Ashland Homes with Heated Garage Parking features

Welcome to Ashland, Oregon – a picturesque gem nestled in the heart of Jackson County. Renowned for its vibrant arts scene, stunning natural landscapes, and a charming small-town atmosphere, Ashland offers an unparalleled quality of life. Home to the prestigious Oregon Shakespeare Festival, this lively city attracts culture enthusiasts from all over the world. With its warm community spirit, delightful downtown shops, and delectable dining options, Ashland is the perfect place for both relaxation and adventure.

For those considering a move to this enchanting city, you’ll be pleased to discover a range of homes featuring heated garage parking. Imagine stepping out of your cozy abode into a warm, welcoming garage, free from the chill of winter mornings or sweltering summer heat. Heated garages not only provide comfort but also protect your vehicles from extreme weather conditions, ensuring they remain in pristine condition year-round.

In Ashland, you’ll find a variety of properties that cater to different lifestyles, from charming bungalows to modern family homes, all with the added luxury of heated garage parking. Whether you’re an outdoor enthusiast eager to explore the nearby hiking trails and scenic parks or a culture lover looking to immerse yourself in the local arts scene, Ashland has something for everyone.

Embrace the opportunity to live in a city that beautifully blends culture, nature, and comfort. Discover your dream home in Ashland, where heated garage parking is just one of the many features that make life here truly special!

Newest Ashland Homes with Heated Garage Parking features

$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

$1,899,000

4 Beds ⋅ 4 Baths ⋅ 220225369 MLS

First time on the market for this one-of-a-kind custom ICF-built home with breathtaking panoramic views! This 4 bed, 3.5 bath, 4,972 sqft home offers a main-level office, multiple large storage rooms, and plenty of space for entertaining. The upper level features a spacious primary suite with a private balcony, plus (2) additional bedrooms and a bonus loft (not included in storage). The lower level is ideal for multigenerational living with a large entertainment area, wet bar, bedroom, bathroom, and bonus office/storage space. Situated on 14.78 acres, (house on 1 acre), 13.8 acres currently in hay production, with rare dedicated unlimited TID irrigation. Propane has been plumbed both interior and exterior to add a fireplace or connect your BBQ if desired. Also includes an approx. 1,500 sqft detached shop, barn with (6) 12x12 stalls, riding arena, plus (2) full RV hookups and 50-amp available at the barn, and endless opportunities for horses, livestock, or hobby farming.

40 Ashland Acres Road, Ashland

$888,000

3 Beds ⋅ 2 Baths ⋅ 220223497 MLS

Tucked in the hills of Ashland, this exquisite light filled home offers a rare blend of elegance, privacy, views and natural beauty. This 3 bedroom, 2 bath house features a large open floorplan, skylights, chef's kitchen with 6 burner gas range and island, expansive great room, double paned windows, dining room, primary suite with walk in closet and so much more. This thoughtfully designed home showcases quality craftsmanship, refined finishes and allows for seamless indoor-outdoor living. The yard features fire safe landscaping, custom organic gardens, dozens of varieties of flowers and trees, Japanese maples, dogwoods, abundant wildlife and a koi pond with waterfall. Enjoy the large 3 car garage and workshop, along with an additional downstairs bonus room and multigenerational living potential. The home has been immaculately maintained, with both a newer roof and HVAC system.

1365 Ponderosa Drive, 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

$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

$1,140,000

3 Beds ⋅ 3 Baths ⋅ 220222186 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

$565,000

5 Beds ⋅ 3 Baths ⋅ 220220823 MLS

Escape to your private retreat on 5 level, wooded acres in the heart of the Highway 66 recreation corridor, minutes from Howard Prairie, Hyatt Lake, and Lake of the Woods. This beautifully maintained, recently updated split-level home blends comfort, privacy, and year-round recreation. A slate entry opens to a spacious living room with bay window and wood-burning stove insert. The kitchen offers granite countertops and tile flooring, while formal and casual living areas provide flexible space for entertaining and everyday life. Features include 5 bedrooms, 3 full baths, formal dining, expansive living and family rooms, each with a fireplace, plus a dedicated office or hobby room. Enjoy a peaceful forest setting near fishing, boating, hiking, mountain biking, and snowmobiling. Ideal as a full-time home, seasonal getaway, retreat, or investment property, this exceptional property captures the best of Southern Oregon living.

12300 Highway 66, Ashland

$828,000

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

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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: