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69550 Deer Ridge Road, Sisters
$1,995,000
5 Beds ⋅ 5 Baths ⋅ 220219250 MLS
SIGNIFICANT PRICE REDUCTION OF OVER $450,000 - AN EXCEPTIONAL OPPORTUNITY FOR BUYERS! Rich in character and charm, this 4,615 sq ft home captures sweeping mountain views and offers five bedrooms, a dedicated office and two wood-burning fireplaces. At its center, a beautifully appointed chef's kitchen open to the living and dining. The primary suite is a serene retreat, featuring a gas fireplace and spa-inspired bath. Enjoy spectacular sunrises and sunsets from the expansive front and back decks. A 2,071 sq ft secondary structure lives like a private mountain sanctuary, complete with four rooms, a full bath, kitchenette, and a dramatic floor-to-ceiling river rock fireplace. The great room evokes a true lodge feel, with expansive windows framing the ponderosas. Additional amenities include a saltwater pool, infrared sauna, four-stall barn and shop. Bring your animals--this 5.85-acre property is fully fenced and cross-fenced with a gated entry, all just 2.3 miles from downtown Sisters.

69550 Deer Ridge Road, Sisters

Listing courtesy of RE/MAX Key Properties.

14987 Buggy Whip, Sisters
$730,000
4 Beds ⋅ 3 Baths ⋅ 220218538 MLS
Ski, walk, or ride into the National Forest! This fenced yard and expansive back deck with hot tub border National Forest. Spanning 2,187 square feet, this 4-bed, 3-bath open floor plan has a great room with a woodstove, spacious dining room, kitchen, laundry room, and 3 bedrooms on the main level, including a second primary suite. The kitchen has granite countertops, stainless appliances, a NEW dishwasher, and back deck BBQ access. Upstairs, the spacious primary suite, bathed in natural light, is an ideal escape, featuring vaulted ceilings, propane fireplace, private balcony, and a luxurious bathroom with a walk-in shower, and walk-in closet. The 2-car detached garage has an EV charger, carport, storage for all your toys, plus a concrete parking pad for additional vehicles or your basketball hoop. Septic 2 years new, Roof 3 years new, Hot tub 5 years new. Tollgate HOA amenities include a pool, tennis courts, basketball, volleyball, snow removal, onsite mail, community hall, and more!

14987 Buggy Whip, Sisters

Listing courtesy of Avenir Realty.

69435 Green Ridge Loop, Sisters
$925,000
5 Beds ⋅ 3 Baths ⋅ 220218327 MLS
Welcome to your own secluded paradise, boasting the ultimate rustic charm and modern convenience. This stunning handcrafted log home offers a serene retreat from the hustle bustle of everyday life. As you step inside, you're greeted by the captivating sight of a log slab spiral staircase, artfully crafted around a majestic tree trunk, leading up to a mezzanine that overlooks the spacious grand room. Perfect for entertaining or simply unwinding in the ambiance of natures embrace. The heart of the home is the open kitchen, exudes warmth and functionality, featuring a cast iron stove that adds to the rustic charm of the log cabin ambiance. The main suite is located on the ground floor, The four upstairs bedrooms have their own vanites. The outbuilding can accommodate a motor home and a car. It also has an aprox. 1100 sq.ft. apt. A greenhouse and chicken coop are a bonus. Recent upgrades include a new well pump and drain field extension. New Wood Stove . New Carport Roof

69435 Green Ridge Loop, Sisters

Listing courtesy of Stellar Realty Northwest.

505 N Pine Street, Sisters
$925,000
3 Beds ⋅ 3 Baths ⋅ 220217696 MLS
The only move-in ready Agate townhome available in the Sisters Woodlands, with generous southern exposure providing ample natural light. Beyond standard high-end Woodlands features, this home includes these upgrades (which makes this list price lower than the current base price with upgrade costs): Wood stove, Larch accent wall, Dining room buffet, In-floor bathroom heat, Heat pump washer/dryer, Instahot, Fancy window shades, Exterior terrace heaters, Maturing landscape. Interior features: Open floor plan; Hardwood/tile floors & quartz counters throughout; Stainless energy star appliances; Ductless/zonal HVAC. Other features: Large covered outdoor elevated terrace; Corrugated metal siding; Full size 2 car garage; Solar & EV ready. High quality design & build is sustainable, durable & efficient for turnkey/low maintenance. Enjoy all Sister's Area offers with easy walkability from this mixed-use community to downtown & wilderness.

505 N Pine Street, Sisters

Listing courtesy of Kizziar Property Co..

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.

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
$479,950
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.

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
$719,000
4 Beds ⋅ 3 Baths ⋅ 220214766 MLS
**Special Financing Available!** Enjoy privacy, space, and the Central Oregon lifestyle on 1.02 acres in the desirable Crossroads community, just minutes from downtown Sisters. Surrounded by thousands of acres of Deschutes National Forest, this firewise neighborhood offers incredible access to horseback riding, hiking, and year-round recreation. The inviting home features 3 traditional bedrooms, 3 full bathrooms, a main-level office with potential as a 4th bedroom, and a generous bonus room ideal for guests, hobbies, or entertainment. Abundant windows bring in natural light, while a wood-burning fireplace adds warmth and character. The primary suite includes a private deck overlooking the peaceful, wooded setting. Mature trees offer exceptional privacy, with room to garden, add a shop, or simply relax outdoors. Short-term rentals are allowed, adding flexibility for personal use or investment potential.

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..

1036 W McKenzie Highway Lot 51 Unit Lot 51, Sisters
$759,950
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..

15624 National Forest Lane, Sisters
$1,095,000
2 Beds ⋅ 3 Baths ⋅ 220213314 MLS
Turnkey Equestrian set up on very private acreage with direct access to USFS land and trails that is also very close to town. This horse property is perfect for equine enthusiasts: 4 stall barn with cement aisle, individual paddocks for each stall, metal roof, tack room, hay storage, feed room, good lighting, and easy access to the home and property, extensive fencing (entire property) and gates. Also includes a well laid out, and structurally sound home with high vaulted tongue and groove ceilings; a primary suite with vaulted ceilings on the main level; New HVAC with zoned mini split system and new propane woodstove. Property additionally features: Large paver patio/gazebo in backyard with complete privacy visually; Hot tub on rear patio; 3 bay shop with metal siding, metal roof, concrete floor; Greenhouse with hydraulic lifting windows; Garden/landscape shed that would make an ideal chicken coop; Extensive front and back landscape; Freshly painted/matching structures on property.

15624 National Forest Lane, 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..

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