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$1,829,900
5 Beds ⋅ 4 Baths ⋅ 220203124 MLS
Recognized as the 2026 COBA Tour of Homes Best of Show winner, this exceptional masterpiece represents the pinnacle of craftsmanship, design, and luxury living in Discovery West. Built by Luxe Homes, a multiple award-winning builder renowned for its uncompromising quality and innovative design, this residence also earned honors for Best Kitchen and Best Interior Finish. Spanning 2,896 sq ft, this thoughtfully designed residence offers 4 bedrooms, 4 baths, and refined living across two levels. The main level features an open-concept great room, designer kitchen, dining area, and a private suite, plus a versatile office/bedroom. Upstairs, enjoy a spacious bonus/media room, loft, and two en-suite bedrooms. Seamless indoor-outdoor living is highlighted by a covered rear deck. Additional features include a 3-car garage with dedicated RV/rec bay, generous storage, and a well-appointed mudroom/laundry. A rare blend of modern design, function, and luxury in one of Bend's premier neighborhoods.

371 NW Crosby Drive Lot 233 Unit Lot 233, Bend

Listing courtesy of Harcourts The Garner Group Real Estate.

$5,890,000
6 Beds ⋅ 9 Baths ⋅ 220202448 MLS
One of the most private & unique offerings in Highlands at Broken Top, this exceptional 10+ acre gated estate combines luxury living with the serenity of a park-like setting just minutes from Bend. Custom built by Norman Building & Design, the 9,197-sq. ft. residence showcases timeless craftsmanship, soaring ceilings, extensive stonework, custom cherry cabinetry, & walls of windows that capture the beauty of the surrounding landscape. Designed for both grand-scale entertaining & comfortable everyday living, the home offers multiple gathering spaces, a main-level primary suite, guest accommodations, & seamless indoor-outdoor living. Resort-style amenities include a pool, detached guest quarters, workshop & extensive garage space, EV charging, & room for collectors, hobbies, and recreation. Surrounded by natural beauty & adjacent to miles of recreation opportunities, this extraordinary estate offers a level of privacy, space, & flexibility rarely found in Bend.Seller financing available.

18883 Sutherland Court, Bend

Listing courtesy of John L Scott Bend.

$1,495,000
3 Beds ⋅ 3 Baths ⋅ 220201956 MLS
Exceptional acreage property featuring a massive heated shop—the ultimate space for hobbies, equipment, vehicles, storage, or a home-based business. Situated on 4.79 private acres in Conestoga Hills, this property offers the perfect blend of functionality and peaceful country living. The home features an updated kitchen with quartz countertops, stainless steel appliances, abundant storage, and comfortable gathering spaces. The main-level primary suite includes a soaking tub, dual sinks, and a walk-in closet. Outdoors, you'll find versatile outbuildings, a custom greenhouse, tool shed, covered RV/boat parking, and a three-car garage with additional storage. Thoughtfully designed landscape lighting accents the paver driveway and welcoming outdoor spaces. Enjoy evenings around the firepit, entertain under the gazebo-covered BBQ area, and take advantage of nearby parks and trails while enjoying the privacy and freedom of acreage living.

23308 Chisholm Trail, Bend

Listing courtesy of Bend Premier Real Estate LLC.

$1,999,000
5 Beds ⋅ 4 Baths ⋅ 220201667 MLS
Welcome to a stunning 34-acre estate where luxury living meets premier equestrian amenities & breathtaking Cascade Mountain views. The impeccably crafted 4,357 sq ft home has elegant finishes & thoughtful design throughout. It offers 5 bdrms, 4 baths, including two spacious primary suites. Enjoy the gourmet kitchen, open floor plan, vaulted ceilings, mudroom, pantry, & more. The main-level primary features a luxurious bath with soaking tub. Perfect for horse enthusiasts, there are 22 irrigated acres, with sought after COID water rights, two ponds, a 7-stall barn with tack room & wash rack, two outdoor arenas, a 60' round pen, 10 paddocks, hay shed, & welded pipe fencing. Ride directly onto miles of BLM land and endless trails. Power & water extends to dry lots and pastures. There is also potential for multigenerational living. This is Central Oregon equestrian living at its best.

24166 Dodds Road, Bend

Listing courtesy of LivOregon Real Estate LLC.

$2,995,000
3 Beds ⋅ 5 Baths ⋅ 220201443 MLS
Beth Dutton would live here! A rare opportunity to secure over 160 acres of private Central Oregon countryside, just beyond Bend's city limits--where space, water, and independence still matter. Surrounded by sweeping mountain views & uninterrupted skies, this estate offers a lvl of privacy + control that is increasingly rare, ideal for those who value long-term security, self-reliance & land ownership with purpose. With 85+ acres of deeded COID water rights, the property is equipped for efficient, modern agricultural use, featuring a state-of-the-art app-controlled pivot system and multiple wheel lines. The custom farmhouse blends refinement and comfort with vaulted ceilings, a chef's kitchen, two primary suites, and a covered deck overlooking the Cascades. A ~10,000 sq. ft. multi-purpose barn w/ bath & huge bar. Four-stall barn, outdoor riding arena, and large concrete event platform provide flexibility for private operations, stewardship, or future vision. Landowner preference tag!

23636 Ten Barr Trail, Bend

Listing courtesy of Cascade Hasson SIR.

$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.

$2,299,000
4 Beds ⋅ 5 Baths ⋅ 220199311 MLS
This exceptional estate in the prestigious Juniper Preserve Resort is nestled within the exclusive Pronghorn Community. Spanning 0.48 acres, it blends luxury, comfort, and elegance for a one-of-a-kind living experience. The 5,118 sq ft home includes a 615 sq ft casita, perfect for guests or a private retreat. The main-level primary suite opens directly to an outdoor spa, while two upper suites access patios with stunning views. There are four opulent bedroom suites in total. The chef's kitchen features a prep pantry and wine cellar. Natural stone and wood accents lend timeless character throughout. A south-facing covered patio with a wood-burning fireplace offers year-round enjoyment. Car enthusiasts will appreciate the 1,328 sq ft garage with room for three cars and a golf cart. Enjoy all the gated community offers, including two championship golf courses at Pronghorn--where luxury meets lifestyle.

23021 Brushline Court, Bend

Listing courtesy of Coldwell Banker Bain.

$1,240,000
4 Beds ⋅ 3 Baths ⋅ 220200307 MLS
Live the good life at Freshfields Farm, located in the Golden Triangle, minutes from Bend and Sisters. This beautifully remodeled, single-level 4 bedroom, 3 bathroom home offers 2,875 sq. ft. feet of living space on a stunning 7.94-acre lot. The property includes a lock-off suite, with full bath, living room, and separate access--ideal for guests. The heart of the home is the commercial grade chef's kitchen with high end appliances, spacious island, abundant counters, and lots of storage. Outside, discover multiple patios perfect for enjoying the views, magical reading nooks, gardens, and sunsets over the pond, all framed by the breathtaking Cascade Mountains. After a day of adventure, unwind in the sauna or hot tub. Additional features include a barn, chicken coop, greenhouse, shed, shop with an office and hobby room, and RV parking. With 7.5 acres of TID irrigation, the possibilities are limitless. Seize the opportunity to own a slice of paradise in the heart of Central Oregon!

19189 Dayton Road, Bend

Listing courtesy of Cascade Hasson SIR.

$1,099,000
3 Beds ⋅ 3 Baths ⋅ 220200217 MLS
Perfect Westside home close to downtown with a highly coveted short term rental permit! Main level features a spacious primary suite with laundry and a guest bedroom with full bath. Well equipped, spacious kitchen, and living room with a cozy gas fireplace. Downstairs features a large second primary suite, living area, kitchenette and laundry, private entrance and patio . Other features include ultra energy efficient ICF construction, newer floors and paint, great natural light. Fully furnished and turn key. Private alley access to parking and single car garage. Live comfortably in this home full-time, or rent nightly for additional income. All this in an ideal location with close proximity to downtown, schools, coffee shops, Drake Park, Newport Market, restaurants, the Deschutes river and more! Call your favorite buyers agent for a tour today. One owner is a realtor licensed in the state of Oregon.

1650 NW 5th Street, Bend

Listing courtesy of Engel & Voelkers Bend.

$599,000
3 Beds ⋅ 2 Baths ⋅ 220199043 MLS
This is the most adorable and completely remodeled single story home! The .23 acre lot feels private with great outdoor space, a nice deck for entertaining, a shed, a green house and a large RV parking area. Walk into this 3 bedroom, 2 bathroom home with updated vinyl plank flooring, newer lighting and interior and exterior paint. The large inviting living room has great built in features with an electric fireplace to keep you cozy. A completely remodeled kitchen has stainless steel appliances, quartz countertops, subway tile backsplash and a great large pantry. The bathrooms are completely updated and feature beautiful tile flooring. Hard to find a large lot with an updated and move-in ready home!

21315 Livingston Drive, Bend

Listing courtesy of Cascade Hasson SIR.

$1,199,900
5 Beds ⋅ 4 Baths ⋅ 220198607 MLS
Escape to this stunning riverfront retreat in the sought-after River Meadows Estates, just south of Sunriver! Nestled along the banks of the Deschutes River, this spacious 5-bedroom, 3.5-bathroom home is the perfect getaway. With a huge bunk room, there's plenty of space for family and friends. Enjoy the private hot tub, expansive outdoor living areas, and breathtaking river views. As part of the River Meadows Estates community, you'll have access to top-notch amenities, including a swimming pool, tennis courts, kids' play area, and a scenic asphalt bike path. Currently operating as a successful Short-Term Rental (STR), this property is a prime investment or personal retreat. With easy access to Mt. Bachelor and all that Central Oregon has to offer, your next adventure is always within reach. A true four-season paradise—don't miss out on this incredible opportunity!

16775 Pony Express Way, Bend

Listing courtesy of Cascade Hasson SIR.

$3,465,000
3 Beds ⋅ 4 Baths ⋅ 220197558 MLS
Discover the natural beauty of Deschutes River Ranch in this remarkable retreat located in Tumalo, Oregon. Spanning an impressive 3,967 square feet, this striking residence features 3 spacious bedrooms, each with a private en-suite bathroom, and an open-concept floor plan bathed in natural light. The chef's kitchen is a culinary delight, equipped with top-of-the-line Thermador appliances, beautiful quartzite and granite countertops, and a hidden butler's pantry, perfect for entertaining. The main level also offers a dedicated home office, and a large family/media room. Enjoy the unique daylight basement, which includes an exceptional nine-car garage (see sample floor plans for other options for this amazing space) accommodating RVs and boats, along with a sound-isolated movie theater. Nestled in a charming community surrounded by the stunning Cascade Mountains and the Deschutes River with scenic walking trails, community parks, and a nearby swimming hole with a covered picnic area.

20334 Arrowhead Drive, Bend

Listing courtesy of Cascade Hasson SIR.

$8,900
1 Beds ⋅ 1 Baths ⋅ 220197385 MLS
Enjoy 8 rotating weeks each year in this coveted Seventh Mountain Condo with cliffside views. This is not a timeshare, but is a deeded 1/6 share. This hard to come by top floor unit is an end unit with big balcony overlooking the valley and surrounding hillsides. It features a spacious living area with fireplace, island kitchen and comes fully furnished. The condo sleeps 4 with the King sized bed in the bedroom and a nice pull out sofa bed in the primary living area. The bathroom has dual access to the bedroom and main living area. HOA's include property maintenance, utilities, snow removal, and all exterior maintenance. Inn of 7th Mountain is a premier resort in Bend and the closest lodging to the Mt. Bachelor ski area. The resort has multiple pools, hot tubs, fitness center, hiking trails, tennis & pickleball courts, playground, ice skating, mini golf, restaurant and more.

18575 SW Century Drive 1537A aka 682 Unit 1537A aka 682, Bend

Listing courtesy of Cascade Hasson SIR.

$1,639,000
3 Beds ⋅ 3 Baths ⋅ 220196979 MLS
This fabulous Mid-century modern home in Northwest Bend is located in the much sought after Discovery West neighborhood. It's soaring ceilings, big windows and skylights flood the home with light. With high end finishes throughout this beauty boasts three bedrooms, an office, a bonus room and a spacious three car garage with one bay to hold your Sprinter van or RV. Discovery Corner, a vibrant community gathering place with small shops and dining, is just a short distance away.

3354 NW Leavitt Lane Lot 275 Unit Lot 275, Bend

Listing courtesy of Harcourts The Garner Group Real Estate.

$95,000
2 Beds ⋅ 2 Baths ⋅ 220196151 MLS
Whether you're seeking a family getaway, 1031 exchange, or a short-term rental, River Ridge at Mt Bachelor Village offers it all. This stunning 2-bdrm, 2-bath condo, perched high above the Deschutes River, is turn-key. 10 weeks annually, Fri-Fri calendar. The condo offers the flexibility to create 2 separate rentals by locking off the 2nd bedroom, an ideal income-generating option. After a day of adventure, unwind in your private hot tub nestled in a peaceful forest setting, listening the river. Amenities include heated pool, hot tubs, Fireside room, & access to the River Trail. Ability to exchange your weeks through RCI for even more travel opportunities. Located near historic downtown Bend & the Old Mill District. Short drive to Mt. Bachelor Ski Resort. Experience the best that Bend has to offer!

19717 Mt Bachelor Dr. 330E Unit 330E, Bend

Listing courtesy of RE/MAX Key Properties.

$1,550,000
3 Beds ⋅ 3 Baths ⋅ 220194374 MLS
This exceptional equestrian estate near downtown Bend offers 2 tax lots,world-class facilities and Cascade Mountain views.The 80'x186' indoor arena features new silica sand and Pro-Tex footing and is complemented by the 175'x250' outdoor arena with a sand-fiber mix.Recently a hunter-jumper facility, it includes a Grand Prix field with a pond and jump/slide bank. Renovated barns offer bright stalls with skylights, groom stalls, and tack rooms.The 3-bedroom,2.5-bath house is ideal for a manager or owner.All of this 40 minutes to the lifts at Bachelor and located near Bend Airport.New office quarter in historic barn with 3 offices, staff lounge, staff breakroom and a full bathroom.This equestrian estate has unmatched access for equestrian enthusiasts while combining luxury,lifestyle,and all the outdoor recreation that Bend has to offer!

22333 Nelson Road, Bend

Listing courtesy of Cascade Hasson SIR.

$1,650,000
3 Beds ⋅ 2 Baths ⋅ 220191801 MLS
This property is a delightful 5± acre equestrian estate near Tumalo and just six miles from Bend. Known for breeding and training top horses in NRCHA, Team Penning, and Sorting competitions, it features a two-story home with three bedrooms and two bathrooms across 2,080± square feet. Highlights include wood-burning stone fireplaces, a wrap-around porch, a 20' x 24' deck, and a permit-ready plan for an expanded primary suite. The property also boasts a 24' x 36' barn, a 10' x 36' equipment shed, and a 12' x 24' run-in shed, all set in a mature landscape with stunning mountain views. Located on a cul-de-sac, Juliet Farm offers a peaceful retreat just 6± minutes from Bend, with easy access to shopping, dining, and skiing at Mount Bachelor. Experience a perfect blend of elegant living and equestrian excellence at this exceptional estate.

65160 Highland Road, Bend

Listing courtesy of Hicks Team - Fay Ranches LLC.

$1,149,000
4 Beds ⋅ 4 Baths ⋅ 220185126 MLS
This custom mountain home is an outdoor paradise. The original structure features beautifully hand-scribed, notched, and hand-hewn logs. Room for 5 cars, RV parking and toys. Trex decking, a water feature, horse corral, and barn. The attached addition includes another great room, space for pool table, 2 bds, office, full bath, private entrance w/ outdoor stairwell, and locked access to the main home, ideal for inlaws or as a rental. A large deck offers backyard views. The main home boasts an open floor plan and vaulted ceilings. The main-level master suite offers a soaking tub, heated floors, dual sinks, tiled shower, and walk-in closet. Upstairs is a bonus loft and a private guest bed/bath. The kitchen has a large island and opens to the great room. The laundry room has an indoor animal wash station. Deschutes NF is out front; back road to Mt. Bachelor makes it 20 min away, with golf, fly fishing, mtn biking, Sunriver dining nearby. Adjacent parcel also for sale.

16864 Covina Road, Bend

Listing courtesy of Cascade Hasson SIR.

$19,900
1 Beds ⋅ 2 Baths ⋅ 220176251 MLS
If your looking for a place with low maintenance to get away, unwind and relax this 1/6 Deeded Fractional Share ownership with 8 weeks per year in 1 Bed, 2 bath condo is the place. Completely furnished end of the building unit on the second floor in building 17 with access to all the resort amenities. Pools, skating rink & golf course. Unit sleeps 4 with 1 bedroom and hide-a-bed in the living room. 40 year fractional rotational share calendar is in effect through 2040. This share uses ''A'' on the share Calendar.

18575 SW Century Drive 1721 Unit 1721, Bend

Listing courtesy of La Pine Realty.

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