Livinginredmond.com Search Results

$1,599,000

Cascade Mountain views & 9.36 acres! Power gated entry & asphalt drive lead to this stunning Sisters Estate. Cozy living room features a river rock fireplace. New kitchen boasts new cabinets, granite counters, new appliances & bar w/wine fridge. Main-level primary suite includes a spa shower, soaking tub & walk-in closet. Upper-level w/2 bedrooms & a fully updated bath w/new cabinets, counters, tile shower & flooring. New laundry cabinets & sink. Oversized 2-car garage has epoxy floors, metal cabinets & a guest/multi-gen living/bonus room above w/private entry & new carpet. Ideal for equestrian lovers: full perimeter fencing & electric cross-fenced pastures connect to barn paddocks & 2 matted stalls, water/power, plus hay storage & tack room. Back deck overlooks a beautifully landscaped pond & fountain. Detached office/exercise studio features mountain views & a private sauna. Serene country living just 10 mins to Sisters & 30 mins to Bend! True privacy with convenient urban access.

3 Beds ⋅ 4 Baths ⋅ 220227675 MLS

Cascade Mountain views & 9.36 acres! Power gated entry & asphalt drive lead to this stunning Sisters Estate. Cozy living room features a river rock fireplace. New kitchen boasts new cabinets, granite counters, new appliances & bar w/wine fridge. Main-level primary suite includes a spa shower, soaking tub & walk-in closet. Upper-level w/2 bedrooms & a fully updated bath w/new cabinets, counters, tile shower & flooring. New laundry cabinets & sink. Oversized 2-car garage has epoxy floors, metal cabinets & a guest/multi-gen living/bonus room above w/private entry & new carpet. Ideal for equestrian lovers: full perimeter fencing & electric cross-fenced pastures connect to barn paddocks & 2 matted stalls, water/power, plus hay storage & tack room. Back deck overlooks a beautifully landscaped pond & fountain. Detached office/exercise studio features mountain views & a private sauna. Serene country living just 10 mins to Sisters & 30 mins to Bend! True privacy with convenient urban access.

17660 Edmundson Road, Sisters

Listing courtesy of Bend Premier Real Estate LLC.

$1,549,900

NEARLY 30 ACRES | GATED SISTERS ESTATE | HOME THEATER | GARAGE/SHOP Beyond the gate, a winding drive beneath towering pines opens to park-like landscaping with sweeping lawns, mature aspens, stone paths and a paver courtyard with hot tub. The theater rivals a private cinema, featuring tiered recliners, a wall-size screen and rich wood-and-brick finishes. Attached and detached garage/shop spaces offer multiple bays, bright work areas, a bath and upper storage for vehicles, equipment and projects. The 4,939-square-foot lodge-style home features hardwood floors, exposed timbers, coffered ceilings, a stone hearth and a chef's kitchen with a large island and Wolf range. The primary suite includes an oversized tiled shower and custom closet. A billiards room, sauna, greenhouse, fenced garden, carport and multiple outbuildings complete this remarkable Sisters property.

2 Beds ⋅ 3 Baths ⋅ 220227737 MLS

NEARLY 30 ACRES | GATED SISTERS ESTATE | HOME THEATER | GARAGE/SHOP Beyond the gate, a winding drive beneath towering pines opens to park-like landscaping with sweeping lawns, mature aspens, stone paths and a paver courtyard with hot tub. The theater rivals a private cinema, featuring tiered recliners, a wall-size screen and rich wood-and-brick finishes. Attached and detached garage/shop spaces offer multiple bays, bright work areas, a bath and upper storage for vehicles, equipment and projects. The 4,939-square-foot lodge-style home features hardwood floors, exposed timbers, coffered ceilings, a stone hearth and a chef's kitchen with a large island and Wolf range. The primary suite includes an oversized tiled shower and custom closet. A billiards room, sauna, greenhouse, fenced garden, carport and multiple outbuildings complete this remarkable Sisters property.

14880 Chickaree Lane, Sisters

Listing courtesy of eXp Realty, LLC.

$895,000

One-of-a-kind Sisters property on nearly 1 acre, where impeccably maintained, park-like grounds meet an extraordinary collection of shops and outbuildings. Mature trees, manicured landscaping, gardens and covered porches create a private Central Oregon retreat--and the exceptional utility spaces make it truly rare. The single level 2-bed, 2-bath + office home has a lodge-like feel with 10' ceilings, wood-burning stove, spacious kitchen/dining area and primary suite. Beyond the home: heated detached 2-car garage with workshop/office; newer 30' x 36' shop with wood stove and stone hearth (tons of possible uses); 12' x 35' covered RV pad; 16' x 24' insulated outbuilding with electrical; plus utility shed and storage building. A standout for gardeners, wood workers, hobbyists, and collectors--exceptionally maintained and hard to duplicate for under $900,000. You really have to see this property in person to appreciate it.

2 Beds ⋅ 2 Baths ⋅ 220227414 MLS

One-of-a-kind Sisters property on nearly 1 acre, where impeccably maintained, park-like grounds meet an extraordinary collection of shops and outbuildings. Mature trees, manicured landscaping, gardens and covered porches create a private Central Oregon retreat--and the exceptional utility spaces make it truly rare. The single level 2-bed, 2-bath + office home has a lodge-like feel with 10' ceilings, wood-burning stove, spacious kitchen/dining area and primary suite. Beyond the home: heated detached 2-car garage with workshop/office; newer 30' x 36' shop with wood stove and stone hearth (tons of possible uses); 12' x 35' covered RV pad; 16' x 24' insulated outbuilding with electrical; plus utility shed and storage building. A standout for gardeners, wood workers, hobbyists, and collectors--exceptionally maintained and hard to duplicate for under $900,000. You really have to see this property in person to appreciate it.

70116 Sorrell Drive, Sisters

Listing courtesy of eXp Realty, LLC.

$699,000

Back on Market-No fault of seller Beautiful Central Oregon charm in this Craftsman move-in-ready 4-bed, 3-bath home in Whychus Canyon Estates, Sisters. Offering 2,675 sq ft on a flat, fully fenced 0.96-acre lot with NO HOA and seller financing available to a qualified buyer. A main-level primary suite, cozy wood-burning stove, and wraparound deck and porch make everyday living a pleasure, and the permitted bonus room above the garage flexes as an office, guest suite, or rec room. Turnkey updates: new range and dishwasher (2024), 50-year roof (2022), upgraded HVAC, flooring, blinds, and new toilets, plus maple cabinets and classic cedar siding. Room for your RV, boat, and all your Central Oregon toys, minutes to downtown Sisters shopping, dining, trails, and outdoor recreation. Come make Sisters your home.

4 Beds ⋅ 3 Baths ⋅ 220226968 MLS

Back on Market-No fault of seller Beautiful Central Oregon charm in this Craftsman move-in-ready 4-bed, 3-bath home in Whychus Canyon Estates, Sisters. Offering 2,675 sq ft on a flat, fully fenced 0.96-acre lot with NO HOA and seller financing available to a qualified buyer. A main-level primary suite, cozy wood-burning stove, and wraparound deck and porch make everyday living a pleasure, and the permitted bonus room above the garage flexes as an office, guest suite, or rec room. Turnkey updates: new range and dishwasher (2024), 50-year roof (2022), upgraded HVAC, flooring, blinds, and new toilets, plus maple cabinets and classic cedar siding. Room for your RV, boat, and all your Central Oregon toys, minutes to downtown Sisters shopping, dining, trails, and outdoor recreation. Come make Sisters your home.

70125 Mustang Drive, Sisters

Listing courtesy of Realty One Group Discovery.

$1,499,000

Welcome to this exceptional custom home with mountain views and beautifully maintained grounds. A must-see 3,177 sq. ft. craftsman home offers an inviting setting for everyday indoor-outdoor living and entertaining. With over $200,000 in upgrades this past two years there are too many to list. This home speaks for itself. You can feel the quality when you first step inside. The great room features soaring vaulted ceilings with timber accents, hardwood flooring, a stunning floor-to-ceiling rock fireplace, and expansive windows showcasing the beautiful surroundings. Gourmet kitchen, office that can also be used as a fourth bedroom, bonus room with extra flex space. Step outside onto the expansive rear deck to an ideal setting. An extended-length, heated 3-car garage completes this truly special home.

4 Beds ⋅ 3 Baths ⋅ 220226890 MLS

Welcome to this exceptional custom home with mountain views and beautifully maintained grounds. A must-see 3,177 sq. ft. craftsman home offers an inviting setting for everyday indoor-outdoor living and entertaining. With over $200,000 in upgrades this past two years there are too many to list. This home speaks for itself. You can feel the quality when you first step inside. The great room features soaring vaulted ceilings with timber accents, hardwood flooring, a stunning floor-to-ceiling rock fireplace, and expansive windows showcasing the beautiful surroundings. Gourmet kitchen, office that can also be used as a fourth bedroom, bonus room with extra flex space. Step outside onto the expansive rear deck to an ideal setting. An extended-length, heated 3-car garage completes this truly special home.

17690 Mountain View Road, Sisters

Listing courtesy of Cascade Hasson SIR.

$655,000

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.

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.

$999,950

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.

$1,450,000

Experience modern farmhouse living at its finest in this beautifully crafted home, nestled on 2 private acres with sweeping mountain views and exceptional privacy. Surrounded by 104 acres of open space, this property offers a peaceful retreat while being just minutes from town. Thoughtfully designed for everyday living and entertaining, the single level floor plan features 3 bedrooms, 2.5 baths, dedicated office, and a spacious living room that opens to a covered patio through oversized sliding doors. The primary suite is tucked away on one side of the home while two bedrooms on the opposite side are connected by a Jack-and-Jill bath. The chef's kitchen features a dedicated bar area with a beverage fridge and large butlers pantry. No detail was overlooked in crafting this home. From the meticulous landscaping and dedicated RV parking to the high end finishes and thoughtful design, this property provides comfort, functionality, and timeless farmhouse appeal in a truly private settin

3 Beds ⋅ 3 Baths ⋅ 220225665 MLS

Experience modern farmhouse living at its finest in this beautifully crafted home, nestled on 2 private acres with sweeping mountain views and exceptional privacy. Surrounded by 104 acres of open space, this property offers a peaceful retreat while being just minutes from town. Thoughtfully designed for everyday living and entertaining, the single level floor plan features 3 bedrooms, 2.5 baths, dedicated office, and a spacious living room that opens to a covered patio through oversized sliding doors. The primary suite is tucked away on one side of the home while two bedrooms on the opposite side are connected by a Jack-and-Jill bath. The chef's kitchen features a dedicated bar area with a beverage fridge and large butlers pantry. No detail was overlooked in crafting this home. From the meticulous landscaping and dedicated RV parking to the high end finishes and thoughtful design, this property provides comfort, functionality, and timeless farmhouse appeal in a truly private settin

70041 Annies Drive, Sisters

Listing courtesy of Stellar Realty Northwest.

$435,000

Welcome to this beautiful, turnkey townhome in a prime Sisters location, perfectly blending mountain charm with low-maintenance convenience in the desirable Village at Cold Springs. Spanning 1,471 sq. ft. with 3 bedrooms and 2.5 baths, this bright, open-concept home features modern finishes, a chef's kitchen with granite countertops, a spacious primary suite, and an upstairs laundry room. A rare find for townhomes, it boasts a 2-car attached garage PLUS an additional 2-car parking pad right behind it--perfect for guests and additional vehicles. Overlooking a scenic community green space and playground, the location offers incredible walkability. Leave your car at home and enjoy an easy stroll to downtown Sisters' iconic coffee shops, local dining, boutiques, and groceries. Whether you are looking for a full-time residence or a lock-and-leave mountain getaway, this property delivers the ultimate Pacific Northwest lifestyle.

3 Beds ⋅ 3 Baths ⋅ 220225003 MLS

Welcome to this beautiful, turnkey townhome in a prime Sisters location, perfectly blending mountain charm with low-maintenance convenience in the desirable Village at Cold Springs. Spanning 1,471 sq. ft. with 3 bedrooms and 2.5 baths, this bright, open-concept home features modern finishes, a chef's kitchen with granite countertops, a spacious primary suite, and an upstairs laundry room. A rare find for townhomes, it boasts a 2-car attached garage PLUS an additional 2-car parking pad right behind it--perfect for guests and additional vehicles. Overlooking a scenic community green space and playground, the location offers incredible walkability. Leave your car at home and enjoy an easy stroll to downtown Sisters' iconic coffee shops, local dining, boutiques, and groceries. Whether you are looking for a full-time residence or a lock-and-leave mountain getaway, this property delivers the ultimate Pacific Northwest lifestyle.

820 N Hindeman Street, Sisters

Listing courtesy of Engel & Voelkers Bend.

$1,299,500

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!

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.

$1,699,900

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.

$899,000

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.

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.

$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.

$599,000

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!

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.

$695,000

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.

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.

$945,000

Enjoy breathtaking views of Mt. Jefferson and Black Butte from this beautifully maintained home on 2.33 private acres. Expansive windows fill the home with natural light, while soaring 20-foot vaulted ceilings in the great room and family room create an impressive sense of space. Generously sized bedrooms provide comfort for family and guests, and the recently built covered TimberTech deck offers the perfect setting for entertaining, outdoor dining, or simply taking in the Cascade views. Recent updates include a new roof (2023), exterior paint (2024), built-in Dacor refrigerator/freezer, and Bosch dishwasher. Additional features include dual-zone heat pump and air conditioning with smart-device controls, central vacuum system, propane fireplaces, Hunter Douglas lifetime-guaranteed shades, a luxurious primary suite with jetted tub and walk-in shower, Firewise landscaping, and a 5-zone irrigation system. A rare combination of privacy, quality, and unforgettable Central Oregon views.

4 Beds ⋅ 3 Baths ⋅ 220223102 MLS

Enjoy breathtaking views of Mt. Jefferson and Black Butte from this beautifully maintained home on 2.33 private acres. Expansive windows fill the home with natural light, while soaring 20-foot vaulted ceilings in the great room and family room create an impressive sense of space. Generously sized bedrooms provide comfort for family and guests, and the recently built covered TimberTech deck offers the perfect setting for entertaining, outdoor dining, or simply taking in the Cascade views. Recent updates include a new roof (2023), exterior paint (2024), built-in Dacor refrigerator/freezer, and Bosch dishwasher. Additional features include dual-zone heat pump and air conditioning with smart-device controls, central vacuum system, propane fireplaces, Hunter Douglas lifetime-guaranteed shades, a luxurious primary suite with jetted tub and walk-in shower, Firewise landscaping, and a 5-zone irrigation system. A rare combination of privacy, quality, and unforgettable Central Oregon views.

70275 Club Road, Sisters

Listing courtesy of Stellar Realty Northwest.

$699,000

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.

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.

$850,000

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.

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.

$689,000

Experience the magic and convenience of downtown living in the scenic mountain town of Sisters, Oregon. Let this home serve as your primary residence, second home 'basecamp', or income-generating rental. The entire interior has been freshly painted, creating a clean, bright, and move-in ready space. Enjoy stunning mountain views from the second story deck. Low maintenance, zero-scape landscaping. Immediate access to all that downtown has to offer. Enjoy community festivals and events, plus access to a multitude of trails, lakes, and the Cascade Mountains. Downstairs features a primary bedroom and bath, kitchen, laundry area, gas fireplace, and inviting living room. Upstairs, you will find two bedrooms, full bathroom, kitchenette, additional laundry room, and a bonus room/flex space. Every detail was meticulously crafted by a renowned custom home builder with quality finishes throughout. An enclosed storage area connected through the garage provides space to store all your gear. No HOA

3 Beds ⋅ 2 Baths ⋅ 220221015 MLS

Experience the magic and convenience of downtown living in the scenic mountain town of Sisters, Oregon. Let this home serve as your primary residence, second home 'basecamp', or income-generating rental. The entire interior has been freshly painted, creating a clean, bright, and move-in ready space. Enjoy stunning mountain views from the second story deck. Low maintenance, zero-scape landscaping. Immediate access to all that downtown has to offer. Enjoy community festivals and events, plus access to a multitude of trails, lakes, and the Cascade Mountains. Downstairs features a primary bedroom and bath, kitchen, laundry area, gas fireplace, and inviting living room. Upstairs, you will find two bedrooms, full bathroom, kitchenette, additional laundry room, and a bonus room/flex space. Every detail was meticulously crafted by a renowned custom home builder with quality finishes throughout. An enclosed storage area connected through the garage provides space to store all your gear. No HOA

353 E Aspenwood Avenue, Sisters

Listing courtesy of Sunriver Realty.

$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.

$2,650,000

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.

$2,995,000

Set against the sweeping backdrop of the Cascade Range in Sisters, this exceptional 6,218-square-foot estate offers a rare combination of privacy, craftsmanship, and versatility -- all just minutes from the charm of downtown. Positioned on 2.09 serene acres, the home was designed to capture both natural light and panoramic mountain views. Expansive windows, soaring ceilings, and timeless finishes create a warm yet refined atmosphere that feels equally suited for everyday living and large-scale entertaining. The chef's kitchen anchors the main living space, featuring premium appliances, custom cabinetry, and generous prep areas ideal for gatherings. The main-level primary suite serves as a private retreat with a spa-inspired bath and substantial closet space. Five additional bedrooms provide flexibility for guests, multi-generational living, or dedicated office and hobby spaces.

6 Beds ⋅ 4 Baths ⋅ 220216913 MLS

Set against the sweeping backdrop of the Cascade Range in Sisters, this exceptional 6,218-square-foot estate offers a rare combination of privacy, craftsmanship, and versatility -- all just minutes from the charm of downtown. Positioned on 2.09 serene acres, the home was designed to capture both natural light and panoramic mountain views. Expansive windows, soaring ceilings, and timeless finishes create a warm yet refined atmosphere that feels equally suited for everyday living and large-scale entertaining. The chef's kitchen anchors the main living space, featuring premium appliances, custom cabinetry, and generous prep areas ideal for gatherings. The main-level primary suite serves as a private retreat with a spa-inspired bath and substantial closet space. Five additional bedrooms provide flexibility for guests, multi-generational living, or dedicated office and hobby spaces.

69205 Hawksflight Drive, Sisters

Listing courtesy of eXp Realty, LLC.

$679,000

Located in a peaceful, newer neighborhood just minutes from downtown Sisters, this single-level home blends small-town charm with contemporary design. Open floor plan with abundant natural light highlights quality finishes and upgrades. Cozy propane fireplace with tiled surround. Primary suite features a large bathroom with private toilet room and spacious walk-in closet. Southern exposure provides sunshine to the fully landscaped and fenced backyard. Front porch overlooks Saddlestone Park with walking paths and playground, and a short walk to Sisters Community Center and local Seed to Table Farm.

3 Beds ⋅ 2 Baths ⋅ 220216121 MLS

Located in a peaceful, newer neighborhood just minutes from downtown Sisters, this single-level home blends small-town charm with contemporary design. Open floor plan with abundant natural light highlights quality finishes and upgrades. Cozy propane fireplace with tiled surround. Primary suite features a large bathroom with private toilet room and spacious walk-in closet. Southern exposure provides sunshine to the fully landscaped and fenced backyard. Front porch overlooks Saddlestone Park with walking paths and playground, and a short walk to Sisters Community Center and local Seed to Table Farm.

1005 E Horse Back Trail, Sisters

Listing courtesy of Realty Net of Central Oregon.

$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.

$2,700,000

Thoughtfully crafted custom home set on a private 2-acre parcel. Ten homesites within an 110-acre wildlife preserve, showcasing sweeping panoramic views of the high desert and the Blue Mountains. A striking Timber-Framed entry opens to a grand great room with soaring cathedral trusses. The gourmet kitchen blends elegance and function with an oversized island, granite countertops, knotty alder cabinetry, and Viking 5 Series appliances. The main level offers three luxurious en-suite bedrooms, two with propane fireplaces, private deck access, and dedicated w&d. Upstairs the loft overlooks the great room, accompanied by two add'l bedrooms, and a full bath. The walk-out lower level includes a wood-burning stove, full bath, flex space, sleeping room, and access to a covered patio with private hot tub. Wraparound deck, three-car garage with EV receptacle, native defensible landscaping. Ideal for Corporate Retreats, STR permit in place. Walk-out basement ideal for ADU.

5 Beds ⋅ 6 Baths ⋅ 220214444 MLS

Thoughtfully crafted custom home set on a private 2-acre parcel. Ten homesites within an 110-acre wildlife preserve, showcasing sweeping panoramic views of the high desert and the Blue Mountains. A striking Timber-Framed entry opens to a grand great room with soaring cathedral trusses. The gourmet kitchen blends elegance and function with an oversized island, granite countertops, knotty alder cabinetry, and Viking 5 Series appliances. The main level offers three luxurious en-suite bedrooms, two with propane fireplaces, private deck access, and dedicated w&d. Upstairs the loft overlooks the great room, accompanied by two add'l bedrooms, and a full bath. The walk-out lower level includes a wood-burning stove, full bath, flex space, sleeping room, and access to a covered patio with private hot tub. Wraparound deck, three-car garage with EV receptacle, native defensible landscaping. Ideal for Corporate Retreats, STR permit in place. Walk-out basement ideal for ADU.

70030 Annies Drive, Sisters

Listing courtesy of Stellar Realty Northwest.

$774,900

This special home in Saddlestone, a very sought after neighborhood in the quaint town of Sisters, Oregon, sits up on the lot and is very private. The front porch/patio faces south for the Central Oregon sunshine, is large (enough room for outdoor dining/entertaining) and looks out onto the Saddlestone Park. Just under 2,000 sq.ft. - 3 Bedrms, 2 1/2 Bathrms plus large loft - Primary on the main floor with ensuite bathroom. Open floor plan includes the living room w/vaulted ceilings, gourmet kitchen w/island/breakfast bar & stainless steel appliances, dining and nice sized entry. Powder rm and laundry room w/folding table downstairs. Upstairs has a large loft, 2 bedrooms and a full bathroom. Kitchen & all bathrooms have solid surfaces. Upgraded hardware (oil rubbed bronze) thru out and upgraded lighting thru out. Beautifully landscaped front yard that adds privacy to the front porch. Fenced side yard. 2 car garage with lots of storage space. This house has been softly lived in .

3 Beds ⋅ 3 Baths ⋅ 220214029 MLS

This special home in Saddlestone, a very sought after neighborhood in the quaint town of Sisters, Oregon, sits up on the lot and is very private. The front porch/patio faces south for the Central Oregon sunshine, is large (enough room for outdoor dining/entertaining) and looks out onto the Saddlestone Park. Just under 2,000 sq.ft. - 3 Bedrms, 2 1/2 Bathrms plus large loft - Primary on the main floor with ensuite bathroom. Open floor plan includes the living room w/vaulted ceilings, gourmet kitchen w/island/breakfast bar & stainless steel appliances, dining and nice sized entry. Powder rm and laundry room w/folding table downstairs. Upstairs has a large loft, 2 bedrooms and a full bathroom. Kitchen & all bathrooms have solid surfaces. Upgraded hardware (oil rubbed bronze) thru out and upgraded lighting thru out. Beautifully landscaped front yard that adds privacy to the front porch. Fenced side yard. 2 car garage with lots of storage space. This house has been softly lived in .

936 E Black Butte Avenue, Sisters

Listing courtesy of Engel & Voelkers Bend.