Livinginredmond.com Search Results

$1,115,000

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.

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

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.

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.

$519,900

Prime corner lot min from the charm of downtown Sisters. Well maintained single-level home, turn-key, xeriscape landscaping & fire pit facing Black Butte -- all fully fenced. Open concept great room w/bamboo flooring, vaulted ceilings & a cozy corner pellet stove anchor the living space. Kitchen ftrs granite counters, ss appliances & is adjacent to a large eating area. Primary suite is complete w/en-suite bath & direct access to the exterior covered deck/sitting area. Guest bedroom w/access to separate full bath. Outside, gated RV/boat parking, shared double carport w/neighbor, locking storage area, & a thoughtfully designed xeriscape yard round out the property. No HOA adds further appeal. Located blocks from shops, galleries, restaurants, & Village Green City Park, this home puts the very best of Sisters at your doorstep. World-class outdoor recreation, from the Three Sisters Wilderness to Black Butte Ranch, is all just min away.

2 Beds ⋅ 2 Baths ⋅ 220222827 MLS

Prime corner lot min from the charm of downtown Sisters. Well maintained single-level home, turn-key, xeriscape landscaping & fire pit facing Black Butte -- all fully fenced. Open concept great room w/bamboo flooring, vaulted ceilings & a cozy corner pellet stove anchor the living space. Kitchen ftrs granite counters, ss appliances & is adjacent to a large eating area. Primary suite is complete w/en-suite bath & direct access to the exterior covered deck/sitting area. Guest bedroom w/access to separate full bath. Outside, gated RV/boat parking, shared double carport w/neighbor, locking storage area, & a thoughtfully designed xeriscape yard round out the property. No HOA adds further appeal. Located blocks from shops, galleries, restaurants, & Village Green City Park, this home puts the very best of Sisters at your doorstep. World-class outdoor recreation, from the Three Sisters Wilderness to Black Butte Ranch, is all just min away.

747 E Black Butte Avenue, Sisters

Listing courtesy of Keller Williams Realty Central Oregon.

$1,749,900

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

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.

$950,000

Enchanting mountain retreat in Sage Woods, just minutes from downtown Sisters. With a lodge-inspired ambiance and access to hiking, biking, and endless outdoor recreation right from your doorstep, this property offers the ideal blend of adventure, comfort, and versatility. This extraordinary and thoughtfully designed home features a spacious kitchen, sunroom/library, fireplace, flexible office or studio space, laundry/pantry room, and abundant storage. Beamed ceilings, hickory floors, and slate accents add warmth and character throughout. The inviting outdoor living area includes a large covered porch, sunny deck, water features, and hot tub. The property also features a deer-proof garden, greenhouse, playhouse, fenced dog area, and workshop. Two adjacent suites, each with its own full bathroom, provide exceptional flexibility and bring the total usable square footage to 2,892 square feet. A rare opportunity to enjoy the Central Oregon lifestyle in a charming and peaceful setting.

2 Beds ⋅ 4 Baths ⋅ 220224218 MLS

Enchanting mountain retreat in Sage Woods, just minutes from downtown Sisters. With a lodge-inspired ambiance and access to hiking, biking, and endless outdoor recreation right from your doorstep, this property offers the ideal blend of adventure, comfort, and versatility. This extraordinary and thoughtfully designed home features a spacious kitchen, sunroom/library, fireplace, flexible office or studio space, laundry/pantry room, and abundant storage. Beamed ceilings, hickory floors, and slate accents add warmth and character throughout. The inviting outdoor living area includes a large covered porch, sunny deck, water features, and hot tub. The property also features a deer-proof garden, greenhouse, playhouse, fenced dog area, and workshop. Two adjacent suites, each with its own full bathroom, provide exceptional flexibility and bring the total usable square footage to 2,892 square feet. A rare opportunity to enjoy the Central Oregon lifestyle in a charming and peaceful setting.

69741 Old Wagon Road, Sisters

Listing courtesy of Stellar Realty Northwest.

$3,350,000

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!

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

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.

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.

$1,775,000

Indian Ford Meadows is less than three miles from Sisters, a six-minute drive, This property is right on the national forest boundary. Nearly 1,000 feet of fence line runs that edge, so you can ride or hike thousands of acres straight from the gate. Two neighbors share the cul-de-sac. It's quiet here. The double-sawn log home sits on flat, cross-fenced acreage built for equestrian use. Three stalls with runouts, two pastures, a feed shed, and a 60-foot round pen. Renovated in 2022, enjoy heated herringbone tile floors, quartz counters, sage green cabinets with brass pulls, KitchenAid appliances, breakfast bar, corner eating nook. Primary suite over 18 feet square, vaulted ceilings, ductless heat pump, pedestal tub, dual vanities. Second primary suite upstairs, another bedroom and bath. Basement prepped for full finish. Three-car garage, nearly double deep, 40-foot RV garage with roll-up door, mud room, tankless water heater. One-bed ADU and detached studio, both steps from main house.

5 Beds ⋅ 5 Baths ⋅ 220223702 MLS

Indian Ford Meadows is less than three miles from Sisters, a six-minute drive, This property is right on the national forest boundary. Nearly 1,000 feet of fence line runs that edge, so you can ride or hike thousands of acres straight from the gate. Two neighbors share the cul-de-sac. It's quiet here. The double-sawn log home sits on flat, cross-fenced acreage built for equestrian use. Three stalls with runouts, two pastures, a feed shed, and a 60-foot round pen. Renovated in 2022, enjoy heated herringbone tile floors, quartz counters, sage green cabinets with brass pulls, KitchenAid appliances, breakfast bar, corner eating nook. Primary suite over 18 feet square, vaulted ceilings, ductless heat pump, pedestal tub, dual vanities. Second primary suite upstairs, another bedroom and bath. Basement prepped for full finish. Three-car garage, nearly double deep, 40-foot RV garage with roll-up door, mud room, tankless water heater. One-bed ADU and detached studio, both steps from main house.

69566 Paint Brush Lane, Sisters

Listing courtesy of Central Oregon Realty Group.

$1,275,000

Exceptional single-level Mid-Century Modern home, featuring two spacious primary en-suites and numerous high-end customizations. Grand Peaks owner-only gated pickleball courts and private park, all right in town. Filled with natural light, the home offers vaulted ceilings, expansive windows, a floor-to-ceiling brick fireplace, and a custom glass entry chandelier. Gourmet kitchen features a huge island, six-burner cooktop, double ovens, beverage drawer, large pantry, abundant storage, and office nook with barn doors. Primary suite includes vaulted ceilings, double walk-in closets, double vanities, soaking tub, tile shower, private toilet room, and direct access to the patio and hot tub. Second en-suite and third bath both feature tile walk-in showers. Wired speaker system, large laundry room with utility sink, and epoxy-floor garage. Extensive outdoor living area includes a covered patio, built-in fireplace, hot tub, water feature, raised garden beds, fruit trees, and mature landscaping

3 Beds ⋅ 3 Baths ⋅ 220223209 MLS

Exceptional single-level Mid-Century Modern home, featuring two spacious primary en-suites and numerous high-end customizations. Grand Peaks owner-only gated pickleball courts and private park, all right in town. Filled with natural light, the home offers vaulted ceilings, expansive windows, a floor-to-ceiling brick fireplace, and a custom glass entry chandelier. Gourmet kitchen features a huge island, six-burner cooktop, double ovens, beverage drawer, large pantry, abundant storage, and office nook with barn doors. Primary suite includes vaulted ceilings, double walk-in closets, double vanities, soaking tub, tile shower, private toilet room, and direct access to the patio and hot tub. Second en-suite and third bath both feature tile walk-in showers. Wired speaker system, large laundry room with utility sink, and epoxy-floor garage. Extensive outdoor living area includes a covered patio, built-in fireplace, hot tub, water feature, raised garden beds, fruit trees, and mature landscaping

471 E Diamond Peak Avenue, Sisters

Listing courtesy of Kizziar Property Co..

$1,200,000

Nestled on acreage with incredible Cascade Mountain Views, this beautifully maintained home, offers the perfect blend of comfort, privacy, and natural beauty. Pride of ownership shines throughout with thoughtfully cared-for spaces both inside and out. The stunning landscaped grounds create a peaceful retreat, complete with tranquil outdoor living areas designed to take in the surrounding scenery. Whether enjoying quiet mornings on the patio or entering guest, this property captures the essence of country living with refined charm. A rare opportunity to own a serene and picturesque setting with space to breathe and views to inspire, less than 15 minutes to down town Sisters!

3 Beds ⋅ 3 Baths ⋅ 220222240 MLS

Nestled on acreage with incredible Cascade Mountain Views, this beautifully maintained home, offers the perfect blend of comfort, privacy, and natural beauty. Pride of ownership shines throughout with thoughtfully cared-for spaces both inside and out. The stunning landscaped grounds create a peaceful retreat, complete with tranquil outdoor living areas designed to take in the surrounding scenery. Whether enjoying quiet mornings on the patio or entering guest, this property captures the essence of country living with refined charm. A rare opportunity to own a serene and picturesque setting with space to breathe and views to inspire, less than 15 minutes to down town Sisters!

17584 Mountain View Road, Sisters

Listing courtesy of Stellar Realty Northwest.

$1,699,000

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.

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.

$1,590,000

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)

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.

$2,795,000

Booming Cascade Mountain and meadow views from all main indoor and outdoor living areas. Very private but also very close to town. Van Sant designed home features: Open living floor plan; Sunroom with private deck; Vaulted ceilings with wood accents; Abundant natural light; Hardwood flooring; Floor to ceiling river rock fireplace; Large ''entertainer'' kitchen with island, walk-in pantry, stainless appliances; First level primary suite with deck access, fireplace, walk-in closet, soaking tub, double vanity, private toilet, walk-in shower; Two large upstairs bedrooms and an additional en-suite, all with mountain views; Huge bonus room with balcony. Exterior features: Indian Ford Creek flows through property; Fenced pasture/meadow; 3 car garage with extra workshop, EV charger outlet; 1 new HVAC system for 1st level; Hardi siding, 50 year presidential roof; Extensive landscape with underground irrigation; Large water feature/pond; Huge rear deck with large covered area; Large paved driveway

4 Beds ⋅ 4 Baths ⋅ 220217892 MLS

Booming Cascade Mountain and meadow views from all main indoor and outdoor living areas. Very private but also very close to town. Van Sant designed home features: Open living floor plan; Sunroom with private deck; Vaulted ceilings with wood accents; Abundant natural light; Hardwood flooring; Floor to ceiling river rock fireplace; Large ''entertainer'' kitchen with island, walk-in pantry, stainless appliances; First level primary suite with deck access, fireplace, walk-in closet, soaking tub, double vanity, private toilet, walk-in shower; Two large upstairs bedrooms and an additional en-suite, all with mountain views; Huge bonus room with balcony. Exterior features: Indian Ford Creek flows through property; Fenced pasture/meadow; 3 car garage with extra workshop, EV charger outlet; 1 new HVAC system for 1st level; Hardi siding, 50 year presidential roof; Extensive landscape with underground irrigation; Large water feature/pond; Huge rear deck with large covered area; Large paved driveway

69485 Deer Ridge Road, Sisters

Listing courtesy of Kizziar Property Co..

$2,450,000

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.

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.

$1,200,000

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!

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.

$1,895,000

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.

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.

$9,750,000

This is a testament to timeless grandeur. Nestled within Deschutes Land Trust's preserve, in the heart of Central Oregon, this remarkable 67 acre estate offers an enduring legacy that will be treasured for generations to come. The primary residence, spanning 5,050 sq ft, boasts three bedrooms, five bathrooms, and a chef's kitchen. Hand-carved hickory and heated stone floors exude warmth, while twenty-foot ceilings and expansive windows provide stunning views. The property features a private-access apartment suite, custom cabinetry, a heated three car garage, and manicured landscaping. Enjoy mountain vistas, an outdoor kitchen, and a fire feature in the courtyard, as well as direct access to private land for fishing and wildlife viewing. On this sprawling estate you will also find two other full residences. Home two is single story with 1,700 sq ft, 2 bed, 2 bath, and a two car garage. Home three is two story with 2,200 sq ft, 3 bed, 2 bath, and a 2 car garage.

8 Beds ⋅ 9 Baths ⋅ 220203639 MLS

This is a testament to timeless grandeur. Nestled within Deschutes Land Trust's preserve, in the heart of Central Oregon, this remarkable 67 acre estate offers an enduring legacy that will be treasured for generations to come. The primary residence, spanning 5,050 sq ft, boasts three bedrooms, five bathrooms, and a chef's kitchen. Hand-carved hickory and heated stone floors exude warmth, while twenty-foot ceilings and expansive windows provide stunning views. The property features a private-access apartment suite, custom cabinetry, a heated three car garage, and manicured landscaping. Enjoy mountain vistas, an outdoor kitchen, and a fire feature in the courtyard, as well as direct access to private land for fishing and wildlife viewing. On this sprawling estate you will also find two other full residences. Home two is single story with 1,700 sq ft, 2 bed, 2 bath, and a two car garage. Home three is two story with 2,200 sq ft, 3 bed, 2 bath, and a 2 car garage.

16465 Suntree Lane, Sisters

Listing courtesy of Engel & Volkers Portland Rose City.