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$799,000
4 Beds 3 Baths 220220538 MLS
Experience premier Central Oregon living in this beautifully appointed single-level home in Crossroads, set on a private one-acre lot bordering Deschutes National Forest. Enjoy direct trail access while remaining just minutes from Downtown Sisters & local schools. Designed with both comfort & functionality in mind, the home features a light-filled open-concept layout. The well-appointed kitchen offers a bar area, double oven, gas range, stainless steel appliances, farmhouse sink, & pantry. A formal dining room & separate breakfast nook provide versatility, while the spacious great room opens to a large deck, ideal for seamless indoor-outdoor entertaining. The home includes four bedrooms (two ensuites), three bathrooms, & a dedicated office for an ideal work-from-home environment. Additional highlights include a three-car garage with shop, luxury vinyl plank flooring, fresh interior paint, fenced & cross-fenced grounds suitable for horses, RV parking, circular driveway & newer roof.

14474 Crossroads Loop, Sisters

Listing courtesy of Ponderosa Properties.

$570,000
3 Beds 3 Baths 220220530 MLS
Don't miss out on this two-story home with private backyard, primary mountain view and 3 car garage. This home is convenient to schools and the festive Sisters downtown. The private, fenced backyard with perennial flowers and raised garden beds feels like an oasis. The first floor's expansive living room, adjoining dining room, and open kitchen with ample counter space, pantry, built-in desk, and half bath add functionality and convenience. The upstairs primary feels luxurious with mountain views, dual vanity and a generous walk-in closet. Two additional bedrooms, each with ample closet space and a shared bathroom. Adding ease and function is the second story laundry room. Enjoy the neighborhood's walking paths, playgrounds, and well cared for community space.

715 N Brooks Camp Road, Sisters

Listing courtesy of Stellar Realty Northwest.

$660,000
2 Beds 2 Baths 220220345 MLS
Relaxed luxury abounds in this modern mountain cottage in Clearpine. Featured on the 2020 COBA Tour of Homes and Earth Advantage Platinum certified, this home offers high-end design and sustainable, low-maintenance living. Light-filled with vaulted ceilings and an open floor plan, it creates a bright, airy feel ideal for living and entertaining. Finishes include Silestone quartz countertops, a Blanco farmhouse sink, custom soft-close cabinetry, and Bosch black stainless appliances. A dry bar with a wine fridge extends the entertaining footprint. The primary suite features a heated tile floor and full custom tile shower. EV charger installed. Prewired for solar. Ductless HVAC. Tankless water heater. Heated two-car garage. Spacious laundry and mudroom with built-in storage. Xeriscaped lot with HOA-covered drip irrigation. Two blocks from National Forest trails, less than a mile to downtown Sisters, refined mountain living at its best, built to COBA Tour of Homes standards.

152 W Clearpine Drive, Sisters

Listing courtesy of Stellar Realty Northwest.

$1,699,000
3 Beds 6 Baths 220220342 MLS
Located on the golf course, with mountain views, this NW lodge style home is in the gated Aspen Lakes Golf Community. Soaring vaulted ceilings & expansive windows drench the interior w/natural light & showcase the stunning scenery. 3 en suite bedrooms on the main level with a large en suite bonus room, w/wet bar & full bath upstairs. Be enveloped by the exceptional craftsmanship. Featuring massive wood beams, beautiful stone fireplace, hickory floors & custom built-ins throughout. Open concept, dining area & timeless kitchen w/ eating bar & dining nook, in addition to the formal dining area.. Golf course views from most every window, designated office, extra wide hallways, enhance comfort & function. The luxury continues outside with teak, wrap around deck with covered areas, ideal for entertaining and taking in the views. Hot tub, circular drive, low maintenance landscaping, water feature and an oversize 3 car, heated garage with workshop.. all on nearly an acre of land.

16921 Lady Caroline Drive, Sisters

Listing courtesy of Stellar Realty Northwest.

$615,950
3 Beds 3 Baths 220220313 MLS
Welcome to Sunset Meadows 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. The Cascade Mountain Range, including the Three Sisters and their magnificent views are along McKenzie Highway - the entrance to this neighborhood. The Coho is a single family home design with 3 bedrooms, primary bedroom w/full bathroom on the main floor along with a 1/2 bath powder room and the laundry room. 2 bedrooms & 1 fully (jack & Jill) bathroom upstairs with a nice sized loft. The main floor is an all open floor plan with large windows to allow the Central Oregon sunlight to shine through. Stainless Steel Kitchenaid appliances & solid surfaces in the kitchen and all the bathrooms add to the elegance of the homes. Just under 1,700 sq.ft. Attached oversized 2 car garage. Your chance to own a brand new, beautiful home in Sisters, Oregon.

1035 W Linda Avenue Lot 38 Unit Lot 38, Sisters

Listing courtesy of Engel & Voelkers Bend.

$395,000
2 Beds 2 Baths 220220297 MLS
Let's be honest. $750 HOA dues are a bit intimidating. In reality, it's a great deal - hear me out. Those dues cover the pool, hot tub, sauna, clubhouse and upkeep of all these perks, the landscaping, the roof, the siding, and here's the Big One - structural fire insurance!! Also included are water, sewer, garbage service, and snow removal. There is nowhere else you could all of that for anywhere near $750 a month. Whether you are seeking ease or logic, this condo is your answer either way! Two primary suites (one w/separate exterior entrance for added flexibility), new flooring and interior paint throughout. Picture yourself retiring to the covered deck to unwind after a day of Central Oregon adventures - summer or winter! Ideally located near Sisters Athletic Club, Five Pines campus, Sisters Movie House, and Three Creeks Brewery. 3 minutes to charming downtown Sisters and all of it's festivities, 30 minutes to Bend or Redmond. Long term (30 day+) rentals allowed.

821 E Desperado Trail UNIT 201 Unit UNIT 201, Sisters

Listing courtesy of Stellar Realty Northwest.

$310,000
220220091 MLS
Tucked into a quiet, tree filled setting, this exceptional homesite offers a rare blend of seclusion and connection in the heart of Sisters. The property backs directly to Whychus Creek and adjacent Oregon State Parks land, creating a naturally private backdrop of flowing water and preserved open space. Despite its peaceful surroundings, everyday convenience is just moments away - just two blocks from the Sisters Park & Recreation District building (pickleball, fitness, daycare), about half a mile to downtown Sisters, and just over a mile to Peterson Ridge Trailhead for hiking and outdoor recreation. This is a rare opportunity to design and build a custom home in a setting that captures the charm, tranquility, and outdoor lifestyle that make Sisters so special.

390 S Timber Creek Drive, Sisters

Listing courtesy of Stellar Realty Northwest.

$1,395,000
4 Beds 5 Baths 220219628 MLS
Experience refined living in this one-owner Johannesen custom home, nestled on a private 1.25-acre lot within the gated Aspen Lakes golf community. This versatile single-level estate features a chef's kitchen equipped with dual Fisher Paykel dishwashers, a warming drawer, & instant hot water. Unwind in the great room by the wood-burning fireplace or retreat to the primary suite, which offers dual walk-in closets, separate vanities, & a jetted tub. The home is designed for flexibility, offering a dedicated office, an upstairs bonus room with a King Murphy bed, & a 39x20 flex room ideal for a studio or suite. For those who value utility, the property includes a heated 1,000 sq. ft. garage with custom cabinets, a workbench, & a golf cart bay. Outside, enjoy an expansive mahogany deck & an oversized Sundance hot tub amidst lush landscaping. Modern comforts include a Vyanet security system, central vacuum, & dual HVAC. This is a rare opportunity for elegant, effortless living in Sisters!

16923 Royal Coachman Drive, Sisters

Listing courtesy of Ponderosa Properties.

$550,000
3 Beds 2 Baths 220219315 MLS
New price and exceptional value in Sisters! Directly across from the neighborhood park and less than a mile to downtown Sisters, this home offers easy access to shops, dining, trails, and community events. Inside, the great room layout features vaulted ceilings, abundant natural light, a cozy fireplace, and great separation of bedrooms. The kitchen is designed for everyday living and entertaining with stainless steel appliances, quartz countertops, rich cabinetry, & a large island that flows into the dining and living areas. The spacious primary suite includes a double vanity, walk-in shower, & two walk-in closets. Additional bedrooms offer flexibility for guests, hobbies, or a home office. The fenced backyard features low-maintenance landscaping and quiet space to relax. From the street, enjoy peekaboo mountain views. Fresh interior paint and a new price make this one of the best values in the neighborhood!

680 McKinney Ranch Road, Sisters

Listing courtesy of Fathom Realty Oregon, LLC.

$2,450,000
5 Beds 5 Baths 220219250 MLS
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, designed for both daily living and effortless entertaining. The primary suite is a serene retreat, featuring a gas fireplace and spa-inspired bath. Enjoy spectacular sunrises and sunsets from the covered front porch and expansive 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.

$295,000
220219195 MLS
Discover 20 acres in McKenzie Canyon just outside Sisters, where privacy, adventure and breathtaking views come together. Bordering BLM land to the east and south, this property stretches from the canyon floor to the rim, with about 5 acres perched on top offering commanding Cascade Mountain vistas and endless high desert skies and abundant wildlife. Access is provided from McKenzie Canyon Road. A small rim-side platform makes the property camp-ready today, while preliminary work has been started to explore future building potential. Whether you envision a private retreat, a modern home overlooking the canyon, or a rugged basecamp for adventure, this land delivers an extraordinary opportunity in Central Oregon.

69740 McKenzie Canyon Road, Sisters

Listing courtesy of Ponderosa Properties.

$1,895,000
4 Beds 5 Baths 220219175 MLS
Unique Aspen Lakes property with extensive custom, high-end finishes. Interior highlights include a gourmet kitchen with copper ceiling, butler's pantry, premium stainless appliances including a Wolf 6-burner range and Sub-Zero refrigerator, large eating island. Koa hardwood floors run through the main living areas, complemented by solid wood doors, trim, wainscoting, and built-ins. The home offers four en-suites, including a spacious main-level primary with private patio access, walk-in tile shower, soaking tub, private toilet room, double vanity, and a huge walk-in closet with built-ins. Additional features include a bonus/media room with wet bar and loads of accessible attic storage. Exterior amenities include brick and stone siding, landscaped setting, water feature, paver driveway, walkways and patios, gas lanterns, oversized three-car garage, copper gutters, greenhouse. Property owners enjoy access to community clubhouse, exercise room, outdoor pool, hot tub, and tennis courts.

17041 Lady Caroline Drive, Sisters

Listing courtesy of Kizziar Property Co..

$1,590,000
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.

$635,000
2 Beds 2 Baths 220218977 MLS
Ask about seller-paid credits toward closing costs or interest rate buy-down with an acceptable offer! Meet ''Pinedrops Cottage,'' a peaceful retreat where low-maintenance living and outdoor adventure come together. This Earth Advantage certified, single-level home offers 2 beds, 2 baths and 1004 SF of easy living in desirable ClearPine. Hardwood floors, vaulted ceilings, quartz counters, and high-end appliances create a bright, welcoming interior that lives larger than its footprint. Relax on the covered back porch overlooking community greens/gardens or enjoy the privacy of the enclosed paver patio. The detached garage provides parking plus room for your gear. HOA maintained common areas make ownership simple, allowing more time to enjoy the Central Oregon lifestyle. With National Forest trails just steps away and downtown Sisters dining, shopping, and year-round events mins from your door, ''Pinedrops Cottage'' is an ideal full-time residence, weekend getaway or lock-and-leave basecamp.

233 W Heising Drive, Sisters

Listing courtesy of Avenir Realty.

$599,900
220218895 MLS
Premium lakefront homesite in Aspen Lakes Golf Estates. This exceptional 1.20-acre parcel (Lot 110) offers a rare combination of water frontage, mature pine trees, and sweeping views across the lake toward the 11th fairway. Utilities are available at the lot line, & protective CC&Rs help maintain the integrity of this upscale gated community. This is one of the finest remaining building sites in Aspen Lakes--ideal for a custom home that captures both privacy & scenery. The setting delivers a true sense of tranquility while still being part of a vibrant, well-designed neighborhood. Residents enjoy access to an 18-hole golf course, clubhouse, fitness center, pool, & on-site dining. Just minutes away, the town of Sisters adds tremendous lifestyle value & features boutique shopping, local restaurants, art galleries, and year-round events including rodeos, festivals, and live music. Live in a peaceful golf course setting while staying connected to everything Central Oregon has to offer.

16887 Golden Stone Drive, Sisters

Listing courtesy of High Desert Realty, LLC.

$575,000
2 Beds 2 Baths 220218888 MLS
Motivated Sellers!! Live where the trails meet the town! This stunning, No-HOA townhome in Sisters' Highland Village offers the ultimate low maintenance lifestyle without sacrificing high end style. Step inside to an open spacious layout with Quartz counters and durable Paradigm flooring. Whether hosting a summer dinner on the covered upper deck or relaxing in your private, paver lined courtyard, outdoor living is a year round reality. The spacious single car garage provides ample room for all your gear. Enjoy the rare perk of being minutes away from the best of Sisters: walk to Three Creeks Brewery, the Movie Theater, or Sisters Athletic Club. Jump directly onto the Peterson Ridge Trail System for a hike/bike. This prime location offers easy walkability to downtown, where you can enjoy restaurants, boutiques, and events like the Quilt Show & Folk Festival. Your mountain basecamp awaits!

923 E Desperado Trail, Sisters

Listing courtesy of Coldwell Banker Sun Country.

$449,000
2 Beds 2 Baths 220218617 MLS
Cascade Mountain views from the living room, dining room and upper terrace of this Pine Meadow Village condo. Condo features include: Open living concept; propane fireplace and vaulted ceilings in living room; abundance of natural light through the numerous large wood framed windows; Primary suite with rear terrace; second good sized bedroom; additional full bathroom; dedicated garage space on the grounds. Located in the heart of Pine Meadow Village with easy access to the community pool and clubhouse,. Additionally, the condo is within a short distance to downtown Sisters, providing convenient access to all the restaurants and amenities the area has to offer. Great set-up for a full-time residence, second home or investment property/mid-term rental. HOA fees cover water/sewer/garbage and all exterior maintenance of the units.

566 W Jefferson Avenue, Sisters

Listing courtesy of Kizziar Property Co..

$410,000
3 Beds 2 Baths 220218574 MLS
Welcome to The Pines in Sisters This wonderful quaint and gated community offers privacy to all its residents and is located near shopping, schools and Historic Downtown Sisters. This light and bright single level home has three bedrooms and two full baths with vaulted ceilings throughout the home. The open and very spacious kitchen/ living room combo has access to the back yard with a deck for relaxing and entertaining. The family/ dining room combo has plenty of natural light and room for family and friends to gather. Located on a corner lot, this home has had the landscaping upgraded in 2022 as well as the sprinkler system in the front yard, side yards and rear yard. The interior of the home has just been finished with all new interior paint on walls and ceiling and all new carpet and padding has been added. The hot water heater was replaced in 2021 and the furnace was just serviced in March 2026. Also installed was a new garage door and opener.

1009 W Yapoah Crater Drive, Sisters

Listing courtesy of Hall Properties Group LLC.

$475,000
3 Beds 2 Baths 220218571 MLS
Experience the perfect blend of mountain-town charm and low-maintenance living at The Pines in Sisters, Oregon's gated 55+ community. This well-maintained, single-level home was originally a Fuqua Homes developer model. Step inside to an open-concept floor plan characterized by high ceilings and lots of natural light. The Great Room: Features French doors open to the rear deck overlooking a peaceful common area. Kitchen: Features a large central island, plenty of cabinetry, and counter space. Primary Suite: Featuring a walk-in closet and a private ensuite bathroom. Additional Features: Three ceiling fans and laminate wood flooring throughout. An attached 2-car garage, extra-wide concrete driveway, and a pull-down ladder leading to attic storage. HOA Perks: Gated community! Monthly dues ($152) cover lawn care and snow removal. Prime Location: Just minutes from downtown Sisters, close to local boutiques, bakeries, dining, neighborhood churches, schools, and trails!

1045 W Collier Glacier Drive, Sisters

Listing courtesy of Avenir Realty.

$1,495,000
3 Beds 3 Baths 220218568 MLS
Looking for a 6-car heated garage with real shop capacity near Sisters? This single-level home on nearly 5 acres in Starr Ranch has it. The attached garage runs 49.6 by 34.9 feet, heated, with 8-ft doors and room for several vehicles plus ample workshop space. A mudroom connects it to the main house. Move-in ready with zero deferred maintenance, the home carries a luxury modern farmhouse feel. Timber-frame vaulted ceilings and a stacked-stone fireplace anchor the great room. The kitchen has dual sinks, a large island, a walk-in pantry, and quartz-topped shaker cabinets. The primary suite has heated floors, custom cabinetry, and a soaking tub. Ten-foot ceilings run throughout, plus a dedicated office. Concrete patios overlook a fenced yard. The acreage is zoned for horses, though no facilities are in place yet. Starr Ranch is a secluded loop of similar large-acreage homes, five minutes from downtown Sisters.

16055 Foothill Lane, Sisters

Listing courtesy of Central Oregon Realty Group.

$760,000
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 lands. 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 and built-in appliances, with 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.

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