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68830 Chestnut Drive, Sisters
$1,645,000
3 Beds ⋅ 3 Baths ⋅ 220230308 MLS
8.5-acre equestrian property with mountain views and only 3 miles to town! Reverse-living home offers an open upstairs living/dining area, kitchen with gas range, new stainless appliances, island & granite counters, plus office & half bath. Downstairs includes a living area with wood-burning rock fireplace, primary suite, 2 bedrooms, full bath & laundry. The 40x72 barn has 3 stalls with automatic waterers, wash rack, tack room, hay storage & trailer parking. Sand riding arena & fenced pastures. A 30x60 garage/shop offers solar panels, bathroom, washer/dryer hookups, 2 parking spaces, dog run, rear deck & flex space for exercise or storage. Above the garage is 1,000 SF of ADU/office space with a separate entrance. Fenced property includes a medicinal garden, greenhouse, RV hookups & dump station.

68830 Chestnut Drive, Sisters

Listing courtesy of Invest in Bend Real Estate.

17660 Edmundson Road, Sisters
$1,599,000
3 Beds ⋅ 4 Baths ⋅ 220227675 MLS
Stunning Cascade Mountain views & 9.36 acres! Power gated entry & asphalt drive leads to this amazing Sisters Estate. Cozy living room features a river rock fireplace. New kitchen boasts new cabinets, granite counters, new appliances & bar w/wine fridge. Main-level primary suite includes spa shower, soaking tub & walk-in closet. Upper-level w/2 bedrooms & fully updated bath w/new cabinets, counters, tile shower & flooring. New laundry cabinets & sink. Oversized 2-car garage has epoxy floors, metal cabinets & a guest/multi-gen living/bonus room above w/private entry & new carpet. Ideal for equestrian lovers: full perimeter fencing & electric cross-fenced pastures connect to barn paddocks & 2 matted stalls, water/power, hay storage & tack room. Back deck overlooks a beautifully landscaped pond & fountain. Detached office/exercise studio features mountain views & a private sauna. Serene country living just 10 mins to Sisters & 30 mins to Bend! True privacy with convenient urban access.

17660 Edmundson Road, Sisters

Listing courtesy of Bend Premier Real Estate LLC.

67376 Peterson Mill Road, Sisters
$3,500,000
4 Beds ⋅ 5 Baths ⋅ 220225659 MLS
Set on approximately 79 private, forested acres bordering Deschutes National Forest, this custom home near Sisters, OR offers 6,366 sq ft, 4 bedrooms, and 4 baths. The great room's massive river rock fireplace, hand-forged ironwork, and cherry cabinetry set the tone, while the kitchen features Sub-Zero, Wolf, Dacor, and Miele appliances alongside a granite island and butler's pantry with wine fridge. Oak hardwood floors, a formal dining room with French glass doors, and a family room with a Jotul wood stove and Brazilian cherry floors add warmth throughout. The primary suite includes a marble trimmed fireplace, soaking tub, and glass-block shower; a downstairs guest suite and upstairs Jack-and-Jill bedroom offer flexible living. Outdoors, enjoy a private pond, flagstone patio, firepit, and an auto irrigation system supplied by a private well. A nearly 3200 sq ft detached garage/shop rounds out this rare forest retreat, minutes from Sisters and surrounded by developed Forest trails.

67376 Peterson Mill Road, Sisters

Listing courtesy of Ponderosa Properties.

69566 Paint Brush Lane, Sisters
$1,595,000
5 Beds ⋅ 5 Baths ⋅ 220223702 MLS
Indian Ford Meadows is less than three miles from Sisters, a six-minute drive, This property is right on the national forest boundary. Nearly 1,000 feet of fence line runs that edge, so you can ride or hike thousands of acres straight from the gate. Two neighbors share the cul-de-sac. It's quiet here. The double-sawn log home sits on flat, cross-fenced acreage built for equestrian use. Three stalls with runouts, two pastures, a feed shed, and a 60-foot round pen. Renovated in 2022, enjoy heated herringbone tile floors, quartz counters, sage green cabinets with brass pulls, KitchenAid appliances, breakfast bar, corner eating nook. Primary suite over 18 feet square, vaulted ceilings, ductless heat pump, pedestal tub, dual vanities. Second primary suite upstairs, another bedroom and bath. Basement prepped for full finish. Three-car garage, nearly double deep, 40-foot RV garage with roll-up door, mud room, tankless water heater. One-bed ADU and detached studio, both steps from main house.

69566 Paint Brush Lane, Sisters

Listing courtesy of Central Oregon Realty Group.

17186 Highway 126, Sisters
$1,795,000
3 Beds ⋅ 2 Baths ⋅ 220222540 MLS
This property is not just a farm... it's a story. Located just minutes from downtown Sisters, this exceptional property features a remodeled classic farmhouse and a separate guest house with expansive Cascade Mountain views. The land includes 40 acres of 1895 water rights through Three Sisters Irrigation District, offering excellent irrigation for pasture or agricultural use. A new standalone office provides flexible workspace. Multiple outbuildings provide flexibility for storage, equipment, or animal shelter. Whether your vision includes gardens, open pasture, or a peaceful homestead, this property offers the space to create it. Interior features include tile walk-in showers, antiqued granite countertops, hardwood flooring, custom tile, and a finished basement ideal for guests or flex space. Outdoor amenities include a wraparound porch, park-like landscaping, patios, a built-in pizza oven, lighted paths, and a 1.5-acre pond with irrigation ditch. Let's make this your story.

17186 Highway 126, Sisters

Listing courtesy of eXp Realty, LLC.

15275 Windigo Trail, Sisters
$2,350,000
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.

67500 Three Creeks Road, Sisters
$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.

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