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3105 O. B. Riley Road, Bend
$10,700,000
220214932 MLS
Rare riverfront hospitality opportunity in Bend, OR. This legacy property includes 151 guest rooms, a single-family residence with lower apartment, and an additional apartment attached to the lobby, all situated on expansive grounds along the Deschutes River. Amenities include multiple pools, hot tubs, saunas, on-site restaurant space, and banquet/event facilities. Originally built in the mid-1980s as what was intended to be Touch of Class, and later operated as the Shilo Inn, this property has long served as a home away from home for travelers and long-term guests in Central Oregon. While the hotel has experienced deferred maintenance and operational inefficiencies, the underlying fundamentals remain compelling, including irreplaceable river frontage, scale, existing infrastructure, and zoning. This is a value-add and repositioning opportunity suited for an experienced operator, developer, or investor seeking to reimagine or redevelop a landmark asset.

3105 O. B. Riley Road, Bend

Listing courtesy of Varsity Real Estate. Selling Office: .

19472 Pine Drive, Bend
$9,995,000
6 Beds ⋅ 6 Baths ⋅ 220221414 MLS
Just 25 feet from the Deschutes River, this rare legacy riverfront estate offers an extraordinary opportunity in Bend. Set on 3.60 private acres, this extraordinary estate offers an irreplaceable connection to the water, where the sound, movement, and beauty of the river become part of everyday life. Designed for privacy, comfort, and unforgettable entertaining, the Northwest modern main residence is complemented by a 2718 sqft. 3-bedroom guesthouse, creating exceptional flexibility for guests or multi-generational living. Walls of glass frame river, canyon, and territorial views, while expansive indoor-outdoor living spaces, riverfront patios, a fire pit, spa, sauna, and serene wooded grounds create a resort-like setting just minutes from the Old Mill and downtown Bend. With a gated approach, refined natural materials, generous gathering spaces, and a setting that could not be recreated today, this is more than a home. It is a once-in-a-generation Deschutes River estate.

19472 Pine Drive, Bend

Listing courtesy of Bend Premier Real Estate LLC. Selling Office: .

18665 Macalpine Loop, Bend
$5,125,000
5 Beds ⋅ 10 Baths ⋅ 220160959 MLS
This elegant and luxurious private estate in The Highlands of Bend, Oregon is an architectural treat designed by renowned Harrison Design. Thoughtfully curated with no expense spared, the level of customization throughout the home and property is unlike any other. Details range from the hand selected stone from Jerusalem to the hand-blown Murano chandeliers; the level of detail continues in every room. Situated on a spectacular 10 acres with explosive 360 degree views that include the Cascade Mountain range. Features include a private guest home, attached 4 car garage, detached 4 car garage and RV garage with hookups and dump. Outside soak in the direct afternoon sun from the pool and entertain from one of the two outdoor kitchen areas, one off the house and the other in the covered cabana that is also home to a changing room and bathroom inclusive of a shower. Located just minutes to downtown, schools, golf, and all the outdoor recreation Bend has to offer. See it to believe it!

18665 Macalpine Loop, Bend

Listing courtesy of Cascade Hasson SIR. Selling Office: .

22 NW Shasta Place, Bend
$4,500,000
5 Beds ⋅ 5 Baths ⋅ 220218836 MLS
Located in Bend, the Desert Rain property is a rare architectural achievement set on a striking basalt outcropping in the heart of downtown. Designed to harmonize with the high desert environment, the home captures natural light, open skies & native landscape, creating a seamless connection between indoors and out. Internationally recognized as the first single-family residence to meet the Living Building Challenge, Desert Rain functions as a fully regenerative home. The compound includes 3 homes arranged around a central courtyard, with curved walls, expansive glass and natural materials that enhance airflow and daylight. The main residence offers 3 bedrooms and 2 baths, complemented by a private 2-bedroom guest house and a separate 1-bedroom ADU~each with its own dedicated garage. Reclaimed wood, locally sourced earth materials & thoughtful craftsmanship by Timberline Construction ground the design in its natural surroundings while creating an immediate connection to all things Bend.

22 NW Shasta Place, Bend

Listing courtesy of Cascade Hasson SIR. Selling Office: .

20450 Arrowhead Drive, Bend
$3,999,000
4 Beds ⋅ 6 Baths ⋅ 220221512 MLS
Perched on a private and serene 2.5 acres with some of the most breathtaking views in Deschutes River Ranch, this masterfully crafted estate by acclaimed architect Jim Rozewski embodies the absolute best of the Central Oregon lifestyle! The 6,635 square foot main residence offers 4 luxurious en-suite bedrooms, refined gathering spaces, a gourmet kitchen with butler's pantry, library/den, media room, office, wine cellar, and an expansive 3-car garage with workbench and gym area. A beautifully appointed barn includes 1,663 square feet of additional living space with a private suite, half bath, and third-level lookout. Soaring ceilings, reclaimed fir and alder, natural stone, elegant finishes, and extraordinary craftsmanship create a retreat that seamlessly blends luxury and everyday living. Multiple covered and fenced entertaining areas, a fully fenced courtyard, and sweeping views of the Cascade Mountains and Deschutes River complete this truly exceptional offering. Welcome home!

20450 Arrowhead Drive, Bend

Listing courtesy of Cascade Hasson SIR. Selling Office: .

19107 Cartwright Court, Bend
$3,900,000
4 Beds ⋅ 5 Baths ⋅ 220210565 MLS
Located at the end of the cul-de-sac of the well sought after neighborhood, Tartan Druim & overlooking Tetherow's prestigious Kidd's Corner is where you will find this elegant custom home. This impressive, light-filled home captures the vast views from top to bottom. Graced w/high end finishes & fun touches, you'll find all the bells & whistles throughout this thoughtfully designed home. On the main level you'll find an airy primary suite w/a dual vanity, heated floors, & a roomy walk in closet, an open great room w/a striking wood burning fireplace, an entertainers kitchen w/top of the line appliances incl. a beverage fridge & built in coffee maker, a secondary en-suite, office, powder room, mud/laundry room, 3 car garage w/storage room, 2 balconies, & a built-in BBQ. The lower level features a bonus room w/a kitchenette, 2 bedrooms & bathrooms, a paver patio & grass area. Whether living here full time or part time, you'll rest easy w/the Lutron smart system. Why live anywhere else?

19107 Cartwright Court, Bend

Listing courtesy of Cascade Hasson SIR. Selling Office: .

61572 Hardin Martin Court, Bend
$3,875,000
4 Beds ⋅ 4 Baths ⋅ 220218603 MLS
Welcome to this Tetherow golf retreat, where contemporary design meets Central Oregon's natural beauty.Set on over half an acre at the end of a quiet cul-de-sac, this masterpiece offers panoramic views of the golf course and National Forest-perfect for nature and golf lovers.Light-filled living spaces feature soaring 25-ft ceilings, expansive windows, and warm modern-industrial finishes. The chef's kitchen boasts a built-in refrigerator/freezer wall, wine fridge, oversized gas range, and rough sawn oak island, ideal for entertaining or gourmet meals. Dining and kitchen areas flow to a covered patio for seamless indoor-outdoor living.The private master suite includes a secluded patio for morning coffee or evening relaxation. Additional highlights: designer tilework, 4-zone climate control, 3-car garage with workbench, and access to Tetherow's pools, fitness, dining, and world-class golf.Perfect as a primary home, getaway, or entertainer's retreat.Seller is a licensed real estate broker.

61572 Hardin Martin Court, Bend

Listing courtesy of Engel & Voelkers Bend. Selling Office: .

19260 Christopher Court, Bend
$3,824,000
4 Beds ⋅ 4 Baths ⋅ 220205062 MLS
Amazing New Gem in Tetherow is now complete!!! Home is located on a gated and quiet cul-de-sac with 7th hole golf course view from the front of the home. The backyard is an entertainer's dream with Expansive Covered outdoor living area with a fire pit, infrared heaters, and paver patio, Diamond Spa Built in Stainless steel Hot Tub, and an outdoor kitchen with dining and living area. Inside, you'll find a luxurious primary bedroom suite with quartzite countertops, porcelain and natural stone tile work, Walk-in Walk-out oversized shower with bench and multiple shower heads, heated floor in bathroom, shower and closet, oversized vanity, and toe-kick accent lighting. There is also a spacious study on the main floor. Upstairs are additional 3 bedrooms with a flex space and a large bonus room with a wet bar. Please see the feature sheet for all of the amazing amenities this home has to offer.

19260 Christopher Court, Bend

Listing courtesy of John L Scott Bend. Selling Office: .

56222 Trailmere Circle, Bend
$3,585,000
6 Beds ⋅ 8 Baths ⋅ 220211749 MLS
Nestled among towering Ponderosa pines, backing to an open meadow, this custom NW Lodge-style home blends natural beauty w/ refined elegance. Exposed wood beams, knotty alder doors & oak hardwood flooring are complemented with quartzite countertops, mosaic tile accents & a heated driveway - a true modern mountain retreat. Dramatic great room w/ soaring ceiling, massive stone fireplace & sweeping forest views. Contemporary kitchen with Thermador appliances & generous island, extends outdoors to a covered fireplace, built-in BBQ & open air firepit for starlit evenings. Main-level primary suite offers coffered ceilings, forest views, and a spa-like bath w/ heated floors, soaking tub & walk-in shower. 2 more suites on the main level + upstairs is an 8-bunk bunkroom, bonus room & 2 additional guest suites—ideal for family retreats or vacation rental. Centrally located, near both the Lake House & Forest House. Built by Envision Development Group with exceptional attention to detail.

56222 Trailmere Circle, Bend

Listing courtesy of Harcourts The Garner Group Real Estate. Selling Office: .

19209 Cartwright Court, Bend
$3,550,000
4 Beds ⋅ 5 Baths ⋅ 220215797 MLS
Tucked on a quiet cul-de-sac with expansive high-desert views, this modern home blends refined finishes with smart, effortless living. A whole-home Control4 system manages AV, lighting, heating, water, security, electric shades, and more--delivering exceptional comfort and efficiency throughout. Sunlit living spaces feature elevated design details, warm wood accents, and seamless indoor-outdoor flow. The chef-inspired kitchen, serene primary suite, and inviting guest rooms evoke an atmosphere of understated luxury. Set within the sought-after Tetherow community, residents enjoy exceptional golf, miles of trails, and a welcoming neighborhood park with barbecue facilities, plus quick access to world-class hiking, biking, and skiing. Just minutes from downtown, vibrant dining, shopping, and everything Bend has to offer, this home is perfectly suited as a full-time residence or an adventure-ready retreat--offering sophistication, convenience, and the very best of Central Oregon living.

19209 Cartwright Court, Bend

Listing courtesy of Engel & Voelkers Bend. Selling Office: .

20324 Rock Canyon Road, Bend
$3,450,000
3 Beds ⋅ 4 Baths ⋅ 220219131 MLS
Stunning Cascade Mountain, river, and pasture views from every room. European modern elegance combines with award-winning luxury. Live connected, luxuriously, amidst unparalleled nature. This 4,329 sq ft smart home is fully app-controlled from anywhere using your smartphone: leak detection, water shut-off, temperature control, lights, blinds, sprinklers, alarm, and cameras. Great room floating fireplace conceals TV, Hammerton lighting, Wolf/Sub-Zero appliances, PITT burners, quartzite countertops, Cleaf cabinetry, butler's pantry, mudroom with dog wash, and wine cellar. 3 en-suite beds, 3.5 baths, heated 3-car garage. Located on a quiet cul-de-sac, just 10 mins to Bend, 15 mins to Redmond Airport. Seed-to-table farm next door: pick veggies for your dinner! Direct access to 32,000 acres of BLM and Deschutes River trail and fly fishing.

20324 Rock Canyon Road, Bend

Listing courtesy of Avenir Realty. Selling Office: .

1746 NW Wild Rye Circle, Bend
$3,360,000
5 Beds ⋅ 6 Baths ⋅ 220196517 MLS
Step inside this remarkable home and be transported to Europe, where every corner tells a story of worldwide inspiration and craftsmanship from another era. With its meticulously curated design, this home offers an unparalleled sense of history and artistry. Perched above Awbrey Glen Golf Course, it boasts sweeping views of the Cascade Mountain Range. Inside you'll discover an expansive gourmet kitchen, complete with a butler's pantry, formal dining room, wine cellar, an executive office/library, game room with a pool table, shuffle board, game table and a movie theater. The heated tile balcony welcomes you with ample room for entertaining and savoring the sunsets. Each bedroom has access to the two story balcony, offering elevated views. This exquisite residence is a masterpiece of design and craftsmanship. A home that must be experienced in person to fully appreciate its beauty and artistry.

1746 NW Wild Rye Circle, Bend

Listing courtesy of Engel & Voelkers Bend. Selling Office: .

61591 Hosmer Lake Drive, Bend
$3,350,000
4 Beds ⋅ 5 Baths ⋅ 220222766 MLS
Experience exceptional Northwest Modern living in one of Tetherow's most coveted settings. Perched along the 13th fairway, this stunning 3,965-square-foot custom residence showcases sweeping Cascade Mountain views, overlooking the course and tranquil pond below. Thoughtfully crafted by Timberline Construction of Bend and designed to embrace its remarkable surroundings, the home offers 4 bedrooms, 4.5 bathrooms, and a highly functional layout anchored by a luxurious main-level primary suite. Expansive windows fill the home with natural light while seamlessly connecting indoor and outdoor living spaces. Clean architectural lines, refined finishes, and timeless craftsmanship create an atmosphere of understated elegance. Located within Bend's premier golf community, this extraordinary retreat offers the perfect balance of privacy, luxury, and access to renowned outdoor recreation

61591 Hosmer Lake Drive, Bend

Listing courtesy of Cascade Hasson SIR. Selling Office: .

66279 Gerking Market Road, Bend
$3,350,000
4 Beds ⋅ 4 Baths ⋅ 220219361 MLS
Welcome to this beautifully renovated home in Tumalo. Perched on 36.5 acres w/2 acres of irrigation & adjoining BLM, this one-of-a-kind property is extremely private & features dramatic mountain views. Completely remodeled to the studs in 2017, no detail was spared in this 4,629 sq ft home. Quality built & tastefully finished inside & out, featuring 4 bd, 3.5 ba, bonus room, office, 2 car att garage, wood beam accents & picturesque windows throughout to frame in the mountain, forest & pond views, a covered deck w/firepit, paver patios, hot tub, a spacious primary bedroom w/double vanity, soaking tub & walk in shower, a designer kitchen w/granite counters, brick accents, Jenn-Air appl, farmhouse sink, prep sink, alder cabinetry & pantry, an open great room w/a wood burning fireplace w/a stone surround. The dreamy 2,180 sq ft finished shop affords an RV bay w/a 13' door, two 10' doors, epoxy floors, woodstove, ½ bath & 200 AMP service. This well-manicured property is a must see!

66279 Gerking Market Road, Bend

Listing courtesy of Cascade Hasson SIR. Selling Office: .

56399 Elk Run Drive 420 Unit 420, Bend
$3,350,000
6 Beds ⋅ 8 Baths ⋅ 220202504 MLS
Experience lake views from this newly completed custom mountain-modern home in Caldera Springs! Designed for memorable gatherings, it features four ensuite bedrooms on the main level, a spacious great room, a gourmet kitchen with a butler's pantry, and a convenient laundry room. Upstairs, discover two additional ensuite bedrooms, bunk room and a versatile bonus room. Relax on the expansive covered patio, complete with a hot tub enclosure. Features include distress wood beams, custom cabinetry, rich woods, solid surfaces, high end appliances, and Central Vacuum with an in-wall hose, built in fridge and wi-fi enabled zoned Central A/C. Schedule a showing with your real estate professional to experience this home today!

56399 Elk Run Drive 420 Unit 420, Bend

Listing courtesy of Cascade Hasson SIR. Selling Office: .

61279 Gorge View Street, Bend
$3,265,000
5 Beds ⋅ 5 Baths ⋅ 220183649 MLS
Set beautifully atop the cliffs of the Deschutes River, this multi-generational trio of structures has a total of 4702 sq feet of usable space and rests on a beautifully manicured double lot. Enjoy 180-degree bird's-eye views of the Cascades, the striking tree-lined gorge below and the winding river that meanders through it all. The primary home is a main hub, with three bedrooms, a chef's kitchen, an additional den (or 4th bedroom), office and a game room/theater space that invites gathering. The second home is an adjacent one-bedroom, one-bath single-level 'Casita' with a kitchenette and access to the custom outdoor kitchen. The third structure is a two-story one-bedroom, one-bath 'Rimessa' with a charming turret and built-in wine room. Offering enduring finishes, state-of-the-art mechanicals, dreamy custom landscaping and breathtaking sunsets, this is a truly special opportunity.

61279 Gorge View Street, Bend

Listing courtesy of Cascade Hasson SIR. Selling Office: .

17737 Everwild Circle 455 Unit 455, Bend
$3,200,000
5 Beds ⋅ 8 Baths ⋅ 220224580 MLS
Welcome to the ultimate mountain retreat in the prestigious community of Caldera Springs. Backing to a serene forest setting on .43 acres, this exceptional residence blends timeless Northwest architecture with resort-style luxury. Designed for effortless living and entertaining, the home offers 5 spacious suites, a den with full bath, bonus room, bunk room, and 7.5 bathrooms. The main level features four suites, dual dining areas, an impressive great room, and a chef's kitchen equipped with Sub-Zero & Wolf appliances plus two dishwashers. Upstairs, you'll find an additional guest suite, den with full bath, and expansive bonus & bunk rooms. Outside, experience your own private retreat with two fire pits, a custom water feature, hot tub, enhanced landscaping, and tranquil forest views. 3 car garage with epoxy floor. Meticulously designed and offered fully furnished, this turnkey luxury home includes access to Caldera Springs' exclusive amenities and an unmatched Central Oregon lifestyle.

17737 Everwild Circle 455 Unit 455, Bend

Listing courtesy of Sunriver Realty. Selling Office: .

62608 Sparrow Hawk Circle, Bend
$3,200,000
3 Beds ⋅ 3 Baths ⋅ 220223274 MLS
Serenity and privacy will be your first thoughts as you unwind in this luxurious, architecturally designed home. Premier location on 0.37 acres in sought after community of Shevlin Commons. Relax and take in the astonishing, uninterrupted Cascade Mountain views from nearly every room in the home, or one of the outdoor patios. Walk seamlessly from patios onto the adjoining public land of Shevlin Park, or take one of the nearby trails. Quiet, dark-sky starlit views with warmth by the fire-pit. Chef's kitchen and wet-bar room ideal for entertaining or head to the cozy wine tasting room. Working from home? Detached bonus office space or the eagle-nest office. Exquisite finishings and attention to detail throughout. It's not just a home, it's a lifestyle.

62608 Sparrow Hawk Circle, Bend

Listing courtesy of Stellar Realty Northwest. Selling Office: .

61454 Cultus Lake Court, Bend
$3,200,000
5 Beds ⋅ 7 Baths ⋅ 220207759 MLS
There's a light that finds its way through the trees in The Parks at Broken Top. Arborelle is where stories begin. Crowned with a brand-new roof and reimagined in 2024 by Design Bar Bend, it blends timeless grace with modern luxury. Inside, sunlight pours across warm oak floors, unveiling a scullery, wine room, loft, junior suite—spaces crafted for living and for dreams. The primary suite becomes a sanctuary—yoga room, spa bath, heated floors—where mornings are unrushed and intentional. Outside, over a half-acre of shade and sky invites pause—firelight dancing in the gas assit fireplace, steam rising from the hot tub, laughter drifting through the trees. Dual garages with 2 spaces each, a guest cottage for loved ones or passive income, endless possibility await. Just minutes from downtown Bend, trails, golf, and skiing, Arborelle isn't just a home. It's the beginning of your next great story.

61454 Cultus Lake Court, Bend

Listing courtesy of The Agency Bend. Selling Office: .

61865 Hosmer Lake Drive, Bend
$3,150,000
4 Beds ⋅ 4 Baths ⋅ 220227237 MLS
Nestled quietly above the Cascade-Highland trail, this modern sanctuary redefines the best of living in Bend. Surrounded by old-growth Ponderosas, the Scandinavian-inspired architectural design and premier Tetherow location offer luxurious, thoughtful, and intentionally low-maintenance living, with a unique level of quality and craftsmanship. Light-filled living spaces and a contemporary kitchen flow into a spacious dining area which cascades into a large living room. Hardwood ceilings extend seamlessly from the open living space to a 470SF elevated deck with outdoor fireplace, offering unparalleled indoor/outdoor living and sunset views. Premium details include zoned radiant-heat floors, Reynaers windows and doors, automatic shades, ductless HVAC, Moen water system, and Equitone siding. An airy primary suite with private deck, 4th bedroom/office, family room with deck, ground-level bonus room with a full bath, laundry room, and oversized 3-car garage complete this one-of-a-kind home.

61865 Hosmer Lake Drive, Bend

Listing courtesy of The Agency Bend. Selling Office: .

19885 7th Street, Bend
$3,134,039
220179846 MLS
Stunning new building with mixed use in downtown Tumalo. Central Oregon architecture mixed with Tuscan inspiration. Currently approved & used for retail, offices, manufacturing & is set up to be divided into three suites with separate HVAC and electrical. Sewer system in the works will open up usage possibilities to virtually anything allowed in the TUC zone, restaurants, boutique hotel, & much more. Rock exterior, copper roof accents & gutters, presidential shingles & raw metal siding make for a beautiful aesthetic & virtually maintenance free building. The interior has $75k worth of light fixtures, solid wood doors and trim. 70+ commercial storefront doors, windows & skylights. Suite 100 is 1190sf retail, 160sf back stock area, 2 bathrooms, custom bar & fireplace. Suite 200 is a large common area with bark, 2 bathrooms, 4 offices & 1100sf conference room. Suite 300 has kitchen, bathroom, & office. All are joined by tunnel with 1300sf reception area, courtyard & parking lot.

19885 7th Street, Bend

Listing courtesy of RE/MAX Key Properties. Selling Office: .

56545 Sunstone Loop 121 Unit 121, Bend
$3,125,000
6 Beds ⋅ 6 Baths ⋅ 220196173 MLS
Welcome to The Yellowstone House! Discover the best value in Caldera Springs with this timeless, custom-built retreat. Designed with warmth and comfort in mind, this home blends rustic elegance with modern luxury. Cathedral beams and hand-crafted ironwork showcase artisan details that never go out of style, while six bedrooms (five en suites), a dream bunk room, and an expansive game room ensure space for everyone. After a day of adventure, gather on the enclosed patio by the fire or unwind in the hot tub under the stars. Practical features like a heated roof + driveway, efficient utilities, and built-in safety systems make this the ultimate ''lock-and-go'' home, providing peace of mind whether you live here full-time or visit seasonally. Backed by open space and steps from world-class amenities including golf, 2 pools, a spa, and a private lake, this property is the perfect primary home, vacation retreat, or high performing investment opportunity, built for making life long memories.

56545 Sunstone Loop 121 Unit 121, Bend

Listing courtesy of Windermere Realty Trust. Selling Office: .

61727 Tam McArthur Loop, Bend
$3,100,000
5 Beds ⋅ 5 Baths ⋅ 220217966 MLS
Serene, private & refined, this Broken Top home offers a rare blend of woodland setting & elevated golf course views on nearly half an acre w/filtered views of lake & clubhouse, creating a sense of connection & seclusion. A dramatic entry opens to great room w/soaring ceilings, exposed timber trusses, striking stone fireplace & walls of glass framing the views, seamlessly connecting to outdoor kitchen, patios & fireplace seating. Inside, the gourmet kitchen is both sophisticated & functional, centered around island w/ bar seating, high-end appliances inc. multiple ovens, refrigerators & dishwashers, butler's pantry & light-filled dining. Privately situated, the primary wing offers tranquil views, outdoor access & luxury bath. Adj office w/ fireplace provides a quiet, comfortable workspace. Guest wing features 4 additional bedrooms, 3 baths, bonus room & theater, reflecting homes exceptional livability. Heated 4-car garage w epoxy-floors & separate carpted/heated wrkout space & basmnt

61727 Tam McArthur Loop, Bend

Listing courtesy of Berkshire Hathaway HomeService. Selling Office: .

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