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14911 Snafflebit, Sisters
$625,000
3 Beds ⋅ 2 Baths ⋅ 220230131 MLS
Enjoy peaceful Central Oregon living in the desirable Tollgate community! Nestled among mature pine trees on a spacious .62-acre lot, this home offers comfortable living space with an inviting great room layout perfect for gathering and entertaining. Fresh new carpet adds to the home's welcoming feel, while the generous lot and beautiful back deck provide an ideal setting to relax, and enjoy the quiet surroundings. Convenient RV parking offers additional flexibility for your Central Oregon adventures. Tollgate residents enjoy an outstanding collection of amenities, including a swimming pool, clubhouse, pickleball & tennis courts, parks, playgrounds, and scenic trails. The community also offers Firewise certification & snow removal services. Just minutes from downtown Sisters, this property offers a wonderful combination of space, privacy, and the Central Oregon lifestyle.

14911 Snafflebit, Sisters

Listing courtesy of RE/MAX Key Properties.

69296 Ladigo, Sisters
$600,000
3 Beds ⋅ 2 Baths ⋅ 220230129 MLS
A fantastic opportunity to enjoy the Central Oregon lifestyle in the desirable Tollgate community! Situated among the pines, this single-level home offers comfortable living space with an inviting great room layout ideal for everyday living. Recent interior updates include new laminate flooring and fresh paint, creating a bright, welcoming atmosphere. The spacious lot offers plenty of potential to personalize the outdoor space and create your own Central Oregon retreat. Tollgate residents enjoy an exceptional collection of amenities, including a swimming pool, clubhouse, pickleball and tennis courts, parks, playgrounds, and scenic trails. The community also offers Firewise certification and snow removal services. Just minutes from downtown Sisters, this property offers an appealing combination of comfortable single-level living, community amenities, and exceptional value!

69296 Ladigo, Sisters

Listing courtesy of RE/MAX Key Properties.

17111 Lady Caroline Drive, Sisters
$1,595,000
3 Beds ⋅ 4 Baths ⋅ 220229530 MLS
First time on the market! Nestled in prestigious Aspen Lakes, this custom-built home pairs breathtaking golf course and serene pond views with a thoughtfully designed layout. Main-level living is effortless here: the light-filled main floor features soaring vaulted ceilings, a dedicated office, a spacious laundry room, and an oversized 3-car garage. The open-concept kitchen flows seamlessly into the dining and great room areas, creating an inviting space for entertaining. The main level also hosts two complete bedroom suites, including a private primary retreat. Upstairs, a third ensuite bedroom and a versatile second living area offer ideal privacy for guests or extended family. Step outside to the covered paver patio--complete with a built-in BBQ--to enjoy outdoor dining with exceptional views. Conveniently located just steps from the community pool, fitness center, and pickleball/tennis courts, this beautiful home is ready for its next chapter.

17111 Lady Caroline Drive, Sisters

Listing courtesy of Ponderosa Properties.

17771 Warrin Road, Sisters
$3,199,000
3 Beds ⋅ 4 Baths ⋅ 220227904 MLS
Perched on a ridge above your own private canyon with dramatic 360-degree views of the Cascades to the west and the Ochocos and Smith Rock to the east, this gated xeriscaped 19.02ac compound makes an exceptional primary residence or 2nd home. Located in the heart of Central Oregon's ''Golden Triangle'' between Bend Sisters and Redmond, the property features a 2071 sq ft custom built single-level smart home; 640 sq ft detached guest house; 720 sq ft separate shop with a heated finished family room; pickleball court; attached 1102 sq ft four-car pull-through RV garage; and a detached cedar storage shed. Enjoy more than 2000 sq ft of paver patios and decking, along with multiple outdoor living areas, including campsites with full RV hookups. Extensive infrastructure is already in place, complemented by unmatched recreational access, four different power sources, Firewise construction and very low monthly utility costs. This special property is truly a unique gem in the heart of C.O.

17771 Warrin Road, Sisters

Listing courtesy of Stellar Realty Northwest.

351 E Diamond Peak Avenue, Sisters
$799,900
3 Beds ⋅ 2 Baths ⋅ 220227967 MLS
SELLER OFFERING UP TO $20,000 TOWARD BUYER'S ALLOWABLE CLOSING COSTS, PREPAIDS, AND/OR MORTGAGE INTEREST RATE BUYDOWN, SUBJECT TO LENDER APPROVAL AND LOAN PROGRAM LIMITS! ESTIMATED COMPLETION NOVEMBER 2026! Discover the best of Central Oregon living in this brand-new home in desirable Grand Peaks in Sisters. Offering 1,715 sq. ft., 3 bedrooms, 2 baths, and stylish custom finishes, this home features a vaulted great room with gas fireplace, a beautifully appointed kitchen with large island, walk-in pantry, and KitchenAid appliances, plus a spacious primary suite with tile shower. Take in mountain views from your backyard and enjoy outdoor living on the covered patio. The fully landscaped yard includes underground sprinklers, and the home comes complete with A/C and Gold Earth Advantage certification. Ideally located near parks, pickleball courts, trails, shopping, dining, and downtown Sisters! Agent is related to the seller and is a licensed real estate broker in Oregon.

351 E Diamond Peak Avenue, Sisters

Listing courtesy of Coldwell Banker Bain.

14842 Stagecoach, Sisters
$574,900
3 Beds ⋅ 2 Baths ⋅ 220227721 MLS
*VA assumable at 5.25%* Tucked into the heart of Central Oregon in the Tollgate Community sits this classic log home bordering Deschutes County National Forest. Open great room w/stone hearth surrounding a cozy wood burning stove, vaulted ceilings & an abundance of natural light. Open kitchen ftrs central island w/brkfst bar seating + addtnl eating area. Downstairs is a main level bedroom w/adjacent bath & upstairs you'll find an addtnl 2 bedrooms, w/one serving as a flex space as a den or home office. Off the back deck is a large groomed outdoor space, garden shed, privacy fence, & plenty of room for RV parking & all your toys. Residents of Tollgate enjoy a saltwater pool, tennis & pickleball courts, basketball courts, & miles of paved walking & biking paths. Snowmobile out your back door in the winter & access endless mountain biking on the nearby Peterson Ridge trail system come summer. Central Oregon lifestyle at its finest: skiing, hunting, world-class fly fishing & much more.

14842 Stagecoach, Sisters

Listing courtesy of Keller Williams Realty Central Oregon.

69877 California Trail, Sisters
$1,763,000
3 Beds ⋅ 3 Baths ⋅ 220227351 MLS
Cascade Mountain Views! Enjoy sunrises and sunsets over the snow-capped mountains from this meticulously maintained log home. New roof and refurbished logs in 2024. Private, quiet cul-de-sac bordered on three sides by protected open space, with the national forest beyond. 3,235 total SF: 2,656 SqFt Main house has 3 beds, 2.5 baths, great room, and loft, PLUS a 579 SF bonus area. Bonus area has a studio, full bath, kitchenette, and balcony: perfect for an office or crafting haven. Greenhouse with drip irrigation, sink, heat, and raised beds awaits your gardening passion. Covered parking for 5 vehicles: 3-car garage and a 2-space carport. Garage includes deck, commode, sink, storage, and 30 Amp RV port. Well pump and casing replaced in 2026, generator ready! Cascade Meadow Ranch features expansive equestrian amenities: Indoor/outdoor arenas, full-care staff, clubhouse, tennis/pickleball courts, ponds, RV/toy storage, and National Forest trail access.

69877 California Trail, Sisters

Listing courtesy of Avenir Realty.

17147 Caddis Court, Sisters
$1,648,000
3 Beds ⋅ 5 Baths ⋅ 220227407 MLS
A rare Aspen Lakes offering, combining privacy, beautiful craftsmanship, and resort-style living. Set on 1.14 acres with views of the 7th fairway, three ponds, and forest beyond, this 3,543 sq ft single-level Craftsman features TWO PRIMARY SUITES, walnut floors, and a heated 3-car garage with workshop. A stone-and-cedar-shake exterior sets the tone. Inside, vaulted tongue-and-groove ceilings, wood built-ins and a dramatic stone fireplace define the great room, opening to a covered patio with built-in BBQ, heaters, and horseshoe pit. The updated kitchen offers quartz counters, new appliances, cream cabinetry, and a large island. All 3 bedrooms are ensuite, plus a dedicated office and 3 full + 2 half baths. Turnkey with TVs, exercise equipment, patio furnishings, and surround sound. Community amenities include clubhouse, pool, hot tub, tennis, gym, restaurant and pickleball. Just minutes from downtown Sisters, with golf, nature, and the best of Central Oregon right outside your door.

17147 Caddis Court, Sisters

Listing courtesy of Coldwell Banker Mayfield Realty.

70208 Viola, Sisters
$749,000
3 Beds ⋅ 3 Baths ⋅ 220226261 MLS
Welcome to your Black Butte Ranch retreat! Located on a rare .99-acre wooded homesite, this inviting 3 bedroom, 3 bath, 2 car garage home offers the perfect blend of comfort, privacy, and recreation. Located near the Upper Glaze Meadow Pool and tennis courts, a peaceful, less-crowded amenity area surrounded by the natural beauty. The thoughtfully designed floor plan features two main-level primary suites, while the upper level offers a spacious loft, bunk room, and full bath, comfortably sleeping up to 8 guests. Expansive living areas, abundant natural light, and an oversized deck overlook a peaceful forest setting with direct access to nearby trails. Whether you're searching for a full-time residence, vacation home, or legacy family retreat, this exceptional property captures the very best of the Black Butte Ranch lifestyle.

70208 Viola, Sisters

Listing courtesy of Duke Warner Realty ERA Powered.

304 W Clearpine, Sisters
$844,900
3 Beds ⋅ 2 Baths ⋅ 220224788 MLS
This single level mid-century modern home in Clearpine stands out with a spacious alley-loaded 3 car garage! South facing orientation & an abundance of thoughtfully placed windows bring in the sun to light up this stunning home w/designer finishes. Easy access to the Deschutes Nat'l Forest trails on west border of Clearpine and community park/playground complete with bocce ball court, covered bbq pavilion, nature path and common ground. Three patio door accesses to multiple outdoor spaces with privacy fencing complete a tranquil living experience for all! Upgrades include rain glass tile walk-in shower, water closet, barn door to dedicated office (or extra sleep space). Handy laundry/mud room adjacent to garage with utility basin and bench, man door from garage to doggy space. Low maintenance native landscaping frees up your time to enjoy recreational pursuits today rather than spending your free time doing yard work!

304 W Clearpine, Sisters

Listing courtesy of Stellar Realty Northwest.

16951 Lady Caroline Drive, Sisters
$1,574,900
4 Beds ⋅ 4 Baths ⋅ 220223064 MLS
Don't miss out; tucked into a pine canopy overlooking Aspen Lakes GC (pool/rec ctr) & Cascade Mtns; this contemporary craftsman home is a unicorn! Vaulted ceilings & enlarged windows offer natural light while framing the breathtaking surroundings. Main-level living, home offers 2 suites, + another bedroom (J&J bath), bunkroom, & theatre upstairs! Exquisite craftsmanship w/ wood beams, corner fireplace, & luxury LVP floors. Fully updated chef's kitchen, blending timeless style with modern functionality w/ premium finishes, abundant workspace, eating bar, & dining nook-all seamlessly connected to the open concept living & formal dining areas. Capture the golf course mtn. views w/ exceptional outdoor living w/ hot tub, water feature pond, and outdoor patio (fireplace & down heater). Front shade deck featuring covered entertaining spaces designed to take in the panoramic scenery. This remarkable property is complete with/ a 3-car garage w/ workshop & golf cart shed all on 1 private acr

16951 Lady Caroline Drive, Sisters

Listing courtesy of Stellar Realty Northwest.

12960 Hawks Beard CHC63 Unit CHC63, Sisters
$699,000
3 Beds ⋅ 2 Baths ⋅ 220223801 MLS
Set among the pines in one of Black Butte Ranch's most coveted locations, Country House Condo 63 enjoys a setting few properties can match. Positioned in a desirable second-row location with adjoining common area, the home overlooks Phalarope Lake, open meadows and the Three Sisters, Mount Washington and Broken Top beyond. Walls of windows on both levels fill the home with natural light and showcase the landscape from nearly every room. A main-level bedroom and full bath are complemented by two upstairs bedrooms connected by a Jack-and-Jill bath, including a bedroom with a walk-in closet and sitting area overlooking the mountain backdrop. Vaulted wood ceilings and warm architectural details reflect mountain lodge design. Offered fully furnished and moments from the Lodge area, Lakeside Bistro, pools, fitness center, pickleball courts and more. Whether envisioned as a private getaway, vacation home or investment opportunity, this retreat is ready to be enjoyed from day one.

12960 Hawks Beard CHC63 Unit CHC63, Sisters

Listing courtesy of Keller Williams Sunset Corridor.

16923 Royal Coachman Drive, Sisters
$1,299,000
4 Beds ⋅ 5 Baths ⋅ 220219628 MLS
Experience refined living in this one-owner Johannesen custom home, nestled on a private 1.25-acre lot within the gated Aspen Lakes golf community. This versatile single-level estate features a chef's kitchen equipped with dual Fisher Paykel dishwashers, a warming drawer, & instant hot water. Unwind in the great room by the wood-burning fireplace or retreat to the primary suite, which offers dual walk-in closets, separate vanities, & a jetted tub. The home is designed for flexibility, offering a dedicated office, an upstairs bonus room with a King Murphy bed, & a 39x20 flex room ideal for a studio or suite. For those who value utility, the property includes a heated 1,000 sq. ft. garage with custom cabinets, a workbench, & a golf cart bay. Outside, enjoy an expansive mahogany deck & an oversized Sundance hot tub amidst lush landscaping. Modern comforts include a Vyanet security system, central vacuum, & dual HVAC. This is a rare opportunity for elegant, effortless living in Sisters!

16923 Royal Coachman Drive, Sisters

Listing courtesy of Ponderosa Properties.

14987 Buggy Whip, Sisters
$730,000
4 Beds ⋅ 3 Baths ⋅ 220218538 MLS
Ski, walk, or ride into the National Forest! This fenced yard and expansive back deck with hot tub border National Forest. Spanning 2,187 square feet, this 4-bed, 3-bath open floor plan has a great room with a woodstove, spacious dining room, kitchen, laundry room, and 3 bedrooms on the main level, including a second primary suite. The kitchen has granite countertops, stainless appliances, a NEW dishwasher, and back deck BBQ access. Upstairs, the spacious primary suite, bathed in natural light, is an ideal escape, featuring vaulted ceilings, propane fireplace, private balcony, and a luxurious bathroom with a walk-in shower, and walk-in closet. The 2-car detached garage has an EV charger, carport, storage for all your toys, plus a concrete parking pad for additional vehicles or your basketball hoop. Septic 2 years new, Roof 3 years new, Hot tub 5 years new. Tollgate HOA amenities include a pool, tennis courts, basketball, volleyball, snow removal, onsite mail, community hall, and more!

14987 Buggy Whip, Sisters

Listing courtesy of Avenir Realty.

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.

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