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SISTERS

One of the most popular communities provided by Christy Symons

SISTERS

About SISTERS

Discover Sisters, Oregon

Welcome to Sisters, Oregon, a charming town nestled at the gateway to the Cascades. Known for its stunning natural beauty and rich Western heritage, Sisters is a must-visit destination for adventurers and tranquility-seekers alike.

Location & Accessibility

Sisters is located in Central Oregon, approximately 22 miles northwest of Bend. Set against the dramatic backdrop of the Three Sisters Mountains, the town is easily accessible via US Highway 20, offering a scenic drive through forests and open plains.

Small Town Charm

Sisters exudes a welcoming, small-town vibe with a population of just over 3,000 residents. The historic downtown features:

Western-themed architecture
Mom-and-pop shops
Art galleries
Local coffee houses
Boutique stores

Explore the friendly main street and discover a vibrant, walkable community.

Outdoor Adventure

Nature lovers will find endless recreation in and around Sisters. Highlights include:

Hiking: Trails in the Three Sisters Wilderness and along the Metolius River
Mountain biking: Peterson Ridge Trail System
Fishing: Renowned fly fishing on the Metolius and Deschutes rivers
Skiing & Snowshoeing: Winter sports at Hoodoo Ski Area, just 20 minutes away
Camping & Horseback Riding: Numerous campsites and equestrian trails in nearby national forests

Arts, Culture & Events

Sisters is a hub for culture and creativity. Notable annual events include:

Sisters Outdoor Quilt Show — The largest outdoor quilt show in the world
Sisters Folk Festival — Celebrating roots music every September
Sisters Rodeo — “The Biggest Little Show in the World”

Local galleries, live music at cozy venues, and a community theater scene keep the arts alive year-round.

Dining & Nightlife

Enjoy a variety of eateries, breweries, bakeries, and cafés. Don’t miss:

Sisters Coffee Company — Famous for its rustic ambiance and expertly roasted coffee
Sisters Bakery — A beloved spot for pastries and bread
Three Creeks Brewing Co. — Craft beer and hearty pub fare

Living in Sisters

Sisters offers a slower pace of life, friendly neighbors, and access to some of Oregon’s best scenery. The community is:

Family-friendly
Surrounded by excellent schools
Active in conservation and sustainability

Housing options range from historic homes to new builds, with neighborhoods emphasizing outdoor space and mountain views.

Why Visit Sisters?

Breathtaking mountain vistas
Thriving arts scene
Year-round adventure
Welcoming, tight-knit community

Plan your visit or make yourself at home—Sisters, Oregon is where the West lives on.

One of the most popular communities provided by Christy Symons

111

# of Listings

3

Avg # of Bedrooms

$620

Avg. $ / Sq.Ft.

$1,191,925

Med. List Price

Browse SISTERS Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

57 Properties Found. Page 3 of 4.

This is hands-down one of the most well-maintained homes you'll ever step into—truly cared for with a level of love and attention that's rare to find. While it may be an older home, it shines with pride of ownership inside and out.

Located in a highly desirable subdivision, the entire subdivision is Firewise certified, offering peace of mind in every season.

The property itself is a dream—meticulously landscaped with a 7-zone sprinkler system, fenced yard, Fiberon composite deck, and a newly chip-sealed and coated driveway with plenty of parking. An RV hookup and dump station make it perfect for adventurers.

Inside, you'll find beautiful pine floors, a cozy yet functional layout, and an actual two-car insulated garage (yes—it really fits two cars comfortably!): 3 bedrooms plus a bonus room. Significant upgrades have been taken care of, including a newer roof (2017), a septic tank replaced in 2020, and a fully restored drainfield.

Mt. Bachelor and HooDoo close by.

Sisters

15689 Paddock Green

3 Beds

2 Baths

1,616 Sq.Ft.

$699,900

MLS#: 220209321

Beautifully maintained 3-bedroom, 2-bath home offering 1,432 sq ft of single-level living PLUS a finished 200 sq ft detached studio with heat and power, perfect for work, hobbies, or guests. Situated on a corner .56-acre lot, this home features vaulted ceilings, open floor plan, propane fireplace, and a dining area off the kitchen. The primary suite includes vaulted ceiling, large organized closet, and an updated bath with walk-in tile shower and stone countertop. An enclosed sunroom off the primary is ideal for a gym or sitting area. Enjoy an easy-care landscaped yard with drip and sprinkler system, metal fencing for fire prevention, patio, gazebo, propane fire pit, and water feature. Asphalt driveway is painted for pickleball. Additional enclosed area includes a sauna and hot tub. Cement tile roof and recent fire-mitigation work complete this move-in-ready home.

Sisters

14860 Checkrein

3 Beds

2 Baths

1,432 Sq.Ft.

$690,000

MLS#: 220211744

Price reduced

Newly built custom home in western-themed Sisters, Oregon. No HOA fees. Features a flexible floor plan with potential lock-off studio and private entrance—ideal for long-term rental. Main level includes tiled propane fireplace with granite hearth, Acacia wood eating bar, quartz countertops, custom Kibak tile, large pantry, and storage room. Powder room located away from living areas. Attached single-car garage. Upstairs offers plush carpet, custom stair railing, open loft/bonus space, two bedrooms, and a full bath with 6' soaking tub. Additional upgrades include solid-core doors, tiled step-in shower with Pebblestone flooring, heat pump, extra insulation, paver stone driveway/walkway, and vintage-style gate. $5,000 seller credit toward mortgage rate buy-down.

Sisters

337 W Jefferson Avenue

3 Beds

2 Baths

1,622 Sq.Ft.

$690,000

MLS#: 220201095

Welcome to Sisters, Oregon! With one of the best performing school districts in the state and endless year-round outdoor opportunities outside your door, it's an easy town to fall in love with! Located just blocks from Downtown and around the corner from Wychus Creek, this home is positioned to enjoy the best of Sisters. A vibrant lawn, limbed up pine trees and open front porch warmly greet you. Inside the home, you'll find a light filled great room with a cozy fireplace and spacious chef's kitchen. Lots of cabinets and counter space along with bar seating. From the dining area a slider flows out to the large, covered side patio allowing all season outdoor entertaining. A vaulted and generous primary suite + two additional bedrooms, laundry and large loft complete the upstairs. A rear loading two car garage is complimented by the additional RV/boat/trailer parking space! Don't miss out on this gem in Sisters' idyllic Timber Creek!

Sisters

952 E Timber Pine Drive

3 Beds

2 Baths

1,787 Sq.Ft.

$675,000

MLS#: 220208845

Price reduced

Furnished Retreat! Spacious 2,513-SF home in Tollgate, Sisters, Oregon - ideal second home or vacation rental, with most furnishings included! Generous 0.57-acre lot, fenced yard, 3 bedrooms, 2.5 baths, 1-car garage, 185-SF storage shed, 85-SF garden shed, and circular driveway. Light fills the bright great room, featuring soaring vaulted ceilings, impressive timber frame trusses, and a propane fireplace, as well as a kitchen, breakfast bar, and a separate dining room. The 2003 addition included the main-level primary suite with a second propane fireplace, jetted tub, and a walk-in closet, plus a 500 SF ''hidden'' upstairs bonus room. Enjoy the serene outdoors on the front deck, covered rear deck, paver patio, or upstairs balcony. The durable Mansard tile roof provides lasting protection. Tollgate amenities are fantastic, featuring a sparkling pool, pickleball/tennis, basketball, park, community hall, snow removal, and more! Enjoy direct access to the National Forest trail system!

Sisters

69301 Lariat

3 Beds

2 Baths

2,513 Sq.Ft.

$649,000

MLS#: 220210975

Turnkey Home & Investment in Tollgate! Discover this inviting 3-bed, 2-bath home in Sisters' desirable Tollgate community, ready for immediate enjoyment or as an income-generating short-term rental. Recently remodeled with new finishes, and updated kitchen/baths, it's truly move-in ready. The large private backyard backs to BLM/National Forest land and trails. Enjoy fantastic Tollgate amenities, including a pool, sports courts, and trails. Conveniently located between Hoodoo and Sisters, very close to Sisters' attractions and outdoor recreation, this property is a prime opportunity for full time living, a second home, or continue use as a top rated AirBnB vacation rental.

Sisters

69322 Hackamore

3 Beds

2 Baths

1,466 Sq.Ft.

$649,000

MLS#: 220205524

Price reduced

NEW PRICE $649,000 - $337 per square foot! 1-Year Home Warranty included at closing. 1,922 SF, 3-bed, 3.5-bath home on a 0.48-acre lot with a fenced backyard, hot tub, fire pit, and more! Prime Location across the street from the community pool, pickleball, and tennis courts in Tollgate, Sisters, Oregon. Short Term Rental Approved Community: Ideal full-time home, vacation getaway, or rental investment. New septic system, new carpet, and fresh interior paint. Metal roof! Flat $75 monthly water fee. Wood-burning fireplace. 2-car attached garage with EVSE electric car charger. Main level primary suite plus great room, dining area, kitchen with an island, breakfast bar, and pantry, laundry room, and a half bath. Upstairs are two spacious bedrooms, two bathrooms, and a flexible bonus room for a family room, home office, playroom, or 4th sleeping area. Tollgate access to National Forest trails for endless Central Oregon fun. Minutes from charming downtown Sisters, Oregon, schools, and more!

Sisters

69362 Lariat

3 Beds

3 Baths

1,922 Sq.Ft.

$649,000

MLS#: 220210295

Tucked away on .25 acre in a quiet neighborhood of bucolic Sisters, Oregon is a serene escape behind your private gate. This one level, 4 bedroom 2 bath ranch home has been given a refresh with clean white walls and cozy lighting. Welcoming sunshine through the windows gives this home a warm feeling, inviting you to curl up with a good book next to the wood stove. The endless options of outdoor space are waiting for your special touches. Greenhouse, raised garden, firepit, backyard camping for the kids or snowman village in winter? Make it your own oasis from season to season. Conveniently located within 5 minutes to Sisters Elementary School.

Sisters

352 N Tamarack Street

4 Beds

2 Baths

1,920 Sq.Ft.

$639,000

MLS#: 220210883

Tucked away on a quiet cul-de-sac, this well-maintained home offers excellent investment and rental potential—ideally located near Sisters Schools and everyday conveniences. The main level features an open-concept layout, a quartz-trimmed kitchen with stainless steel appliances, and a versatile bedroom or office plus a full bath.

Upstairs, the primary suite enjoys mountain views, a large walk-in closet, and a spacious ensuite with soaking tub and dual vanity. Two additional bedrooms, a full bath, and a convenient laundry room complete the upper level.

The fully fenced, landscaped backyard and HOA-maintained front yard (including snow removal) make this a low-maintenance option for an investment portfolio. A great opportunity for investors seeking a quality rental property before year-end.

Sisters

746 N Roundhouse Court

4 Beds

3 Baths

2,026 Sq.Ft.

$620,000

MLS#: 220212390

Primary bedroom on the main! This better than new 3-bed, 2.5-bath with loft offers the ease of main-level living with a spacious primary suite. Inside, enjoy updated carpet, fresh interior paint, and a large entry with an extra-wide staircase. The airy kitchen layout blends naturally into the central living space ideal for entertaining. Upstairs features a loft-style landing, two additional bedrooms, and a full bathroom, offering flexibility for guests, family, or a home office. Outside, relax in the landscaped yard with storage shed, and a designated space for a utility trailer. HOA cares for front lawn care and community parks/trails. Just minutes from downtown Sisters, you'll enjoy easy access to great schools, the famous rodeo, vibrant quilting community, and charming local shops. Come see why everyone loves the Village at Cold Springs!

Sisters

1602 W Hill Avenue

3 Beds

2 Baths

1,889 Sq.Ft.

$615,000

MLS#: 220208573

#220205755

Sisters

1011 W Linda Avenue 35

3 Beds

2 Baths

1,680 Sq.Ft.

$609,950

MLS#: 220205755

#220210161

Sisters

947 W Linda Avenue 29

3 Beds

2 Baths

1,680 Sq.Ft.

$609,000

MLS#: 220210161

Price reduced

With room for your RV, boat, and all your Central Oregon gear, this corner-lot home offers both comfort and adventure-ready space. Located in the quiet community of Wychus Canyon Estates, this single-level 3-bedroom, 2-bathroom home sits on just under an acre and features low-maintenance stucco siding, a tile roof, an enclosed front courtyard, and an enclosed rear courtyard/patio for private outdoor living. Inside, enjoy vaulted ceilings, new skylights, new carpet, and newer appliances in a light-filled layout. A newer whole-house generator adds peace of mind. Recent updates include tree removal and a new asphalt driveway. The partially fenced yard and outdoor storage add function and convenience. This well-cared-for home is solid, spacious and ready for you to enjoy the Central Oregon lifestyle.

Sisters

70120 Mustang Drive

3 Beds

2 Baths

1,572 Sq.Ft.

$600,000

MLS#: 220209156

Welcome to your genuine log home, where rustic charm meets modern comfort. As you enter, the inviting river-rock hearth and the warmth of the wood stove greet you, creating a cozy atmosphere. Relax in your comfortable chair and admire the tongue and groove wood-beamed ceiling. Unwind on the expansive cedar deck as you enjoy the lush, irrigated lawn and mature Ponderosa Pines. This two-story residence spans 1,592 square feet and features three bedrooms and two bathrooms, offering ample space on its 0.54-acre lot. The generous property provides plenty of room to build a garage or shop and a has new in 2024 upgraded septic system. Nestled in the highly desirable Tollgate community, this location is surrounded by public lands and conveniently positioned just 2 miles west of Sisters via Highway 20. Tollgate's amenities, including a paved bike and walking trail, swift access to public lands, a swimming pool, club house, tennis & pickleball basketball court, and a park. A must see home!

Sisters

14842 Stagecoach

3 Beds

2 Baths

1,592 Sq.Ft.

$599,000

MLS#: 220210068

Welcome to your peaceful getaway in the woods! This cozy 508 sq ft studio CABIN is perfectly situated on a 4.65-acre corner lot, located on the paved portion of the road for easy year-round access.
The open-concept cabin features vaulted ceilings that enhance the sense of space, a full kitchen, 1 bathroom, and a sleeping area without interior walls—keeping the layout simple, open, and full of natural light. A wraparound deck invites you to relax and enjoy the quiet, private setting surrounded by nature.
Enjoy year-round comfort with a Mitsubishi ductless split system providing both efficient heating and cooling. Additional features include a private well (680 feet deep), standard septic system with a 1,000-gallon concrete tank, and plenty of room for future expansion or outdoor living projects.
Whether you're looking for a weekend retreat, vacation rental opportunity, or a place to live while you build, this one-of-a-kind cabin offers the perfect balance of simplicity and space.

Sisters

16840 Buck Horn Drive

1 Beds

1 Baths

508 Sq.Ft.

$599,000

MLS#: 220206730

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