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$2,450,000
5 Beds ⋅ 5 Baths ⋅ 220219250 MLS
Rich in character and charm, this 4,615 sq ft home captures sweeping mountain views and offers five bedrooms, a dedicated office and two wood-burning fireplaces. At its center, a beautifully appointed chef's kitchen open to the living and dining, designed for both daily living and effortless entertaining. The primary suite is a serene retreat, featuring a gas fireplace and spa-inspired bath. Enjoy spectacular sunrises and sunsets from the covered front porch and expansive back decks. A 2,071 sq ft secondary structure lives like a private mountain sanctuary, complete with four rooms, a full bath, kitchenette, and a dramatic floor-to-ceiling river rock fireplace. The great room evokes a true lodge feel, with expansive windows framing the ponderosas. Additional amenities include a saltwater pool, infrared sauna, four-stall barn and shop. Bring your animals--this 5.85-acre property is fully fenced and cross-fenced with a gated entry, all just 2.3 miles from downtown Sisters.

69550 Deer Ridge Road, Sisters

Listing courtesy of RE/MAX Key Properties.

$600,000
1 Beds ⋅ 1 Baths ⋅ 220218511 MLS
Welcome to your peaceful getaway in the woods! This cozy 508 sq ft studio CABIN is perfectly situated on a 4.65-acre corner lot, located on the PAVED portion of the road for easy year-round access. The open-concept cabin features vaulted ceilings that enhance the sense of space, a full kitchen, 1 bathroom, and a sleeping area without interior walls--keeping the layout simple, open, and full of natural light. A wraparound deck invites you to relax and enjoy the quiet, private setting surrounded by nature. Enjoy year-round comfort with a Mitsubishi ductless split system providing both efficient heating and cooling. Additional features include a private well (680 feet deep), standard septic system with a 1,000-gallon concrete tank, and plenty of room for future expansion or outdoor living projects. Whether you're looking for a weekend retreat, vacation rental opportunity, or a place to live while you build, this one-of-a-kind cabin offers the perfect balance of simplicity and space.

16840 Buck Horn Drive, Sisters

Listing courtesy of Stellar Realty Northwest.

$799,000
3 Beds ⋅ 3 Baths ⋅ 220218490 MLS
Whychus Creek rim setting w/Cascade views, National Forest access, Detached shop/garage. The thoughtfully designed home features a formal dining room, den, breakfast nook, and an inviting great room with a wood-burning fireplace. The open kitchen offers stainless steel appliances, a pantry, eating bar, and warm laminate wood floors. The primary suite is a peaceful escape with deck access, dual closets, an attached den, and a well-appointed bath with soaking tub, shower, and double sinks. A spacious laundry room with a half bath adds convenience. The detached oversized two-car garage includes covered RV parking and unfinished bonus space above. With a new septic tank (2014) and drain field (2025), low HOA fees, a community water system, and access to miles of National Forest and canyon trails, this is a rare Central Oregon retreat.

16959 Canyon Crest Drive, Sisters

Listing courtesy of Cascade Hasson SIR.

$949,000
5 Beds ⋅ 3 Baths ⋅ 220218327 MLS
Welcome to your own secluded paradise, boasting the ultimate rustic charm and modern convenience. This stunning handcrafted log home offers a serene retreat from the hustle bustle of everyday life. As you step inside, you're greeted by the captivating sight of a log slab spiral staircase, artfully crafted around a majestic tree trunk, leading up to a mezzanine that overlooks the spacious grand room. Perfect for entertaining or simply unwinding in the ambiance of natures embrace. The heart of the home is the open kitchen, exudes warmth and functionality, featuring a cast iron stove that adds to the rustic charm of the log cabin ambiance. The main suite is located on the ground floor, The four upstairs bedrooms have their own vanites. The outbuilding can accommodate a motor home and a car. It also has an aprox. 1100 sq.ft. apt. A greenhouse and chicken coop are a bonus. Recent upgrades include a new well pump and drain field extension. New Wood Stove . New Carport Roof

69435 Green Ridge Loop, Sisters

Listing courtesy of Stellar Realty Northwest.

$850,000
2 Beds ⋅ 1 Baths ⋅ 220218120 MLS
Set on 2 private acres just minutes from downtown Sisters, this authentic full-log home captures the soul of a true Central Oregon mountain lifestyle. With no drywall, the handcrafted log construction delivers the warmth, character, and thermal mass of a timeless mountain lodge--an artisan home built to endure for generations. Inside, Acacia engineered hardwood, parquet flooring, and custom-fabricated steel fixtures blend rustic craftsmanship with modern design, all beneath a durable metal roof. Breathtaking views from the living room frame the surrounding landscape, creating a setting that feels both peaceful and inspiring. The massive RV shop/outbuilding offers exceptional space for adventure rigs, projects, or a workshop, while 110-volt camper pedestals welcome visiting guests. A legacy landholding where land, craftsmanship, and lifestyle come together--an unforgettable property designed to be enjoyed today and passed down for generations.

16011 Old Juniper Road, Sisters

Listing courtesy of Nexus 360 Realty.

$625,000
3 Beds ⋅ 2 Baths ⋅ 220217345 MLS
Turnkey Home & Investment in Tollgate! Discover this inviting 3-bed, 2-bath home in Sisters' desirable Tollgate community, ready for immediate enjoyment or as an income-generating short-term rental. Recently remodeled with new finishes, and updated kitchen/baths, it's truly move-in ready. The large private backyard backs to BLM/National Forest land and trails. Enjoy fantastic Tollgate amenities, including a pool, sports courts, and trails. Conveniently located between Hoodoo and Sisters, very close to Sisters' attractions and outdoor recreation, this property is a prime opportunity for full time living, a second home, or continue use as a top rated AirBnB vacation rental.

69322 Hackamore, Sisters

Listing courtesy of Harcourts Home Oregon Coast.

$2,450,000
4 Beds ⋅ 5 Baths ⋅ 220217038 MLS
Experience mountain living perfection in the premier equestrian community of Cascade Meadow Ranch. This 4,448 SqFt custom estate on 2.29 private acres boasts stunning Cascade Mountain views & seamless main-floor living. The 4 bed, 5 bath home features soaring vaulted ceilings, exquisite woodwork & Montana river rock fireplaces. A gourmet chef's kitchen offers a Thermador 6 burner range & premium appliances, while the main-level primary suite serves as a luxury retreat with a soaking tub & propane fireplace. Dual stairwells lead to a versatile bonus room, bedrooms & bunk room. The property includes an attached 2 car garage plus a detached 1,510 SqFt shop with a finished upstairs bonus room & 3 car garage. Enjoy a new roof, redwood siding, & covered cedar decks overlooking a landscaped yard with a tranquil waterfall & pond. This gated community provides indoor/outdoor arenas, horse stalls, 3 RV spots, clubhouse, tennis/pickleball & direct access to public lands.

15275 Windigo Trail, Sisters

Listing courtesy of Ponderosa Properties.

$2,995,000
6 Beds ⋅ 4 Baths ⋅ 220216913 MLS
Set against the sweeping backdrop of the Cascade Range in Sisters, this exceptional 6,218-square-foot estate offers a rare combination of privacy, craftsmanship, and versatility -- all just minutes from the charm of downtown. Positioned on 2.09 serene acres, the home was designed to capture both natural light and panoramic mountain views. Expansive windows, soaring ceilings, and timeless finishes create a warm yet refined atmosphere that feels equally suited for everyday living and large-scale entertaining. The chef's kitchen anchors the main living space, featuring premium appliances, custom cabinetry, and generous prep areas ideal for gatherings. The main-level primary suite serves as a private retreat with a spa-inspired bath and substantial closet space. Five additional bedrooms provide flexibility for guests, multi-generational living, or dedicated office and hobby spaces.

69205 Hawksflight Drive, Sisters

Listing courtesy of eXp Realty, LLC.

$749,900
3 Beds ⋅ 2 Baths ⋅ 220216304 MLS
Beautifully maintained home on 2.28 acres off desirable Cloverdale Rd in Sisters! This light-filled 3 bed, 2 bath home features a spacious layout with a family room, dining area, and living room featuring a cozy gas fireplace and office. The spacious kitchen features an island, breakfast bar, and a convenient butler's pantry. The oversized primary suite offers a large walk-in closet and ensuite bath with double vanity and abundant natural light. An attached 2-car garage adds convenience. Enjoy outdoor living with inviting front and back decks, perfect for relaxing or entertaining. The property includes a heated shop with an attached dog run, a 30x48 pole barn with 11' clearance, ideal for RVs, toys, or future horse setup and a 12x12 storage shed. While not currently set up for horses, it's easily adaptable. Easy access to Sisters, Bend, and Redmond plus all of Central Oregon's outdoor recreation. A must-see to fully appreciate this wonderful home and property.

17415 Kent Road, Sisters

Listing courtesy of Stellar Realty Northwest.

$1,200,000
4 Beds ⋅ 4 Baths ⋅ 220214803 MLS
A rare find! Proven short-term rental + documented income, this multi-generational home borders forest offers privacy and hard-to-find living options. 69288 Stetson is custom-built, has 4 beds (including primary on the main with oversized shower and walk-in closet,) 3.5 baths and 3,295 SF of total living space with a versatile lock-off layout. Flexible loft offers potential for 5th bedroom; conceptual layout ideas/estimates available! Interior highlights include hickory hardwood floors, knotty alder trim and cabinetry, floor-to-ceiling Tibetan stone fireplace. Connected second living area has 2 beds, 1 bath, kitchenette, and private entrance. Set back from the street and forest-adjacent, this property feels like a true retreat! Outdoor amenities: hot tub, fully fenced backyard, gas fire pit, garden area, greenhouse, drip irrigation, shed + RV parking. 1,152 SF 3+ car attached garage with workshop/office. New septic in 2021. Come experience the ease and beauty of life in Sisters!

69288 Stetson, Sisters

Listing courtesy of Avenir Realty.

