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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.

$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.

$1,495,000
3 Beds ⋅ 3 Baths ⋅ 220226703 MLS
First time ever on the market! This expansive one-level home offers soaring living room ceilings, wide tiled hallways, and skylights that fill the home with natural light. Partial views of the 3 Sisters Mtns. from the living room. The spacious floor plan includes a second primary bedroom with an ensuite bath, a dedicated art room or office, and a large family den perfect for relaxing or entertaining. The oversized laundry room features a gift-wrapping station. Enjoy a spacious kitchen with a large island, breakfast nook, and wood floors, plus a flexible dining room that can easily accommodate hobbies, a library, or additional living space. A stunning rock fireplace anchors the living area, with a cozy sitting nook and wet bar tucked behind it. The bonus room off the garage is ideal for a pool table, game room, media room, or private retreat for kids and grandkids. Completing the home is an oversized 2.5-car garage with room for vehicles, storage, toys, or a golf cart. 9th fairway views

16863 Royal Coachman Drive, Sisters

Listing courtesy of Avenir 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.

$349,000
2 Beds ⋅ 2 Baths ⋅ 220224220 MLS
Located in the desireable 4th Sister Condominiums, this 2 bedroom suite condo is in the heart of Sisters! Bring your designer ideas to this unit that features 2 primary suites, a full kitchen and great room living with a cozy fireplace. The covered deck is perfect for enjoying the lovely grounds or a BBQ. This location offers a fantastic Sisters location close to all the Sister's amenities and outdoor activities. Whether it is a full time residence, a relaxing getaway or an income generating investment this main floor unit is the condo for you!

897 E Desperado Trail UNIT 102 Unit UNIT 102, Sisters

Listing courtesy of Cascade Hasson SIR.

$1,699,900
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.

$899,000
3 Beds ⋅ 2 Baths ⋅ 220224322 MLS
Don't miss the opportunity to own this meticulously crafted home in the desirable Pine Meadow Village community. This move-in-ready home offers the convenience of single-level living with three bedrooms and two bathrooms on the main floor, plus a spacious bonus room upstairs showcasing beautiful Cascade Mountain views. Perfectly positioned on a corner lot, the property offers exceptional curb appeal, ample parking, a two-car garage, and a fully fenced backyard. Quality craftsmanship is evident throughout with high-end finishes including quartz countertops, hardwood flooring, custom cabinetry, and a tile steam shower. Vaulted ceilings and large wood-framed windows fill the home with natural light, creating a bright and inviting atmosphere, while the covered front porch provides the perfect place to enjoy the surroundings. Ideally located in the heart of Sisters, this home offers easy access to charming downtown shops, restaurants, parks, and endless outdoor recreation.

301 S Pine Street, Sisters

Listing courtesy of Cascade Hasson SIR.

$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.

$766,500
3 Beds ⋅ 2 Baths ⋅ 220223050 MLS
This beautifully appointed, single-level home in the Crossroads community offers the premier Central Oregon living experience. Set on a private, one-acre lot with direct trail access, this like-new property built in 2020 perfectly blends comfort and functionality just minutes from Downtown Sisters and local schools. The light-filled, open-concept layout features a spacious great room that opens to an outdoor deck, making it ideal for seamless indoor-outdoor entertaining. At the heart of the home is a well-appointed kitchen complete with stainless steel appliances, a pantry, and a bar area, complemented by both a formal dining room and a separate breakfast nook for versatile dining options. With three bedrooms, two bathrooms, a two-car garage, and a dedicated office/den providing the perfect work-from-home environment, this residence is designed to accommodate every lifestyle need.

14431 Crossroads Loop, Sisters

Listing courtesy of Ponderosa Properties.

$409,000
220222675 MLS
Welcome to a rare opportunity in the prestigious Aspen Lakes Golf Course community. Set on a beautiful 1.23-acre lot, this property offers the perfect setting for your custom dream home. Enjoy a sunny, open homesite with desirable southern exposure, peaceful fairway views, and filtered views of the North and Middle Sisters. With water and power available at the lot and septic approval already completed, much of the groundwork is in place. Imagine waking up to serene golf course scenery, enjoying wide-open space, and relaxing in a private setting surrounded by natural beauty. Whether you're planning a full-time residence or a special retreat, this exceptional lot offers the ideal blend of luxury, convenience, and Central Oregon lifestyle.

17057 Golden Stone Drive, Sisters

Listing courtesy of Premiere Property Group, LLC.

$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.

$395,000
2 Beds ⋅ 2 Baths ⋅ 220220297 MLS
Lock-and-go, high perks, low-maintenance condo is the perfect home base for your adventures! Two suites, one with exterior entrance and ability to lock off for flexibility. New flooring and interior paint. Large, covered deck. Amenities include: structural fire insurance, roof, all exterior maintenance, pool, clubhouse, sauna, snow removal, water sewer and garbage. Picture yourself retiring to the covered deck to unwind after a day of Central Oregon adventures - summer or winter! Ideally located near Sisters Athletic Club, Five Pines campus, Sisters Movie House, and Three Creeks Brewery. 3 minutes to charming downtown Sisters and all of it's festivities, 30 minutes to Bend or Redmond. Long term (30 day+) rentals allowed.

821 E Desperado Trail UNIT 201 Unit UNIT 201, 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.

$515,000
2 Beds ⋅ 1 Baths ⋅ 220219264 MLS
If you've been dreaming of a getaway ''cabin in the woods'', your dream awaits in Sisters, OR. Private .65 acre setting offering quiet serenity. Relax on huge back deck where you're hidden from the world except for birds & wildlife. After your respite, cozy up to the woodburning fire or enjoy Tollgate community amenities: saltwater swim pool, pickleball/tennis, hiking/biking path easily accessible to US forest land yet oh-so-convenient to town. Lightly used as a second home. Could sleep 6 with two queens plus trundle - furnished! Includes newer GE stacked washer/dryer. Second deck off upstairs bedroom. Don't delay, call today!

69307 Scabbard, Sisters

Listing courtesy of Stellar Realty Northwest.

$740,000
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 lands. 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 and built-in appliances, with 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.

$395,000
220218514 MLS
Lot 86 at Aspen Lakes Golf Estates. Ready for your dream home! End of cul-de-sac privacy on highly desirable Caddis Court which features some of the finest homes in Central Oregon. Views of the 6th green, 7th tee box and fairway and lake. Developer's suggested building site is marked by a green metal T-post with white top. Broker owned.

17167 Caddis Court, Sisters

Listing courtesy of Stellar Realty Northwest.

$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.

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