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1536 Pinecrest Terrace, Ashland
$595,000
3 Beds ⋅ 3 Baths ⋅ 220224168 MLS
Welcome to this stunning 1993-built home on a private .29-acre lot. Dramatic floor-to-ceiling windows flood the front rooms with natural light and frame the gorgeous scenery. The main floor features 2 bedrooms, including a large primary suite and walk-in closet, a main-level office/3rd bedroom with built in Murphy bed, 2 full baths, a cozy den, a sunroom, a huge front living room with vaulted ceilings and separate dining space. The eat-in kitchen offers plentiful storage in a serene setting overlooking the hills. The basement has an additional room with a craft room already set up to be a photographer's dark room with ventilation, a sink, and a half bath. Outside is a terraced backyard with gazebo and a huge half wrap around deck all providing spectacular views. Complete with an attached 2-car garage. A Newer roof, washer, dryer, dishwasher, and Air conditioning unit all installed/replaces in 2023 and 2024. Minutes from hiking trails, parks, schools, and shopping! Move in ready.

1536 Pinecrest Terrace, Ashland

495 Chestnut Street 24 Unit 24, Ashland
$305,900
3 Beds ⋅ 2 Baths ⋅ 220223687 MLS
*Seller Motivated - will entertain all reasonable offers!* Affordable Ashland living in desirable Tudor Heights! This spacious 3-bedroom, 1.5-bath condo offers 1,392 sqaure feet of comfortable living space with mountain and territorial views from a private upper-corner location. The main level features a bright living room with a 60s style fireplace, kitchen, half bath, and flexible den perfect for a home office, guest space, or potential 4th bedroom! Upstairs you'll find three bedrooms, a full bath, and laundry area. Recent improvements include new carpet and a new water heater. Enjoy a private patio, detached carport, and additional storage. Conveniently located near downtown Ashland, Lithia Park, restaurants, shopping, and the hospital. HOA covers water, sewer, trash, landscaping, exterior maintenance, and exterior insurance for easy, low-maintenance living! Ownership occupancy only - no rental opportunities available at this time.

495 Chestnut Street 24 Unit 24, Ashland

590 Taylor Street, Ashland
$695,000
2 Beds ⋅ 3 Baths ⋅ 220223937 MLS
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

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

100 Belle Fiore Lane, Ashland

200 Belle Fiore Lane, Ashland
$12,000,000
7 Beds ⋅ 19 Baths ⋅ 220223437 MLS
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

22494 Jefferson Road, Ashland
$2,140,000
5 Beds ⋅ 5 Baths ⋅ 220223401 MLS
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

163 Hitt Road, Ashland
$335,000
220222249 MLS
Prime Ashland location just off Strawberry Lane in an area of fine homes. Perched above neighboring properties, this exceptional .28-acre parcel captures sweeping valley and mountain views, expansive skies, and abundant natural light. The setting is both inspiring and serene, with mature oaks and conifers creating a beautiful natural backdrop. Thoughtfully positioned to take full advantage of its elevated location, the property enjoys remarkable view protection and a sense of openness that is increasingly difficult to find. With no homes immediately on either side, privacy is enhanced while still being just minutes from Ashland's celebrated Plaza, Lithia Park, and the extensive North Ashland trail system. Whether envisioning a contemporary showpiece or a timeless custom residence, this is a rare opportunity to build in one of Ashland's most sought-after locations and enjoy views that will be treasured for years to come.

163 Hitt Road, Ashland

1969 Colestin Road, Ashland
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 220222210 MLS
Rare opportunity to own 160 private acres on the outskirts of Ashland, offering extreme end-of-the-road seclusion, breathtaking panoramic views, and endless potential for recreation, hunting, and homesteading. Surrounded by nature and abundant wildlife, this remarkable mountain retreat delivers the peace and privacy that are increasingly difficult to find. Located just 30 minutes from Mt. Ashland and approximately 45 minutes to downtown Ashland, the property offers the perfect balance of remote living and convenient access to dining, culture, and outdoor adventure. The custom-built home features a stunning great room that truly must be experienced in person, with soaring ceilings, warm finishes, and walls of windows framing the surrounding landscape. A spacious primary suite, inviting guest accommodations, large barn, and substantial shop space make this property ideal as a full-time residence, legacy ranch, or unforgettable weekend mountain escape.

1969 Colestin Road, Ashland

312 Sky Ridge Road, Ashland
$899,000
220221479 MLS
312 Sky Ridge Road offers 164 acres in the hills above Ashland, combining privacy, natural beauty, and usable land in a premier Southern Oregon setting. Zoned EFU, the property features a blend of moderately sloping terrain, open ground, and native landscape ideal for recreation, investment, or an exceptional estate setting. Approximately 2,220 feet of Cove Creek frontage adds scenic beauty and recreational appeal. A strong 48 GPM well, per 2018 well log, provides an excellent water source for future improvements. A fully paved drive leads to the property, with plans underway for a custom luxury entrance designed to complement the scale and quality of the setting. Elevations ranging from approximately 2,120 to 2,520 feet capture panoramic views in nearly every direction, creating a remarkable sense of space and connection to the surrounding mountains and valleys. Conveniently located near Medford, outdoor recreation, public lands, and Southern Oregon amenities.

312 Sky Ridge Road, Ashland

500 Ashland Loop Road, 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

1020 Walker Avenue, Ashland
$715,000
3 Beds ⋅ 3 Baths ⋅ 220221008 MLS
Back on the market through no fault of the property! Custom-built home on a private .69-acre lot in Ashland with breathtaking valley and mountain views. This versatile property offers a primary bedroom on the main level, vaulted ceilings, fireplace, built-ins, and spacious living areas designed for comfort and entertaining. Large kitchen with breakfast nook and abundant storage throughout. The primary suite features double sinks, separate shower, and a jetted soaking tub with its own hot water system. Downstairs includes a finished daylight basement with separate entrance and plumbing in place ideal for guest quarters, multi-generational living, or future mother-in-law suite potential. Enjoy the fenced garden with raised beds, TID irrigation water, oversized 2-car garage, easy-care landscaping, and a new roof installed in 2023. Rare blend of privacy, flexibility, and stunning views.

1020 Walker Avenue, Ashland

575 Dogwood Way, Ashland
$769,000
4 Beds ⋅ 3 Baths ⋅ 220220097 MLS
It's the home you've dreamed of with astounding views of the valley and mountains from living and dining rooms and all four bedrooms! Designed by Jerry Toney it's been well cared for and improved over time with meaningful updates including terraced lawn with sundeck, two kitchen sinks, 16 (owned) solar panels and more! A large room on the first floor with built-in shelves is suitable for use as media, gym, or library. Garage has storage room plus workbench and sink. On the main level, vaulted ceilings and oversized windows running the length of the home create a spacious feeling that invites the valley below indoors. The primary suite boasts a walk-in closet/dressing area and a tiled bathroom complete with two-person soaking jacuzzi. The kitchen opens onto the main outside deck facilitating meals outside or barbecuing meals for inside. Throughout the home, custom western maple cabinetry and quality woodwork add warmth and character. Call your Realtor for a private showing today!

575 Dogwood Way, Ashland

COLESTIN RD, 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

852 Oak 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

2205 Ashland Street 210 Unit 210, 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

483 Strawberry Lane, Ashland
$435,000
220215800 MLS
Is this Ashland's best neighborhood? We certainly think so! This prime ½-acre lot, located in the desirable Strawberry Meadows Subdivision, is surrounded by stunning high-end homes. The gently rolling terrain is bordered by protected common areas to the west and south, offering added privacy and natural beauty. Lightly treed with expansive views of the Rogue Valley and surrounding mountain vistas, this property is a true gem. Just minutes above Ashland's vibrant plaza--home to charming shops, acclaimed restaurants, the renowned Shakespeare Festival, and picturesque Lithia Park--you'll enjoy the perfect balance of nature and culture. All city utilities are available, including public sewer, water, power, cable, and fiber optics. A well-managed homeowners association preserves the common areas and the character of the neighborhood, ensuring a lifestyle you'll love.

