Jackson Homes with Chalet Style

Jackson Homes with Chalet Style

Welcome to Jackson County, Oregon, a stunning area that perfectly blends natural beauty and vibrant community life. Nestled in the heart of the Rogue Valley, Jackson County is renowned for its picturesque landscapes, including the majestic peaks of the Cascade Range and the meandering rivers that enhance the region's charm. With a rich history, diverse culture, and an abundance of outdoor activities, Jackson County is a dream destination for nature lovers and adventure seekers alike.

One of the most captivating architectural styles you’ll find in this region is the chalet-style home. Inspired by the rustic charm of the Swiss Alps, these homes are characterized by their steeply pitched roofs, expansive balconies, and cozy interiors that invite warmth and comfort. Imagine coming home to a beautifully crafted chalet, where large windows frame breathtaking views of the surrounding mountains and forests. These homes are not just about aesthetics; they are designed for functionality, featuring open floor plans that seamlessly blend living spaces with nature.

Whether you’re sipping coffee on your balcony while watching the sunrise over the Siskiyou Mountains or hosting friends in your spacious living area, a chalet-style home in Jackson County offers a unique lifestyle that celebrates both comfort and adventure. With easy access to hiking, skiing, and charming local towns filled with artisan shops and gourmet dining, your new home here is more than just a residence; it’s a gateway to a vibrant and fulfilling life. Discover the enchanting allure of Jackson County and find your perfect chalet-style retreat today!

Newest Jackson Homes with Chalet Style

$3,995,000
2 Beds ⋅ 1 Baths ⋅ 220225545 MLS
The Four Corners Ranch offers 897.32 acres of productive timberland on the south side of Mount Ashland, near the California border. This is a rare legacy holding that pairs a strong timber inventory with live water, recreation, and several structural improvements. Elevations range from 3,600 to 4,900 feet across varied topography, supporting consistent, reliable timber growth. Current stocking is estimated at 7.7 MMBF Douglas fir, 4 MMBF white fir, 5.9 MMBF pine, and just under 1 MMBF cedar. Located in the Rogue hunting unit, an area known to produce quality black-tailed deer, the ranch is ideal for hunting and outdoor recreation. Live water, diverse terrain, and direct access to vast public lands add to its appeal. Whether acquired for merchantable timber value or held as a generational asset, the Four Corners Ranch is a genuine opportunity to own a productive expanse of land in Southern Oregon. Additional documentation available upon request.

Hungry Ridge, Ashland
$475,000
3 Beds ⋅ 3 Baths ⋅ 220224437 MLS
Nestled on 6.1 wooded acres, this charming chalet-style retreat offers a blend of privacy, character, & functionality. Abundant natural light, & large windows that showcase the surrounding natural beauty. Architectural details include a spiral staircase leading to a loft and additional bedroom + bath, stained glass accents, honed granite countertops, & a warm, inviting atmosphere throughout. Recent updates include newer decks, windows, & durable metal roofs. Stay cozy year-round w/ a certified wood stove. The detached 2-car garage includes versatile flex space w/ a bathroom, perfect for a home office. Detached outbuilding w/ electricity. Ample room for equipment, recreational vehicles, and outdoor toys, this property is perfect for those seeking space and adventure. Conveniently located near BLM land, river access, and Shady Cove amenities, this tranquil property captures the best of Southern Oregon living.

238 Citadel Road, Trail
$2,950,000
5 Beds ⋅ 6 Baths ⋅ 220223587 MLS
Stunning mansion located in Southern Oregon! This home was fully completed in 2015 with millions of dollars in infrastructure and high-end finishes. Recently finished high end pool was put in for you to enjoy as you take in the breathtaking 360-degree views of the Rogue Valley. This property comes with over 20 acres of land, partially usable with room for animals, fully paved + gated entrance gives you security and peace of mind. This home features over 1800 sqft of garage space (6 cars) and could fit more. This is truly an entertainer's home with plenty of room in the front yard for large gatherings, or in the backyard on the patio and in the pool - Or downstairs in your bar/wine cellar! With 5 bedrooms, and 5.5 bathrooms + office + entertainment rooms. Built with 13'' ICF walls maximizing efficiency. Also - a sauna, wine cellar, concrete safe room, bar and so much more. Too much for a short description - Please inquire for more information, come and tour it to see the rest!

15202 Richards Way, Eagle Point
$235,000
2 Beds ⋅ 1 Baths ⋅ 220223508 MLS
The cabin of your dreams is waiting for you just 35 minutes from downtown Ashland at The Cabins at Hyatt Lake. Tucked into the trees near the shores of the Lake, this peaceful mountain getaway offers the kind of escape people search for and rarely find. With one of the larger and more desirable layouts, the added bump-out creates extra room to relax, gather, and enjoy every season. Vaulted wood ceilings, warm natural light, and a spacious open living area create an inviting place to unwind after a day on the lake, hiking nearby trails, or winter adventures in the snow. Step outside to the wraparound deck, enjoy coffee in the crisp mountain air, soak in the hot tub, and take in the quiet forest setting. Never used as a rental, this fully furnished retreat is truly turnkey. Main-level bedroom and bath, loft sleeping space above, and an oversized shared 2-car garage for boats, gear, and toys complete the package. Just a short walk to the lake and endless outdoor recreation year-round.

7979 Hyatt Prairie Road 42 Unit 42, Ashland
$699,000
220223307 MLS
Check out this Chalet-style triplex with R-2 zoning offering both short- and long-term rental possibilities just minutes from downtown Ashland. Units 1 & 3 are one-bedroom, unit 2 is 2 bedroom, all units have tile flooring, a kitchen with granite countertops and breakfast bar, a full bathroom with tile shower, and generous living area. Private decks provide outdoor living space, while the upper unit enjoys spectacular views. The property includes off-street parking, one space per unit, plus basement with shared laundry facilities and additional storage. Two units are currently vacant, creating flexibility for an owner-occupant, investor, or those seeking a combination. Updates completed in 2016 include ductless heating and cooling system, electrical improvements, and interior finishes. The metal roof has been recently painted, decks have been updated and water heaters were new in '23. This is a rare opportunity to own a versatile income-producing property in a desirable location.

326 N Main Street, Ashland
$1,049,900
3 Beds ⋅ 3 Baths ⋅ 220223070 MLS
Tranquil & pristine Mountain oasis on over 121 acres with a campground, marketable timber, Greenhouse, stream w/waterfall, springs and amazing scenic views of Mt Shasta & Pilot Rock. Amazing main home w/tile entry & stained-glass w/3 bedrooms, 2.5 baths, 2145 SQ FT with open beam vaulted ceilings in the great rm w/ huge stone staircase. Kitchen w/granite counters, tile floors opens to dining & great rm loft area. 2 primary suites overlooking the deck and creek. The other primary suite has a door to lg covered deck. Detached 2 car garage. Off grid secluded unpermitted cabin by waterfall and campground. Woodshed w/Japanese architectural elements, on-site fire suppression. Next to Forest Lands w/private hiking trails; Pacific Trail, wildlife, berries and mushroom hunting. Enjoy unobstructed star gazing, snow shoeing, sledding and more just 20 minutes from downtown Ashland. Owner will carry with $500,000 Down, 6.5% for 3-5 years w/Sellers' approval of Buyer. Last house before the Lodge.

500 Mt Ashland Ski 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
$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
$475,000
2 Beds ⋅ 2 Baths ⋅ 220220635 MLS
Attention investors!! If you're looking for a cozy getaway close to all the recreational activities Southern Oregon has to offer, this is the one for you! Currently an active short term rental and providing a strong return to the owners, this two-story charmer features 2 bedrooms plus loft area, 2 bathrooms, 1472 sq ft, 1.64 wooded acres, open floor plan, vaulted ceilings, hardwood flooring, metal roofing, attached 2 car garage, detached shop/garage, fenced yard, enclosed porch, certified woodstove, main level living, & much more! Living room, kitchen, and bedrooms are spacious as well! Can't go wrong with this property if you like to hike, fish, kayak, atv, bike, or simply enjoy a forested ambiance. Only seconds away from Hyatt Lake! This one won't last long on the market, so contact your agent today for a personal tour, before it's too late! No drive-by's allowed and this property is appt only.

7550 Hyatt Prairie Road, Ashland
$845,000
3 Beds ⋅ 3 Baths ⋅ 220219802 MLS
Stunning Chalet Retreat with Breathtaking Mt. Ashland Views! Nestled on 7.51 private acres, this gorgeous 2,306-sq-ft chalet offers unparalleled views of the Colestin Valley and Mt. Ashland. The thoughtfully designed interior features 3 spacious bedrooms, 3 full baths, and a versatile bonus room. Uniquely permitted for short-term rentals, this property is a proven income-producer and an ideal part-time residence or year-round sanctuary. Located just 15 minutes from the culture of downtown Ashland and minutes from world-class skiing, it perfectly balances seclusion with convenience. High-quality infrastructure includes a robust 16 GPM well and a state-of-the-art Advantex septic system. Whether you are seeking a mountain getaway, a savvy investment, or a private estate, this home delivers the best of Southern Oregon living. Experience ultimate privacy without sacrificing proximity to the city. A rare find in an iconic setting--this mountain masterpiece is ready for its next owner!

12673 Highway 99 S, Ashland
$499,900
4 Beds ⋅ 3 Baths ⋅ 220219093 MLS
Bring your vision to this spacious tri-level home on 10 acres. 2 wells, 450 AMP dual power sources, In ground pool, 2,600 sq. ft. deck. A 1,800 sq. ft. shop. The 3,013 sq. ft. home features 4 bedroom, 2.5 bathrooms. The second well is on the parcel of land across the road from the main house. This home has solid bones, offering a rare opportunity to personalize it to yours needs with endless possibilities. Home is being sold AS IS. Potential buyers must be prequalified for Cash or Private money lender. Private and only 10 mins from downtown Rogue River.

4196 E Evans Creek Road, Rogue River
$1,199,900
3 Beds ⋅ 5 Baths ⋅ 220219449 MLS
One of the most extraordinary private lakefront estates in Southern Oregon, located in gated Gold Rey Estates on 1.68 acres just minutes to town. A rare Oregon Dream property and absolute MUST SEE. Set on a 4 acre pond w/ private dock and pontoon boat, this property offers stunning lake views from nearly every room. Custom built home w/ open floor plan, 18 ft vaulted beam ceilings, expansive windows and main level primary suite w/ deck access. Incredible 1,360 sq ft shop built in 2024 w/ mezzanine, epoxy floors and RV door. Multiple new decks, professional landscaping and mature trees. Roundabout driveway w/ water feature and huge RV parking. Incredible kitchen w/ cherry cabinets, granite, Viking oven, refrigerator and Thermador cooktop. Lower-level w/ custom wood bar, addl bedrooms and bath. Finished 3 car garage w/ built ins. Truly one of a kind.

8959 John Day Drive, Gold Hill
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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: