Jackson Co: Ashland Real Estate

Welcome to Ashland, Oregon, a charming gem nestled in the heart of Jackson County. Famous for its vibrant arts scene, stunning natural landscapes, and a welcoming community, Ashland offers a unique blend of small-town charm and cultural sophistication.

Known as the home of the renowned Oregon Shakespeare Festival, Ashland attracts visitors and residents alike with its lively theater performances and rich artistic heritage. The festival draws theater enthusiasts from around the globe, making the town a cultural hub where creativity thrives. Beyond the stage, Ashland boasts a variety of galleries, music venues, and annual events that celebrate the arts, ensuring there’s always something to experience.

Nature lovers will find Ashland equally enchanting. Surrounded by the majestic Cascade Mountains and the picturesque Rogue River, outdoor adventures await at every turn. Whether you enjoy hiking the scenic trails of Lithia Park, skiing at nearby Mount Ashland, or exploring the stunning landscapes of the Rogue Valley, this region is a paradise for those who appreciate the great outdoors.

The community in Ashland is as warm and inviting as the climate. With a diverse range of dining options, from farm-to-table restaurants to cozy cafes, residents can indulge in the local culinary scene that emphasizes fresh, seasonal ingredients. Additionally, the town is home to excellent schools, making it an ideal place for families to settle down.

In Ashland, you’ll find not just a place to live, but a lifestyle filled with culture, adventure, and community spirit. Come explore the beauty and charm of Ashland, where every day feels like a celebration of life!

Newest Listings in Jackson Co: Ashland

$699,000

4 Beds ⋅ 2 Baths ⋅ 356025262 MLS

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 AVE, Ashland

$950,000

2 Beds ⋅ 1 Baths ⋅ 161774949 MLS

Rare opportunity -- 4.39 acres of open pastoral land within the Eagle Point Urban Growth Boundary. The City of Eagle Point has indicated this parcel is a strong candidate for rezoning from RR-5 to R-2, potentially allowing approximately 31 residential home sites. Wide, sweeping views stretch west across the valley toward the mountains -- the quiet, spacious feel that defines Southern Oregon living at its best. Just two miles from the Golf Club at Eagle Point Golf Course, with shopping and dining minutes away in Medford. Eagle Point is one of Southern Oregon's most actively growing communities, currently processing annexations under Oregon's SB 1537 housing initiative. This parcel sits inside the UGB with city-indicated rezoning support -- an advantage few land listings can claim. Developers, builders, and long-view investors will want to look closely. Buyers to conduct own due diligence with the City of Eagle Point regarding rezoning, annexation timeline, and all development requirements.

963 STEVENS RD, Eagle Point

$4,000,000

794757614 MLS

A landmark downtown Ashland land offering. Just one block from Ashland's Plaza, this rare 1.18-acre commercial development site represents one of the last opportunities of its scale & prominence in the downtown corridor. Located within the Employment Zoning District, the property offers exceptional potential for hotel, conference center, mixed-use, luxury residential, retail, offices, or destination development. Extensive prior approvals include architectural, engineering, landscaping, utility, and entitlement plans for an 8-building mixed-use project with ground-level commercial spaces and luxury residences above. Current approvals expire Summer 2026 and may be eligible for renewal. With virtually no remaining undeveloped commercial land of this size in downtown Ashland, this offering combines exceptional visibility, strong street presence, & outstanding walkability to the Plaza, acclaimed restaurants, theaters, galleries, and Lithia Park. Rare scale. Rare location. Rare opportunity.

165 WATER ST, Ashland

$1,140,000

3 Beds ⋅ 2 Baths ⋅ 221762307 MLS

Set privately back on 5+ acres in the Sunny Oaks community, this custom 3 bed + office, 2.5 bath, 2644 sq ft home pairs open mountain views with easy access to town -- 15 min from Downtown Ashland and near Emigrant Lake. The groundwork for comfortable rural living is in place: a dedicated 1-gigabit fiber line, 300 amp electrical, whole-home water filtration, 2021 Lennox HVAC, irrigation rights, a large cedar-fenced area, and a roof under six years old. Inside, natural light fills an updated kitchen with quartz counters and hardwood floors, opening to a great room, with a separate family room, office, and laundry on the main level. Upstairs, the primary suite offers vaulted ceilings and a balcony framing the same sweeping mountain views as the wraparound deck below, plus two more bedrooms and a full bath. Outside, a gravel RV pad offers water, power, and internet, and a barn with corrals stands ready for horses. With over $200K in updates, the property is move-in ready.

7130 HIGHWAY 66, Ashland

$439,000

3 Beds ⋅ 2 Baths ⋅ 706062451 MLS

Charming, fully remodeled home in the heart of Ashland! This beautifully updated 3-bedroom, 2-bath residence offers 1,291 sq ft of comfortable living space on a spacious .28-acre lot. Enjoy peace of mind with a newer roof (approximately 3-4 years old) and updated ducting. The interior features fresh paint throughout, brand-new carpet, and stylish tile flooring in the kitchen and bathrooms. The modern kitchen shines with quartz countertops and stainless steel appliances, perfect for everyday living and entertaining. With ample outdoor space for gardening, relaxing, or potential expansion, this move-in-ready home combines quality upgrades with a desirable location. Don't miss this exceptional Ashland property!

540 OAK KNOLL DR, Ashland

$745,000

1 Beds ⋅ 1 Baths ⋅ 735184840 MLS

Elevated downtown living in one of Ashland's most desirable addresses. This top-floor, end-unit residence at Plaza West offers a rare blend of privacy, sophistication, & sweeping views of Grizzly Peak & the valley beyond. Light-filled & beautifully appointed, the single-level design features hardwood floors, quartz countertops, stainless appliances, & a spacious kitchen with dining bar and walk-in pantry, all flowing seamlessly into the main living areas. A gas fireplace adds warmth, while the view balcony invites relaxed indoor-outdoor living. Built in 2014 & rarely lived in, this home presents like new. Generous primary suite offers views, a spa-like bath with soaking tub, step-in shower, & large walk-in closet. Stylish den/media room, half bath, & laundry complete the layout. LEED Platinum certified building with secure entry, video intercom access for guests, underground parking, EV charging, storage & elevator. Just steps to dining, theater, & Ashland's vibrant downtown.

175 LITHIA WAY Unit #303, Ashland

$299,000

693671412 MLS

Step into a world of pristine natural beauty, remarkable solitude, and boundless potential with this extraordinary ±78-acre property, nestled in the heart of Southern Oregon’s picturesque Colestin Valley. Offering commanding panoramic views, rich ecological diversity, and a peaceful ambiance that feels worlds away from the bustle of daily life, this land is more than just real estate—it’s a legacy in the making.Bordering the western edge of the renowned Cascade-Siskiyou National Monument, this unique parcel features a stunningly varied topography that includes a prominent knoll-top view site, gently undulating hills, timbered draws, and open meadows. Whether you're drawn by the call of nature, inspired by the land’s tranquility, or envisioning a future full of off-grid potential, this property delivers on every front. Outdoor enthusiasts will relish the opportunity to hike, hunt, camp, and rockhound on their own land, all while sharing space with abundant wildlife such as deer, wild turkey, black bear, and even the occasional elk.Just minutes from the iconic Pacific Crest Trail and a short drive to some of the region’s most treasured destinations—including Pilot Rock, Mt. Ashland Ski Area, Emigrant Lake, and majestic Mt. Shasta—this property is perfectly positioned for adventure and exploration. Whether you're seeking seclusion or inspiration, you’ll find both here. Buyer to perform and satisfy all due diligence regarding the property and its permitted uses.

COLESTIN RD, Ashland

$1,295,000

4 Beds ⋅ 3 Baths ⋅ 660672633 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 ST, Ashland

$1,650,000

5 Beds ⋅ 3 Baths ⋅ 444414247 MLS

Addressed as 309 and 311 Granite Street, this exceptional estate is tucked above Lithia Park on nearly six private acres, blending timeless European elegance with the tranquility of a forested retreat. Surrounded by mature trees, stone pathways, outdoor patios, and serene water features, the property feels secluded and intentional, yet remains just minutes from downtown Ashland, the Oregon Shakespeare Festival, and the historic Ashland Plaza.Inside, the architecture immediately impresses with vaulted ceilings, dramatic wood craftsmanship, custom detailing, stained glass accents, and expansive windows that fill the home with natural light. Rich textures and thoughtful design elements create a warm, old-world atmosphere that is both grand and inviting.The main residence is centered around a generous open great room with a striking rock fireplace, flowing into an informal dining area and an oversized kitchen ideal for gathering. Multiple living spaces—including a formal dining room, den, and additional sitting rooms—allow flexibility for everyday living or entertaining on a larger scale.The primary residence offers 4,479 square feet, plus 2,364 square feet of flexible ground-level space. A second residence provides 844 square feet for guests or extended living, along with a separate 1,153 square foot multi-purpose room and carport. In total, the estate encompasses approximately 8,840 square feet of versatile living space.Ideally located near Mt. Ashland Ski Resort, Crater Lake National Park, the Britt Music & Arts Festival, and Rogue Valley wineries, this is a rare opportunity to own a private, architectural estate that seamlessly blends refined craftsmanship, natural beauty, and an exceptional cultural lifestyle.

309 GRANITE ST, Ashland

$1,100,000

428863147 MLS

Great development opportunity at the first major I5 intersection as one arrives from California to Ashland, Oregon. This high-traffic corridor property is perfectly positioned for maximum exposure to tens of thousands of vehicles daily. Potential uses include hotel/lodging, retail, restaurant, or mixed-use development—subject to local zoning approvals. An annexation for the development of a hotel is supported by Economic Data provided in Ashland's Comprehensive Plan and within the economic data provided since last Ashland Comprehensive Plan update. Required for annexation is a zone change from RR-5 to C1. Data and information from City of Ashland should align & justify the development request and address the shortage of adequate retail/commercial in the City. Perfect site for hotel with restaurant and conference facilities or an array of other commercial facilities.

HWY 66, Ashland

$965,000

597339018 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 and 152 Maple ST, Ashland

$4,500,000

2 Beds ⋅ 3 Baths ⋅ 371788226 MLS

Centrally located along the west coast I-5 corridor, this spectacular one-of-a-kind home, on 700 awe-inspiring acres, offers magnificent sanctuary and adventure, as well as convenience. One of the most naturally beautiful regions of the country, this area of southern Oregon is known for a developing wine industry and phenomenal outdoor recreation opportunities. Characterized by four distinct seasons and mild winters, the climate is one of the most sought-after in North America. Designed to reflect and honor the majesty of this natural environment, this home sits on a high bench with open terraces that bring the view so close, you feel like you could reach out and touch it. Unique features like all rounded corners and smooth edges, a perfectly balanced use of the natural elements, and purposeful architectural design, create a remarkable effect, both peaceful and expansive. This home is beyond custom: it is a work of art. This property is an unparalleled place to rejuvenate and become inspired. A few minutes drive from I-5, the property immediately embraces you in a sanctuary of wilderness, where magnificent elk herds can be seen roaming the rolling meadows and oak savanas. Two enormous rock faces rise from a blanket of green and greet you as you gently climb higher and approach this spectacular home. This astonishing home is one of a kind. Earthen tiles cascade down four distinct, rounded rooves crowned with small cupolas, capturing the geometrical beauty of Byzantine architecture. Beneath the tiles, the outer walls are smooth stucco, accented with a myriad of windows, rounded and flowing, reminiscent of the graceful and curvaceous architecture of Antoni Gaudi. Domes and crests of stucco stand against the sky, giving the impression of a white-washed chapel on the island of Mykonos. Despite its references to world-class art and architecture, this home also has its own distinct and extraordinary style.

2700 N Valley View RD, Ashland

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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: