Ashland Homes with Cascade Mountains View

Welcome to Ashland, Oregon, a charming city nestled in the heart of Jackson County, where the beauty of the Cascade Mountains serves as a breathtaking backdrop to everyday life. Known for its vibrant arts scene, historic downtown, and proximity to stunning natural landscapes, Ashland offers a unique blend of culture and outdoor adventure that captivates residents and visitors alike.

As you explore the real estate opportunities in Ashland, you'll discover homes that boast spectacular views of the majestic Cascade Mountains. Imagine waking up each morning to the sight of snow-capped peaks against a clear blue sky, or winding down your day with a stunning sunset casting a golden hue over the mountains. These homes not only provide a picturesque setting but also create a serene atmosphere that enhances your quality of life.

Ashland is renowned for its rich cultural offerings, including the famous Oregon Shakespeare Festival, lively art galleries, and delightful local eateries that celebrate farm-to-table dining. The city also embraces outdoor enthusiasts with an array of recreational activities, from hiking and biking trails to nearby skiing in the winter months.

With a strong sense of community and a commitment to preserving its natural beauty, Ashland is more than just a place to live—it's a lifestyle. Whether you're looking for a cozy cottage or a spacious family home, the properties with Cascade Mountain views in Ashland promise to elevate your living experience. Come and discover the magic of Ashland, where your dream home awaits amidst nature's grandeur.

Newest Ashland Homes with Cascade Mountains View

$950,000

3 Beds ⋅ 3 Baths ⋅ 220225745 MLS

Tremendous 360 view on 5.75 flat white fenced acres & walking distance to Emigrant Lake. You have 3 acres of water rights on open EFU land, a 36'x36' barn with loft, a 14' RV bay door, workshop & attached office. Behind the barn is a single horse stall. To the side is a gazebo to enjoy those wonderful summer outside nights. This home is greeted by a paved & gated 800' driveway leading to a drive-through that takes you to the front entrance. Brand new wrap around porch greets you so you can sit in awe at the beauty of your surroundings or sit under your backyard gazebo and say, ''Do I really live here''? Perched on a small knoll, this 2,934 sq ft 4/3 home, has 2 bonus rooms, with open floor plan, large entertaining living room with woodstove insert fireplace & kitchen with abundant cabinets & island. Ten-foot ceilings provide ample sunlight for all occasions. The upstairs primary suite has a fireplace, en-suite bathroom with soaking tub & walk-in closet. Country comfort at its best.

5597 Highway 66, Ashland

$1,350,000

5 Beds ⋅ 6 Baths ⋅ 220225703 MLS

Live the Southern Oregon Dream! Welcome to an extraordinary Ashland estate where breathtaking views of Mount Ashland, the Cascades, downtown Ashland, and surrounding vineyards create a spectacular backdrop. Nestled behind a private gated entrance on 5 acres, 3 TID irrigated, this custom-built 5 bedroom, 6 bath home offers luxury, privacy, and versatility. Whether you're seeking a peaceful retreat, a multigenerational home, or space to operate a home-based business, this property adapts to your lifestyle. The thoughtfully designed floor plan features TWO private suites with their own entrance, ideal for extended family, a professional office, or creative studio. Garden beds, fruit trees, space for horses, animals, a 28 GPM well, RV hookups w/220, abundant parking, just minutes from the Shakespeare Festival, galleries, wineries and award-winning restaurants. You'll enjoy the best of country living without sacrificing convenience. Luxury. Privacy. Self-sufficiency. Endless possibilities.

808 Pompadour Drive, 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

$795,000

3 Beds ⋅ 3 Baths ⋅ 220224946 MLS

Enjoy expansive views of the 9th fairway at Oak Knoll Golf Course, Grizzly Peak, and surrounding vineyards from this inviting 3-bedroom, 2.5-bath home. Located on a quiet cul-de-sac, the 1,995 sq.ft. residence offers peaceful golf course living with direct cart access. This well-maintained home features a new roof (January 2026), a large deck perfect for entertaining, and RV parking. Inside, you'll find both a living room and a spacious family room with an open vaulted ceiling, plus a kitchen with a new double oven and gas cooktop. The primary bedroom and bath are generous, with elegant cultured marble counters and shower surround. Additional highlights include HVAC with an advanced air scrubber filtration system and ADA accessibility. Ideal for those seeking a single-level lifestyle with stunning golf course and mountain views in a highly desirable Ashland location. A rare opportunity to own a golf-front home in one of Southern Oregon's most beautiful areas.

738 Fairway Court, Ashland

$1,200,000

5 Beds ⋅ 3 Baths ⋅ 220224554 MLS

One-of-a-kind Southern Oregon retreat just minutes from Ashland! A remarkable property offering a rare blend of privacy, craftsmanship and income potential in a private park-like setting with mature trees. This custom-built 5 bedroom home showcases soaring ceilings, walls of windows with views of Emigrant Lake/Grizzly Peak, large breakfast nook, custom pine log features/dramatic curved staircase, hardwood floors, granite/travertine countertops, floor-to-ceiling fireplace, large 3rd floor bonus wing, 1900+ sq. ft. wraparound cedar deck, workshop, charming playhouse and covered carport. The 1st floor ADU currently operates as a successful AirBNB with 2 bedrooms, beautiful kitchenette, granite countertops, stunning tile bathroom, ADA access, private driveway and entrance, for use as continued rental income or separate multigenerational family living. A former homesite offers additional potential. Rarely does a property combine this level of quiet privacy, quality and versatility.

4567 Old Highway 99 S, 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

$685,000

4 Beds ⋅ 3 Baths ⋅ 220222972 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 Avenue, Ashland

$789,000

2 Beds ⋅ 1 Baths ⋅ 220224351 MLS

Experience the rural southern Oregon lifestyle on 7.34 acres of mostly flat, park-like property bordered by BLM. This custom built home features passive solar design, hardwood floors throughout and an open floor plan with a finished basement ideal for a guest space or studio. A unique third floor office tower provides an inspiring workspace with elevated views. The property is well-equipped for a variety of uses with a large, wood framed 3,400 square foot shop including 220 power, a 10 foot roll up door and 1,000 sq ft of loft space. Detached cabin with power has a completely remodeled exterior with Hardie board siding. Extensive tree thinning and fire prevention work has been done over the years to help provide a ''park like'' feel on the property as well as defensible space. Conveniently located just 10 minutes to Emigrant lake and 20 minutes to downtown Ashland, this property offers privacy, recreation and opportunity for a homestead or retreat. See list of upgrades attached.

1700 Tyler Creek Road, Ashland

$650,000

3 Beds ⋅ 3 Baths ⋅ 220224225 MLS

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

$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

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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: