Sisters, Oregon listings for sale

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$3,999,000 - Sisters, OR
17945 Mountain View Road Sisters, OR - 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.
1982 | 4 | 6 | 7,663 sqft.
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$3,375,000 - Sisters, OR
69223 Crooked Horseshoe Road Sisters, OR - This private & pristine, 10-acre Scandinavian Farmhouse Estate located 1 mile from Sisters. Tastefully updated with high quality finishes & attention to detail. It includes a gourmet chef's kitchen, Viking & SubZero appliances, equine facilities, indoor pool w/ lap lane, Finlandia sauna, home gym, 2023 Master Spa Phelps Legend Spa, 4 en-suite bedrooms, bonus rooms, guest quarters w/ kitchenette, perfect for multi-generational living. Game room, elevator, 4-car garage, pottery/arts & crafts room. This wonderfully serene property is fully fenced & cross-fenced w/ a long, gated, stately driveway, 6 stall barn w/ attached paddocks, heated washroom, tack room, office, 3/4 bath, kitchenette & attic space for possible barndominium, arena & round pen with footings, 3 large pastures & equipment garage, enclosed garden area w/ chicken coops. 7.2 acres of underground, automated irrigation, 2 wells, 2 septic systems, rear 5 acres w/ barn & equine facilities could possibly be partitioned off.
1994 | 4 | 6 | 10,463 sqft.
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$3,150,000 - Sisters, OR
69205 Hawksflight Drive Sisters, OR - 69205 Hawksflight Dr, Sisters, OR 97759 Where majestic mountain views meet unparalleled craftsmanship, this extraordinary 6,218 square foot residence stands as a testament to refined mountain living. Nestled on a secluded 2.09-acre parcel in prestigious Sisters, Oregon, this remarkable estate offers an elevated lifestyle that seamlessly blends luxury with nature's splendor. Cross the threshold into a grand foyer where soaring ceilings and expansive windows frame breathtaking views of the Cascade Range. The heart of this home features a chef's kitchen designed for both intimate family meals and grand entertaining, complete with premium appliances and handcrafted cabinetry. The main-level primary suite serves as a private retreat with a spa-inspired bathroom and generous closets. Five additional bedrooms provide ample space for family and guests, each appointed with the same attention to detail found throughout this remarkable home.
1999 | 6 | 4 | 6,218 sqft.
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$2,899,000 - Sisters, OR
69019 Holmes Road Sisters, OR - Indulge in the epitome of ranch living on this expansive 63-acre property, featuring a grand 4,797 square-foot main residence, a private guest home, a distinct apartment, and picturesque mountain vistas. Enjoy an array of opulent amenities amidst the tranquil beauty of the surroundings. The main home features multiple en-suite bedrooms and spacious outdoor areas, perfect for relaxation and entertainment. Explore landscaped paths leading to three tranquil ponds and enjoy panoramic vistas of the Three Sisters and Broken Top Mountains. This exceptional estate includes an 8-stall horse barn, garden, greenhouse, pet kennels, and a large workshop. With room for up to 14 cars and 4 RVs, it caters to car enthusiasts. Wildlife enthusiasts will delight in observing deer, elk, bald eagles, and more. Additionally, 56 acres of hay fields with 1895 senior water rights ensure ample irrigation. Water distribution is managed efficiently through a pressurized system.
1979 | 4 | 3 | 4,797 sqft.
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$2,850,000 - Sisters, OR
69550 Deer Ridge Road Sisters, OR - CUSTOM ESTATE WITH TWO STUNNING HOMES, NESTLED ON A PRIVATE, GATED 5.85 ACRE LOT WITH MOUNTAIN VIEWS! The beautifully renovated Farmhouse is light filled and spacious. 4,615 sq ft, 5 bedrooms, chefs kitchen with butlers pantry, luxurious primary suite with fireplace and spa like bathroom. The 2,071 sq ft 3 bedroom guest house feels like a mountain retreat, with vaulted open living and gorgeous floor to ceiling stone fireplace for cold winter nights. This rare and unique property is perfect for multigenerational living. Each home has their own separate power supply and septic system. The property features a solar heated in ground salt water pool, hot tub, infrared sauna, a 1,300 sq ft shop, barn w/4 stalls, greenhouse and chicken coop. The setting is idyllic for meeting today's need for the simpler pleasures in life, where nature & space are the new luxury, yet minutes (2.5 miles) from the charming western town of Sisters!
1992 | 5 | 4 | 4,615 sqft.
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$2,450,000 - Sisters, OR
69482 Panoramic Drive Sisters, OR - Nestled in 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, for a thoughtful design and functionality. Main house boast 4 spacious bedrooms (3 are Ensuite) and 4.5 baths, providing ample space for family and guests 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 equally impressive, featuring a 3-stall barn,tack room, & storage for hay & equipment. Automatic underground sprinkler & irrigation systems, a reliable well and a septic system. It has pet-friendly floors, a fully fenced yard, and an outdoor kennel. Currently operating as a successful short-term rental on Airbnb it provides a steady income for the owner
1977 | 6 | 4 | 5,279 sqft.
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$1,850,000 - Sisters, OR
16900 Green Drake Ct Sisters, OR - One acre Aspen Lakes property where charm & elegance meet on the golf course. This home blends seamlessly with its natural surroundings. Architectural elegance greets you at every turn, from the grand entrance to the french doors taking you to the spacious backyard. A gourmet kitchen awaits while the spacious 2-story living room accommodates your large gatherings. Additional luxuries include a generous bonus room, roomy mud room, office space, & a tranquil sitting area off the kitchen. What sets this property apart? It's all on 1-level except the bonus room, every bedroom has an en suite, a floorplan that creates privacy where needed & enormous sunfilled windows. Indulge in a lifestyle where you can immerse yourself in the hiking, biking, fishing and skiing. Or stay in the community and golf, swim, play pickleball & tennis. What about the commute? The home is conveniently located near the entrance, and downtown Sisters is 4 miles, Redmond is 15 miles and Bend is 25 mile
2004 | 3 | 4 | 4,250 sqft.
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$1,780,000 - Sisters, OR
68050 Fryrear Road Sisters, OR - Dream View Property-Private Luxury Living & Stunning views of the Three Sisters and Broken Top. Custom home features 3 bedroom, 2.5 bath, plus a huge bonus room that can be customized to suit your needs. Surrounded by public lands on 3 sides. Oversized attached garage plus 2 car detached garage. A large outbuilding that is versatile and can serve as a shop or be adapted for horse or dog kennel use. Master ensuite has access to private hot tub, dual master closets a custom tile shower & clawfoot tub. Professionally landscaped - easily maintained with complete sprinkler and drip system. Custom waterfall feature. Covered Trex decking in back and front entry.
2017 | 3 | 2 | 2,967 sqft.
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$1,750,000 - Sisters, OR
16900 Green Drake Court Sisters, OR - Unparalleled value in Aspen Lakes! This stunning home offers the one of most competitive price per sq ft homes in Aspen Lakes in the last few yrs -- what an incredible opportunity! Thoughtfully designed, the expansive layout ensures every inch is well-utilized, from the generously sized bedrooms to the spacious bonus room and airy great room. High ceilings, abundant natural light, and quality finishes create a warm yet sophisticated ambiance, perfect for both everyday comfort and elegant entertaining. Elegance greets you at every turn, from the grand entrance to the french doors taking you to the spacious backyard. A gourmet kitchen awaits while the 2-story living room accommodates your large gatherings. Additional luxuries include a roomy mud room, office space, & a tranquil sitting area off the kitchen. What sets this property apart? It's all on 1-level except the bonus room, a floorplan that creates privacy where needed & enormous sun filled windows
2004 | 3 | 4 | 4,250 sqft.
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$1,711,000 - Sisters, OR
16941 Lady Caroline Drive Sisters, OR - Immaculate high-end custom home built by renowned R&H Construction, proudly featured in Builder/Architect Mag, Central Oregon edition. This stunning residence is a showcase of sophistication, craftsmanship and design, highlighted by rich Brazilian cherry wood floors and an abundance of natural light throughout. Blending timeless elegance with distinctive style, the home features a hammered copper bar top, limestone slab countertops, creating a unique contrast that exudes sophistication. Every corner of this property is filled with character. Enjoy a spa-like experience with a steam shower and retreat-worthy primary suite with Mountain Views. An oversized garage offers ample space for vehicles, gear, golf cart, etc. Step outside to a beautifully landscaped yard complete with a tranquil water feature, this outdoor space is prefect for relaxation or entertaining. Nestled in a private, golf course community offering exclusive amenities including a pool, clubhouse, and pickleball courts.
2003 | 3 | 4 | 3,632 sqft.