Ashland Homes with Courtyard Exterior features

Ashland Homes with Courtyard Exterior features

Welcome to Ashland, Oregon—a charming city nestled in the heart of Jackson County, renowned for its vibrant arts scene, stunning natural landscapes, and a warm, welcoming community. With its picturesque streets lined with historic buildings and lush parks, Ashland offers a unique blend of small-town charm and cultural richness. This scenic locale is home to the famous Oregon Shakespeare Festival, attracting theater enthusiasts from around the globe, while the nearby Ashland Creek and surrounding mountains provide ample opportunities for outdoor adventures.

One of the most appealing aspects of Ashland's real estate market is the availability of homes featuring exquisite courtyard exterior designs. These properties not only enhance the aesthetic appeal of the neighborhood but also create a serene outdoor oasis for residents. Imagine stepping into your own private courtyard, beautifully landscaped with vibrant flowers and cozy seating areas—perfect for morning coffee or evening gatherings with friends and family.

These homes with courtyard exteriors are designed to foster a sense of community while providing a peaceful retreat from the hustle and bustle of daily life. Whether you’re looking for a charming bungalow or a modern family home, Ashland offers a variety of options to suit your lifestyle. The courtyard serves as an extension of your living space, ideal for entertaining or simply enjoying the tranquility of nature.

Discover the magic of Ashland and explore the unique homes that embody the spirit of this enchanting city. Your dream home awaits in this idyllic corner of Oregon!

Newest Ashland Homes with Courtyard Exterior features

$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
$1,200,000
2 Beds ⋅ 3 Baths ⋅ 220225582 MLS
Experience refined living just one block from downtown Ashland in this custom-built 2012 luxury home designed for comfort and ease. Rich oak and red oak floors and cabinetry pair beautifully with custom metalwork and soaring wood-paneled ceilings in the great room. The chef's kitchen features a 6 burner Wolf cooktop, wall oven, speed oven, Sub Zero refrigerator, exposed edge granite countertops and custom pot racks. Spa inspired bathrooms include heated tile floors, dual vanities, tiled showers and abundant natural light, one with a soaking tub. An elevator and 36 inch doorways provide seamless accessibility throughout. The oversized finished two car garage offers space for a workshop, gym and storage with additional laundry, sink and gas heater. The private flagstone courtyard with gas BBQ, is perfect for relaxing and outdoor entertaining with lovely, low maintenance landscaping.

400 Allison Street, Ashland
$1,300,000
3 Beds ⋅ 3 Baths ⋅ 220223946 MLS
An Ashland jewel, this architecturally designed & built home enjoys an exceptional setting above Lithia Park with stunning views and timeless craftsmanship. Intentionally designed, with high-performance systems throughout, showcasing exceptional interior and exterior finishes. Main level has 3 bedrooms, 2 full baths, open floor plan, den, and dedicated office space; all designed to capture abundant natural light and beautiful views. The gourmet island kitchen flows seamlessly into the living and dining areas, creating an inviting space for entertaining. Enjoy the private deck, perfect for morning coffee or twilight dining. A fully furnished 1-bedroom ADU provides flexibility for guests, extended living, or income potential, while the finished shop is ideal for a studio, workshop, or hobbies. A rare opportunity to own one of Ashland's most distinctive and notable properties.

5 Scenic Drive, Ashland
$650,000
3 Beds ⋅ 2 Baths ⋅ 220224343 MLS
Stylish and thoroughly updated single-level Craftsman home in a desirable neighborhood near Ashland Creek Park. New roof with 3.60 kW solar array, central AC, high-efficiency gas furnace and water heater, hickory hardwood floors, interior paint, designer lighting, fixtures, and hardware throughout - all within the last six years. Vaulted great room with gas fireplace and dining area with skylight, remodeled kitchen with quartz counters, maple cabinets with custom pull-outs and displays, stainless appliances including gas range, sculptural breakfast bar, and sliding glass door to pebbled concrete patio with retractable awnings. Primary with walk-in closet, renovated full ensuite bathroom, dual quartz vanity, and shower with custom tiled surround. Two guest bedrooms with closets, updated full guest bath with tub shower, laundry mudroom, and two-car garage. Mature drought-tolerant plantings, ornamental trees, and garden beds with new automated irrigation system. Inquire for details!

414 Parkside Drive, Ashland
$313,000
2 Beds ⋅ 2 Baths ⋅ 220223565 MLS
Welcome to 965 Golden Aspen in the sought-after Mountain Meadows community in Ashland. This beautifully maintained condo offers comfortable, low-maintenance living with an inviting floor plan, abundant natural light, and thoughtfully designed living spaces. The spacious living and dining areas provide an ideal setting for both everyday living and entertaining. Enjoy beautiful courtyard views that bring a sense of tranquility and natural beauty into the home. Step outside to the serene patio space, perfect for morning coffee, reading, or relaxing outdoors. Well-sized bedrooms, ample storage, and convenient access to community amenities enhance the appeal. Residents enjoy beautifully landscaped grounds and easy access to Ashland's dining, shopping, cultural attractions, and outdoor recreation. A wonderful opportunity to enjoy comfort, convenience, and community in one exceptional setting.

965 Golden Aspen Place, 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
$379,000
2 Beds ⋅ 1 Baths ⋅ 220221178 MLS
Ashland Garden Cottages boast Earth Advantage Platinum Status with Owned Solar Panels. Energy Star appliances, efficient layout of 2 bedrooms, 1 bathroom, stackable washer/dryer, and a living area to include the kitchen, dining area, and living room. Covered front porch, no common walls, quartz countertops, tile shower, and designer lighting. All appliances shown are included in the sale.

162 Mountain View Drive, Ashland
$799,200
3 Beds ⋅ 3 Baths ⋅ 220221136 MLS
Enjoy this practically new, sophisticated, energy-efficient home just one mile from downtown Ashland. Thoughtfully designed for main-level living, it features a primary suite with walk-in closet, tile shower, dual sinks, and tile flooring, plus an office, half bath, laundry, kitchen with walk in pantry and extended storage/coffee bar, dining area, vaulted living room with gas fireplace with access to the back patio. Upstairs offers a spacious landing/bonus area, two bedrooms, one with walk-in closet, and a large bathroom with dual sinks and tub/tiled shower combo. Quartz countertops, custom cabinetry, and window shutters are found throughout. Engineered hardwood spans the main living areas, with carpet in bedrooms and stairs. The fenced, landscaped backyard includes covered patio, a paver courtyard, retractable awning, and drip irrigation. Owned solar and EV charger complete this exceptional home. Check it out today!

396 Randy Street, Ashland
$585,000
3 Beds ⋅ 3 Baths ⋅ 220218209 MLS
The minute you enter this one level home you will say WOW! Gorgeous light and bright remodel with prefinished hardwood floors, open living concept with gourmet cooks delight kitchen with island and room for bistro table and chairs. Open floor plan including vaulted ceilings in living, kitchen and dining. Gas fireplace. Primary suite with walk in closet, double sinks, amazing shower. A bonus sunroom/family room. Two more good size bedrooms, second full bath and one half bath. Double garage and large laundry room. Beautiful landscaping, covered back patio, side patio with pavers. Low voltage lighting and drip watering system. Across the street from the Oak Knoll pond and trails for the neighborhood to enjoy. Just 3 blocks to golf course. Large shed for extra storage and subdivision parking bays for visitors. Take your time to see all the details of this home and enjoy!

1057 Oak Knoll Drive, 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: