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15275 Windigo Trail, Sisters
$2,350,000
4 Beds ⋅ 5 Baths ⋅ 220217038 MLS
Experience mountain living perfection in the premier equestrian community of Cascade Meadow Ranch. This 4,448 SqFt custom estate on 2.29 private acres boasts stunning Cascade Mountain views & seamless main-floor living. The 4 bed, 5 bath home features soaring vaulted ceilings, exquisite woodwork & Montana river rock fireplaces. A gourmet chef's kitchen offers a Thermador 6 burner range & premium appliances, while the main-level primary suite serves as a luxury retreat with a soaking tub & propane fireplace. Dual stairwells lead to a versatile bonus room, bedrooms & bunk room. The property includes an attached 2 car garage plus a detached 1,510 SqFt shop with a finished upstairs bonus room & 3 car garage. Enjoy a new roof, redwood siding, & covered cedar decks overlooking a landscaped yard with a tranquil waterfall & pond. This gated community provides indoor/outdoor arenas, horse stalls, 3 RV spots, clubhouse, tennis/pickleball & direct access to public lands.

15275 Windigo Trail, Sisters

Listing courtesy of Ponderosa Properties.

69205 Hawksflight Drive, Sisters
$2,995,000
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.

412 N Desert Rose Loop, Sisters
$475,000
2 Beds ⋅ 1 Baths ⋅ 220216839 MLS
SELLER CONCESSION UP TO $10,000, toward buyers allowable closing costs, pre-paid expenses, and/or interest rate buy down, subject to lender's approval. ADORABLE cottage-style home full of charm and character. This turnkey property is move-in ready and offers a cozy welcoming atmosphere perfect for a small family, first-time homebuyer, downsizers, or anyone seeking a peaceful retreat. The open living room, dining area, and kitchen flow seamlessly together creating a welcoming space for family and friends to gather. This sweet home is ready for its next chapter. Fencing is permitted, subject to HOA and local regulations. The garage is deep, with room for a car, outdoor toys and shelving. Beyond the back and side yard, the open spaces are maintained by the HOA. This home is close to all Sister's schools, shopping, the Deschutes National Forest, the Metolius River and downtown Sisters.

412 N Desert Rose Loop, Sisters

Listing courtesy of Avenir Realty.

17415 Kent Road, Sisters
$749,900
3 Beds ⋅ 2 Baths ⋅ 220216304 MLS
Beautifully maintained home on 2.28 acres off desirable Cloverdale Rd in Sisters! This light-filled 3 bed, 2 bath home features a spacious layout with a family room, dining area, and living room featuring a cozy gas fireplace and office. The spacious kitchen features an island, breakfast bar, and a convenient butler's pantry. The oversized primary suite offers a large walk-in closet and ensuite bath with double vanity and abundant natural light. An attached 2-car garage adds convenience. Enjoy outdoor living with inviting front and back decks, perfect for relaxing or entertaining. The property includes a heated shop with an attached dog run, a 30x48 pole barn with 11' clearance, ideal for RVs, toys, or future horse setup and a 12x12 storage shed. While not currently set up for horses, it's easily adaptable. Easy access to Sisters, Bend, and Redmond plus all of Central Oregon's outdoor recreation. A must-see to fully appreciate this wonderful home and property.

17415 Kent Road, Sisters

Listing courtesy of Stellar Realty Northwest.

1024 W McKenzie Highway Lot 52 Unit Lot 52, Sisters
$819,950
4 Beds ⋅ 3 Baths ⋅ 220216047 MLS
The 2026 COBA Tour of Homes Model in Sunset Meadows in the charming town of Sisters Oregon! This stunner w/fabulous Cascade Mountain views including the Three Sisters has many upgrades making it a show stopper! Built by the Award Winning Builder Woodhill Homes. The Contemporary Modern Mountain Chalet design of the houses gives the neighborhood the look & feel of a mountain resort. A single family home just under 2,000 sq.ft. w/4 bdrms & 2 1/2 baths. Main floor open floorplan w/large windows & high vaulted ceilings to allow the Central Oregon sunlight to shine thru. Primary Bdrm w/ensuite bath on the main floor. Stainless Steel KitchenAid appliances & solid surfaces in kitchen & all the bathrms. Powder rm & laundry rm are downstairs. 3 bdrms & a full bath are upstairs. Attached 2 car garage. This is your chance to own a brand new, stunning home w/views of the Cascade Mountains. Watch the sun set over the Cascade Mountains from your living room!

1024 W McKenzie Highway Lot 52 Unit Lot 52, Sisters

Listing courtesy of Engel & Voelkers Bend.

1080 W Linda Avenue Lot 3 Unit Lot 3, Sisters
$517,450
3 Beds ⋅ 3 Baths ⋅ 220215537 MLS
Select home credit incentive $10,000.00 This is your chance to own a new townhouse - The Kokanee - in the popular new development in Sisters, Oregon! Sunset Meadows is close to downtown Sisters & the Sisters Elementary, Middle & High school campuses. The Kokanee is a 3 Bedroom, 2 1/2 Bathroom townhouse. All the bedrooms - with vaulted ceilings - are upstairs w/primary bathroom en suite & additional bathroom. Large Laundry room is also upstairs. This is an open floor plan design w/kitchen, living room, dining area and powder room downstairs. Kitchen has all stainless steel, Kitchen Aid appliances, solid surfaces in the Kitchen & all 3 bathrooms. 2 car Garage is alley loaded. Front yard & nice size side yard (with patio outside the sliding glass door) are landscaped using low maintenance native plants. All of the houses in Sunset Meadows are Certified & Registered Energy Star Rated! Come live the Central Oregon, special Sisters, lifestyle.This house comes with a fully fenced yard!

1080 W Linda Avenue Lot 3 Unit Lot 3, Sisters

Listing courtesy of Engel & Voelkers Bend.

1086 W Linda Avenue Lot 2 Unit Lot 2, Sisters
$489,950
3 Beds ⋅ 3 Baths ⋅ 220215536 MLS
This is your chance to own a new townhouse - The Kokanee - in the popular new development in Sisters, Oregon! Sunset Meadows is close to downtown Sisters & the Sisters Elementary, Middle & High school campuses. The Kokanee is a 3 Bedroom, 2 1/2 Bathroom townhouse. All the bedrooms - with vaulted ceilings - are upstairs w/primary bathroom en suite & additional bathroom. Large Laundry room is also upstairs. This is an open floor plan design w/kitchen, living room, dining area and powder room downstairs. Kitchen has all stainless steel, Kitchen Aid appliances, solid surfaces in the Kitchen & all 3 bathrooms. 2 car Garage is alley loaded. Front yard & nice size side yard (with patio outside the sliding glass door) are landscaped using low maintenance native plants. Houses in Sunset Meadows are Certified & Registered Energy Star Rated! Come live the Central Oregon. This house comes with a fully fenced yard.

1086 W Linda Avenue Lot 2 Unit Lot 2, Sisters

Listing courtesy of Engel & Voelkers Bend.

17945 Mountain View Road, Sisters
$3,999,000
4 Beds ⋅ 7 Baths ⋅ 220214782 MLS
Nestled in a breathtaking location, this timeless estate offers sweeping views of the majestic Cascade Mountains and Whychus Creek Canyon. Surrounded by luxurious gardens, the home stands in contrast to the low-maintenance high desert landscapes that dominate the nearly 40-acre property and the sparsely developed land around it. With European-inspired elegance, this estate boasts an array of exceptional features, including a lighted tennis court, three stunning rock fireplaces, and expansive aggregate patios--both covered and uncovered. Additional highlights include a heated dog kennel, solarium, sunroom, formal and informal dining spaces, and an oversized family room. The home offers four bedrooms, each with an ensuite bathroom, including a main floor primary suite with two full baths, separate closets, and a chef's kitchen with a large pantry. Enjoy the convenience of a three-car garage with ample attic storage for all your toys.

17945 Mountain View Road, Sisters

Listing courtesy of Ponderosa Properties.

14450 Mountain View Loop, Sisters
$729,000
3 Beds ⋅ 3 Baths ⋅ 220214766 MLS
**Special Financing Available, rates as low as 5.95%**. Nestled on 1.02 private acres in the desirable Crossroads community, this inviting home offers the perfect blend of comfort, space, and the Central Oregon lifestyle. Surrounded by thousands of acres of Deschutes National Forest, enjoy endless opportunities for horseback riding, hiking, and outdoor recreation right from the neighborhood. Inside, you'll find 3 bedrooms, 3 full baths, a main-level office that could easily serve as a 4th bedroom, and a spacious bonus room for guests, hobbies, or a media room. Large windows fill the home with natural light, while the cozy wood-burning fireplace creates a warm gathering space. The primary suite features its own private deck, and mature trees provide exceptional privacy with room to garden, add a shop, or simply enjoy the peaceful setting just minutes from downtown Sisters.

14450 Mountain View Loop, Sisters

Listing courtesy of High Desert Realty, LLC.

67500 Three Creeks Road, Sisters
$5,950,000
3 Beds ⋅ 4 Baths ⋅ 220214681 MLS
Cascadia Ranch near Sisters, Oregon is available for sale for the first time in over 50 years: 700+/- acres of farm, ranch and timber land at the foot of the Cascades with unobstructed mountain views. This unique property has 80 acres of exclusive water rights, sourced from three springs, a two-story barn, corrals, large ranch house, rustic cabin, equipment and hay sheds, a large swimming pond, fenced fields for horses or livestock, and additional wildlife ponds. Surrounded by public lands, the ranch accesses miles of adjacent horseback and mountain bike trails. Approved to divide into 4 parcels. New building site with commanding mountain views and utilities in place. Enjoy privacy, solitude, wildlife, fresh air, dramatic rock outcrops and open skies, only minutes to the Western town of Sisters, and 30 minutes to Bend. This is one of the Northwest's truly exceptional properties, which could be perfect as a horse farm, mountain retreat or build your dream custom home.

67500 Three Creeks Road, Sisters

Listing courtesy of Cascade Hasson SIR.

620 W Sprout Lane Lot #132 Unit Lot #132, Sisters
$747,000
2 Beds ⋅ 3 Baths ⋅ 220214596 MLS
Sisters Woodlands Overstory Cottage has a two floor layout with a wide open upper living concept and a huge upper outdoor living terrace. Cottages are carefully sited to save 100's of pine trees & complement the natural environment. High quality design & build is sustainable, durable & efficient for turnkey/very low maintenance dwellings. Enjoy all Sister's Area offers with easy walkability from this mixed use community to downtown & wilderness. Interior features: Hardwood/tile floors & quartz counters throughout; Stainless energy star appliances; Ductless/zonal HVAC. Exterior features: Larch Shou Sugi Ban burnt siding (fire/pest resistant); Metal roof; Private front/rear patio; 2 car garage; Direct connection to private landscape & common amenity area; Solar/EV charger ready. Pictures are of prior completed Overstory model. Visit model home (East on Barclay off the roundabout/take the first right/model home first home on corner). Homes being pre-sold prior to construction.

620 W Sprout Lane Lot #132 Unit Lot #132, Sisters

Listing courtesy of Kizziar Property Co..

70030 Annies Drive, Sisters
$2,700,000
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.

69150 Butcher Block Boulevard, Sisters
$1,795,000
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 above shop apartment. 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.

69150 Butcher Block Boulevard, Sisters

Listing courtesy of Bend Premier Real Estate LLC.

1036 W McKenzie Highway Lot 51 Unit Lot 51, Sisters
$789,950
3 Beds ⋅ 3 Baths ⋅ 220213845 MLS
Sunset Meadows new development in the charming town of Sisters, Oregon. Built by Award Winning Builder Woodhill Homes. The Contemporary Modern Mountain Chalet design of the homes give the neighborhood the look & feel of a mountain resort. Cascade Mountain Range, including the Three Sisters are directly in front of this property! This home is a single family home just under 2,000 sq.ft. w/3 bedrooms & 2 1/2 baths. The main floor is an all open floorplan w/large windows & high vaulted ceilings to allow the Central Oregon sunlight to shine through. Primary Bedroom w/ensuite bathroom is on the main floor. Stainless Steel KitchenAid appliances and solid surfaces in the kitchen and all the bathrooms - 1/2 bath powder room & laundry room are downstairs and 2 bedrooms, a full bath and a large loft are upstairs. Attached 2 car garage. Your chance to own a brand new, beautiful home in Sisters, Oregon and start living the Central Oregon Lifestyle.

1036 W McKenzie Highway Lot 51 Unit Lot 51, Sisters

Listing courtesy of Engel & Voelkers Bend.

610 W Sprout Lane Lot #131 Unit Lot #131, Sisters
$747,000
3 Beds ⋅ 3 Baths ⋅ 220213494 MLS
Sisters Woodlands Old Growth Cottage has 2 floor layout with 3 ensuite bedrooms & open living concept (alternative 2 bedroom option available with larger primary bedroom/office). Cottages carefully sited to save 100's of pine trees & complement natural environment. High quality design/build is sustainable, durable & efficient for very low maintenance dwellings. Enjoy all Sister's offers with easy walkability from this mixed use community to downtown & wilderness. Interior features: Hardwood/tile floors & quartz counters; Stainless energy star appliances; Ductless/zonal HVAC. Exterior features: Larch Shou Sugi Ban burnt siding (fire/rot/pest resistant); Large upper terrace; Metal roof; Private front/rear patio; 2 car garage & attached storage; Direct connection to private landscape & common amenity area; Solar/EV charger ready. Pictures are of prior completed Old Growth. Visit model home (631 N Sisters Woodlands Way)

610 W Sprout Lane Lot #131 Unit Lot #131, Sisters

Listing courtesy of Kizziar Property Co..

533 W Sisters Park Drive Lot #129 Unit Lot #129, Sisters
$697,000
2 Beds ⋅ 2 Baths ⋅ 220213312 MLS
Sisters Woodlands Limestone Townhome is far and away the largest single level home in the Woodlands. A generous sized primary en-suite; open living floor plan; large outdoor courtyard. High quality design & build is sustainable, durable & efficient for turnkey/very low maintenance dwellings. Interior features: Hardwood/tile floors & quartz counters throughout; Stainless energy star appliances. Exterior features: Corrugated metal siding; Solar & EV ready. Townhomes carefully sited to save 100's of pine trees & complement the natural environment. Enjoy all Sister's Area offers with easy walkability from this mixed use community to downtown & wilderness. Visit model home (631 N Sisters Woodlands Way) for open houses on Saturdays from 12:00 to 4:00. Photos are from a previously finished home. Homes being pre-sold prior to the commencement of construction.

533 W Sisters Park Drive Lot #129 Unit Lot #129, Sisters

Listing courtesy of Kizziar Property Co..

630 W Sprout Lane Lot #133 Unit Lot #133, Sisters
$747,000
3 Beds ⋅ 3 Baths ⋅ 220213278 MLS
Sisters Woodlands Canopy Cottage has upper primary living space, allowing the architecture to unlock a unique relationship with surrounding trees. Upper level has an open floor plan, connected to a large exterior deck. High quality design & build is sustainable, durable & efficient for turnkey/low maintenance dwellings. Enjoy all Sister's Area offers with easy walkability from this mixed use community to downtown & wilderness. Interior features: Hardwood/tile floors & quartz counters throughout; Stainless high-end appliances; Ductless HVAC. Exterior features: Larch Shou Sugi Ban burnt siding (fire/pest resistant); Metal roof; Private front/rear patio; 2 car garage; Direct connection to private landscape & common amenity area; Solar/EV charger ready. 3 bedroom or 2 bedroom (larger primary) option. Pictures are of prior completed Canopy. Visit model home at 631 N Sisters Woodlands Way. Homes being pre-sold prior to construction.

630 W Sprout Lane Lot #133 Unit Lot #133, Sisters

Listing courtesy of Kizziar Property Co..

643 Sisters Park Drive Lot #122 Unit Lot #122, Sisters
$727,000
2 Beds ⋅ 3 Baths ⋅ 220213188 MLS
Sisters Woodlands Opal Townhome has a two floor layout with main living upstairs, two downstairs bedrooms, two car garage, and a huge covered deck. High quality design & build is sustainable, durable & efficient for turnkey/very low maintenance dwellings. Interior features: Hardwood/tile floors & quartz counters throughout; Stainless energy star appliances. Exterior features: Corrugated metal siding; Option for large outdoor patio on ground level; Solar & EV ready. Townhomes carefully sited to save 100's of pine trees & complement the natural environment. Enjoy all Sister's Area offers with easy walkability from this mixed use community to downtown & wilderness. Visit model home (631 N Sisters Woodlands Way) to see finishes and other available models. Homes being pre-sold prior to the commencement of construction.

643 Sisters Park Drive Lot #122 Unit Lot #122, Sisters

Listing courtesy of Kizziar Property Co..

278 N Wheeler Loop, Sisters
$385,000
3 Beds ⋅ 2 Baths ⋅ 220210772 MLS
Seller offering $3,000 in credit to buyer to help with closing costs! Welcome to this beautifully refreshed single-level home in The Pines, a gated 55+ community in the heart of Sisters. Offering 3 bedrooms and 2 baths across 1,500 square feet, this residence features brand-new interior paint and updated flooring throughout, giving it a bright and inviting feel. The open floor plan provides effortless flow between the kitchen, dining, and living areas; perfect for everyday comfort or hosting friends. Enjoy the peace of mind that comes with low-maintenance living, with the HOA covering landscaping and snow removal. Conveniently located near shopping, dining, and all that downtown Sisters has to offer, this home combines comfort, convenience, and community in one appealing package. Home to be sold as-is

278 N Wheeler Loop, Sisters

Listing courtesy of Keller Williams Realty Central Oregon.

16465 Suntree Lane, Sisters
$9,750,000
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.

69482 Panoramic Drive, Sisters
$1,800,000
6 Beds ⋅ 5 Baths ⋅ 220200531 MLS
Owners willing to carry and are motivated. Central Oregon, is the Red Barn Farm offering a blend of rustic charm & modern amenities. This 4,279 sq ft primary residence, is complemented by a 1,000 sq ft mother in- law suite,totally seperate from Main house by the oversized 3 car garage. The Main house boast 4 spacious bedrooms (3 are Ensuite) and 4.5 baths, providing ample storage for family and guests all on 5.77 irrigated acres. Main floor houses 1 master and an office. The ADU, has a full kitchen, lg living room, 2 bedrooms, 1 baths, and climate control mini-splits. It offers versatility as a guest suite, rental opportunity, or private retreat. The property's exterior features a 3-stall barn,tack room, & storage for hay & equipment. Automatic underground sprinkler & irrigation systems, a reliable well and septic system Heated Dog Kennel with fenced dog yard. Property is perimeter fenced and gated. Official sized tennis court. 12 X 24 Pasture run-in shelter. Furnishing are negotiable

69482 Panoramic Drive, Sisters

Listing courtesy of John L Scott Bend.

17400 Spur Drive, Sisters
$800,000
220195581 MLS
40.29 acres of manicured Ponderosa forested property just minutes from downtown Sisters. It truly feels like your very own private park. This is the perfect setting for a family legacy estate with an abundance of Ponderosa trees, and your very own herd of Mule deer. The owner has marked a potential building site that has views of North and Middle Sister all while being tucked into an gorgeous grove of old growth Ponderosa trees creating a lovely homesite. Views of Black Butte from the property. The owner just completed a thorough thinning/fire fuel reduction project removing hundreds of Juniper trees and underbrush creating a healthy fire resistant forest. Brand new compacted gravel driveway leading to the building site installed. Since the property is zoned RR10 no CUP is needed and building permits can be applied for immediately. Power is at the street and septic feasibility has been approved. A private well will be needed. Call for a private showing.

17400 Spur Drive, Sisters

Listing courtesy of Knightsbridge International.

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