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$725,000
3 Beds 2 Baths 220226206 MLS
Beautiful updated one-story home in Sisters tucked into a cul-de-sac! This modern 3-bed, 2-bath floorplan lives large across 1,800 sq ft, + grand Cascade Mountain Range views right from the windows and backyard. Upgrades: Quartz in both baths, LVP, tiled floors in baths, laundry, primary shower, fireplace, hot tub outlet, BBQ stub. Open floorplan with natural light beams in kitchen and offers generous counters, large walk-in pantry, Island, breakfast bar, flowing easily into the living and dining area for entertaining. The primary suite is a true retreat, with dual vanities, soaking tub, walk-in shower, and an enormous walk-in closet. Sizeable second bedrooms share the second full bath. Outside, enjoy one of the largest fenced-in landscaped backyards in the neighborhood, ready for play, raised garden beds, covered patio and those same Cascade views. Steps from the front door offer access to Deschutes National Forest, 25-mile Peterson Ridge Trail System, Village Green Park, Downtown. Come see today!

1949 W Williamson Avenue, Sisters

Listing courtesy of Bend Premier Real Estate LLC.

$1,115,000
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.

$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.

$699,000
3 Beds 2 Baths 220224904 MLS
Discover the privacy and beauty of McKenzie Canyon on this exceptional 10-acre retreat with sweeping pastoral valley and rimrock views. Built with quality and custom craftsmanship, the home is thoughtfully designed to capture the surrounding views. The main-level bedroom features French doors opening to the outdoors, 2 additional bedrooms, a loft space and abundant storage provide flexible living space. The open kitchen includes a breakfast nook, flowing seamlessly into the main living areas and out to the covered porch. Native landscaping and a fire pit create inviting outdoor spaces to relax and entertain. Additional features include RV parking with hookups, a 1,400-square-foot shop/garage, animal shelters and fencing. Experience this incredibly unique, secluded and peaceful location bordering public land that offers the perfect balance of comfort, privacy, and outdoor adventure!

70090 McKenzie Canyon Road, Sisters

Listing courtesy of LivOregon Real Estate LLC.

$498,000
3 Beds 3 Baths 220224477 MLS
Steps from Deschutes National Forest trails and minutes from downtown Sisters, this turnkey home offers a modern, lock-and-leave lifestyle. The bright, open-concept main floor features tall ceilings, luxury vinyl plank floors, and custom built-ins. A spacious kitchen boasts quartz countertops, ample cabinetry, and a large island flowing into the living and dining areas. A convenient half bath is on the main level. Upstairs, there are 3 spacious bedrooms: the private primary ensuite features a walk-in closet, separated from two flexible guest bedrooms/office spaces and a convenient laundry room. An attached two-car garage provides plenty of room for all your Central Oregon gear. Enjoy park views, HOA-maintained landscaping, and endless outdoor recreation right outside your front door. Perfect as a full-time residence or vacation retreat!

950 N Hindeman Avenue, Sisters

Listing courtesy of Avenir Realty.

$1,749,900
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.

$3,350,000
3 Beds 4 Baths 220223836 MLS
Discover one-of-a-kind living in this low energy, one-level, stepless smart home, completed in 2020 & designed as a legacy property. Set in the golden triangle on 19 low-to-no-maintenance acres w/direct public-land access, the estate offers panoramic sunrise and sunset views, unmatched privacy, & only minutes to Bend, Sisters, & Redmond. Designed for indoor-outdoor living, it features approx. 2,000 square feet of stamped concrete patios & decks, a timber-covered outdoor living area w/fireplace, BBQ area, & hot tub--ideal for entertaining or relaxing under the stars. The property includes an attached 1102 sq ft RV garage, 720 sq ft shop, guest house w/bedroom & loft, & a finished multi-purpose gathering room, 2 full RV hookups, dry-camp areas, walking paths w/scenic viewpoints, a labyrinth, pickleball, solar, & more. A rare retreat combining luxury, privacy, recreation, convenience, & it meets all defensible space requirements. This is a perfect full time, part time, or vacation home!

17771 Warrin Road, Sisters

Listing courtesy of Cascade Hasson SIR.

$740,000
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.

$1,995,000
6 Beds 6 Baths 220223800 MLS
Exceptional 5-Acre Multigenerational Estate in Sisters! This unique, fully fenced and gated property features two separate residences connected by an oversized dream shop, making it perfect for multigenerational living or rental income. The centerpiece is a luxury barndominium featuring three bedrooms, each with its own private en-suite bathroom. Connected through the shop is the second residence, a beautifully maintained traditional home with three bedrooms and two and a half bathrooms. At the heart of it all is the massive central shop, a hobbyist's dream equipped with a vehicle lift and abundant storage. The five-acre grounds offer ultimate privacy, professional landscaping, a stunning koi pond, multiple garage spaces, and ample room for RVs or pets. Offering unmatched versatility and shop-focused living, this rare estate delivers the ultimate Central Oregon lifestyle just minutes from town.

16440 Fair Mile Road, Sisters

Listing courtesy of Ponderosa Properties.

$619,000
3 Beds 2 Baths 220223779 MLS
Located just a few short blocks to downtown Sisters, this lovely Cottonwood Condo has been tastefully updated and is ready for the next fortunate owner. The welcoming floor plan has a well appointed kitchen with solid surface counters, energy star appliances & hardwood flooring. Quality construction through out with solid wood windows and doors, paver patio and upstairs deck with views towards the Cascades. Comfortable living room on the main level with a flex room that can be used as a bedroom or office. Upstairs is a 2nd primary suite, 3rd bedroom & a bonus room with cozy fireplace and private deck. The detached two car garage has plenty of room for Central Oregon gear & two vehicles. Ease of living with more time to enjoy the outdoors & vibrant Sisters downtown out your front door. Community features include Firewise certification, pool, two tennis courts, paths, community center, park & much more. Don't miss this opportunity to secure one of only 5 Cottonwood condos built!

547 W Jefferson Avenue, Sisters

Listing courtesy of Cascade Hasson SIR.

$729,000
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.

$850,000
2 Beds 2 Baths 220222513 MLS
Turnkey equestrian property just minutes from downtown Sisters! Situated on 2.3 fully fenced and cross-fenced acres, this move-in ready hobby farm offers the ideal blend of country living and convenience. The thoughtfully maintained home features updated luxury vinyl plank flooring, heat pump with A/C, wraparound porch, hot tub, and a functional loft space with closet overlooking the great room with soaring ceilings and stone fireplace. Designed with horse enthusiasts in mind, the property includes a 3-stall Noble shelter, tack shed, hay storage, round pen, cross-fenced pastures, chicken coop, dog run, horseshoe pit, fire pit, electric gated entry, and paved road access. Detached 2-car garage/shop offers a finished flex/man cave space, upstairs storage, and additional enclosed side storage rooms. Whether you're bringing horses, hobbies, or simply looking for room to spread out, this rare Sisters property offers the Central Oregon lifestyle you've been dreaming of.

16738 Pine Tree Lane, Sisters

Listing courtesy of Realty One Group Discovery.

$633,000
3 Beds 2 Baths 220222058 MLS
This single level, open floor plan, Crossroads subdivision home, built in 2014, on 1 acre, offers so much! 24 X 30 insulated shop w/ 200 Amp and double attached garage w/ 400 Amp service. Both with ductless heat pumps! Plus, covered RV Parking. Totally fenced with 2 gates and plenty of parking. The entire interior freshly professionally painted. Home is light and bright with 4 Solatube skylights. Waterproof vinyl plank flooring. Kitchen features 2-year-old smart stainless-steel appliances. gas stove with convection, air fryer, dehydration modes. Smart high efficiency hybrid heat pump hot water heater. The open floor plan has a primary bedroom and two additional bedrooms. Another bonus, ADA Pergola front deck with heated concrete, and ADA back deck. Shop attic with pull-down stairs and attic ventilator fan. Items included: brand new snow blower, flatbed trailer. tractor, riding mower with cart. The septic replaced 2014.

14866 Bluegrass Loop, Sisters

Listing courtesy of Stellar Realty Northwest.

$915,000
3 Beds 2 Baths 220221899 MLS
Discover a perfect blend of elegance and serene Central Oregon living in this beautifully updated single-level home in the highly sought-after Sage Meadow community. Inside you'll find a welcoming floor plan with all new lighting to showcase beautiful hickory and Saltillo tile floors. The updated kitchen is a chef's dream, featuring new countertops, and newer appliances. Each detail has been thoughtful, from updated baths and new fixtures to a main electric panel. PLUS a $25,000 concession for a NEW roof! The fenced yard is a sanctuary with a gorgeous pollinator garden and mature Ponderosa Pines that create a majestic backdrop for the sunlight. Entertain on the expansive, new fire-resistant deck (2025) while enjoying your beautifully landscaped, Firewise-certified property. Home offers a new septic system (2024), newer garage doors and a 16'x12' shed with power. Enjoy peace of mind and easy access to USFS trails for hiking and biking, all just 3.2 miles from charming Sisters.

69986 W Meadow Parkway, Sisters

Listing courtesy of Keller Williams Realty Central Oregon.

$899,000
3 Beds 2 Baths 220220765 MLS
This sanctuary in the heart of Sisters, Oregon, is nestled within 19.4 acres of Ponderosa pines and has access to National Forest trails. Enjoy views of Black Butte and Mt. Jefferson as you wake and sip your morning coffee from the new wrap-around deck. Step inside the beautifully remodeled 1,793 SF 3-bedroom, 2-bath cabin with a bright, open interior featuring a great room and an office. New windows, hardwood and laminate flooring, tongue-and-groove wood ceilings accented by ambient lighting, and fresh paint inside and out. Enjoy your hobbies in the versatile 30'x40' shop with a 30'x16.5' RV bay and two insulated 22'x14' rooms -- perfect for a home office, game room, fitness studio, craft space, or more! The 2-car oversized garage has heated storage, dedicated wood storage, and a storage room. Plus a pump house/greenhouse combo for the gardening enthusiast. 9.4 of the total acres are in forest deferral for only $13 in taxes, totaling $2,006.80 for the entire property!

15020 Remuda Road, Sisters

Listing courtesy of Avenir Realty.

$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
Let's be honest. $750 HOA dues are a bit intimidating. In reality, it's a great deal - hear me out. Those dues cover the pool, hot tub, sauna, clubhouse and upkeep of all these perks, the landscaping, the roof, the siding, and here's the Big One - structural fire insurance!! Also included are water, sewer, garbage service, and snow removal. There is nowhere else you could all of that for anywhere near $750 a month. Whether you are seeking ease or logic, this condo is your answer either way! Two primary suites (one w/separate exterior entrance for added flexibility), new flooring and interior paint throughout. 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.

$1,590,000
3 Beds 3 Baths 220218997 MLS
A dream view property on 18.8 private acres with stunning views of the Three Sisters and Broken Top. Extremely private and bordered on three sides by 180,000 acres of public land. This custom-built home offers 3 bedrooms, 2.5 baths, plus a large bonus room for flexible use. The primary suite features a custom tile shower, clawfoot tub, dual closets, and private hot tub access. Professionally landscaped with low-maintenance sprinkler and drip systems, plus a custom waterfall feature. Enjoy covered, Trex decks. In addition to the oversized attached garage, there is a detached 2-car garage and a spacious 36x48 outbuilding ideal for a shop, horses, or kennel use. Centrally located between Sisters, Redmond & Bend. (Broker Owned)

68050 Fryrear Road, Sisters

Listing courtesy of Stellar Realty Northwest.

$635,000
2 Beds 2 Baths 220218977 MLS
Ask about seller-paid credits toward closing costs or interest rate buy-down with an acceptable offer! Meet ''Pinedrops Cottage,'' a peaceful retreat where low-maintenance living and outdoor adventure come together. This Earth Advantage certified, single-level home offers 2 beds, 2 baths and 1004 SF of easy living in desirable ClearPine. Hardwood floors, vaulted ceilings, quartz counters, and high-end appliances create a bright, welcoming interior that lives larger than its footprint. Relax on the covered back porch overlooking community greens/gardens or enjoy the privacy of the enclosed paver patio. The detached garage provides parking plus room for your gear. HOA maintained common areas make ownership simple, allowing more time to enjoy the Central Oregon lifestyle. With National Forest trails just steps away and downtown Sisters dining, shopping, and year-round events mins from your door, ''Pinedrops Cottage'' is an ideal full-time residence, weekend getaway or lock-and-leave basecamp.

233 W Heising Drive, Sisters

Listing courtesy of Avenir Realty.

$599,900
220218895 MLS
Premium lakefront homesite in Aspen Lakes Golf Estates. This exceptional 1.20-acre parcel (Lot 110) offers a rare combination of water frontage, mature pine trees, and sweeping views across the lake toward the 11th fairway. Utilities are available at the lot line, & protective CC&Rs help maintain the integrity of this upscale gated community. This is one of the finest remaining building sites in Aspen Lakes--ideal for a custom home that captures both privacy & scenery. The setting delivers a true sense of tranquility while still being part of a vibrant, well-designed neighborhood. Residents enjoy access to an 18-hole golf course, clubhouse, fitness center, pool, & on-site dining. Just minutes away, the town of Sisters adds tremendous lifestyle value & features boutique shopping, local restaurants, art galleries, and year-round events including rodeos, festivals, and live music. Live in a peaceful golf course setting while staying connected to everything Central Oregon has to offer.

16887 Golden Stone Drive, Sisters

Listing courtesy of High Desert Realty, LLC.

$575,000
2 Beds 2 Baths 220218888 MLS
Motivated Sellers!! Live where the trails meet the town! This stunning, No-HOA townhome in Sisters' Highland Village offers the ultimate low maintenance lifestyle without sacrificing high end style. Step inside to an open spacious layout with Quartz counters and durable Paradigm flooring. Whether hosting a summer dinner on the covered upper deck or relaxing in your private, paver lined courtyard, outdoor living is a year round reality. The spacious single car garage provides ample room for all your gear. Enjoy the rare perk of being minutes away from the best of Sisters: walk to Three Creeks Brewery, the Movie Theater, or Sisters Athletic Club. Jump directly onto the Peterson Ridge Trail System for a hike/bike. This prime location offers easy walkability to downtown, where you can enjoy restaurants, boutiques, and events like the Quilt Show & Folk Festival. Your mountain basecamp awaits!

923 E Desperado Trail, Sisters

Listing courtesy of Coldwell Banker Sun Country.

$475,000
3 Beds 2 Baths 220218571 MLS
Experience the perfect blend of mountain-town charm and low-maintenance living at The Pines in Sisters, Oregon's gated 55+ community. This well-maintained, single-level home was originally a Fuqua Homes developer model. Step inside to an open-concept floor plan characterized by high ceilings and lots of natural light. The Great Room: Features French doors open to the rear deck overlooking a peaceful common area. Kitchen: Features a large central island, plenty of cabinetry, and counter space. Primary Suite: Featuring a walk-in closet and a private ensuite bathroom. Additional Features: Three ceiling fans and laminate wood flooring throughout. An attached 2-car garage, extra-wide concrete driveway, and a pull-down ladder leading to attic storage. HOA Perks: Gated community! Monthly dues ($152) cover lawn care and snow removal. Prime Location: Just minutes from downtown Sisters, close to local boutiques, bakeries, dining, neighborhood churches, schools, and trails!

1045 W Collier Glacier Drive, Sisters

Listing courtesy of Avenir Realty.

$760,000
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.

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