$3,999,000
4 Beds ⋅ 7 Baths ⋅ 220214782 MLS
Nestled in a breathtaking location, this timeless estate offers sweeping views of the majestic Cascade Mountains and Whychus Creek Canyon. Surrounded by luxurious gardens, the home stands in contrast to the low-maintenance high desert landscapes that dominate the nearly 40-acre property and the sparsely developed land around it. With European-inspired elegance, this estate boasts an array of exceptional features, including a lighted tennis court, three stunning rock fireplaces, and expansive aggregate patios--both covered and uncovered. Additional highlights include a heated dog kennel, solarium, sunroom, formal and informal dining spaces, and an oversized family room. The home offers four bedrooms, each with an ensuite bathroom, including a main floor primary suite with two full baths, separate closets, and a chef's kitchen with a large pantry. Enjoy the convenience of a three-car garage with ample attic storage for all your toys.

17945 Mountain View Road, Sisters

Listing courtesy of Ponderosa Properties.

$739,900
3 Beds ⋅ 3 Baths ⋅ 220214766 MLS
Nestled on 1.02 private acres in the desirable Crossroads community, this inviting home offers the perfect blend of comfort, space, and the Central Oregon lifestyle. Surrounded by thousands of acres of Deschutes National Forest, enjoy endless opportunities for horseback riding, hiking, and outdoor recreation right from the neighborhood. Inside, you'll find 3 bedrooms, 3 full baths, a main-level office that could easily serve as a 4th bedroom, and a spacious bonus room for guests, hobbies, or a media room. Large windows fill the home with natural light, while the cozy wood-burning fireplace creates a warm gathering space. The primary suite features its own private deck, and mature trees provide exceptional privacy with room to garden, add a shop, or simply enjoy the peaceful setting just minutes from downtown Sisters.

14450 Mountain View Loop, Sisters

Listing courtesy of High Desert Realty, LLC.

$5,950,000
3 Beds ⋅ 4 Baths ⋅ 220214681 MLS
Cascadia Ranch near Sisters, Oregon is available for sale for the first time in over 50 years: 700+/- acres of farm, ranch and timber land at the foot of the Cascades with unobstructed mountain views. This unique property has 80 acres of exclusive water rights, sourced from three springs, a two-story barn, corrals, large ranch house, rustic cabin, equipment and hay sheds, a large swimming pond, fenced fields for horses or livestock, and additional wildlife ponds. Surrounded by public lands, the ranch accesses miles of adjacent horseback and mountain bike trails. Approved to divide into 4 parcels. New building site with commanding mountain views and utilities in place. Enjoy privacy, solitude, wildlife, fresh air, dramatic rock outcrops and open skies, only minutes to the Western town of Sisters, and 30 minutes to Bend. This is one of the Northwest's truly exceptional properties, which could be perfect as a horse farm, mountain retreat or build your dream custom home.

67500 Three Creeks Road, Sisters

Listing courtesy of Cascade Hasson SIR.

$1,145,000
2 Beds ⋅ 3 Baths ⋅ 220213314 MLS
Turnkey Equestrian set up on very private acreage with direct access to USFS land and trails that is also very close to town. This horse property is perfect for equine enthusiasts: 4 stall barn with cement aisle, individual paddocks for each stall, metal roof, tack room, hay storage, feed room, good lighting, and easy access to the home and property, extensive fencing (entire property) and gates. Also includes a well laid out, and structurally sound home with high vaulted tongue and groove ceilings; a primary suite with vaulted ceilings on the main level; New HVAC with zoned mini split system and new propane woodstove. Property additionally features: Large paver patio/gazebo in backyard with complete privacy visually; Hot tub on rear patio; 3 bay shop with metal siding, metal roof, concrete floor; Greenhouse with hydraulic lifting windows; Garden/landscape shed that would make an ideal chicken coop; Extensive front and back landscape; Freshly painted/matching structures on property.

15624 National Forest Lane, Sisters

Listing courtesy of Kizziar Property Co..

$1,825,000
6 Beds ⋅ 5 Baths ⋅ 220200531 MLS
Owners willing to carry and are motivated. Dropped $190,000!!Central Oregon, is the Red Barn Farm in Sisters,Oregon, offering a blend of rustic charm & modern amenities. This 4,279 sq ft primary residence, is complemented by a 1,000 sq ft mother in- law suite,totally seperate from Main house. The Main house boast 4 spacious bedrooms (3 are Ensuite) and 4.5 baths, providing ample storage for family and guests all on 5.77 irrigated acres. Main floor houses 1 master and an office. The ADU, has a full kitchen, lg living room, 2 bedrooms, 2 baths, and climate control mini-splits. It offers versatility as a guest suite, rental opportunity, or private retreat. The property's exterior is impressive, featuring a 3-stall barn,tack room, & storage for hay & equipment. Automatic underground sprinkler & irrigation systems, a reliable well and septic system. With pet-friendly floors, a fully fenced yard, and an outdoor kennel. Currently operating as a successful short-term rental on VRBO/Airbnb.

69482 Panoramic Drive, Sisters

Listing courtesy of John L Scott Bend.

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