath w/ mudroom entry. RV parking area w/ hookups. Outside is a covered patio, garden area, & sprinkler system. Minutes from hiking, dining, 2 wineries, Emigrant Lake County Park. 8 minutes from shopping center.

2809 Dead Indian Memorial Road, Ashland

$500,000
3 Beds 2 Baths 220213463 MLS 2,256 SqFt. 182,952 Sqft. Lot 4.2 Acres
Sold Only...for statistical purposes only. 1950s farmhouse set on 3.14 level acres zoned RR-5 with adjoining 1.06-acre parcel, also zoned RR-5. The home retains some vintage character with wood floors and cozy living room fireplace with woodstove insert. The main level offers a spacious primary bedroom with an updated bath featuring wainscoting, vinyl flooring, a clawfoot tub, and a small shower, plus two guest bedrooms with knotty pine paneling and wood floors. The kitchen has laminate counters and vinyl flooring, with a large utility room and laundry sink nearby. Upstairs includes two additional rooms with built-ins. Outside has a large shop building with well, miscellaneous sheds and pasture areas ideal for animals and/or crops. The adjoining 1.06 has a greenhouse and gardening area.

340 Normal Avenue, Ashland

$1,795,000
4 Beds 3 Baths 220213243 MLS 2,790 SqFt. 217,800 Sqft. Lot 5 Acres
5 magazine quality acres, masterfully landscaped with expansive emerald, green lawns, mature trees, ponds & waterfalls create the perfect setting, built with enduring quality. The walls are solid 4x6 Canadian Western Red Cedar, offering style & durability. Large open-floor plan is perfect for gatherings. Earthy materials feature Saltillo tile flooring, rich cherry custom cabinetry, Milgard wood-cased windows, & vaulted, beamed ceilings add substance & style. Upper-level primary has a private deck overlooking the estate style grounds & mountains. Guest house features dual porches, carport, & sits beside one of five waterfalls. A 22' x 44' greenhouse with raised cedar beds. Nearly a mile of crushed granite paths wind through the landscape. 3-car garage, full RV hook-ups, & a 20'x45' shop. A true paradise. Main home is 3/2, guest home is 1/1.

4896 Highway 66, Ashland

$785,000
5 Beds 4 Baths 220213217 MLS 3,018 SqFt. 218,235 Sqft. Lot 5.01 Acres
Experience the ultimate Ashland lifestyle at this remarkable 5-acre estate, located just three miles from the Plaza yet below the snowline for year-round ease. This 3,370-sqft residence balances understated elegance with authentic country charm. The expansive interior boasts 5 beds and 3.5 bths, designed for flexibility. The main level offers three spacious bedrooms, a cozy family room, and a gourmet kitchen featuring granite surfaces, stainless appliances, and a sunlit breakfast nook. A distinct advantage is the private guest suite with a separate garage entrance, ideal for multi-generational living. Upstairs, retreat to the massive rec room or the private primary suite. Outside, the property shines as an equestrian paradise with irrigation, cross-fencing, and a 4-stall barn / detached shop with power. If you have been waiting for a property that truly has it all, this is it!

2101 Dead Indian Memorial Road, Ashland

$540,000
3 Beds 3 Baths 220212828 MLS 2,833 SqFt. 223,462 Sqft. Lot 5.13 Acres
Versatile, spacious, and thoroughly updated home on private wooded acreage in the Cascade-Siskiyou National Monument - just 14 miles from Ashland! Main level features a new kitchen with granite counters and island, walk-in pantry, glass-fronted display cabinets, all new stainless appliances, informal and formal dining areas, double-height vaulted ceilings, living room with built-in entertainment system, wood cooking stove with soapstone surround, family room, and powder room. Upper level with three vaulted bedrooms including primary with private balcony, two powder rooms with access to soaking tub and tiled shower, plus a loft area with skylights. Lower-level workshop or office studio with French doors and utility storage room. Solid frame construction with strawbale insulated walls, radiant heated floors, energy-efficient double-paned windows, concrete stucco exterior, and metal roof. High-speed internet via Greensprings Broadband Coop. Inquire for details!

827 Tyler Creek Road, Ashland

$265,000
220211972 MLS 7,257,096 Sqft. Lot 166.6 Acres
Step into your private oasis on 166.6 beautiful acres of gorgeous views and scenery! Two separate tax lots are ready for you to build the home of your dreams. The septic is approved, the shared well is up and running, there is power at the road and has a spring near the top of the mountain. This secluded property features a vibrant mix of mature trees and colorful wildflowers. Abundant wildlife roams the land, with deer, elk, turkeys, and much more frequently spotted, making it ideal for hunting enthusiasts. The property boasts merchantable trees, adding potential value. Offering plenty of privacy, it's perfect for recreation, hiking, and exploring the great outdoors. A truly unique opportunity for anyone seeking a peaceful and adventurous retreat within minutes from the airport and amenities in Ashland.

639 Cove Road, Ashland

$210,000
220211332 MLS 1,333,807 Sqft. Lot 30.62 Acres
Are you looking to construct the home of your dreams? If you're tired of searching unsuccessfully for a pre-built residence that suits your needs, consider building it yourself. We are proud to present this stunning 30-acre parcel located 8 miles from the beautiful city of Ashland, Oregon. From the top of the ridge, the views of Mt Ashland and the city below will take your breath away. Boasting varied topography, oak groves and cooler temperatures in the summer and above the fog during winter days, this spot is ideal for living off-the-grid without sacrificing proximity to great restaurants, shopping, cultural experiences like the Oregon Shakespeare Festival and more. Buyer due diligence recommended; applications for a homesite have already been submitted.

Dead Indian Memorial Road 1400 Unit 1400, Ashland

$2,900,000
220211191 MLS 422,967 Sqft. Lot 9.71 Acres
PRICE REDUCED-$2,900,000. A rare opportunity to acquire ±9.71 acres of prime, developable land within Ashland's adopted Normal Neighborhood Plan, the city's designated area for sustainable, mixed-use growth. Three contiguous parcels with direct East Main Street frontage lie just outside city limits yet within the Urban Growth Boundary, contiguous to existing city limits and services -- the only parcel in the Plan area with stand-alone annexation-readiness in the chain of contiguity, providing a clear, efficient path to Type III annexation. The City may establish an Advance Financing District (AFD) to help offset infrastructure costs such as sewer oversizing and frontage improvements, reducing upfront expense. The site also carries the only commercial overlay (NN-1-3.5-C) in the entire 93-acre Plan area. With utilities at frontage and anticipated zoning of NN-1-5, NN-1-3.5, and NN-1-3.5-C, the assemblage suits a blend of residential and neighborhood-scale commercial uses.

2082 E Main Street, Ashland

$850,000
2 Beds 3 Baths 220211093 MLS 2,007 SqFt. 1,230,134 Sqft. Lot 28.24 Acres
Imagine creating your dream farm on 28+ acres of EFU farmland, surrounded by breathtaking views of the valley and mountains! The main home boasts three levels, each with its own bathroom and a deck to take in the stunning views. The radiant floor heating throughout ensures warmth in Winter and there are washer / dryer hookups on the lower floor. The potential for each level to be a separate rental unit provides a lucrative opportunity. The impressive ag building includes a room w/roll up door, a guest room with a full bathroom, a farm office space above and a deck to take in stunning views. Both structures are powered by solar energy. A large chicken house is ready for commercial chicken production or a great multi-use structure. Property is fenced and cross-fenced, ready for your animals, and features a fenced garden area. Good well flow per seller. All this and only a 5 minute drive to amenities and 10 minutes to downtown Ashland.

3152 Siskiyou Boulevard, Ashland

$10,775,000
12 Beds 10 Baths 220210683 MLS 11,456 SqFt. 41,760,972 Sqft. Lot 958.7 Acres
New Frontier Ranch - A storied and truly one-of-a-kind legacy property encompassing 958 breathtaking acres surrounded by pristine wilderness. Steeped in rich history, this remarkable ranch includes a charming farmhouse, museum building, expansive Great Hall, and a private campground with commercial kitchen and bath facilities. Scattered across the land are three rustic cabins, multiple barns and outbuildings, two reservoirs, and irrigated meadows ideal for livestock or crops. Miles of trails wind through forests, meadows, and a preserved ghost town reminiscent of the Old West. Existing resort approvals and extensive infrastructure make it perfect for corporate retreats, events, weddings, festivals, or a destination resort. With unlimited recreation—hiking, horseback riding, ATV adventures, and fishing—this ranch offers both adventure and serenity. A rare opportunity to own a vast wilderness retreat where history, nature, and imagination unite to create something truly extraordinary.

16799 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: