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4567 Old Highway 99 S, Ashland
$1,175,000
5 Beds ⋅ 3 Baths ⋅ 220224554 MLS ⋅ 4,918 SqFt. ⋅ 219,106 Sqft. Lot ⋅ 5.03 Acres
One of a kind Southern Oregon retreat just 15 minutes from downtown Ashland, offering privacy, exceptional craftsmanship, sweeping views & proven income in a peaceful park like setting. A true money maker, the fully permitted first floor 2 bedroom/ 1 bath ADU currently operates as a successful Airbnb, generating approximately $25,000 a year in net income, per seller. The custom one owner main home features soaring ceilings, walls of windows framing Emigrant Lake and Grizzly Peak, a dramatic curved staircase, custom pine log accents, hardwood floors, granite and travertine finishes, floor to ceiling fireplace, kitchen with breakfast nook, third floor bonus wing & over 1,900 sq. ft. of wraparound cedar decking. Also includes workshop, playhouse and covered carport. The Airbnb has its own private driveway and entrance, ADA access, kitchenette with granite counters and a custom bath, ideal for rental income, guests or multigenerational living.

4567 Old Highway 99 S, Ashland

1509 Woodland Drive, Ashland
$850,000
4 Beds ⋅ 3 Baths ⋅ 220224544 MLS ⋅ 2,712 SqFt. ⋅ 12,196 Sqft. Lot ⋅ 0.28 Acres
Professionally designed & extensively remodeled, with construction completed by Agakhanov Homes in 2022, this stunning 4BR/3BA, 2,712 SF home offers sweeping Grizzly Peak views & thoughtfully curated living spaces throughout. Vaulted ceilings, expansive windows & a dramatic floor-to-ceiling wood-burning fireplace anchor the open-concept great room, where the family room, dining area & designer kitchen create an ideal space for entertaining. Step outside to the spacious view deck & enjoy the breathtaking Grizzly Peak views. The main level features a primary suite with ensuite bath, 2 additional bedrooms & a full bath. Downstairs offers a 4th bedroom, full bath, laundry area, family/bonus room with access to the lower deck & backyard, plus a dedicated home gym or flexible space for an office, studio or hobby room. Conveniently located near shopping, restaurants, parks & schools.

1509 Woodland Drive, Ashland

492 Herbert Street, Ashland
$560,000
3 Beds ⋅ 2 Baths ⋅ 220224331 MLS ⋅ 1,418 SqFt. ⋅ 6,534 Sqft. Lot ⋅ 0.15 Acres
Charming and tastefully updated 1965 Ashland bungalow with exceptional curb appeal. Thoughtful improvements throughout include new flooring, fresh interior paint, and a beautifully remodeled primary suite featuring a spacious walk-in closet and updated bathroom. The inviting living room showcases a striking wood-burning ,rock fireplace creating a warm and welcoming gathering space. The kitchen has been refreshed with new hardware and charming beadboard wainscoting, blending character and functionality. Outside, the backyard is a true standout with newly terraced landscaping, retaining walls, and raised garden beds designed for both beauty and function. Enjoy relaxing or entertaining on the private patio, the perfect spot for morning coffee or an evening beverage. Conveniently located near hiking trails, a park and Ashland's outdoor recreation opportunities, this move-in ready home combines classic character with modern updates in a desirable setting.

492 Herbert Street, Ashland

225 Grandview Drive, Ashland
$1,700,000
4 Beds ⋅ 5 Baths ⋅ 220224430 MLS ⋅ 4,234 SqFt. ⋅ 28,749 Sqft. Lot ⋅ 0.66 Acres
Rarely does a property of this caliber come to market. Completed in 2016 by Steve Asher, this custom Earth Advantage Platinum view home offers 4 bedrooms, 4.5 baths, and 4,234 sf of total living, including a 3,537 sf main house and a detached 697 sf guest studio, half a mile from downtown Ashland. A wall of glass frames unobstructed views of Grizzly Peak. The main level is anchored by a gourmet kitchen with a Gen-Aire double oven, cooktop, and granite island, flowing into a living room with gas fireplace and bar, plus an office, half-bath, and primary suite featuring a soaking tub, spa shower, and walk-in closet. A mudroom opens onto the patio and grilling area, steps from the guest studio with its own entrance and kitchenette. Downstairs, the main house offers a second living room with wet bar, gas stove, and outdoor jacuzzi tub, two en-suite guest rooms, and a flex room (not included in sf). Direct access to the Ditch Trail and Strawberry-Hald Park rounds out this turnkey offering.

225 Grandview Drive, Ashland

345 Fair Oaks Avenue, Ashland
$657,000
4 Beds ⋅ 3 Baths ⋅ 220222972 MLS ⋅ 2,170 SqFt. ⋅ 4,791 Sqft. Lot ⋅ 0.11 Acres
Built in 2007, this inviting 4 bedroom, 2.5 bath home offers 2,170 SF of thoughtfully designed space with beautiful mountain views. Main-level living room showcases Brazilian cherry floors, exposed beams, and a gas fireplace that opens to the deck. The kitchen features granite countertops, stainless steel appliances, custom cherry cabinetry, a full butler's pantry, and an adjacent dining area perfect for gatherings. A spacious primary suite includes a sitting area, walk-in closet and generous bathroom. Complemented by a separate laundry room and convenient half bath. Upstairs, three large bedrooms and a full bath provide excellent separation of space. Lush landscaping, gated yard and generous deck create an ideal outdoor area. With solid wood doors, mixed carpet, hardwood and tile flooring, and a central vacuum system, this home blends luxury, comfort & craftsmanship in a coveted Ashland location near Kestrel Park, Bear Creek, and nearby trails.

345 Fair Oaks Avenue, Ashland

1700 Tyler Creek Road, Ashland
$725,000
2 Beds ⋅ 1 Baths ⋅ 220224351 MLS ⋅ 1,864 SqFt. ⋅ 319,730 Sqft. Lot ⋅ 7.34 Acres
OWNER CARRY AVAILABLE.Experience the Southern Oregon lifestyle on 7.34 acres of mostly level, park-like land bordering BLM. This custom passive solar home features hardwood floors, an open floor plan, a finished basement ideal for guests or a studio, and a unique third-floor office with elevated views. Built in 2016, the insulated 3,400 sq ft shop features Hardie siding, 220 power, a 10-ft roll-up door, 1,000 sq ft loft, ductless mini-split heating and cooling upstairs, custom trim, tongue-and-groove ceilings, and a wraparound driveway. A detached cabin with power has a remodeled Hardie exterior. Extensive fire mitigation creates a beautiful park-like setting with defensible space, complemented by 6,000 gallons of water storage. Just 10 minutes to Emigrant Lake and 20 minutes to downtown Ashland. See attached upgrades list.

1700 Tyler Creek Road, Ashland

425 Merrill Circle, Ashland
$869,000
4 Beds ⋅ 3 Baths ⋅ 220224308 MLS ⋅ 2,553 SqFt. ⋅ 10,454 Sqft. Lot ⋅ 0.24 Acres
This stunner has incredible views from the kitchen, which has granite counters, high-end appliances, and walks out to the deck to enjoy the view or entertain. Not only does this home have 4 bedrooms, but it also has an office as well as a den/media room! High-end finishes throughout, including hardwood everywhere, sconces with lighting to display artwork, a built-in entertainment center and bookshelves. The split two-car garage has tons of storage, as well as two separate workshop areas! The yard is fully fenced with mature Japanese maples, big bushes for privacy, and even a small synth-lawn for a dog. Solar array offsets a major portion of the monthly electric bills! The small HOA for this quiet cul-de-sac is only $880/year.

425 Merrill Circle, Ashland

430 Wiley Street, Ashland
$610,000
3 Beds ⋅ 3 Baths ⋅ 220224225 MLS ⋅ 1,860 SqFt. ⋅ 12,632 Sqft. Lot ⋅ 0.29 Acres
Charming custom home with panoramic mountain views on a spacious and private 0.29-acre flag lot located above the boulevard within six minutes of Ashland's downtown plaza. All new low-pile berber wool carpets and fresh interior paint in 2026, new central AC system in 2019, and new roof c. 2016. Main level with solid oak hardwood floors, living room with bay window and gas fireplace, formal dining with French door to concrete paver patio with fire pit, kitchen with tiled counters and backsplash, powder room, laundry closet, and two-car garage with extensive built-in storage cabinets. Versatile upper level with two guest bedrooms, a very spacious primary suite with private office or nursery, two full ensuite bathrooms, and three sets of French doors to the backyard. Abundant natural light with Eastern exposure - dormer windows throughout. Established trees and hedges, mature plantings, and grass lawns with automated drip and sprinkler irrigation. Inquire for details!

430 Wiley Street, Ashland

155 Westwood Street, Ashland
$712,500
4 Beds ⋅ 4 Baths ⋅ 220224216 MLS ⋅ 3,438 SqFt. ⋅ 25,264 Sqft. Lot ⋅ 0.58 Acres
Nestled in the highly desirable southwest hills of Ashland, Oregon. This is an incredible opportunity w/ so much potential for the next owner to enjoy and make their own. The contemporary ranch-style main home features over 2,600 sq. ft., 3 bedrooms, 3 bathrooms, soaring wood-vaulted ceilings, an open floor plan, abundant windows, skylights, and beautiful natural light. A charming 800 sq. ft. cottage-style ADU (built in 2003) includes its own address, metered separately, private patio, and garden making it ideal for guests, rental income, or multi-generational living. The detached three-car garage includes a studio space with a bathroom. Additional amenities include a screened sleeping deck, greenhouse, storage sheds, and firewood storage. There is an owned solar panel system and solar hot water heater for high efficiency and keeping low carbon print. This one-of-a-kind property is a gardener's dream and a rare opportunity to create your own private retreat.

155 Westwood Street, Ashland

565 Altamont Street, Ashland
$755,000
3 Beds ⋅ 2 Baths ⋅ 220224162 MLS ⋅ 1,647 SqFt. ⋅ 7,405 Sqft. Lot ⋅ 0.17 Acres
Located in one of Ashland's most sought-after neighborhoods less than a mile from downtown, this beautifully updated single-level home offers 3 bedrooms, 2 full bathrooms, and nearly 1,700 square feet of thoughtfully designed living space on a .17-acre corner lot. A studs-out remodel completed in 2018 brought modern style and quality updates throughout. Oak hardwood flooring extends through the main living areas, while both bathrooms feature tile flooring and contemporary finishes. The primary suite includes an ensuite bath with a tiled walk-in shower. Expansive living room windows frame Cascade Mountain views. Enjoy the scenery from the view deck or relax among meticulously maintained grounds with a tranquil water feature. Owned solar adds efficiency and value. Move-in ready and ideally located near downtown Ashland, parks, dining, and shopping. Tour today!

565 Altamont Street, Ashland

426 Parkside Drive, Ashland
$565,000
3 Beds ⋅ 2 Baths ⋅ 220223926 MLS ⋅ 1,538 SqFt. ⋅ 6,534 Sqft. Lot ⋅ 0.15 Acres
Welcome to this wonderful Craftsman-style home in one of Ashland's most desirable neighborhoods, complete with its own charming neighborhood park. A spacious covered front porch sets an inviting tone from the moment you arrive. Once inside, natural light fills the home through custom windows and skylights, creating a warm and welcoming atmosphere throughout. The floor plan offers a formal dining room plus an open-concept kitchen and living area, ideal for both everyday living and entertaining. The kitchen features a gas range and generous counter space, while the living room centers around a cozy gas fireplace and access to the backyard. The expansive primary suite includes skylights, a large walk-in closet, and direct backyard access. Outside, enjoy one of the larger yards in the neighborhood, featuring a flower garden, two patios and a lovely lawn area perfect for relaxing, gardening, or gathering with friends.

426 Parkside Drive, Ashland

953 Spring Way, Ashland
$650,000
4 Beds ⋅ 3 Baths ⋅ 220224018 MLS ⋅ 2,062 SqFt. ⋅ 4,791 Sqft. Lot ⋅ 0.11 Acres
Nicely upgraded and well-maintained view home with thoughtfully curated interior finishes located on a corner lot directly across from Hamilton Creek greenspace. New roof, siding, HVAC, designer lighting, flush-mounted LEDs, water heater, updated fixtures and hardware, and fresh interior paint throughout within the last three years. Main level with solid oak floors, vaulted living area with gas fireplace, kitchen with new stainless steel refrigerator and sink, gas range with new built-in hood, covered back deck and front patio, two bedrooms with closets, full bathroom with shower, laundry room with utility sink, and two-car garage. Upper level with vaulted primary suite, private covered view balcony, full ensuite bathroom with double vanity and curbless tiled shower, fourth bedroom with closet, and third full bathroom with tub shower. Small association maintains common area landscaping. Inquire for details!

953 Spring Way, Ashland

590 Taylor Street, Ashland
$695,000
2 Beds ⋅ 3 Baths ⋅ 220223937 MLS ⋅ 2,172 SqFt. ⋅ 11,325 Sqft. Lot ⋅ 0.26 Acres
Beautifully Maintained Custom Ashland View Home! This property offers a blend of distinctive architecture and serene privacy with custom windows and natural beauty throughout. Step-down living room with gas fireplace, dining room has built-in shelving; house has engineered hardwood flooring and carpeted bedrooms; kitchen has newer 36'' gas range and built-in desk. Spacious ground-floor master bedroom, separate office that could be used as a guest bedroom, second upstairs bedroom, plus upstairs laundry room. View decks for indoor-outdoor living, mature landscaping and peaceful setting that includes patio, firepit, walking paths and fully fenced backyard. Quality upgrades include Karastan wool carpeting, newer roof, high-efficiency 2-stage HVAC, fresh interior paint, oversized garage with workshop/bonus area, central vac, 220v for EV charging and great storage throughout. Lovely hillside home on a quiet cul-de-sac just minutes from downtown with EZ access to Ashland's trail system.

590 Taylor Street, Ashland

1423 E Main Street, Ashland
$505,000
3 Beds ⋅ 2 Baths ⋅ 220223843 MLS ⋅ 1,576 SqFt. ⋅ 8,712 Sqft. Lot ⋅ 0.2 Acres
Charming Ashland home tucked behind a solar-powered privacy gate + fully fenced front & back yard. Solar panels, double paned windows, zoned AC, hardwired internet, analog electric meter & new water heater. Stunning hardwood floors in the living room, highlighted by a beautiful brick mantle that adds character to the space. The galley-style kitchen features a gas range, tile backsplash, tile flooring, reverse osmosis system at the sink, & located adjacent to the dining area w/ a cozy wood stove. Primary suite w/ heated floor in the ensuite bath + a tile shower. Oversized covered back deck overlooking the backyard & bonus guest quarters/office space. Additional features include mature landscaping, well (buyer to do their own due diligence), organic garden, oversized 2-car garage w/ workshop space +220 voltage, and a large driveway with abundant parking, including room for an RV. This is a property you truly must see to appreciate, ideally situated in a prime close to downtown location.

1423 E Main Street, Ashland

307 N Main Street, Ashland
$749,000
3 Beds ⋅ 2 Baths ⋅ 220223795 MLS ⋅ 1,847 SqFt. ⋅ 10,454 Sqft. Lot ⋅ 0.24 Acres
Vintage Craftsman with an exceptional location, just five easy blocks from the Ashland Plaza and Lithia Park. Welcoming covered front porch entry is just an example of the many period details of the original portion of the home. The living and dining area includes many light capturing windows, beautiful wide moldings, vintage tile surround gas fireplace, solid wood flooring, antique light fixtures and a wall of built-ins that encase a lovely stained-glass window and built-in hutch. Cheerful kitchen has black and white tiled flooring and a cozy breakfast nook. Current owners added a spacious ''lock off'' primary suite that was perfectly integrated to fit the overall feel of the home. R-2 zoning has allowed for a live/ work use and provides so much versatility depending on one's needs. Lovely, paved patio and mature landscaping compliment the overall picture. Plenty of storage between the basement and detached single car garage. This is a great opportunity for the next owner to enjoy.

307 N Main Street, Ashland

565 Henley Way, Ashland
$621,000
3 Beds ⋅ 2 Baths ⋅ 220223772 MLS ⋅ 2,009 SqFt. ⋅ 13,939 Sqft. Lot ⋅ 0.32 Acres
Tucked in a private cul-de-sac, this thoughtful home offers character & beautiful views of the surrounding hills, on a third-acre lot near hiking trails & convenient access to town. Custom hand-crafted cherry cabinetry, bamboo and hickory hardwood floors create an inviting atmosphere. High ceilings, tall windows & fireplace anchor the spacious living room, while the split-level layout adds flexibility with a lofted reading nook, dedicated office w/ French doors, & an open kitchen. Designed for both everyday living & entertaining, the kitchen features Corian countertops, brand-new fridge, soft-close cabinetry. Primary suite opens to a private balcony. Outside, enjoy the pool, hot tub, multiple decks, and plenty of space to gather or take in the views. Well maintained w/ numerous system updates, including HVAC, furnace, service panel, and vinyl double-pane windows. Bonus attic storage room & RV parking available. A welcoming home filled with craftsmanship, comfort & space to relax.

565 Henley Way, Ashland

624 Crowson Road, Ashland
$475,000
2 Beds ⋅ 2 Baths ⋅ 220223679 MLS ⋅ 1,448 SqFt. ⋅ 49,658 Sqft. Lot ⋅ 1.14 Acres
NEW PRICE- $475,000, a $24,000 price reduction! 1.18 ACRES WITH CREEK, SHOP, and EASY I-5 access! It's hard to find this much land this close to Ashland at this price! This 1974 home offers two bedrooms, two bathrooms, a dedicated office and 1448 ft.² along with a large shop, paid irrigation rights, and a flowing creek along the lower back of the property. Enjoy room for horses, animals, gardening, hobbies, or future possibilities, with no neighbors directly behind. The home offers a great foundation for someone looking to update and make it their own. Conveniently located just minutes from I-5, approximately 10 minutes to the plaza, with a golf course at the end of the street. Bring your vision, your contractor, and your offers. This special piece of Ashland is ready for its next chapter!

624 Crowson Road, Ashland

162 Crocker Street, Ashland
$375,000
3 Beds ⋅ 3 Baths ⋅ 220223627 MLS ⋅ 1,361 SqFt. ⋅ 1,742 Sqft. Lot ⋅ 0.04 Acres
Tucked into the desirable Chautauqua Trace neighborhood in Ashland, this well-maintained home was made for indoor-outdoor living. The real showstopper is the spacious private deck, accessed right off the dining area through a sliding glass door, creating an effortless flow from kitchen to open air. Picture slow morning coffee, summer dinners under the sky, and easy evenings hosting the people you love, all in your own peaceful retreat. Inside, easy-care laminate flooring runs throughout the main level, and the home offers three bedrooms and two and a half bathrooms with tiled baths that add both style and durability. The kitchen keeps everything within reach thanks to a large pantry. Beyond your doorstep, walking paths and open space invite you outside, while shopping and the YMCA sit just minutes away. Come experience it in person and picture yourself settling in.

162 Crocker Street, Ashland

143 Granite Street, Ashland
$789,000
5 Beds ⋅ 2 Baths ⋅ 220223588 MLS ⋅ 1,935 SqFt. ⋅ 13,939 Sqft. Lot ⋅ 0.32 Acres
Offered for the first time in generations, this extraordinary fourth-generation Ashland treasure presents a rare opportunity. Own a piece of local history just steps away from world-renowned Lithia Park. This timeless two-story residence sits on beautifully landscaped .32 acre lot. It offers 5 bedrooms, 2 bathrooms, and a character that cannot be replicated. This home is rich in charm and architectural detail. It showcases the craftsmanship of a bygone era, while providing ample space for modern living. Enjoy peaceful mornings on the porch, stroll through Lithia Park, and easy access to downtown Ashland's theaters, galleries, restaurants, and cultural attractions. Homes of this caliber, location, and historical significance seldom become available. This is a once-in-a-generation opportunity to continue the legacy of one of Ashland's cherished homes.

143 Granite Street, Ashland

45 Brooks Lane, Ashland
$495,000
3 Beds ⋅ 3 Baths ⋅ 220223487 MLS ⋅ 1,638 SqFt. ⋅ 3,920 Sqft. Lot ⋅ 0.09 Acres
Beautifully maintained detached home featuring 3 bedrooms, 2.5 baths, and a 2-car garage. The open-concept floor plan includes a main-level primary suite with an oversized closet, sliding-door access to the backyard, and peaceful greenbelt views. Upstairs, two generously sized bedrooms share a full bath and enjoy picturesque scenery. The kitchen offers quartz countertops, a gas range, abundant cabinetry, and a pantry, with convenient access to the laundry area. The dining room is filled with natural light from large windows that frame stunning mountain views and the beautifully landscaped backyard. Outdoor amenities include a garden, patio, and additional parking. Situated alongside a riparian area ideal for birdwatching, this home also features numerous upgrades, including crown molding, a 2022 roof, a newer heat pump providing efficient heating and cooling, and a hybrid water heater.

45 Brooks Lane, Ashland

1100 Beswick Way, Ashland
$665,000
4 Beds ⋅ 3 Baths ⋅ 220223464 MLS ⋅ 2,268 SqFt. ⋅ 13,068 Sqft. Lot ⋅ 0.3 Acres
Step into this beautifully designed 4-bedroom, 2.5-bathroom home offering the perfect blend of modern comfort and natural serenity. Boasting 2,268 square feet of thoughtfully planned living space, this property is situated on a premier 0.3-acre fenced corner lot in an exceptionally quiet, private neighborhood. From the moment you walk through the front door, you'll be greeted by expansive vaulted ceilings and large windows that flood the home with bright, natural light. The open-concept feel creates an inviting atmosphere perfect for both lively entertaining and cozy family nights. The master bedroom with ensuite bath are upstairs, as is the 1/2 bath. Downstairs features 3 bedrooms, a bathroom, and a tv area with a sliding door to the back yard which is spacious for a corner lot. This thoughtfully landscaped fenced yard features a variety of mature fruit trees, flowers, and plants. There is also TID. All of this and less than a 10-minute walk from the Oredson-Todd trailhead.

1100 Beswick Way, Ashland

75 Dewey Street, Ashland
$500,000
2 Beds ⋅ 1 Baths ⋅ 220223449 MLS ⋅ 1,326 SqFt. ⋅ 6,098 Sqft. Lot ⋅ 0.14 Acres
First time on the market in 30 years, this super sweet cottage in the historic Siskiyou-Hargadine district is full of charm and artistic character. This thoughtfully designed 2 bedroom, 1 bath home offers approximately 1,326 sq ft of light-filled living space with an open feel, vaulted ceilings, and abundant natural light throughout. Recent updates include a beautifully remodeled kitchen and bathroom in 2025, along with a new roof in 2026. The home features inviting sitting, living, and dining areas, plus an attached studio/office with a separate entrance -- perfect for creative space or home office. The fully deer-fenced, pet-secure yard was completed in 2026 and includes mature landscaping, a peaceful water feature, sitting deck, and gazebo ready for a hot tub. Additional highlights include 2 off-street parking spaces and 3 custom utility sheds for storage or gardening needs.

75 Dewey Street, Ashland

200 Belle Fiore Lane, Ashland
$12,000,000
7 Beds ⋅ 19 Baths ⋅ 220223437 MLS ⋅ 19,908 SqFt. ⋅ 773,190 Sqft. Lot ⋅ 17.75 Acres
Chateau at Belle Fiore is one of Oregon's most extraordinary estates. Spanning over 17,400 sqft across 4 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 17+ acres, including 12+ 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, 4-car garage, prep kitchen, and grand gathering spaces complete this iconic estate. Business assets and inventory available, subject to applicable licensing and regulatory requirements.

200 Belle Fiore Lane, Ashland

200 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 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.

200 Belle Fiore Lane, Ashland

22494 Jefferson Road, 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

457 Walnut Street, Ashland
$650,000
3 Beds ⋅ 4 Baths ⋅ 220223382 MLS ⋅ 2,606 SqFt. ⋅ 14,374 Sqft. Lot ⋅ 0.33 Acres
Enjoy exceptional privacy and beautiful views in this single-family retreat, nestled on a tree-lined 0.33-acre lot in one of Ashland's most desirable neighborhoods. A welcoming front deck leads to the 2,270 sq ft home featuring 3 bedrooms and 3 full bathrooms. The grand living room showcases expansive windows framing stunning trees, the valley and mountain views. The rear deck overlooks a professionally designed/built backyard with a charming gazebo. A versatile 336 sq ft house addition featuring a private half bath and a valley-view picture window is ideal for guests, a home office, or multi-generational living. The oversized 2-car garage provides ample storage and workspace. The garage backdoor leads to a custom Catio porch... Despite its peaceful and secluded setting, this home is conveniently located just minutes from downtown, the hospital, and Lithia Park, offering the perfect combination of tranquility and accessibility.

457 Walnut Street, Ashland

307 Hillcrest Street, Ashland
$750,000
4 Beds ⋅ 4 Baths ⋅ 220223301 MLS ⋅ 3,159 SqFt. ⋅ 7,405 Sqft. Lot ⋅ 0.17 Acres
Custom view home with charming detached guest cottage located just above downtown between Lithia Park and the Ashland Public Library. Main level great room with vaulted double-height ceiling, walls of windows, reclaimed clear-grain fir trim, solid-core doors, refinished oak floors, kitchen with composite dining bar, tile counters and backsplash, cabinets with solid wood interiors and custom pull-outs, dining room with glass door to view deck with gas BBQ hookup, bedroom with closet and full ensuite bath, and pantry with washer and dryer. Upper level primary with skylights, hanging closet, French doors to private balcony, and full ensuite bath with jetted tub. Versatile lower guest suite or family room with French doors to paver patio, full bathroom with oversized shower, storage cellar with stainless utility sink, and one-car garage. Detached cottage with permitted kitchen, living area, full bathroom, loft bedroom, and private gated entrance from Terrace Street. Inquire for details!

307 Hillcrest Street, Ashland

117 High Street, Ashland
$850,000
3 Beds ⋅ 2 Baths ⋅ 220223214 MLS ⋅ 2,499 SqFt. ⋅ 6,534 Sqft. Lot ⋅ 0.15 Acres
Located in the heart of downtown Ashland, just two blocks from the plaza, this idyllic, recently renovated Victorian home offers classic Victorian curb appeal with modern upgrades throughout the home. A brand-new remodeled kitchen is finished with quartz countertops, solid wood cabinets, and stainless-steel appliances. An open-concept floor plan and an ample family room provide endless potential for families and entertaining. Step outside to the elegant hardscape patio with a covered gazebo, granite countertop, and outdoor cooking area, complete with an outdoor beverage refrigerator, designed for an immersive outdoor living experience. Upstairs, the ample master bedroom with wall-to-wall closet space is adjacent to a second den/reading nook. Step outside onto the spacious rooftop sun porch with views of Mt Ashland and the gorgeous mature landscaping below. The property also includes a detached finished shop/studio space with a sleeping loft, alley access and private parking.

117 High Street, Ashland

2334 Black Oak Way, Ashland
$690,000
3 Beds ⋅ 2 Baths ⋅ 220223188 MLS ⋅ 2,122 SqFt. ⋅ 12,632 Sqft. Lot ⋅ 0.29 Acres
This well-maintained single-level home rests on a generous 0.29-acre corner lot with a large fenced backyard, mature trees (including fruit trees), lush landscaping, and a TID sprinkler system for easy care. The private primary suite is a standout retreat featuring vaulted ceilings, skylights, sliding doors to the backyard, an ensuite bathroom with jetted soaking tub and tiled shower, a spacious walk-in closet with built-ins, and a bonus office space. Inside, enjoy an open-concept great room with a wood-burning fireplace, a spacious kitchen with breakfast bar and gas range, and a dining area that opens to the rear patio. Hardwood and tile floors flow throughout the home. The hallway offers two additional bedrooms, a full bath with tub/shower, a large office or media room with French doors, and a convenient laundry room. A 2-car attached garage provides additional storage and parking.

2334 Black Oak Way, Ashland

11871 Highway 66, Ashland
$775,000
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

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:

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