483 Strawberry Lane, Ashland

220 Nutley 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

461 Waterline Road, Ashland
$766,000
4 Beds ⋅ 4 Baths ⋅ 220211772 MLS
Tucked away on a quiet, tree-lined street, this beautiful home strikes the perfect balance of space, comfort, and mountain charm. Boasting 3,404 square feet, 4 bedrooms (plus an office) and 3 bathrooms, it offers plenty of room for both relaxation and entertaining. The open main level flows easily from the spacious living and dining areas to a warm, inviting kitchen with rich wood cabinetry, generous counter space, and windows that frame peaceful forest views. New front and rear cedar decks (2022) extend your living space outdoors, perfect for morning coffee or evening gatherings. The lower level hosts the primary suite and three additional bedrooms, three with private deck access and peaceful vistas. A large basement provides easy access to nearby trails and could be finished for extra living space, while also offering convenient access to the home's major systems. With a clean pre-listing inspection and thoughtful updates throughout, this home truly embodies refined mountain living.

461 Waterline Road, Ashland

Dead Indian Memorial Road 1400 Unit 1400, Ashland
$210,000
220211332 MLS
Are you looking to construct the home of your dreams? If you're tired of searching unsuccessfully for a pre-built residence that suits your needs, consider building it yourself. We are proud to present this stunning 30-acre parcel located 8 miles from the beautiful city of Ashland, Oregon. From the top of the ridge, the views of Mt Ashland and the city below will take your breath away. Boasting varied topography, oak groves and cooler temperatures in the summer and above the fog during winter days, this spot is ideal for living off-the-grid without sacrificing proximity to great restaurants, shopping, cultural experiences like the Oregon Shakespeare Festival and more. Buyer due diligence recommended; applications for a homesite have already been submitted.

Dead Indian Memorial Road 1400 Unit 1400, Ashland

381 Clinton Street, Ashland
$991,800
3 Beds ⋅ 3 Baths ⋅ 220210724 MLS
Stunning new construction in Ashland's Magnolia Meadows! This exceptional 3-bedroom home features a unique design and thoughtful use of space, making it a true neighborhood gem. Enjoy a pitched roof ready for solar panels, a fully fenced yard with drip irrigation, and beautiful landscaping with views of Grizzly Peak. Inside, benefit from top-of-the-line heating and cooling, on-demand hot water, and heated flooring in the primary bath. Elegant vaulted ceiling with skylights and clear story windows that envelope rooms with light. Gas fireplace serves as a focal point, complemented by 8-foot rift oak doors. Single-story living with no carpeting, deluxe primary suite, beautiful wide planked hardwood oak floors with the expansive living and dining area featuring custom built-ins, quartz countertops, and gourmet kitchen with a 36'' Bosch induction range, wine cooler, and more. Discover your dream home today!

381 Clinton Street, Ashland

1440 E Nevada Street, Ashland
$3,750,000
5 Beds ⋅ 5 Baths ⋅ 220206087 MLS
A private retreat setting where nature meets luxurious living. The 5BR/5BA Contemporary home captures the Siskiyou mtn range at every turn. The main level offers floor to ceiling windows, hardwood floors, living & dining room & Chef's kitchen appointed w/ island, wet bar, pantry, double ovens, wolf stove & more! Upstairs the main bedroom suite is an oasis unto itself w/views, decking & spa. A second primary suite, 2 add'l bedrooms/bath & laundry room w/abundant storage are downstairs. Each room has custom finishes & exquisite views to ensure a lifestyle of privacy & relaxation. Outside you're met w/soothing soundscape of a tiered cascading creek, lagoon waterfall style pool, cabana area, outdoor kitchen & bath, for ease of entertaining. Equestrian, livestock or agricultural enthusiasts will delight w/the endless possibilities. Fruit trees, garden beds, greenhouses, chicken coop & workout room complete this singular estate. 1BD/1BA guest apartment is a bonus to this luxe property.

1440 E Nevada Street, Ashland

1249 N Valley View Road, 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,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 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:

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