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Craftsman Homes for Sale in Sisters, OR

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  • /83

    $1,499,000

    • 4 Beds
    • 2.5 Baths
    • 3,177 Sq Ft

    17690 Mountain View Rd, Sisters, OR 97759

    Welcome to this exceptional custom home with stunning mountain views and beautifully maintained grounds. A blend of craftsmanship, and comfort, this 3,177 sq. ft. home offers an inviting setting for everyday indoor-outdoor living and entertaining. The great room features soaring vaulted ceilings with timber accents, hardwood flooring, a stunning floor-to-ceiling rock fireplace, and expansive

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    Joanna Cooley

    Cascade Hasson SIR

    17690 Mountain View Rd, Sisters, OR 97759
  • /51

    $2,995,000

    • 6 Beds
    • 4 Baths
    • 6,218 Sq Ft

    69205 Hawksflight Dr, Sisters, OR 97759

    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

    Jayson Mitchell eXp Realty, LLC

    69205 Hawksflight Dr, Sisters, OR 97759
  • /40

    $850,000

    $35K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,668 Sq Ft

    16738 Pine Tree Ln, Sisters, OR 97759

    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

    Jenelle McCleary Realty One Group Discovery

    16738 Pine Tree Ln, Sisters, OR 97759
  • /94

    $2,795,000

    $405K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 5,093 Sq Ft

    69485 Deer Ridge Rd, Sisters, OR 97759

    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,

    Tim Kizziar Kizziar Property Co.

    69485 Deer Ridge Rd, Sisters, OR 97759
  • /53

    $1,590,000

    • 3 Beds
    • 2.5 Baths
    • 2,967 Sq Ft

    68050 Fryrear Rd, Sisters, OR 97759

    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

    Geff Kinnaman Stellar Realty Northwest

    68050 Fryrear Rd, Sisters, OR 97759
  • /51

    $1,495,000

    • 3 Beds
    • 5 Baths
    • 3,569 Sq Ft

    70160 Doggie Dr, Sisters, OR 97759

    First time on the market! This custom-built, mostly single-level masterpiece features high-end finishes throughout, all nestled on over two acres with no HOA just minutes from downtown Sisters. The expansive great room boasts vaulted ceilings and a cozy propane fireplace, flowing seamlessly into the dining area and gourmet kitchen. Designed for privacy, the main level features a split-bedroom

    Thomas Arends Ponderosa Properties

    70160 Doggie Dr, Sisters, OR 97759
  • /39

    $599,000

    $46K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,556 Sq Ft

    547 W Jefferson Ave, Sisters, OR 97759

    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

    Bryant Green Cascade Hasson SIR

    547 W Jefferson Ave, Sisters, OR 97759
  • /35

    $659,000

    $80K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,745 Sq Ft

    944 E Creek View Dr Unit Lot 66 Block, Sisters, OR 97759

    Tucked into the sought-after Timber Creek neighborhood, this inviting single-level home offers the perfect blend of comfort, convenience, and the relaxed Central Oregonlifestyle. Featuring 3 bedrooms, 3 baths, two fireplaces, a private primary suite, Wood and tile floors, Heatpump AC with a custom patio, it's designed for easy living bothinside and out. The garage workshop provides extra

    Geff Kinnaman Stellar Realty Northwest

    944 E Creek View Dr Unit Lot 66 Block, Sisters, OR 97759
  • /18

    $689,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,807 Sq Ft

    1005 E Horse Back Trail, Sisters, OR 97759

    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

    Greg Messick Realty Net of Central Oregon

    1005 E Horse Back Trail, Sisters, OR 97759
  • /50

    $1,475,000

    • 3 Beds
    • 2.5 Baths
    • 2,580 Sq Ft

    70041 Annies Dr, Sisters, OR 97759

    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,

    Shelbi Hodges Stellar Realty Northwest

    70041 Annies Dr, Sisters, OR 97759
  • /47

    $719,000

    $6K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,550 Sq Ft

    353 E Aspenwood Ave, Sisters, OR 97759

    Experience the magic of downtown living in the scenic mountain town of Sisters, Oregon. This home can serve as your primary residence, a second home 'basecamp'' for skiing, biking, and hiking, or an income-generating rental property. Recently Appraised. Separate lockout provides access to the upper level with stunning Mountain views from the newly stained private deck. Low maintenance and

    Debra Mortimore Sunriver Realty

    353 E Aspenwood Ave, Sisters, OR 97759
  • /70

    $1,299,500

    • 4 Beds
    • 2.5 Baths
    • 2,717 Sq Ft

    751 S Redwood, Sisters, OR 97759

    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

    Joey Morgan eXp Realty, LLC

    751 S Redwood, Sisters, OR 97759
  • /44

    $699,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    1949 W Williamson Ave, Sisters, OR 97759

    Beautiful updated one-story home in Sisters tucked into a cul-de-sac! This modern 3-bed, 2-bath floorplan lives large across 1,800 sq ft, + grand Cascade Mountain views right from windows and backyard. Upgrades: Quartz in both baths, LVP, tiled floors baths, laundry, primary shower, fireplace, lighting, undercabinet, hardware, BBQ stub. Open floorplan + natural light beams in kitchen and offers

    Sheri Hilton Bend Premier Real Estate LLC

    1949 W Williamson Ave, Sisters, OR 97759
  • /31

    $1,115,000

    • 3 Beds
    • 3.5 Baths
    • 3,042 Sq Ft

    17084 Lady Caroline Dr, Sisters, OR 97759

    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

    Karen Malanga RE/MAX Key Properties

    17084 Lady Caroline Dr, Sisters, OR 97759
  • /26

    $699,000

    $26K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,090 Sq Ft

    15634 Ponderosa Ln, Sisters, OR 97759

    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

    Joe Nickelson Real Broker

    15634 Ponderosa Ln, Sisters, OR 97759
  • /69

    $1,995,000

    • 6 Beds
    • 5.5 Baths
    • 4,910 Sq Ft

    16440 Fair Mile Rd, Sisters, OR 97759

    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

    Thomas Arends Ponderosa Properties

    16440 Fair Mile Rd, Sisters, OR 97759
  • /48

    $1,499,000

    $100K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,590 Sq Ft

    16927 Highway 126, Sisters, OR 97759

    Tucked away on 20 private acres just minutes from Sisters, this custom built property offers exceptional privacy, usable land and a thoughtfully positioned home with breathtaking mountain views. With 11.6 acres of valuable H2O rights, it is well suited for a variety of uses. Inside, oversized windows fill the home with light and showcase the mtn backdrop. Rich cherry, oak and pine finishes

    Shelbi Hodges Stellar Realty Northwest

    16927 Highway 126, Sisters, OR 97759
  • /46

    $1,195,000

    $55K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,378 Sq Ft

    16514 Wren Ln, Sisters, OR 97759

    Custom-built cedar home with a detached shop and RV garage on beautifully landscaped acreage in Junipine Acres. Interior features include an updated kitchen with granite counters, custom cabinets, stainless appliances, hardwood floors, wood-frame windows, and solid wood doors throughout. The main-level primary suite offers a walk-in closet, custom tile shower, tile floors, and granite counters.

    Tim Kizziar Kizziar Property Co.

    16514 Wren Ln, Sisters, OR 97759
  • /41

    $899,000

    Open Sat 11AM - 2PM $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,092 Sq Ft

    301 S Pine St, Sisters, OR 97759

    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

    Jenna Williamson Cascade Hasson SIR

    301 S Pine St, Sisters, OR 97759
  • /44

    $615,000

    $34K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,726 Sq Ft

    14485 Mountain View Loop, Sisters, OR 97759

    Set on a full acre corner lot, this single-level ranch blends space, comfort, and thoughtful updates in a way that just feels right. Vaulted ceilings and abundant natural light create an open, inviting atmosphere, while a cozy pellet stove adds warmth and character to the main living space. Recent improvements throughout the home make it truly move-in ready, including new interior paint and

    Jenna Swain Ninebark Real Estate

    14485 Mountain View Loop, Sisters, OR 97759
  • /60

    $1,200,000

    $150K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,295 Sq Ft

    69288 Stetson, Sisters, OR 97759

    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;

    Suzanne Carvlin Avenir Realty

    69288 Stetson, Sisters, OR 97759
  • /54

    $699,000

    • 3 Beds
    • 2.5 Baths
    • 1,707 Sq Ft

    1035 E Horse Back Trail, Sisters, OR 97759

    Move-in ready and impeccably maintained, this beautifully updated craftsman home in the heart of Sisters, offers the perfect blend of comfort and style. Thoughtfully designed with a desirable primary suite on the main level, this home features numerous upgrades including quartz countertops, designer updated lighting, and tasteful finishes throughout. Enjoy light-filled living spaces and step

    Corrie Lake Stellar Realty Northwest

    1035 E Horse Back Trail, Sisters, OR 97759
  • /47

    $749,000

    $46K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,784 Sq Ft

    70483 Ponderosa Ln Unit GM 116, Sisters, OR 97759

    Tucked into the peaceful setting of Black Butte Ranch, this classic cabin showcases one of the Ranch's original and most beloved floor plans--blending timeless character with thoughtful modern updates. Recently refreshed on the exterior, the home features a new metal roof, new siding, fresh paint, updated windows, and brand-new front and rear decks perfect for enjoying the surrounding. Inside,

    Ross Kennedy Stellar Realty Northwest

    70483 Ponderosa Ln Unit GM 116, Sisters, OR 97759
  • /50

    $699,000

    • 4 Beds
    • 2.5 Baths
    • 2,695 Sq Ft

    70125 Mustang Dr, Sisters, OR 97759

    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

    Kimberly Patterson Realty One Group Discovery

    70125 Mustang Dr, Sisters, OR 97759
  • /36

    $774,900

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,991 Sq Ft

    936 E Black Butte Ave, Sisters, OR 97759

    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/patiofaces 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. - 3Bedrms, 2 1/2 Bathrms plus large loft - Primary on the

    Kimberly Gorayeb Engel & Voelkers Bend

    936 E Black Butte Ave, Sisters, OR 97759
  • /35

    $499,000

    $36K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 1,973 Sq Ft

    840 N Hindeman St, Sisters, OR 97759

    Experience the best of Sisters living in this beautiful end-unit townhome. Because this is an end unit right next to a large green park, you get more light and more privacy than a standard home. The layout is built for easy living with two main bedrooms, including one on the first floor and one on the second. This makes it perfect for guests or for staying on the main level as you get older.

    Carol Zosel Keller Williams Realty Central Oregon

    840 N Hindeman St, Sisters, OR 97759
  • /48

    $669,000

    • 3 Beds
    • 2 Baths
    • 1,837 Sq Ft

    69341 Silver Spur, Sisters, OR 97759

    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

    Ross Kennedy Stellar Realty Northwest

    69341 Silver Spur, Sisters, OR 97759
  • /55

    $449,900

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,471 Sq Ft

    820 N Hindeman St, Sisters, OR 97759

    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

    Marcel Dolak Engel & Voelkers Bend

    820 N Hindeman St, Sisters, OR 97759
  • /58

    $995,000

    • 4 Beds
    • 2.5 Baths
    • 2,728 Sq Ft

    70275 Club Rd, Sisters, OR 97759

    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

    Ross Kennedy Stellar Realty Northwest

    70275 Club Rd, Sisters, OR 97759
  • /57

    $709,900

    $35K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 1,698 Sq Ft

    446 S Cottonwood, Sisters, OR 97759

    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

    Khiva Beckwith Coldwell Banker Mayfield Realty

    446 S Cottonwood, Sisters, OR 97759
  • /98

    $1,724,900

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,888 Sq Ft

    16951 Lady Caroline Dr, Sisters, OR 97759

    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,

    Scott Cruikshank Stellar Realty Northwest

    16951 Lady Caroline Dr, Sisters, OR 97759
  • /111

    $2,700,000

    • 5 Beds
    • 5.5 Baths
    • 6,146 Sq Ft

    70030 Annies Dr, Sisters, OR 97759

    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

    Connie Mitchell Stellar Realty Northwest

    70030 Annies Dr, Sisters, OR 97759
  • /80

    $2,450,000

    • 4 Beds
    • 4.5 Baths
    • 4,448 Sq Ft

    15275 Windigo Trail, Sisters, OR 97759

    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

    Thomas Arends Ponderosa Properties

    15275 Windigo Trail, Sisters, OR 97759
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