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$1,290,000
4 Beds 3 Baths 220222673 MLS
Turnkey 5-acre property in SE Bend with 2 acres of irrigation rights, offering privacy, functionality, and stunning natural beauty. Framed by sweeping Cascade Mountain views, the 2,770 sq. ft. home features 4 bedrooms, 2½ baths, and mid-century charm throughout. Well maintained and filled with natural light, the home offers warm, inviting spaces with picturesque views from nearly every window. Outside, a tranquil pond, mature landscaping, and peaceful setting create a true retreat. Equestrian enthusiasts will appreciate the 1,296 sq. ft. four-stall barn, storage outbuildings, and room to ride, with nearby public lands. A rare opportunity to own horse property with space, serenity, and unforgettable mountain views just minutes from Bend.

60376 Arnold Market, Bend

Listing courtesy of Cascade Hasson SIR.

$975,000
3 Beds 3 Baths 220222195 MLS
Welcome to Woodside Ranch in SE Bend. Where big trees, big lots, star filled skies and privacy take center stage. This custom built home adds the benefit of an extra 3 car garage/ SHOP with abundant storage and places to park boats and RV's There is ALSO an attached 3 car garage. This home has been loved by the same owners since it was built in 1978. Upgrades and maintenance have always been done, and for the last 25 years, it has been a part time residence. Wood floors, builtins, and a seamless flow from the main living area to a generous outdoor living space that offers mature landscaping and abundant privacy. Upstairs are 3 bedrooms, plus double French doors to an office/ den. Closets and storage are plentiful in this home. Woodside Ranch is served by two Roats Water wells. Have a glass of water from the tap when you tour this home. If you are looking for a home with elbow room, but you appreciate good neighbors (at a distance) and high quality don't miss this one.

20423 Heritage Avenue, Bend

Listing courtesy of Cowgirl Properties.

$2,895,000
3 Beds 2 Baths 220220953 MLS
A rare offering of quality and lifestyle, w/direct access to BLM, this 19.7 acre estate is within a short drive to the conveniences of NE Bend. The property features a light-filled 2,459 sq. ft. single level custom home + a lawfully established 1,304 sq. ft. second dwelling. The main residence showcases contemporary style with the timeless beauty of sand-in-place white oak floors, custom walnut cabinetry, a chef's kitchen, walk-in pantry, quartz & stainless surfaces & premium appliances. Spa-inspired baths offer radiant heated tile floors & a steam shower, complemented by a dedicated mudroom and a 1,014 sq. ft. heated/cooled 3 car garage. With 8.3 acres of COID water rights, in-ground electrical services, 2 irrigation ponds, an automated irrigation system, a 50' round pen, a 200' x 150' outdoor arena, a 1,100 sq. ft. barn/shop w/tack room & multiple outbuildings, this property checks all the boxes for the equestrian enthusiast.

23420 Bear Creek Road, Bend

Listing courtesy of Coldwell Banker Bain.

$1,225,000
4 Beds 3 Baths 220222435 MLS
Escape to an unparalleled Equestrian Retreat! Beautiful log home on 5+acres behind private gate, bordering National Forest Land for endless riding & adventure! The elegant residence features Acacia floors & loft balcony in the expansive lodge-style home. Stamped concrete patios & magnificent water feature at the entry provide a seamless indoor-outdoor lifestyle. Large pond at the rear of the property creates a tranquil focal point for outdoor entertaining. This premier property is a horse lover's dream, offering a 160x300 arena built in 2018, a 4-stall barn, hay shelter, & well-maintained pristine grounds! Land is perimeter & cross-fenced, creating 3 separate pastures. Paved driveway provides easy access to the gated entry. For added convenience, the property incl. RV storage, garage, & large shop with a concrete floor. Located just 2 mi S of the coveted Sisters School District, this estate offers the perfect blend of secluded country living w/ easy access to Central Oregon amenities!

16443 Dea Drive, Bend

Listing courtesy of Jeff Larkin Realty.

$949,900
5 Beds 2 Baths 220222405 MLS
Discover your dream retreat in Bend, Oregon, with this exquisite single-level home boasting five spacious bedrooms and two well-appointed bathrooms across approximately 2,326 square feet. Nestled on 2.5 lush acres, including 1.5 acres equipped w/irrigation, this property features a light-filled open-concept great room, versatile bonus room, and charming wraparound porch offering serene views of the surrounding forest and tranquil pond. The fully fenced yard w/gated entry ensures privacy, while being just minutes from downtown Bend allows for easy access to community amenities & scenic outdoor trails. Enjoy a modern lifestyle enhanced by energy-efficient updates, new HVAC system (2020), & new septic system (2018).New roof 2026. Additionally, the property includes a barn w/stalls & carport, chicken coop, dog kennel w/ doghouse, and spacious 768sf storage shop, making it perfect for hobbyists & animal lovers alike.

63425 Deschutes Market Road, Bend

Listing courtesy of Stellar Realty Northwest.

$395,000
220222337 MLS
Rare buildable acreage minutes from downtown Bend -- 3.29-acre legal lot of record (confirmed August 2025, File 247-25-000412-LR) with senior COID irrigation water rights and a 2022 onsite wastewater site evaluation supporting a 1-to-4 bedroom residence. Zoned MUA-10 (Multiple Use Agricultural) for residential, agricultural, and accessory uses. Established 25-foot driveway easement off Dobbin Road. Open pasture, gentle topography, mature setting -- ready for a custom build, hobby farm, or equestrian setup. Existing irrigation system, pump, and sprinkler infrastructure available from adjacent owner, offering a meaningful head start versus building from scratch. In-close Bend acreage with confirmed water rights and verified buildability is genuinely scarce inventory. Bring your builder, plans, or vision.

61855 Dobbin Road, Bend

Listing courtesy of Berkshire Hathaway HomeService.

$2,850,000
5 Beds 4 Baths 220222189 MLS
Set above downtown Tumalo on just over 7 acres, this legacy estate in Winston Ranch is the kind of property that rarely comes available. Mornings open to 180-degree Cascade Mountain views, afternoons unfold by the pool, and evenings settle into a private movie theater or the one-of-a-kind office and den wrapped in spectacular woodwork. Freshly updated throughout with new interior and exterior paint, hardwood flooring, new carpet, updated fixtures, and a reworked primary ensuite, the home feels both timeless and ready. The ground-level primary suite frames an incredible mountain view with a large walk-in closet, picture-perfect tub, and dual vanities, while cherry cabinetry and an open-concept kitchen and living space anchor everyday life. A finished shop with bathroom and workspace and a 44' RV bay deliver rare flexibility. HOA-managed underground irrigation, a 1-mile private loop, and an underground dog fence make country living effortless. Call for a private tour.

20180 Winston Loop, Bend

Listing courtesy of Cascade Hasson SIR.

$1,295,000
4 Beds 3 Baths 220221871 MLS
Move-in ready horse property in the heart of Tumalo with stunning Cascade Mountain views and exceptional equestrian amenities. This beautifully updated 4bed/3ba home offers an open-concept layout filled with natural light, featuring quartz countertops, stainless steel appliances, an induction range, woodstove, and a spacious primary suite with vaulted ceilings and a custom tile shower. A second en suite bedroom with private deck access provides ideal flexibility for guests or multigenerational living. The home includes a newer furnace and heat pump, a newer roof, private well with filtration system, and a 3-car tandem garage with workshop space. Set up perfectly for horse enthusiasts with 4.5 acres of irrigation rights, and fully automated underground sprinklers. The fenced and cross-fenced acreage features a 3-stall barn, tack room, hay barn, loafing shed, and additional outbuilding with fenced dog run. Surrounded by mature landscaping and offering outstanding privacy!

19800 Connarn Road, Bend

Listing courtesy of Cascade Hasson SIR.

$1,350,000
4 Beds 3 Baths 220220862 MLS
Beautiful country estate on 9.52 acres in desirable Northeast Bend with 2.5 acres of irrigation. Built in 2016, this 2184 sq ft farmhouse offers 4 bedrooms, 2.5 bathrooms, and a welcoming wrap around deck, with the primary suite conveniently located on the main level. The impressive 4,300 sq ft shop is a standout feature, complete with a huge bridge crane for easily moving heavy items. Additional amenities include a charming art studio, a separate office with ADU potential, irrigation pond, RV hookup and various storage sheds. With easy access to Highways 20 & 97, this property offers the perfect blend of country living, convenience, and functionality. A wonderful family property with room for animals, hobbies, equipment storage, and wide-open Central Oregon living.

63639 Gentry Loop, Bend

Listing courtesy of Ninebark Real Estate.

$1,425,000
3 Beds 3 Baths 220221451 MLS
Beautiful single-level retreat on 2.38 acres blending country charm with a little rock & roll. This thoughtfully designed home features a spacious primary suite with dual walk-in closets and a recently remodeled spa-inspired ensuite. Formal living and dining spaces pair perfectly with the cozy great room, fireplace, and gourmet kitchen designed for gathering and entertaining. Outside, enjoy a park-like setting with mature landscaping, a lovely pond, fully fenced back yard, and magical nights under the stars from the hot tub. Car enthusiasts, hobbyists, and adventurers will love the incredible shop space, including a 1,300 sq ft detached 4-car garage built in 2004 and an enormous 1,692 sq ft RV garage/shop built in 2005. Wraparound outdoor living and peaceful privacy create the perfect balance of comfort, function, and lifestyle.

20407 Pine Vista Drive, Bend

Listing courtesy of Harcourts The Garner Group Real Estate.

$2,100,000
2 Beds 2 Baths 220221921 MLS
147 ACRES bordering BLM--an extraordinary, one-of-a-kind retreat where adventure & serenity meet, just 15 minutes from Sunriver. Imagine owning your own landmark - THE ROCK - with sweeping 360 degree views then returning to a luxury custom two-story cabin nestled in the woods with a charming loft that enhances its warm, inviting character. Designed in harmony with nature, this exceptional home showcases artisan craftsmanship with hand-carved railings & posts in and out, foraged iron custom lighting, maple flooring, and custom tilework. The dramatic great room features a floor-to-ceiling stacked stone wood-burning fireplace, soaring vaulted pine ceilings, skylights, and abundant windows framing peaceful forest views. The kitchen offers raw-edge granite slab counters and a breakfast bar. Fish the nearby Fall River or venture to ''The Rock'' and beyond - 147 acres! Complete with 2 bedrooms, 2 baths, and a metal roof--your private wilderness sanctuary awaits. Schedule your private showing!

54655 Jack Pine Road, Bend

Listing courtesy of Sunriver Realty.

$1,279,000
4 Beds 3 Baths 220221863 MLS
Welcome to your Central Oregon homestead, ideally located between Bend and downtown Tumalo. Tucked back behind a canopy of trees, this private 6.73-acre ranch offers Cascade Mountain views, peaceful surroundings, and the perfect setup for country living. The charming 1994 farmhouse blends original farmhouse character with thoughtful updates, including a beautifully remodeled kitchen, inviting front porch, formal living and dining rooms, spacious family room, and large country kitchen. The 3,018 sq ft home features 4 bedrooms, 2.5 baths, plus a bonus room upstairs. Built for a true working ranch lifestyle, the property is fully fenced and cross-fenced with 3 pastures ft in-ground sprinklers, pond, 4.6 acres of timed Swalley irrigation, .25-acre garden, and setup for horses or livestock. A 24x36 heated & plumbed shop and oversized driveway complete this rare Central Oregon retreat. Don't wait- schedule your tour today!

64080 Highway 20, Bend

Listing courtesy of Cascade Hasson SIR.

$1,175,000
220221809 MLS
Discover your ideal retreat in Bend, Oregon, where breathtaking Cascade Mountain views await you. This exceptional 6.47-acre property offers a unique opportunity to create your dream home overlooking Tumalo State Park. It features a charming 462-square-foot cabin with potential for an accessory dwelling unit, along with a workshop equipped with five open stalls perfect for toys, horses, or creative projects. Enjoy the serene view gazebo, ideal for relaxation, and benefit from 4.3 acres of Swalley irrigation rights, complete with ponds, risers, and sprinklers. The level, partially fenced pasture is perfect for a hobby farm, equestrian pursuits, or a private sanctuary. Embrace the tranquility and beauty of Bend while exploring the potential for a multi-dwelling compound in this picturesque setting.

64141 US 20, Bend

Listing courtesy of Cascade Hasson SIR.

$2,329,000
4 Beds 3 Baths 220221777 MLS
Multi-generational custom home on 2.61 private & elevated acres in Lane Knolls Estates. Completed in 2019, this luxuriously appointed home boasts a central open great room with massive vaulted ceilings and custom wood beam accents. Anchored by the home's chef kitchen with massive island, the great room is book-ended with a formal dining area/living room on the SE wing and a cozy family room overlooking the home's fenced & beautifully landscaped courtyard on the NW side. The main home boasts a main-level primary suite, two guests rooms & large bonus room up over the attached 3-car garage PLUS RV garage! Walking through the shared laundry room with dog wash station, you'll enter the secondary residence, which can be incorporated into the main home or used separately. Featuring its own attached 2-car garage, the eastern wing features a full kitchen, living room, bedroom, & spacious bath.

61465 White Peaks Court, Bend

Listing courtesy of The Agency Bend.

$1,700,000
4 Beds 3 Baths 220221453 MLS
Sweeping Cascade Mountain views define the setting for this single-level custom home on 4.53 private, fully fenced acres with 3 acres of irrigation rights, minutes from Downtown Bend. Fully remodeled interiors showcase vaulted ceilings, Acacia wood floors, quartz surfaces, a mahogany grand entry, and a dramatic floor-to-ceiling Montana stone fireplace. The expanded primary suite features a light-filled sunroom wrapped in walls of glass, creating an elegant home office, sitting room, or private retreat. Recent enhancements include updated electrical, smart home systems, garage workshop, refined landscaping, metal cross fencing, and new designer primary closet. Designed for luxury acreage living, the property offers a fenced orchard, pond, room for horses, RV parking with hookups, a north electronic gate, four-car garage with climate-controlled gym, and a 1,440 SF shop with 13' doors on its own electric panel. A rare Bend acreage where refined living, privacy, and versatility converge.

61885 Ward Road, Bend

Listing courtesy of Cascade Hasson SIR.

$1,325,500
3 Beds 3 Baths 220221576 MLS
Minutes from downtown Bend, but it feels like you've escaped the world. Just over 2 fenced, irrigated acres with professional landscaping -- the kind of place you pull into after a long day and just exhale. The backyard was made for living -- private patio, hot tub, fire pit, water feature, and an outside bar. Inside, everything flows easily with an open floor plan, game room, and a big utility/mud room that actually gets used. The detached garage has a loft and shop area for all your projects. The mother-in-law suite is completely separated from the main living area -- use it as a primary bedroom or run it as an Airbnb for extra income. Three horse stables, a greenhouse, a 29x31 covered carport, and a garden round out the property. There's room here for horses, hobbies, guests, and income -- all on one piece of land. Pristine and one of a kind. Don't miss it.

22539 Martee Lane, Bend

Listing courtesy of Duke Warner Realty ERA Powered.

$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.

$2,495,000
4 Beds 6 Baths 220221476 MLS
This extraordinary, 18.95 acre Luxury Estate sits in a park like setting with tall pines, sparkling pond and panoramic mountain views! Offering endless options for the lifestyle you desire, there is room to create a wellness pavilion, car collection, home business, equestrian set up, yoga, gym or artist studio! Great Room features dual flanking Greystone fireplaces, wood beams, Brazilian cherry floors and bar area for entertaining. Huge Chef's kitchen features slab granite and large picture window and flows into an elegant dining room with climate controlled wine room. Second floor Primary Suite is a private sanctuary w/sitting room, fireplace and covered balcony that showcases the cinematic landscape. Main floor Guest Suite includes a bedroom, bath and Bonus room. Two additional guest rooms and two office/flex spaces w/private entrances are perfect for multigenerational living or work from home. Outbuildings include a huge 5 bay RV/shop, detached 2 car garage and dog kennel.

21725 Rickard Road, Bend

Listing courtesy of Cascade Hasson SIR.

$4,950,000
5 Beds 3 Baths 220221468 MLS
A riverfront sanctuary that comes to market once in a generation. Encompassing nearly three acres and 400 feet of low-bank frontage on the Deschutes River, this property represents one of the largest riverfront parcels in all of Bend - set along one of the Northwest's most iconic waterways, with a sweeping stretch of shoreline unlike anything else on the market. The River Home spans nearly 4,000 sq ft with multiple indoor and outdoor living spaces, a private primary wing, and a guest wing - all with unobstructed river views. Here, the Deschutes National Forest is your closest neighbor - and the cherished mountain town of Bend is just minutes away. Step from your back door to cast a line, host a gala, or watch the seasons change from the bank. Family weddings, holiday events, and legendary dinner parties have graced these grounds for years. As the current owners will tell you: no one ever turns down an invitation, and guests are reluctant to leave. It's hard to put a price on magic.

18880 Baker Road, Bend

Listing courtesy of Stellar Realty Northwest.

$1,989,999
3 Beds 5 Baths 220220868 MLS
Some homes are built to live in. This one is built to gather. From the moment you pass through the gate of Sunset View Estates and the Cascade Mountains fill your windshield, you know you've arrived somewhere special - and the home delivers at every turn. Outdoor kitchen, covered patios, cascading water feature, fire pit, and exterior fireplace -designed for evenings that stretch late into a Central Oregon summer. Inside: bonus room with wet bar, pool table & grand piano included. The kind of space that makes any night feel like an event. Daily life is just as compelling. Radiant-heated white oak floors, Brazilian granite, custom built-ins, and multiple gas fireplaces throughout. The main-level primary suite is a sanctuary - private office, balcony, jacuzzi with Cascade Mountain views. 4,596 sq ft, 1.7 private acres, golf course and mountain views. Heated 4-car garage with RV hookup. New roof, fresh paint, move-in ready. This is Bend's luxury market at its finest - and it's ready now.

20112 Starfire Ridge, Bend

Listing courtesy of Cascade Hasson SIR.

$2,499,000
3 Beds 4 Baths 220221303 MLS
Tucked within the exclusive enclave of Pacific Cascade Heights in a prime NW Bend location, this extraordinary 9.88-acre estate offers a rare blend of privacy, luxury, and convenience - just minutes from Bend's thriving north end. Soon, residents will enjoy direct access to the Riley Ranch Nature Preserve, Deschutes River Trail, and Tumalo State Park. Completed in 2020, the 3,771 sq ft custom residence features vaulted ceilings, abundant natural light, and seamless indoor-outdoor living with a custom roll-up door opening to an expansive covered patio. The chef's kitchen is outfitted with Thermador appliances, a wet bar, and exceptional butler's pantry. The main-level primary suite offers a spa-inspired retreat, while upstairs guest suites and a bonus room enjoy panoramic views from a private cantilevered deck. A park-like backyard and oversized 3-car garage are impressive in size and functionality. Horses are permitted, allowing you to bring your equestrian dreams to life.

20055 Pacific Heights Road, Bend

Listing courtesy of Stellar Realty Northwest.

$1,299,000
3 Beds 2 Baths 220220970 MLS
Experience the beauty of Central Oregon living on this picturesque 10-acre property featuring a completely remodeled, turnkey single-level home with sweeping panoramic views of the Cascade Mountains. Designed for comfort and lifestyle, this exceptional acreage offers unforgettable sunsets, lush landscaping, mature fruit trees, established gardens, and irrigation water ideal for hobby farming, animals, or sustainable living. The property is fenced for critters and provides the perfect blend of privacy, functionality, and natural beauty. A spacious barn with flex space above creates more room for guests, a home office, art studio, or creative retreat. Peaceful and private, this one-of-a-kind Bend property captures the essence of country living while still being conveniently located near town amenities, recreation, and outdoor adventure.

21837 Repine Drive, Bend

Listing courtesy of Bend Premier Real Estate LLC.

$1,099,000
3 Beds 3 Baths 220221154 MLS
Nestled on 12.55 acres with a COID canal running through the property, this 2,602 sq ft two-story home offers privacy, space, and a Central Oregon lifestyle. A 30 X 50 shop (1,500 sq ft) includes RV hookups with cleanout, loft storage, and workspace. Built in 1999, 9ft ceilings and features 3 lower-level bedrooms plus a large upstairs bonus room with full bath ideal as a 4th bedroom or second living space. The primary suite fully remodeled in 2025 with a jetted tub, walk-in shower, and custom closet. Recent updates include new partial interior paint and partial carpet (2026), updated heat pump, and refreshed front & back decks with rear retaining wall (2024). The kitchen offers granite counters and stainless appliances. Features: a pond, underground irrigation (COID 1.83 acres), water pump, irrigated fenced garden area, front, and back with sprinklers, playground set, and a freshly seal-coated driveway and updated insta-hot water (2026). Well and septic in place! Septic & Well reports!

21821 Butler Market, Bend

Listing courtesy of Sunny in Bend 1% Realty.

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