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$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.

$1,425,000
3 Beds 3 Baths 220225624 MLS
Irrigated equestrian retreat on 9.18 acres near Sisters, with 9 acres of TSID pressurized irrigation. The 3,176 sq ft custom home offers 3 bedrooms, 2.5 baths, an open great-room layout, and an 852 sq ft finished garage. Upgrades include newer heat pump, air exchanger, and 16-panel solar array, with a new roof scheduled for installation. The equestrian setup is turnkey: horse barn with 4 matted stalls, tack room, and grooming area; 90x160 outdoor arena with washed arena sand; and a large lean-to with two 12x12 stalls plus additional hay storage. Lush irrigated pasture is lined with new wood-post woven wire fence with top rail. Property is cross-fenced throughout. Zoned EFUSC with farm tax deferral in place. Minutes to Sisters and area trail systems, with Bend and Redmond an easy drive. A rare chance to own productive irrigated ground with quality improvements in one of Central Oregon's most sought-after corridors.

69175 Holmes Road, Sisters

Listing courtesy of Berkshire Hathaway HomeService.

$899,000
3 Beds 2 Baths 220224918 MLS
This beautifully maintained home features a durable lightweight concrete tile roof, newer windows, fresh interior paint, and brand-new carpet, making it truly move-in ready. The spacious primary suite offers a private retreat with an en-suite bathroom, walk-in closet, and direct access to your own secluded patio and beautifully landscaped backyard. Enjoy low-maintenance, meticulously cared-for landscaping with underground sprinklers in both the front and rear yards. Relax outdoors while listening to the soothing sounds of the backyard water fountain, creating a peaceful setting for morning coffee or evening gatherings. Additional highlights include a spacious two-car garage with 2 workbenches, an outdoor storage shed that stays with the property, and dedicated space for RV or boat parkingâ€''providing plenty of room for your hobbies, toys, and storage needs.

69700 Old Wagon Road, Sisters

Listing courtesy of William Johnson, Broker.

$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.

$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.

$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.

$1,750,000
5 Beds 3 Baths 220223387 MLS
Highly private and peaceful waterfront acreage with approximately 1200' of accessible Whychus Creek frontage located a short distance from downtown Sisters. Interior of home features: Open floor plan; Large entertainer kitchen with locally crafted Cedar cabinets, granite and black walnut counters, maple hardwood floors leading into dining and living rooms which all have unobstructed views of Whychus Creek; Primary en suite and an additional bedroom/bathroom on the main level; Three remaining bedrooms, full bathroom, large bonus room are downstairs along with large utility room. Exterior features: Huge upper and lower decks with Creek views; 3.5 irrigated acres, flat pasture for hay production; EFU zoning with low taxes and multiple possible farm uses; Feeder barn, pole barn and detached garage for all covered storage and/or farm animals; Great mixture of Ponderosa Pine trees and Aspen tree groves. Home functions as a permanent home or also has a terrific vacation rental history.

16430 Highway 126, Sisters

Listing courtesy of Kizziar Property Co..

$725,000
4 Beds 2 Baths 220223095 MLS
Nestled among towering Ponderosa pines on a beautifully maintained 1.01-acre lot, this inviting single-level home offers the perfect blend of privacy, comfort, and Central Oregon charm. Filled with abundant natural light from expansive windows, the home features real hardwood floors, spacious living areas, and a cozy gas stove that creates a warm gathering space year-round. The oversized primary suite includes a generous bedroom and bath, while large decks extend the living space outdoors, overlooking the fenced backyard and peaceful park-like setting. A durable metal roof, oversized detached garage, circular driveway, and separate outbuilding--ideal as a home office, studio, or hobby shop--add versatility and value. Thoughtfully maintained inside and out, this property offers the quiet lifestyle you've been looking for while remaining just minutes from downtown Sisters.

15634 Ponderosa Lane, Sisters

Listing courtesy of Real Broker.

$849,500
3 Beds 2 Baths 220222856 MLS
Very private 5-acre country property offers Cascade Mountain views, and room to spread out, with the added benefit of bordering larger neighboring parcels (40 acres and 70 acres) as well as bordering BLM land corner-to-corner. Built in 2020, this light and bright Northwest Energy Efficient home features a great room floor plan, 9' ceilings, abundant windows with views in every direction, heat pump, WiFi-enabled thermostat, stainless appliances, eat-in nook, and laundry room with pantry storage. Spacious primary suite plus two additional bedrooms. Fresh exterior paint, new septic, and irrigation system. Enjoy mountain views from the large 50-year Trex deck, perfect for entertaining. The property includes a large shop/barn with RV plug, attached double garage with furnace, solar exterior lighting, landscaped grounds with native sagebrush, and newly planted apple trees. Close to town, minutes from golf, and no HOA.

69592 Lake Drive, Sisters

Listing courtesy of Kizziar Property Co..

$949,000
4 Beds 2 Baths 220222581 MLS
Beautifully remodeled and lovingly cared for 2300sf 4bed home tucked in a quiet cul-de-sac in the sought-after Sage Meadow community, just minutes from downtown Sisters. Warm and inviting with a cozy rustic feel, this thoughtfully updated home offers spacious living areas inside & out designed for both relaxing and entertaining. Expansive windows bring in natural light and frame the Mountain views, while vaulted ceilings and a wood stove create a comfortable atmosphere year-round. Fully remodeled kitchen, quality updates throughout, and an ideal floor plan make this home truly move-in ready. Enjoy peaceful outdoor living with room to gather, unwind, and barbecue, all bordering National Forest land. Attached 2-car garage plus detached shop provide excellent room for hobbies, projects, storage, or recreation. A rare combination of privacy, charm, updates, and location in one of Sisters' most desirable neighborhoods.

15917 Pinion Jay Lane, Sisters

Listing courtesy of High Desert Realty, LLC.

$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.

$1,750,000
4 Beds 3 Baths 220221266 MLS
Tucked among open farmland with sweeping mountain views, this nearly 7-acre Central Oregon property offers a rare blend of privacy, flexibility, and everyday comfort. Designed for connection and entertainment, the home features soaring vaulted ceilings, generous gathering spaces, and an easy flow for hosting inside and out. The layout lives beautifully as a single level, with the main living areas, primary suite, office, and guest bedroom all on the main floor, plus one bonus room upstairs. The attached casita features its own private entrance, creating an ideal setup for guests, extended family, a workspace, or added privacy when hosting. A spacious garage adds function, while the peaceful acreage provides room to spread out and take in the views. Additional adjacent offerings may be available separately, including up to 6+ irrigated acres and a 2+ acre fishing pond with dock (shown in photos). Please inquire with listing agents for more details.

71285 Holmes Road, Sisters

Listing courtesy of Cascade Hasson SIR.

$799,000
3 Beds 3 Baths 220221028 MLS
Extremely well-maintained ranch-style home with solid oak hardwood floors throughout most of the home, vaulted ceilings, and arched doorways. The living room features a custom juniper mantle and woodburning fireplace. The kitchen offers granite counters, tile backsplash, stainless steel appliances, farmhouse sink, eating nook, and separate dining area. The primary suite includes walk-in closet, double vanity, walk-in tile shower. Radiant heated tile floors in both full bathrooms. Bonus room with half bath, separate entry, and sound wiring offers flexible use for guests, office, or media space. Mini splits in main living areas provide efficient heating and cooling. Off the kitchen is a large storage room with sink and access to the back deck. The park-like backyard is fully fenced with drip irrigation, extensive landscaping, raised garden beds, two sheds and covered deck. Large paved driveway, an additional RV parking area and an oversized 2-car garage with workshop.

70064 Appaloosa Drive, Sisters

Listing courtesy of Kizziar Property Co..

$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.

$2,450,000
5 Beds 5 Baths 220219250 MLS
Rich in character and charm, this 4,615 sq ft home captures sweeping mountain views and offers five bedrooms, a dedicated office and two wood-burning fireplaces. At its center, a beautifully appointed chef's kitchen open to the living and dining, designed for both daily living and effortless entertaining. The primary suite is a serene retreat, featuring a gas fireplace and spa-inspired bath. Enjoy spectacular sunrises and sunsets from the covered front porch and expansive back decks. A 2,071 sq ft secondary structure lives like a private mountain sanctuary, complete with four rooms, a full bath, kitchenette, and a dramatic floor-to-ceiling river rock fireplace. The great room evokes a true lodge feel, with expansive windows framing the ponderosas. Additional amenities include a saltwater pool, infrared sauna, four-stall barn and shop. Bring your animals--this 5.85-acre property is fully fenced and cross-fenced with a gated entry, all just 2.3 miles from downtown Sisters.

69550 Deer Ridge Road, Sisters

Listing courtesy of RE/MAX Key Properties.

$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.

$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.

$799,000
3 Beds 3 Baths 220218490 MLS
Whychus Creek rim setting w/Cascade views, National Forest access, Detached shop/garage. The thoughtfully designed home features a formal dining room, den, breakfast nook, and an inviting great room with a wood-burning fireplace. The open kitchen offers stainless steel appliances, a pantry, eating bar, and warm laminate wood floors. The primary suite is a peaceful escape with deck access, dual closets, an attached den, and a well-appointed bath with soaking tub, shower, and double sinks. A spacious laundry room with a half bath adds convenience. The detached oversized two-car garage includes covered RV parking and unfinished bonus space above. With a new septic tank (2014) and drain field (2025), low HOA fees, a community water system, and access to miles of National Forest and canyon trails, this is a rare Central Oregon retreat.

16959 Canyon Crest Drive, Sisters

Listing courtesy of Cascade Hasson SIR.

$850,000
2 Beds 1 Baths 220218120 MLS
Set on 2 private acres just minutes from downtown Sisters, this authentic full-log home captures the soul of a true Central Oregon mountain lifestyle. With no drywall, the handcrafted log construction delivers the warmth, character, and thermal mass of a timeless mountain lodge--an artisan home built to endure for generations. Inside, Acacia engineered hardwood, parquet flooring, and custom-fabricated steel fixtures blend rustic craftsmanship with modern design, all beneath a durable metal roof. Breathtaking views from the living room frame the surrounding landscape, creating a setting that feels both peaceful and inspiring. The massive RV shop/outbuilding offers exceptional space for adventure rigs, projects, or a workshop, while 110-volt camper pedestals welcome visiting guests. A legacy landholding where land, craftsmanship, and lifestyle come together--an unforgettable property designed to be enjoyed today and passed down for generations.

16011 Old Juniper Road, Sisters

Listing courtesy of Nexus 360 Realty.

$499,000
2 Beds 2 Baths 220218040 MLS
Income-generating investment 2-suite condominium meets mountain charm. Located in the desirable 4th Sister Condominiums in Sisters, Oregon, this single-level, main-floor unit offers a rare turnkey opportunity with an option to keep a long-term tenant in place. The open floor plan features two primary suites, including a versatile lock-off studio with its own exterior entrance -- perfect for maximizing rental potential. Inside, enjoy an open living area with a cozy fireplace, a dining area, a kitchen with a breakfast bar, and a built-in coffee bar. A stacking washer/dryer unit is included. Outside, your private patio overlooks the beautifully manicured common-area park, clubhouse, and pool. 2 assigned parking spots; 1 is covered. Situated within steps of the Sisters Movie House, Shibui Spa, Three Creeks Brewery, Creekside Park, and the new Sisters Park pickleball courts, this property is a cornerstone for any portfolio. Bonus: Furnishings are available for purchase outside of escrow.

813 E Desperado Trail UNIT 102 Unit UNIT 102, Sisters

Listing courtesy of Avenir Realty.

$2,450,000
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.

$1,895,000
5 Beds 5 Baths 220213955 MLS
Rare 45.6-acre private estate in Sisters' premier Cloverdale area, one of Central Oregon's most coveted acreage properties. This turn-key compound offers a 4,230 sq ft main residence with a NEW 2026 roof, 5 beds, 4.5 baths, plus an attached studio apartment and detached ADU. A massive shop, machine shed, and RV/boat storage make this the ultimate hobby ranch or entrepreneur's retreat. 38.7 acres of pressurized irrigation rights deliver exceptional agricultural and equestrian value. Cascade Mountain views frame every sunrise. Flexible floor plan supports multi-generational living, remote work, and extended guest stays. No HOA. Horse property. Minutes to Sisters. Sisters' Oregon acreage for sale, this is the irreplaceable Central Oregon legacy estate you've been searching for. $1,895,000.

69150 Butcher Block Boulevard, Sisters

Listing courtesy of Bend Premier Real Estate LLC.

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