Bend Homes with Chalet Style

Bend Homes with Chalet Style

Welcome to Bend, Oregon, a stunning gem nestled in the heart of Deschutes County. Known for its breathtaking natural beauty, Bend offers a unique blend of outdoor adventure and vibrant community life. With the majestic Cascade Mountains as a backdrop, residents enjoy year-round recreational activities, from skiing and snowboarding in the winter to hiking, biking, and river sports in the warmer months. The city is also home to a thriving arts scene, charming boutiques, and an array of craft breweries, making it a perfect place for those who appreciate both nature and culture.

One of the standout features of Bend's real estate market is its enchanting chalet-style homes. These distinctive properties exude warmth and character, often characterized by their inviting wooden beams, stone accents, and expansive decks that seamlessly blend indoor and outdoor living. Chalet-style homes in Bend are designed to capture the essence of mountain living, making them ideal for those who seek a cozy retreat after a day of exploring the great outdoors.

Imagine sipping your morning coffee on a sun-drenched deck, surrounded by towering pines and the sounds of nature, or hosting friends for a barbecue in your spacious backyard. The charm of these homes extends beyond their aesthetic appeal; they offer a lifestyle that embraces the serene beauty of the surrounding landscape. Whether you’re looking for a permanent residence or a vacation getaway, a chalet-style home in Bend is more than just a property; it’s an invitation to experience the magic of Oregon living at its finest. Come discover your dream home in this picturesque city and let the adventures begin!

Newest Bend Homes with Chalet Style

$999,900
2 Beds ⋅ 3 Baths ⋅ 220225285 MLS
Both lots need to be sold together, currently an older home on lot 1, and an older shop on the other. The site is adjacent to a commercially zoned neighborhood and can also be classified as Neighborhood Commercial with expanded allowed uses. 1 Block off 3rd street. Office and repair service uses appear to be permitted in this zone and appraisal has been done on these properties, and being sold as is. Adorable 2 bedroom 2 bath, plus 2 additional finished rooms in the basement house, along with a adu over a shop on 1 lot, and a nice sized shop on the other tax lot. Shop has several seperate offices,,storage and loads of open space to use to work on your projects to work. And fenced parking space galore

195 SE Roosevelt Avenue, Bend

Listing courtesy of Stellar Realty Northwest.

$429,900
2 Beds ⋅ 2 Baths ⋅ 220223686 MLS
Wake up, grab a kayak, and walk one block to the Deschutes. Come home to a hot tub and a property that already has 140+ five-star reviews doing the work for you. This fully furnished 2BD/1.5BA in River Meadows has been thoughtfully maintained with newer carpet, windows, cedar deck, electric fireplace, and refreshed bath. Active Airbnb Guest Favorite grossing $38-40K annually! Plus the listing, furnishings and newer hot tub transfer with sale! Pet friendly, single car garage with EV charger, and private neighborhood boat launch are just steps away. Four seasons of demand: skiing at Mt. Bachelor, summer river float trips, autumn hiking in Deschutes National Forest. Community pool, tennis, pickleball, fitness center, marina, and RV/boat storage. HOA covers sewer too. 20 min to Mt. Bachelor, 12 min to Sunriver, 25 min to Bend.

16693 Wagon Trail, Bend

Listing courtesy of Real Broker.

$1,675,000
4 Beds ⋅ 4 Baths ⋅ 220222812 MLS
Brisk activity-don't wait or you'll miss out! $200K+ in luxury updates - unrivaled panoramas! This turnkey retreat is nestled in a 1,000-year-old juniper forest at a private lane's end in Pronghorn at Juniper Preserve. Perched on the 17th Fazio fairway, the home captures postcard-perfect Cascade views. Inside, natural light fills the spaces, complete with a den, tasting room, and a secret door leading to a wine cellar. The palatial primary suite boasts a fireplace, sitting enclave, wet bar, spa bath, spacious wardrobe suite and private view deck. Perfect for hosting, the expansive outdoor spaces feature a courtyard fireplace, fire pit, built-in Twin Eagles BBQ, and turf games area. Accommodate guests in the separate 2-bedroom lock-off suite. Features a 2-car garage + golf cart bay. Short-term rental potential. Enjoy premier resort amenities: pools, Member's Lounge, pickleball, and fine dining. $115K Premier Membership is included! Ultimate exclusivity just 20 minutes to downtown Bend.

22887 Ghost Tree Lane, Bend

Listing courtesy of Stellar Realty Northwest.

$1,049,000
4 Beds ⋅ 3 Baths ⋅ 220216127 MLS
Welcome to the ultimate Sunriver retreat where adventure, relaxation, and investment potential meet. This beautifully furnished 4-bed, 3-bath home sits minutes from Sunriver Village and 20 minutes to the slopes of Mt. Bachelor. Step outside to experience what truly sets this property apart: a private wiffle ball field, custom mini-golf course, and play structure for the kids. Entertain on the expansive deck, then unwind beneath the stars in the hot tub after a day on the mountain or river. The light-filled interior features fresh paint and new carpeting throughout. Gather around the cozy fireplace or head to the loft, perfect for movie nights and extra sleeping space. The detached garage even includes a bonus bunk house for guest flexibility. With a proven track record as a successful short-term rental, this property is an ideal income-producing investment, vacation getaway, or family compound. Experience the full Sunriver lifestyle--come see what makes this home truly special.

17039 Cooper Drive, Bend

Listing courtesy of Real Broker.

$1,150,000
2 Beds ⋅ 2 Baths ⋅ 220214685 MLS
Tranquility on Tumalo Creek! This chalet in the historic Skyliner neighborhood is the private retreat you've been searching for. Nestled among towering old-growth Ponderosa pines with 100 feet of creek frontage, it feels a world away yet is only 10 minutes from Bend's west side. Whether you're curled up by the fire in winter, enjoying a summer evening on the deck, or unwinding in the barrel sauna, the setting is pure serenity. The home features a main-level primary suite plus an additional suite upstairs. The kitchen has been tastefully updated with modern appliances and concrete countertops. Tall windows frame year-round views of the water and forest, bringing the outdoors in. With Tumalo Falls just 3 miles away and Skyliner Sno-Park a short stroll down the road, hiking, biking, skiing, and snowshoeing are right out your door. A rare blend of waterfront tranquility and convenient access to Bend's best recreation and amenities. Come experience how peaceful life can be!

16330 Skyline Drive, Bend

Listing courtesy of Stellar Realty Northwest.

$275,000
2 Beds ⋅ 3 Baths ⋅ 220212969 MLS
Discover incredible income potential with this fully furnished, turn-key duplex-style condo at Seventh Mountain. Offering two separate units that can be rented together or individually, this property has a strong history of both short-term and long-term rental success. Located in one of the last buildings constructed, the layout maximizes space with a larger kitchen, expanded living area, oversized balcony, and a Murphy bed in the main unit. The upstairs loft features a bath, vaulted ceilings and sunrise views, while the studio includes its own bath, balcony, and space for a mini-kitchen setup. This unit has earned $4,000-$6,000 per month as a STR in peak summer or $3,300 monthly as a long-term rental. HOA dues include all utilities, exterior maintenance, building insurance, landscaping, snow removal, cable, and HVAC service. Enjoy resort amenities including pools, hot tubs, fitness center, pickleball and tennis courts, sauna, ice rink (seasonal), and more.

18575 SW Century Drive 2035, 2036, Bldg. 20 Unit 2035, 2036, Bldg. 20, Bend

Listing courtesy of Stellar Realty Northwest.

$297,750
1 Beds ⋅ 2 Baths ⋅ 220211226 MLS
magine having your own Central Oregon getaway that's ready whenever you are--and earning income when you're not. This beautifully updated top-floor condo combines Units #1233 and #1234, offering 1 bedroom, 2 full baths, and comfortable sleeping for six. Turn-key and fully furnished with high-end furnishings, linens, and complete kitchenware, this thoughtfully designed retreat features modern finishes, solid surface countertops, and a private deck overlooking the forest. Flexible lockout capability allows you to rent one or both sides, maximizing short-term rental income potential. Enjoy heated pools, hot tubs, tennis, pickleball, scenic trails, and year-round resort amenities just minutes from Mt. Bachelor and the Deschutes River. HOA dues include utilities, internet, exterior maintenance, landscaping, and full resort access, making ownership simple, carefree, and ready to enjoy. Call for your private tour today!

18575 SW Century Drive # 1233/1234 Unit # 1233/1234, Bend

Listing courtesy of Cascade Views Realty, LLC.

$1,950,000
3 Beds ⋅ 3 Baths ⋅ 220208345 MLS
Picturesque lake and 17th-fairway views from this beautifully remodeled single-level Broken Top home, set on a mature landscaped lot with front and back water features adding to the peaceful ambiance. Interiors intertwine luxury with comfortable living spaces, where the spacious living area's wall of windows showcases the outdoors and custom built-ins add warmth. A cheerful breakfast nook adjoins the gourmet kitchen with 2 Wolf ovens, Fisher & Paykel dishwasher, island with gas cooktop, wine fridge & breakfast bar; an elegant dining room sits nearby. The floorplan provides an ideal separation of space, offering an office large enough to double as a den, complete with cozy fireplace. The primary suite, with its own private golf-course-view patio, includes a luxurious remodeled bath & walk-in closet. On the opposite end of the home, the guest wing features two bedroom suites with adjoining sitting area. Expansive laundry room & large 3-car garage complete this remarkable home.

19490 Green Lakes Loop, Bend

Listing courtesy of Berkshire Hathaway HomeService.

$695,000
2 Beds ⋅ 3 Baths ⋅ 220200652 MLS
Great shop + modern ski chalet! Welcome to your ultimate private escape, featuring a massive, fully-equipped shop—perfect for all your toys, tools, and big projects which includes a bathroom and potential living space! Then step inside the brand-new custom-built home, designed with both comfort and efficiency in mind. Enjoy the luxury of radiant floor heating throughout, keeping every room warm and inviting during all seasons. Clean, modern finishes blend seamlessly with natural surroundings, creating a perfect harmony of comfort and rustic charm. The soaring tongue and groove ceilings round out the ski chalet vibe! Whether you're a builder, artist, outdoors enthusiast, or someone who just wants space to live and dream big—this property offers it all! Set on a wooded lot with neighborhood river access for kayaking, fishing, or simply soaking in nature's tranquility, come see why this is more than a home — it's a lifestyle! Seller terms available.

16932 Upland Road, Bend

Listing courtesy of Cascade Hasson SIR.

Start Your Search

The content relating to real estate for sale on this website comes in part form the MLS of Central Oregon. Real Estate listings held by Brokerages other than Selling Central Oregon, LLC are marked with the Reciprocity/IDX logo, and detailed information about these properties includes the name of the listing Brokerage. © MLS of Central Oregon (MLSCO). This content was last updated on . Some properties which appear for sale on this website may subsequently have sold or may no longer be available. All information provided is deemed reliable but is not guaranteed and should be independently verified. All content displayed on this website is restricted to personal, non-commercial use, and only for ascertaining information regarding real property for sale. The consumer will not copy, retransmit not redistribute any of the content from this website. The consumer is reminded that all listing content provided by automatic transmission by MLSCO is © MLS of Central Oregon (MLSCO).