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$1,600,000
3 Beds 4 Baths 220228137 MLS
Dramatic 3,888 sq. ft. custom home beautifully sited on a private 1-acre lot with panoramic fairway views. Lush landscaping surrounds a tranquil private courtyard, BBQ area, and expansive paver patios, creating an ideal setting for outdoor entertaining and relaxation. The thoughtfully designed single-level floor plan features three luxurious primary suites, a den/office, and 3.5 baths. The gourmet kitchen with breakfast nook flows seamlessly into the formal dining area, cozy family room, and spectacular great room--perfect for both intimate gatherings and entertaining on a grand scale. Rich architectural details include abundant wood, stone, and tile throughout. The property also borders a spacious common area, offering an added sense of privacy and open space. A truly gorgeous Aspen Lakes retreat that combines custom craftsmanship, stunning views, and effortless single-level living.

17094 Lady Caroline Drive, Sisters

Listing courtesy of Stellar Realty Northwest.

$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.

$574,900
3 Beds 2 Baths 220227721 MLS
Tucked into the heart of Central Oregon in the highly desired 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 on the Metolius, & more!

14842 Stagecoach, Sisters

Listing courtesy of Keller Williams Realty Central Oregon.

$860,000
4 Beds 3 Baths 220227649 MLS
Escape to your own private oasis where the backyard meets the National Forest! Set on .52 acres, this fun and inviting property offers privacy, space, and plenty of places to unwind. The fenced courtyard features a charming water feature, creating a peaceful retreat for morning coffee or evening cocktails. Enjoy outdoor dining, a back porch off the primary bedroom overlooking the forest, and multiple spots to soak up the serenity. Inside, vaulted ceilings fill the great room and kitchen with light and air, thanks to French doors at both the front and back. The bright kitchen showcases unique ''Memory Lanes'' bowling alley wood countertops and island, while a whitewashed river rock fireplace anchors the great room. A 584 SF ADU is perfect for guests or extended family, plus there's a large workshop/storage shop. Total living space is 2,557 SF. Come enjoy the space, privacy, and forest-at-your-backdoor lifestyle!

14911 Conestoga, Sisters

Listing courtesy of Stellar Realty Northwest.

$1,688,000
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.

$655,000
3 Beds 2 Baths 220226563 MLS
Nestled among the towering Ponderosa pines in the highly sought-after Tollgate community, just two miles from downtown Sisters, this inviting home offers the perfect blend of comfort and adventure. The light-filled kitchen features beautiful oak cabinetry and hardwood floors, opening seamlessly to the spacious great room with vaulted ceilings and a cozy wood stove. A separate living room provides the ideal space for entertaining or hosting guests. The primary suite includes a large walk-in closet and a beautifully tiled walk-in shower. Step outside to a private back deck surrounded by nature, or take advantage of the detached garage--perfect for extra storage, hobbies, crafts, or a woodworking shop. Tollgate residents enjoy a swimming pool, tennis and pickleball courts, sport courts, miles of scenic trails, and direct access to the National Forest, making this one of the most desirable communities in the Sisters area.

69341 Silver Spur, Sisters

Listing courtesy of Stellar Realty Northwest.

$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.

$999,950
3 Beds 4 Baths 220226074 MLS
Enjoy single-level living in the desirable Aspen Lakes Golf Community with stunning fairway views and endless potential. This HUD-owned home is ideally situated on the golf course, offering a peaceful setting and an opportunity to create your dream home. The spacious floor plan is filled with natural light and captures beautiful views of the course from the main living areas. A separate guest quarters or mother-in-law unit, located just off the four-car garage, provides flexible space for extended family, guests, a private office, or hobbies. The oversized garages offers abundant room for vehicles, golf carts, and recreational gear. While the home does need repairs and updates, it presents an exceptional opportunity to build equity in one of Sisters' most sought-after golf communities. Just minutes from downtown Sisters, enjoy championship golf, mountain views, miles of recreation, and the relaxed Central Oregon lifestyle. HUD Home sold As-Is.

17084 Lady Caroline Drive, Sisters

Listing courtesy of RE/MAX Key Properties.

$1,299,500
4 Beds 3 Baths 220224591 MLS
Stunning custom home with mountain views in Pine Meadow - walking distance to downtown Sisters. Quality construction and attention to detail are evident throughout: hardwood floors, wood beams, fireplace with stone hearth, heated tile bathroom floors, etc. The open-concept lower level connects the great room, dining area, and kitchen (featuring a generous island and beautiful cabinetry). A dedicated office, large laundry/mudroom, and oversized 2-car garage complete the downstairs layout. The upstairs master suite features a spa-like bathroom with 2 shower heads, a walk-in closet, plus a spacious covered deck with stunning mountain views. There are 3 guest bedrooms upstairs as well. The lot is exceptionally private, bordered by common area (and the irrigation pond/stream) on two sides - preserving those views. Exterior features include: wraparound front porch; back paver patio; built-in BBQ; fire-pit area. Brand new heat pump, freshly painted/stained, all furnishings negotiable!

751 S Redwood Street, Sisters

Listing courtesy of eXp Realty, LLC.

$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.

$695,000
2 Beds 3 Baths 220223685 MLS
One owner, custom built, meticulous condition, this Pine Meadow Village gem is the one you've been waiting for. 1,698 sq ft of open living with windows that pull in the mountain light, hardwood floors, and quartz countertops. The main level features a dedicated office or flex space with a full bath, perfect for guests or working from home. Upstairs, you'll find a second bedroom and the primary suite, which captures stunning mountain views. Three full baths total. Single car garage plus a covered porch for soaking in that Sisters air. Pine Meadow Village delivers the lifestyle: pool, hot tub, clubhouse, trails, and tennis/pickleball courts, all walking distance to downtown Sisters. Whether you're simplifying, investing, or planting roots in Central Oregon, this one is move-in ready and waiting for its next chapter.

446 S Cottonwood Street, Sisters

Listing courtesy of Coldwell Banker Mayfield Realty.

$1,299,000
4 Beds 3 Baths 220223615 MLS
If you've been waiting for the right Black Butte Ranch opportunity, this is it. Set on nearly half an acre, this fully furnished 3,482 sq ft retreat offers 4 bedrooms, 3 baths, multiple gathering spaces, soaring wood ceilings, exposed beams, and a stunning stone fireplace that has anchored decades of memories. Beautifully preserved with authentic Northwest character, it is ready to enjoy the day you close while leaving room to make it your own over time. Major investments are already complete, including a newer roof and a brand new $61,000 composite wraparound deck built for years of gathering under the pines. Imagine mornings with coffee on the deck, afternoons playing pickleball, golfing, or biking the trails, relaxing by the pool, evenings around the fireplace, and weekends spent making memories. Whether you're creating your own mountain retreat or taking advantage of Black Butte Ranch's full service rental program, this is the kind of place people return to year after year.

13800 Balsam Root, Sisters

Listing courtesy of Real Broker.

$1,699,000
3 Beds 6 Baths 220220342 MLS
Located on the golf course, with mountain views, this NW lodge style home is in the gated Aspen Lakes Golf Community. Soaring vaulted ceilings & expansive windows drench the interior w/natural light & showcase the stunning scenery. 3 en suite bedrooms on the main level with a large en suite bonus room, w/wet bar & full bath upstairs. Be enveloped by the exceptional craftsmanship. Featuring massive wood beams, beautiful stone fireplace, hickory floors & custom built-ins throughout. Open concept, dining area & timeless kitchen w/ eating bar & dining nook, in addition to the formal dining area.. Golf course views from most every window, designated office, extra wide hallways, enhance comfort & function. The luxury continues outside with teak, wrap around deck with covered areas, ideal for entertaining and taking in the views. Hot tub, circular drive, low maintenance landscaping, water feature and an oversize 3 car, heated garage with workshop.. all on nearly an acre of land.

16921 Lady Caroline Drive, Sisters

Listing courtesy of Stellar Realty Northwest.

$1,395,000
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.

$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.

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