Livinginredmond.com Search Results

$3,199,000

Perched on a ridge above your own private canyon with dramatic 360-degree views of the Cascades to the west and the Ochocos and Smith Rock to the east, this gated xeriscaped 19.02ac compound makes an exceptional primary residence or 2nd home. Located in the heart of Central Oregon's ''Golden Triangle'' between Bend Sisters and Redmond, the property features a 2071 sq ft custom built single-level smart home; 640 sq ft detached guest house; 720 sq ft separate shop with a heated finished family room; pickleball court; attached 1102 sq ft four-car pull-through RV garage; and a detached cedar storage shed. Enjoy more than 2000 sq ft of paver patios and decking, along with multiple outdoor living areas, including campsites with full RV hookups. Extensive infrastructure is already in place, complemented by unmatched recreational access, four different power sources, Firewise construction and very low monthly utility costs. This special property is truly a unique gem in the heart of C.O.

3 Beds ⋅ 4 Baths ⋅ 220227904 MLS

Perched on a ridge above your own private canyon with dramatic 360-degree views of the Cascades to the west and the Ochocos and Smith Rock to the east, this gated xeriscaped 19.02ac compound makes an exceptional primary residence or 2nd home. Located in the heart of Central Oregon's ''Golden Triangle'' between Bend Sisters and Redmond, the property features a 2071 sq ft custom built single-level smart home; 640 sq ft detached guest house; 720 sq ft separate shop with a heated finished family room; pickleball court; attached 1102 sq ft four-car pull-through RV garage; and a detached cedar storage shed. Enjoy more than 2000 sq ft of paver patios and decking, along with multiple outdoor living areas, including campsites with full RV hookups. Extensive infrastructure is already in place, complemented by unmatched recreational access, four different power sources, Firewise construction and very low monthly utility costs. This special property is truly a unique gem in the heart of C.O.

17771 Warrin Road, Sisters

Listing courtesy of Stellar Realty Northwest.

$1,763,000

Cascade Mountain Views! Enjoy sunrises and sunsets over the snow-capped mountains from this meticulously maintained log home. New roof and refurbished logs in 2024. Private, quiet cul-de-sac bordered on three sides by protected open space, with the national forest beyond. 3,235 total SF: 2,656 SqFt Main house has 3 beds, 2.5 baths, great room, and loft, PLUS a 579 SF bonus area. Bonus area has a studio, full bath, kitchenette, and balcony: perfect for an office or crafting haven. Greenhouse with drip irrigation, sink, heat, and raised beds awaits your gardening passion. Covered parking for 5 vehicles: 3-car garage and a 2-space carport. Garage includes deck, commode, sink, storage, and 30 Amp RV port. Well pump and casing replaced in 2026, generator ready! Cascade Meadow Ranch features expansive equestrian amenities: Indoor/outdoor arenas, full-care staff, clubhouse, tennis/pickleball courts, ponds, RV/toy storage, and National Forest trail access.

3 Beds ⋅ 3 Baths ⋅ 220227351 MLS

Cascade Mountain Views! Enjoy sunrises and sunsets over the snow-capped mountains from this meticulously maintained log home. New roof and refurbished logs in 2024. Private, quiet cul-de-sac bordered on three sides by protected open space, with the national forest beyond. 3,235 total SF: 2,656 SqFt Main house has 3 beds, 2.5 baths, great room, and loft, PLUS a 579 SF bonus area. Bonus area has a studio, full bath, kitchenette, and balcony: perfect for an office or crafting haven. Greenhouse with drip irrigation, sink, heat, and raised beds awaits your gardening passion. Covered parking for 5 vehicles: 3-car garage and a 2-space carport. Garage includes deck, commode, sink, storage, and 30 Amp RV port. Well pump and casing replaced in 2026, generator ready! Cascade Meadow Ranch features expansive equestrian amenities: Indoor/outdoor arenas, full-care staff, clubhouse, tennis/pickleball courts, ponds, RV/toy storage, and National Forest trail access.

69877 California Trail, Sisters

Listing courtesy of Avenir Realty.

$629,000

Nestled on 2.26 acres, this charming 2-bedroom, 1-bath home offers privacy, functionality, and room to enjoy the outdoors. The cozy living room features a wood stove, creating a warm and inviting gathering space, while the covered front porch is the perfect place to relax and take in the peaceful surroundings. The property includes an attached single-car garage, a covered carport/shed for additional vehicle or equipment storage, and a versatile 18' x 20' detached wood-framed studio with power and plumbing (not currently connected), offering excellent potential for guest quarters, a home office, or hobby space. An attached shed provides additional storage and/or covered parking for one vehicle. Additional features include a durable tile roof and plenty of open space on the 2.26-acre parcel for gardening, recreation, or simply enjoying the Central Oregon lifestyle.

2 Beds ⋅ 1 Baths ⋅ 220225706 MLS

Nestled on 2.26 acres, this charming 2-bedroom, 1-bath home offers privacy, functionality, and room to enjoy the outdoors. The cozy living room features a wood stove, creating a warm and inviting gathering space, while the covered front porch is the perfect place to relax and take in the peaceful surroundings. The property includes an attached single-car garage, a covered carport/shed for additional vehicle or equipment storage, and a versatile 18' x 20' detached wood-framed studio with power and plumbing (not currently connected), offering excellent potential for guest quarters, a home office, or hobby space. An attached shed provides additional storage and/or covered parking for one vehicle. Additional features include a durable tile roof and plenty of open space on the 2.26-acre parcel for gardening, recreation, or simply enjoying the Central Oregon lifestyle.

16664 Pine Tree Lane, Sisters

Listing courtesy of Stellar Realty Northwest.

$349,000

Located in the desireable 4th Sister Condominiums, this 2 bedroom suite condo is in the heart of Sisters! Bring your designer ideas to this unit that features 2 primary suites, a full kitchen and great room living with a cozy fireplace. The covered deck is perfect for enjoying the lovely grounds or a BBQ. This location offers a fantastic Sisters location close to all the Sister's amenities and outdoor activities. Whether it is a full time residence, a relaxing getaway or an income generating investment this main floor unit is the condo for you!

2 Beds ⋅ 2 Baths ⋅ 220224220 MLS

Located in the desireable 4th Sister Condominiums, this 2 bedroom suite condo is in the heart of Sisters! Bring your designer ideas to this unit that features 2 primary suites, a full kitchen and great room living with a cozy fireplace. The covered deck is perfect for enjoying the lovely grounds or a BBQ. This location offers a fantastic Sisters location close to all the Sister's amenities and outdoor activities. Whether it is a full time residence, a relaxing getaway or an income generating investment this main floor unit is the condo for you!

897 E Desperado Trail UNIT 102 Unit UNIT 102, Sisters

Listing courtesy of Cascade Hasson SIR.

$1,195,000

Wake up every morning to a front-and-center view of the Three Sisters, with South Sister and Broken Top perfectly framed from the primary suite. Set on 6.24 fully fenced, gated, and irrigated acres, this lifestyle property blends comfort, function, and unforgettable scenery. The grounds are ''park-like'' with mature landscape. Rich log-look siding and a wraparound covered porch create classic Northwest appeal. Inside, you'll find a knotty pine kitchen with a center island, gas range, walk-in pantry, laminate flooring, and a propane stove. Two primary suites, a dedicated hobby room, craft/laundry room with built-ins, and an oversized two-car garage provide flexible living. **New composite roof installed May 2026.** The insulated 6,500± sq. ft. shop features LED lighting, 200-amp service, RV parking, two large lean-tos, a custom whiskey bar, and a half bath. Zoned for horses, chickens, and more, this is the complete Central Oregon lifestyle.

3 Beds ⋅ 3 Baths ⋅ 220224230 MLS

Wake up every morning to a front-and-center view of the Three Sisters, with South Sister and Broken Top perfectly framed from the primary suite. Set on 6.24 fully fenced, gated, and irrigated acres, this lifestyle property blends comfort, function, and unforgettable scenery. The grounds are ''park-like'' with mature landscape. Rich log-look siding and a wraparound covered porch create classic Northwest appeal. Inside, you'll find a knotty pine kitchen with a center island, gas range, walk-in pantry, laminate flooring, and a propane stove. Two primary suites, a dedicated hobby room, craft/laundry room with built-ins, and an oversized two-car garage provide flexible living. **New composite roof installed May 2026.** The insulated 6,500± sq. ft. shop features LED lighting, 200-amp service, RV parking, two large lean-tos, a custom whiskey bar, and a half bath. Zoned for horses, chickens, and more, this is the complete Central Oregon lifestyle.

17521 Forked Horn, Sisters

Listing courtesy of Central Oregon Realty Group.

$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.

$499,000

Wonderful 2-Suite Condo in the heart of Sisters! Located in the desirable 4th Sister Condominiums, this unit features two primary suites, a full kitchen, and a cozy wood-burning fireplace. The 1-bed, 1-bath 2nd primary has its own exterior door and can be locked off and rented out separately as a studio. Enjoy views of the beautiful grounds and pool from your private outdoor space -- perfect for dining al fresco. This prime location puts you within walking distance of the Sisters Movie House, Shibui Spa, and local favorites like Three Creeks Brewery. Whether as a full-time residence or a mountain getaway, this condo offers unbeatable access to all Sisters' amenities and outdoor excursions.

2 Beds ⋅ 2 Baths ⋅ 220222892 MLS

Wonderful 2-Suite Condo in the heart of Sisters! Located in the desirable 4th Sister Condominiums, this unit features two primary suites, a full kitchen, and a cozy wood-burning fireplace. The 1-bed, 1-bath 2nd primary has its own exterior door and can be locked off and rented out separately as a studio. Enjoy views of the beautiful grounds and pool from your private outdoor space -- perfect for dining al fresco. This prime location puts you within walking distance of the Sisters Movie House, Shibui Spa, and local favorites like Three Creeks Brewery. Whether as a full-time residence or a mountain getaway, this condo offers unbeatable access to all Sisters' amenities and outdoor excursions.

807 E Desperado UNIT 202 Unit UNIT 202, Sisters

Listing courtesy of Avenir Realty.

$430,000

Easy living at it's finest with an upstairs 2 bedroom, 2 bath condominium in Sisters. Imagine enjoying this year round with friends and family with little to no maintenance. In the summer months the pool and hot tub are a welcome sight on those warm days, from spring to fall downtown has many festivals and craft fairs, then in the winter you can cozy up to the fireplace after a day in the snow at Hoodoo, only 30 minutes away. This adorable unit has been updated including new tiled showers, vanities and flooring in both bathrooms with the primary offering heated flooring. A ceiling fan and can lighting was added to the great room. Kitchen is open with a breakfast bar and additional storage over the washer and dryer. Additional features include a large pantry, double paned vinyl windows, additional blown in insulation in ceiling, assigned carport parking, lock out option for a single bedroom/bath, and the community amenities including a pool and clubhouse.

2 Beds ⋅ 2 Baths ⋅ 220220563 MLS

Easy living at it's finest with an upstairs 2 bedroom, 2 bath condominium in Sisters. Imagine enjoying this year round with friends and family with little to no maintenance. In the summer months the pool and hot tub are a welcome sight on those warm days, from spring to fall downtown has many festivals and craft fairs, then in the winter you can cozy up to the fireplace after a day in the snow at Hoodoo, only 30 minutes away. This adorable unit has been updated including new tiled showers, vanities and flooring in both bathrooms with the primary offering heated flooring. A ceiling fan and can lighting was added to the great room. Kitchen is open with a breakfast bar and additional storage over the washer and dryer. Additional features include a large pantry, double paned vinyl windows, additional blown in insulation in ceiling, assigned carport parking, lock out option for a single bedroom/bath, and the community amenities including a pool and clubhouse.

827 E Desperado Trail UNIT 202 Unit UNIT 202, Sisters

Listing courtesy of Keller Williams Realty Central Oregon.

$395,000

Lock-and-go, high perks, low-maintenance condo is the perfect home base for your adventures! Two suites, one with exterior entrance and ability to lock off for flexibility. New flooring and interior paint. Large, covered deck. Amenities include: structural fire insurance, roof, all exterior maintenance, pool, clubhouse, sauna, snow removal, water sewer and garbage. 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.

2 Beds ⋅ 2 Baths ⋅ 220220297 MLS

Lock-and-go, high perks, low-maintenance condo is the perfect home base for your adventures! Two suites, one with exterior entrance and ability to lock off for flexibility. New flooring and interior paint. Large, covered deck. Amenities include: structural fire insurance, roof, all exterior maintenance, pool, clubhouse, sauna, snow removal, water sewer and garbage. 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.

$740,000

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!

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.

$499,000

Income-generating investment 2-suite condominium meets mountain charm. Located in the desirable 4th Sister Condominiums in Sisters, Oregon, this single-level, main-floor unit offers a rare turnkey opportunity with an option to keep a long-term tenant in place. The open floor plan features two primary suites, including a versatile lock-off studio with its own exterior entrance -- perfect for maximizing rental potential. Inside, enjoy an open living area with a cozy fireplace, a dining area, a kitchen with a breakfast bar, and a built-in coffee bar. A stacking washer/dryer unit is included. Outside, your private patio overlooks the beautifully manicured common-area park, clubhouse, and pool. 2 assigned parking spots; 1 is covered. Situated within steps of the Sisters Movie House, Shibui Spa, Three Creeks Brewery, Creekside Park, and the new Sisters Park pickleball courts, this property is a cornerstone for any portfolio. Bonus: Furnishings are available for purchase outside of escrow.

2 Beds ⋅ 2 Baths ⋅ 220218040 MLS

Income-generating investment 2-suite condominium meets mountain charm. Located in the desirable 4th Sister Condominiums in Sisters, Oregon, this single-level, main-floor unit offers a rare turnkey opportunity with an option to keep a long-term tenant in place. The open floor plan features two primary suites, including a versatile lock-off studio with its own exterior entrance -- perfect for maximizing rental potential. Inside, enjoy an open living area with a cozy fireplace, a dining area, a kitchen with a breakfast bar, and a built-in coffee bar. A stacking washer/dryer unit is included. Outside, your private patio overlooks the beautifully manicured common-area park, clubhouse, and pool. 2 assigned parking spots; 1 is covered. Situated within steps of the Sisters Movie House, Shibui Spa, Three Creeks Brewery, Creekside Park, and the new Sisters Park pickleball courts, this property is a cornerstone for any portfolio. Bonus: Furnishings are available for purchase outside of escrow.

813 E Desperado Trail UNIT 102 Unit UNIT 102, Sisters

Listing courtesy of Avenir Realty.

$739,900

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.

3 Beds ⋅ 3 Baths ⋅ 220214766 MLS

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.