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$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
$3,800,000
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
$935,000
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
$1,195,000
220220575 MLS
Hard to find 4 plex plus separate home on large R-2 lot. Walking distance to downtown. The units have been updated and are well maintained. Fully rented. One unit is rented fully furnished . The main home was remodeled 4 years ago. All units have private rear yards that are newly fenced. One of the apartments is complimented with a tile shower plus separate bathtub. Washers and dryers included in all units. Ample parking for tenants.

67 Woolen Way, Ashland
$2,250,000
220220428 MLS
Ten, six, or four-unit investment opportunity in Ashland's Hillview Condominiums near Scenic Park and Asante Ashland. Seller-carried financing available at ~3.99% AFR with 50% down, interest-only payments, with balloon due in three years. Each unit ranges from 1,034 to 1,174 SqFt with two bedrooms, one full bath, open living and dining space, high ceilings, in-unit laundry, kitchen with granite counters and all appliances included, dedicated parking, storage, and access to landscaped common areas. Ground-level units with fully fenced private backyards and poured concrete patios. Current gross monthly income is $15,730 across all ten units following rent increases effective August 1st, 2026. Stable tenancy averaging four-plus years, room for further rent growth, and association-maintained exterior building components including roofs, siding, paint, and landscaping. Complete investment analysis, rent roll, association documents, and due diligence materials available upon request.

230 Grant Street, Ashland
$950,000
5 Beds ⋅ 3 Baths ⋅ 220220148 MLS
Enchanting oasis property,½ acre of lush landscaping, abundant flora waterfalls and swimming pond with its own filtration system. Main house with large wrap around deck to take in the wonderful, secluded backyard and mountain views. Lots of skylights and space with high ceilings welcomes you to your relaxing living room with custom exotic wood built-in and rock fireplace. Large primary bedroom with views via 20 windows. Primary bathrooms includes steam shower. Just outside primary bedroom you can retreat onto a private covered deck with 1 yr old spa. 2 more bedrooms on main floor then journey downstairs to 2 very large additional bonus rooms. Solar system provide total electricity for entire main house. Also, a 3-car garage. A separate addressed 915 sq ft ADU with 2 bedrooms, 2 parking spots, fireplace, vaulted knotty pine ceilings, Corian countertops in bath and kitchen, tile & oak flooring with mahogany trim wood and its own private deck that is included for family or rental options.

610 Orchard Street, Ashland
$130,000
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
$744,000
4 Beds ⋅ 3 Baths ⋅ 220218224 MLS
Welcome to Billings Ranch, one of Ashland's most desirable communities. This stylish 3,184 sq ft, 4 bed, 3 bath home blends comfort and functionality with standout spaces for spring and summer entertaining. Upon entry you are greeted with a sweeping spiral staircase and 20-ft vaulted ceilings that create a grand open atmosphere. The main level offers a spacious living room, a dedicated dining area, and a beautifully appointed kitchen with two gas stoves, granite countertops, and ample prep space making it perfect for gatherings. Enjoy warm-weather living on the private back patio with a built-in gas firepit and grapevine-covered pergola, ideal for outdoor dining, relaxing evenings, and hosting year-round. A main-level bedroom, full bath and den complete the comfort of the downstairs. Upstairs, are three additional bedrooms, including a luxurious primary suite with its own gas fireplace, a spa-like ensuite bathroom with a jetted tub and a generous walk-in closet.

692 Vansant Street, Ashland
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 220217927 MLS
Platinum Earth Advantage home just minutes from downtown, offering 2,750 sq ft of thoughtfully designed 4BR, 3BA + office living space with stunning views of Grizzly Peak and the Cascades. This light-filled residence features 12' ceilings, expansive windows, quartz surfaces, designer lighting, and blonde wide-plank hardwood floors. The main level features two ensuite bedrooms, highlighted by a luxurious primary suite with radiant heated floors, dual shower system, and two walk-in closets. The chef's kitchen boasts an 11-ft island, double ovens, gas cooktop, beverage fridge, and walk-in pantry. Enjoy seamless indoor-outdoor living with an 8' slider to a spacious view deck. Lower level offers 2 bedrooms, office, second laundry, and potential for separate living. Professionally landscaped, private setting with detached 2-car garage, EV charging, and energy-efficient 2-zone HVAC system. Home designed by Vadim Agakhanov.

852 Oak Street, 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
$2,250,000
220216457 MLS
Prime investment opportunity in Ashland, Oregon! This 44-room motel is conveniently located just off the freeway at 50 Lowe Road, offering excellent visibility and accessibility for travelers. The property features beautiful mountain views and includes a well-maintained swimming pool, currently not open to the public, providing significant value-add potential. The property also includes a fully equipped restaurant space that is currently not in operation but offers the infrastructure needed to reopen or repurpose according to a new owner's vision. With its strategic location, existing amenities, and strong upside potential, this property presents an exceptional opportunity for investors or hospitality operators ready to bring new life and creativity to this motel.

50 Lowe Road, Ashland
$1,050,000
220216014 MLS
Located directly across the street from Asante Ashland Community Hospital, this well-maintained 3,925 SF medical office building offers an exceptional opportunity for healthcare users and investors seeking a premier Ashland location. Built in 1977 and in good condition, the property is currently configured as an orthopedic medical office and features a highly functional single-level layout--ideal for patient flow, accessibility, and efficient clinical operations. Ample on-site parking supports both staff and patient needs, adding to the convenience and strong appeal of the site. Situated in the Ashland Health Care zoning designation, the building is well-positioned for a variety of medical and professional healthcare uses, with immediate proximity to hospital services, referral networks, and a strong community healthcare base.

269 Maple Street, 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
$2,100,000
220215747 MLS
This 1880 farmhouse was originally converted into a bed and breakfast in 1983. The Morical House Garden Inn has a rich history and now has 9 bedrooms and 10 bathrooms. The main house has original red fir floors and much of the Victorian era woodwork and other features have been maintained over the years. The carriage house was added in 1995, and the Inn created a luxurious experience for its clients for more than two decades. Although day-to-day operations ceased in 2020, the Morical stands ready to resume its role as a high-end boutique hotel or move on to its next adventure.

668 N Main Street, Ashland
$2,100,000
9 Beds ⋅ 10 Baths ⋅ 220215748 MLS
This 1880 farmhouse was originally converted into a bed and breakfast in 1983. The Morical House Garden Inn has a rich history and now has 9 bedrooms and 10 bathrooms. The main house has original red fir floors and much of the Victorian era woodwork and other features have been maintained over the years. The carriage house was added in 1995, and the Inn created a luxurious experience for its clients for more than two decades. Although day-to-day operations ceased in 2020, the Morical stands ready to resume its role as a high-end boutique hotel or move on to its next adventure.

668 N Main Street, Ashland
$500,000
2 Beds ⋅ 2 Baths ⋅ 220215328 MLS
Stunning 2022 transformation of a classic 1920s single-level cottage situated on a spacious third-acre parcel, ideally located between Lithia Park and Hald-Strawberry Park and only moments from downtown Ashland. Comprehensive updates include new roof, foundation, windows, waterproof LVP flooring, full electrical rewire, modern plumbing, and new sewer line. The open kitchen showcases vaulted ceilings, butcher-block island, granite sink, marble backsplash, and a copper-accented range hood. Primary suite offers private deck access, designer lighting, and a spa-like bath with clawfoot tub. Vaulted living room flows to an expansive deck with mountain views. Versatile second bedroom/office, efficient mudroom laundry, and full guest bath complete the interior. Outside enjoy terraced landscaping, TID irrigation, fresh paving and multiple outbuildings. A rare opportunity in a prime Ashland location--contact today for more information!

220 Nutley Street, Ashland
$1,249,000
8 Beds ⋅ 9 Baths ⋅ 220212846 MLS
Just blocks from downtown, this historic gem blends charm and flexibility. Original fir floors, built-ins, high ceilings, and abundant natural light pair with modern updates. Enjoy the welcoming lawn, pollinator garden, and large covered front porch. The main level offers spacious living and dining areas, kitchen, half bath, and generous entry spaces. A 1-bedroom apartment with interior and private exterior access--includes a kitchen, laundry and full bathroom--a separate additional en-suite bedroom with exterior entry adds versatility. Upstairs are four lovely en-suite bedrooms, one with a balcony, all with updated Renewal by Andersen windows and balcony door. A detached 704 sq ft, 2 bedroom, 1.5 bath, single level cottage with its own address and electric meter provides added flexibility or income potential. With six paved off-street parking spaces, sheds, on-street parking, and alley access, this property offers exceptional possibilities for multi-generational living or investors.

451 N Main Street, Ashland
$715,000
4 Beds ⋅ 4 Baths ⋅ 220212305 MLS
Freshly renovated turn of the century home set on over a third of an acre lot with views and gorgeous mature evergreens. Large covered wraparound front porch leads to the front facing living room w/ wood floors & picture windows allowing for an abundance of natural light. Spacious country kitchen has stainless steel appliances. There's a covered enclosed back porch style room w/ bathroom. There are two bedrooms, one of which is ensuite on the main level. Versatile upstairs space has a light filled landing, one bedroom suite and another huge space w/ great architectural features, views and a full bathroom. Plus, a detached oversized two car garage, lots of parking and a relatively level yard that has a ton of potential for gardening or future development. Just above the hospital and within the Health Care Services zoning district. This is a charming property awaiting the next owner to enjoy!

527 Chestnut Street, 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
$565,500
220197023 MLS
Rare Opportunity to own a beautifully remodeled and well taken care of 2,800 SF Office building in the heart of Ashland Oregon. This versatile space features an open floor plan, an ADA-accessible entry, and is ideal for a variety of end uses. (Check with City Planning) A true standout in Ashland, this property includes 12 dedicated parking spaces- an exceptional find in this sought-after area, a highly desirable and rare future in Ashland. Close to SOU university off the corner of Siskiyou Blvd makes this property easily accessible. Call now to tour this exceptional opportunity.

747 Normal Avenue, Ashland
$646,000
3 Beds ⋅ 2 Baths ⋅ 220197028 MLS
Fall in love with this home of luminous spaces and serene views in a beautiful Ashland neighborhood perched above it all, with fresh air and plenty of quiet • Huge, main, open-layout room with dining area and cabinetry • Sunroom for casual dining & games • Irrigation system • Wood-burning fireplace • Full city services This 2332sf home mirrors the tranquility of its wooded surroundings--its vistas across the Rogue Valley will leave you and your guests beauty-struck and smiling. Sunlight floods the interior; Acacia wood floors add luxe and warmth. The MBR suite is spacious with scenic views. Two BDRMS face west: 1 carpeted, 1 office w/ skylight. The 2+car garage with storage. An expansive backyard deck connects the living space to the mountainside above, with direct access to Siskiyou Mtn Park trails and protected-from-development, watershed land. The house sits uphill from Siskiyou Blvd., between SOU and The Plaza, minutes from everything, and only 30 minutes to Mt. Ashland skiing.

932 Morton Street, 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: