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$1,950,000
3 Beds ⋅ 3 Baths ⋅ 220228333 MLS
Welcome to Red's Cabin, an original homestead on Howard Prairie Lake, never before offered for sale. Held by the family since 1889, this 9.12-acre lakefront estate spans five generations. Built in 2008 to honor that legacy, the 2,907 SF, 3 bed, 3 bath home showcases custom juniper woodwork, exposed timber, vaulted ceilings, a dramatic stone fireplace and an upstairs loft/game room. Offered fully furnished, the home is on-grid with security panels for all main-level windows. A balcony off the bunk room overlooks an impressive permitted pond fed by a year-round spring-fed stream you can hear from the house. A covered outdoor fireplace sits streamside, joined by a bocce court and detached garage. The estate includes 4.1 acres of water rights, adding to its rare combination of water, recreation and mountain setting. Gated with direct access to public lands, Howard Prairie Lake and the shoreline trail, this is a rare opportunity to own a generational Southern Oregon legacy property.

3665 Hyatt Prairie Road, Ashland
$950,000
3 Beds ⋅ 4 Baths ⋅ 220228020 MLS
Set on more than 37 private acres in the Siskiyou Mountains, this property offers space, privacy minutes from Ashland and the Rogue Valley. Mt. Ashland Ski Area, Emigrant Lake and the Pacific Crest Trail are nearby, putting Southern Oregon recreation close at hand. The main residence features soaring wood-clad ceilings, exposed beams, expansive windows and a stone fireplace. The open great room flows into a gourmet kitchen with cabinetry, full-size refrigerator and freezer, double ovens and island. A media room, geothermal heating and cooling, and hard-wired generator add comfort and peace of mind. A detached four-car garage provides spaces, while the auxiliary building offers an open area, kitchen, full bath and three-car garage--ideal for a studio, workshop, recreation or guest space. A loft studio, greenhouse, gardens, water storage, creek, rock outcroppings and wildlife complete this Southern Oregon retreat.

5831 Old Highway 99 S, Ashland
$950,000
3 Beds ⋅ 4 Baths ⋅ 786738387 MLS
Set among more than 37 private acres in the beautiful Siskiyou Mountains, this remarkable property offers space, privacy and versatility within easy reach of Ashland and the Rogue Valley. Mt. Ashland Ski Area, Emigrant Lake and the Pacific Crest Trail are all just minutes away, putting some of Southern Oregon’s best outdoor recreation close at hand.The thoughtfully designed main residence captures the warmth and character of its surroundings. Soaring wood-clad ceilings, exposed beams, expansive windows and a striking stone fireplace create a dramatic yet inviting great room filled with natural light. The open layout flows into a spacious gourmet kitchen with abundant cabinetry and prep space, full-size refrigerator and freezer, double ovens and a generous island—equally suited to everyday living or gathering with family and friends. A dedicated media room provides another comfortable place to relax, while geothermal heating and cooling and a hard-wired generator add year-round comfort and peace of mind. A detached four-car garage offers exceptional space for vehicles, storage and more.A substantial auxiliary building adds another dimension to the property, featuring a large finished open area, kitchen, full bath and three-car garage. With room for hobbies, recreation, a studio, workshop or a variety of other uses, the space provides tremendous flexibility to adapt to your needs.Additional features include a charming loft studio, greenhouse, garden areas and abundant water storage. Wooded acreage, natural rock outcroppings, a creek and abundant wildlife create a peaceful setting with room to explore, garden or simply enjoy the natural beauty that surrounds you.Thoughtfully designed, quality built and carefully maintained, this distinctive property combines the space and privacy of a rural setting with convenient access to Ashland, the Rogue Valley and all that Southern Oregon has to offer.

5831 OLD HIGHWAY 99, Ashland
$565,000
3 Beds ⋅ 3 Baths ⋅ 220225252 MLS
Welcome home to this wonderful 3 bedroom 2.5 bath property in the delightful Oak Knoll Neighborhood! Upon arrival, the beautifully landscaped front yard welcomes you in. The main level is perfect for entertaining with an updated kitchen, separate dining room and living room, cozy wood-burning fireplace and family room that looks out over the seasonal creek and oak trees. Upstairs you will find the three bedrooms including the primary suite! With abundant square footage and a large private lot, this home is sure to delight. Recent update include HVAC system in (June 2026) new roof (2025), exterior paint (2025) and Timbertech deck (2024).

775 Oak Knoll Drive, Ashland
$499,000
2 Beds ⋅ 2 Baths ⋅ 220223679 MLS
$16,000 Price Reduction! 1.18 acres in Ashland with Creek & Shop / Renovation Potential. Rare opportunity! Now offered at $499,000. $76,000 below the original $575,000 list price! It's incredibly hard to find acreage this close to town at this price point. This 1974 home offers two bedrooms, two bathrooms plus a dedicated office space and 1,448 sq ft. Features include a large shop, paid irrigation rights, and a flowing creek along the back of the property. Enjoy space with no HOA and room for horses, animals, gardening, hobbies, or expansion. The home requires substantial repairs and updates and is being sold As-Is. Ideal for an investor, contractor, or renovation - minded buyer. Bring your offers- this opportunity won't last long!

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

100 Belle Fiore Lane, Ashland
$26,000,000
220223435 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is for sale 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, a 4-stop elevator, vineyard, 2 bedroom 2500+ sqft carriage house, 4-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 with 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. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

100 Belle Fiore Lane, Ashland
$949,808
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
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 220222210 MLS
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
$899,000
220221479 MLS
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
$695,000
220219785 MLS
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
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
$1,500,000
220218919 MLS
Fully Entitled Waterfront Youth Camp. Set in the mountains above Ashland, Oregon, this 349-acre holding represents a rare convergence of scale, water, privacy, and federally protected surroundings -- with a fully approved youth camp entitlement already in place. Spanning two tax lots, the property offers mature forest, majestic ridgelines, and nearly one mile of year-round Baldy Creek, along with additional frontage on Emigrant Creek. The landscape is a one-of-a-kind experience; it feels expansive and immersive -- a setting defined by natural character rather than nearby development. What sets this offering apart is its direct boundary with the Cascade-Siskiyou National Monument.

2829 Buckhorn Springs Road, Ashland
$230,000
220218615 MLS
Great Recreational Property! 160 acres close to Howard Prairie and Hyatt Lake. Jenny Creek runs on the edge of the property and usually runs year round. Wide open meadows, wooded hillside, diverse terrain, springs and seasonal ponds are a few features of this recreational property. This acreage provides privacy and seclusion for outdoor enthusiasts are looking for. This property does border the Cascade Siskiyou National Monument and the Pacific Crest Trail. There is a 50 gpm well. The property does have deed restriction with regards to the homesite approval. Escape to your own private 160 acre outdoor haven. All off Grid! One of the Sellers is licensed Realtor in the State of Oregon.

Jenny Cr Road, Ashland
$995,000
5 Beds ⋅ 4 Baths ⋅ 220216782 MLS
Available for the first time, 2004-built custom home in Ashland's Strawberry Meadows. This 3,105 sq. ft. 5 bed/4 bath house sits on a private .46-acre lot bordering an oak-lined creek open space. Main level includes double-height entry with skylights, living room with wood-fire insert, dining room, well-planned kitchen with large pantry, and a primary suite with deck. Upper level offers four bedrooms, 3 with walk-in closets, and large family room with balcony overlooking the creek. Versatile layout accommodates expansive family life and home office space. Additional features include a 2-car garage, robust storage, an approx 200 sq ft finished bonus room not included in the square footage, and a generous patio off the dining/kitchen area with perennial gardens enclosed in a custom deer fence. Situated in a Firewise-certified neighborhood near Lithia Park with access to local hiking trails. This private and quiet property offers a rare opportunity for a special home in a coveted setting.

523 Strawberry Lane, Ashland
$1,795,000
4 Beds ⋅ 3 Baths ⋅ 220213243 MLS
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
$480,000
3 Beds ⋅ 3 Baths ⋅ 220212828 MLS
Priced to sell with instant equity - recent appraisal of $600,000 from June 2026! Versatile, spacious, and updated home on private acreage in the Cascade-Siskiyou National Monument - just 14 miles to Ashland. Solid frame construction with strawbale insulated walls, radiant heated floors, double-paned windows, concrete stucco exterior, and metal roof. 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, cooking stove with soapstone surround, family room, powder room, and two-car garage with EV charging. Three upper-level bedrooms including primary with private balcony, two powder rooms with access to soaking tub and tiled shower, plus a loft area with skylights. French doors from exterior to lower shop or office and utility room. High-speed internet via Greensprings Broadband Coop. Inquire for details!

827 Tyler Creek Road, Ashland
$10,775,000
12 Beds ⋅ 10 Baths ⋅ 220210683 MLS
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
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 220209743 MLS
Private tranquility in the treetops 4 min. to downtown Ashland. Views of Lithia Park w/soothing sounds of Ashland Creek flowing. Style meets sophistication on this beautiful architecturally designed home w/over ½ acre. $400K in new updates in the last 2 years. Private gated courtyard entry. Hardwood floors throughout, tile bathrooms floors, over 100 windows to bring in abundant light & cement balconies w/copper railings w/unobstructed views. Many trails close by. New massive artisan river rock wood burning fireplace in great rm. Chef's kitchen w/built in refrigerator, 6 burner gas cook top, dbl ovens, wine refrigerator, granite counters w/lg island. Formal dining & breakfast rm. 3 bdrms + lg office/meditation rm; 2 bdrm en-suites; Primary w/2 walk in closets, quartz counters, glass sinks, steam shower, air jetted tub, water closet & private balcony. 4 car garage, 2nd courtyard patio off entry. Home allows for an abundance of natural light w/vaulted ceilings & skylights.

545 Ashland Creek Drive, Ashland
$230,000
220195695 MLS
Unique Secluded Dream Home in Pompadour Estates: Welcome to a once-in-a-lifetime opportunity to own a one-of-a-kind property in the prestigious Pompadour Estates. This rare and exclusive listing is the only property in the neighborhood that has access to a tranquil creek, offering peace, privacy, and unparalleled natural beauty. Private 88-Foot Bridge: There are approved plans for an 88-foot bridge ensuring that your sanctuary remains untouched and separated from the hustle and bustle. Exclusive Creekfront Location: Nestled alongside the creek, this property is designed to provide serene views and the peaceful, soothing sound of the flowing water. Ideal for those who value privacy, relaxation, and nature. The property comes with all necessary permits, including the bridge permit and home permit, so you can begin building your dream home with peace of mind. Due to its close proximity to the Ashland Airport, this makes it great for airplane owners to store their aircraft.

141 Majestic Lane, 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: