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$649,000
3 Beds 2 Baths 220225730 MLS
Set back from the street on a flag lot, this lovely home offers a quiet and private retreat, bordering open space and Ashland Creek. Conveniently located a short distance from downtown Ashland, the trailhead to the Bear Creek Greenway and Lithia Park, the property combines a natural, scenic setting with easy access to local amenities. The main living and dining areas feature large windows that capture natural light and frame peaceful outdoor views. A sliding glass door opens to a large back deck, well-suited for enjoying the mountain views and entertaining. There is a nice separation of space with the three bedrooms sitting away from the living area. A daylight 500 sf basement (not included in square footage), with mini split heating and cooling, offers many options for overflow guests, art studio, media room or home office. With a unique balance of privacy, creek-side borders and proximity to Ashland's central attractions, this home is a fantastic opportunity.

1111 Oak Street, Ashland

$564,900
3 Beds 2 Baths 220225550 MLS
'One Property. Four Possibilities. Less than a mile from downtown Ashland, this classic Victorian offers exceptional flexibility with versatile zoning and mountain views. Enjoy it as a spacious 3-bedroom, 2-bath home, a duplex with two long-term rental units, a residence with a currently licensed short-term rental, or a live/work property with a private entrance ideal for an attorney, counselor, massage therapist, or other home-based business. Features include a spacious upstairs primary suite with full bath, basement storage, dry sauna, washer, dryer, refrigerator, an inviting patio, and three deeded off-street parking spaces. Historic charm meets modern opportunity in this truly one-of-a-kind Ashland property.'

508 N Main Street, Ashland

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

1249 N Valley View Road, Ashland

$1,200,000
220224634 MLS
Rare Ashland investment opportunity, three modern townhomes built in 2016, each on its own separate tax lot, offered together as a package. Every unit is a spacious 3-bedroom, 2-full-bath, a hard-to-find configuration in the local rental market. Unit 1173 offers 1,280 sf and a two-car garage, while 1169 and 1171 each offer 1,188 sf and a one-car garage. Turnkey interiors feature stainless steel appliances, warm shaker cabinetry, and 100% solid surface flooring, no carpet anywhere. Current rents total $6,605/month with near-zero vacancy since construction, a track record of dependable income that speaks for itself. Individual tax lots offer long-term flexibility that is rarely found in multi-unit properties. Ideal for the investor seeking newer, low-maintenance construction, or an owner-occupant living in one unit while the other two help pay the mortgage. Close to SOU, downtown, and everyday amenities. Not to be sold separately.

1169 Iowa Street, Ashland

$1,700,000
4 Beds 5 Baths 220224430 MLS
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

$14,000,000
220223436 MLS
Offered for sale for the first time ever, Belle Fiore Estate Winery is a premier Southern Oregon winery and event destination situated on 51+ acres, including 37+ irrigated acres and an established vineyard with 14 grape varieties. The estate encompasses more than 27,000 square feet and features multiple tasting rooms, a ceremonial barrel room, elegant ballroom, full-service restaurant, expansive terraces, and outdoor dining areas overlooking the vineyard and valley. The production facility is designed for commercial-scale operations with eight barrel-storage bays, refrigerated wine storage, soaring ceilings, and extensive infrastructure. Hosting more than 50,000 visitors annually, Belle Fiore is a recognized destination for wine tourism, weddings, corporate retreats, and private events. The combination of established vineyard production, hospitality operations, event revenue, and significant growth potential creates a rare opportunity to acquire Oregon's most significant vineyard esta

100 Belle Fiore Lane, Ashland

$12,000,000
7 Beds 19 Baths 220223437 MLS
Offered for sale for the first time ever, Chateau at Belle Fiore Estate Winery is one of Oregon's most extraordinary residential estates. Spanning over 17,400 sqft across four levels, this French-inspired masterpiece offers 7 bedrooms, 19 bathrooms, and exceptional craftsmanship throughout. An elevator services all floors, including an 8,000 sqft lower level with a wine room, game room, gentleman's lounge, multiple wine bars, and expansive entertaining spaces. Premium finishes include custom cumaru flooring, granite surfaces, and intricate architectural detailing. Set on over 17 acres, including 12.1 irrigated acres and a producing vineyard, the estate is ideal for private enjoyment, weddings, retreats, and special events. Exterior features include hand-chiseled golden granite, a hand-cut slate roof, custom copper gutters, dormers, and downspouts. A 2,500+ sqft carriage house, four-car garage, prep kitchen, and grand gathering spaces complete this iconic Southern Oregon estate.

200 Belle Fiore Lane, Ashland

$26,000,000
220223435 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is being offered for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,800 sqft; it has four levels, 5 bedrooms, 19 bathrooms, elevator service, a vineyard, a 2 bedroom 2500+ sqft carriage house, four-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard featuring 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights, a priceless feature of this one of one opportunity to own Oregon's most significant vineyard estate.

100 Belle Fiore Lane, Ashland

$26,000,000
7 Beds 19 Baths 220223434 MLS
Belle Fiore Estate Winery and Chateau is Oregon's most extraordinary vineyard estate and is being offered for the first time ever. The French-inspired Chateau is one of the largest homes in Oregon, spanning over 17,400+ sqft; it has four levels, 5 bedrooms, 19 bathrooms, elevator service, a vineyard, a 2 bedroom 2500+ sqft carriage house, four-car garage, resort style pool, hand-cut slate roof, custom copper detailing, and one of a kind craftsmanship throughout. ~ Separately, the Winery features a 32-acre vineyard featuring 14 distinguished grape varietals. The 27,000+ sqft Italian basilica-inspired facility includes tasting rooms, a ceremonial barrel room, ballroom, restaurant, outdoor dining areas, panoramic views of the Rogue Valley, and a commercial production facility with extensive refrigerated wine storage. Set on nearly 70 acres, this offering includes 49+ acres of water rights, a priceless feature of this one of one opportunity to own Oregon's most significant vineyard estate.

200 Belle Fiore Lane, Ashland

$419,000
3 Beds 3 Baths 220222380 MLS
Exceptional end-unit townhome less than 1 mile from Southern Oregon University! Originally built as the developer's personal residence, this thoughtfully designed home offers approximately 30% more living space than other units in the community. Inside, you'll find rich Brazilian cherry hardwood floors, elegant Italian mosaic tile accents, new interior paint, and stainless-steel kitchen appliances. The spacious kitchen features granite countertops, abundant cabinetry, and a walk-in pantry, opening to a comfortable living area with a gas stove. The main level also includes a half bath, laundry area, and access to a private fenced patio with additional storage. Upstairs, the generous primary suite captures beautiful mountain views and offers a spa-inspired bath with dual sinks, soaking tub, walk-in shower, and two closets. A detached garage, deeded parking space, community pool, exterior maintenance, and landscaped common areas complete this outstanding property.

820 Park Street, Ashland

$679,900
3 Beds 3 Baths 220222330 MLS
Lovely Ashland View Home above the boulevard, ideally situated close to downtown, the Oregon Shakespeare Festival and Lithia Park. This beautifully maintained 2,043 square foot stand-alone home offers a great floor plan, 3 bedrooms, 2.5 baths, hardwood and tile flooring throughout the main living spaces, all complemented by a cozy gas fireplace and abundant natural light. The kitchen and baths feature granite tile counters, nice cabinetry and quality finishes, along with custom window coverings throughout. The upper-level primary suite is quite spacious with vaulted ceilings, walk-in closet, private view deck, and an ensuite bath with a relaxing jetted tub. Enjoy the covered front porch and a charming back deck overlooking the private fenced backyard with a slate patio, mountain views, crawling vines, and mature plantings--perfect for low-maintenance outdoor living. Single garage, small monthly HOA fee. This is a wonderful spot to call HOME.

472 Scenic Drive, Ashland

$965,000
7 Beds 5 Baths 220222015 MLS
Rare opportunity to own 2 residences plus a studio on one tax lot. Offers exceptional flexibility for multigenerational living, rental income, live-work, or guest accommodations. The 1,720 SF main residence was fully renovated in 2018, including a new poured foundation, and has 4 bedrooms, 2 baths, open living spaces, a kitchen with crisp white cabinets, subway tile backsplash & a main level bedroom. The main residence includes a double garage with a 480 SF upper-level studio with a full bath. A separate second 1,070 SF residence, built in 2018, offers stylish & charming single-level living with high ceilings, 2 bedrooms, 2 baths, & contemporary finishes. Situated in an established historic neighborhood with mature trees, the property has off-street parking, modern systems, and is close to Ashland's downtown. This R-2-zoned property features separate addresses & meters & allows for 2 Airbnb units with owner occupancy on premises. Request property offering details.

563 Rock Street, Ashland

$2,500,000
5 Beds 7 Baths 220220624 MLS
Discover this extraordinary Southern Oregon Luxury 2 acre estate perched above downtown Ashland w/views & incredible privacy. This custom built Pagnini home 5313 SQ FT, 5 bdrms, 5.5 bthms, 5 Car Garage + an additional 720 sq ft detached guest quarters. Grand entry, stunning wood floors, soaring ceilings, multiple fireplaces & walls of windows to take in the incredible views & abundant natural light. Gourmet kitchen w/quartz countertops, skylights & SS appliances w/double ovens. Main level primary suite w/ terrace access offers a soaking tub & steam shower. 2 upstairs guest suites both come complete w/private balcony & breakfast bar. Additionally this incredible home features a slate roof, sauna, elevator, a spacious office w/ en-suite + so much more. European-style terrace w/big natural boulders, fruit trees, a dog run, greenhouse, and manicured gardens along w/ abundant wildlife- no expense was spared on this remarkable Ashland retreat & it truly shows

500 Ashland Loop Road, Ashland

$393,000
3 Beds 3 Baths 220220980 MLS
Stylish turn-key condominium with an excellent central location in beautiful Ashland, OR. Welcoming entryway sets the tone for a calming vibe from the moment you enter. The main living and dining areas have bamboo flooring. The kitchen has stainless steel appliances and granite countertops including a large center island with breakfast bar. There is a cozy gas fireplace with tile surround and large bay window with views out to the private, fenced patio area. Upstairs there are three bedrooms including a spacious primary bedroom suite with balcony, walk-in closet and tastefully updated bathroom. The two additional bedrooms share a bathroom. Laundry is also on this level. HOA fees cover all exterior maintenance as well as exterior insurance. Location is ideal with proximity to schools, parks, the bike path and a relatively level and short distance to everything downtown Ashland has to offer.

62 N Mountain Avenue, Ashland

$4,500,000
5 Beds 6 Baths 220220674 MLS
Set on 3.48 private acres just 500 ft from Lithia Park and within a 1/2 mile of downtown Ashland, 237 Granite is a rare, legacy estate inspired by the timeless design principles of Greene & Greene Architects. Showcasing over 5,700 sq ft of refined living, this 5-bedroom, 5.5-bath residence embodies the essence of The Arts and Crafts Movement with exceptional craftsmanship, rich walnut flooring throughout, and a seamless connection to its natural surroundings. The grounds are a destination unto themselves--featuring a solar-heated pool, tranquil Japanese gardens with tea house, two waterfalls, a koi pond, and direct access to nearby hiking trails. Main level living w/ 871 sq ft primary wing, private caretaker quarters, and a separate 676 sq ft guest cottage with 1 bed, 1 bath, 2-car garage--offering flexibility for guests or extended living. ''The Gamble House'' of Ashland, this is the largest private estate of its kind in such close proximity to the cultural and natural heart of Ashland.

237 Granite Street, Ashland

$950,000
3 Beds 3 Baths 220220668 MLS
Quality custom view home in a private natural setting above the boulevard, just six minutes to Ashland's downtown plaza. Abundant natural light and airflow with operable wood-wrapped casement windows, high vaulted ceilings, solid core doors, and unique architectural view corridors throughout. Great room with solid Brazilian cherry flooring, gas fireplace, formal dining with built-in buffet, French doors to wrap-around view deck, kitchen with granite dining counter and stainless appliances, open family and informal dining room, powder room, laundry with utility sink, and two-car garage. Step-down primary suite with French doors to private balcony, walk-in closet, full ensuite bathroom with travertine double vanity, jetted tub, shower, and water closet. Upper loft with mountain views and stairwell skylights. Two lower-level guest bedrooms, full bath with tub shower, den, and French doors to pebbled concrete patio and organic garden. Newer HVAC and exterior paint. Inquire for details!

602 Ashland Street, Ashland

$140,000
1 Beds 1 Baths 220219091 MLS
Step into a bright, beautifully cared-for top-floor condominium featuring a vaulted living room ceiling, expansive windows, and a seamless flow that makes the space feel both open and inviting. The well-appointed kitchen offers generous counter space, ample cabinetry, and a cozy dining area. Step outside onto your private balcony--perfect for relaxing evenings and fresh air. The spacious bedroom connects easily to a well-designed bathroom with a low-step shower and built-in linen storage, while a full-size washer and dryer add everyday convenience. Located just moments from the clubhouse and fitness center, with easy elevator access to parking and storage, this home blends accessibility with comfort. Enjoy a vibrant, amenity-rich lifestyle with beautifully maintained grounds, walking paths, gardens, an indoor pool, fitness center, and a welcoming calendar of social events, gatherings, and activities.

943 Mountain Meadows Circle, Ashland

$1,466,000
2 Beds 4 Baths 220218853 MLS
You'll be in a prime spot right in Ashland's Railroad District/Spur Rail Subdivision, a super desirable area! Just hop on the elevator to the top! This place has a fantastic modern design, with 770 square feet of first-floor commercial space and a luxurious 2-story home on the 2nd and 3rd floors. You'll find premium finishes everywhere, a huge rear patio, vaulted ceilings, big windows, an open floor plan, and materials that are easy to take care of, so they last. Plus, the property is set up to get the most out of solar panels. You'll have amazing views of Grizzly Peak to the north and Mt. Ashland to the south--it's truly a dream location. The property is zoned E1 commercial (Ashland Employment District with Residential Overlay). There's a single-car garage, EV charging, and the square footage has grown. The windows have also been upgraded to Milgard Fiberglas;, each parcel comes with a 1/6th interest in the parking lot next door.

138 Clear Creek Drive, Ashland

$379,900
3 Beds 3 Baths 220217759 MLS
Nicely updated 2000-built Ashland townhome, offering 1,388 square feet of comfortable, two-level living. Hardwood floors, a cozy gas fireplace and attractive finishes create a warm, inviting feeling throughout. The well-designed kitchen includes gas range, great cabinetry, good built-in storage, an attached eating area, and an open layout to the living spaces--ideal for relaxed living. The home has three bedrooms, two full baths and convenient powder room with pedestal sink. Enjoy lovely views in this active friendly community, a covered porch with plenty of sitting area, a small front and side garden plots for your plantings, a one-car garage and one separate assigned parking space. The professionally managed HOA offers low dues of just $75 a month. Excellent access to schools, shopping, transit and Ashland's renowned amenities--this well priced property is perfect for a starter home, rental investment, or part-time getaway. Stop by for a look!

827 Blackberry Lane, Ashland

$1,350,000
3 Beds 4 Baths 220217132 MLS
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

$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

$325,000
1 Beds 1 Baths 220215889 MLS
This 1 br/1bath 2nd-floor corner condo greets you w/ sunlight pouring through generous windows, illuminating the inviting finishes that give the space its timeless, easy charm. Its open floor plan unfolds naturally, with the living area flowing into the kitchen with abundant counter space, ample storage, & brand-new appliances waiting to be used for the very first time. You'll love spending your mornings on your private balcony gazing out toward the Cascade Mountains as the light shifts across the peaks. Even workdays feel lighter here, thanks to a dedicated office nook that keeps productivity close to comfort. With its own dedicated laundry area & built-in storage, even the practical parts of life feel organized & beautifully tucked away. Perfectly located minutes from downtown Ashland, the Oregon Shakespeare Festival, shopping, dining, & scenic hiking/ biking trails -- with quick access to I-5 & just 30 minutes north of the California state line -- you're moments from everything!

2205 Ashland Street 210 Unit 210, Ashland

$255,000
2 Beds 2 Baths 220214906 MLS
Nestled within a quiet, well-kept complex, this charming 960 sq ft end-unit condominium, built in 2002, offers a comfortable blend of privacy and convenience. The home features 2 bedrooms and 2 full baths, a generously sized laundry and pantry room, a dedicated dining area, and an inviting living space ideal for everyday living. The kitchen is well appointed with abundant cabinetry for storage, and a stackable washer and dryer are included. The primary bedroom offers a peaceful retreat with an ensuite bath and spacious closet, while a secondary bedroom and full bath provide flexibility for guests, a home office, or creative pursuits. Situated on the second floor with no neighbors above and only one adjoining unit, the condo enjoys a sense of calm and seclusion. A one-car garage and large storage unit add practicality, while the location—close to shopping, Southern Oregon University, restaurants, and scenic hiking trails—makes this affordable Ashland home especially appealing.

790 Park Street, Ashland

$850,000
2 Beds 3 Baths 220211093 MLS
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

$799,000
1 Beds 2 Baths 220200581 MLS
It's all about the beautiful 13.39 contiguous acres with 12.6 acres of TID irrigation, panoramic views and just minutes to downtown Ashland. Family owned since 1964, the original home was built in 1915. There are 3 separate tax lots, one with the original home,6-stall horse barn and workshop (5.81 acres), one that has a non-expiring homesite (confirm with county) with fantastic panoramic views (4.53 acres) and the third with a large barn (3.05 acres) and separate access. All 3 may be sold separately (check with Jackson County Planning). Tax lot #700 has a small home, large shop, a 8-stall barn, tack room and small living quarters in the back. There is a 2-story barn on tax lot #300. The portion of the property growing grass and clover for hay produces approximately 600 bales and has wheel line irrigation. There are many other potentials for this EFU property.

1249 N Valley View Road, 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: