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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

All listings

$250,000 - $500,000

111 Properties Found. Page 4 of 8.

#220211562

Sisters

69388 Tollgate

4 Beds

3 Baths

2,315 Sq.Ft.

$790,000

MLS#: 220211562

Beautifully crafted single-level mid-century modern home offering 1,972 SqFt of stylish, open-concept living in the heart of Sisters. The great room features vaulted ceilings and abundant natural light, flowing seamlessly into the dining area and gourmet kitchen with custom cabinetry, high-end appliances, and a full-height tile backsplash. The luxurious primary suite includes a spacious walk-in closet with built-ins and a spa-like bath with walk-in tile shower and dual vanities. Two additional bedrooms, a full bath, laundry/mudroom, and attached two-car garage complete the home. Located in the sought-after ClearPine community with access to trails, a neighborhood park, local coffee shops, and just minutes from downtown Sisters. Welcome to the best of Central Oregon living!

Sisters

242 W Lundgren Mill Drive

3 Beds

2 Baths

1,972 Sq.Ft.

$790,000

MLS#: 220208537

Sisters Woodlands Sandstone Townhome has a two floor layout with primary suite & main living downstairs. Two upstairs bedrooms & 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. 2-10 year Homebuyer Warranty. Townhomes carefully sited to save 100's of pine trees & complement natural environment. 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. Visit model home (631 N Sisters Woodlands Way). Open house Friday through Saturday from 12:00 to 4:00. Homes being pre-sold prior to construction.

Sisters

475 N Pine Street Lot #158

3 Beds

2 Baths

1,534 Sq.Ft.

$787,000

MLS#: 220195506

Sisters Woodlands Sunstone Townhome is the only available, move-in ready home, in the community. This model has a two floor layout with primary suite and two additional bedrooms downstairs. Main living, including a huge covered deck upstairs. Developers offering a 10k credit toward purchase. Homes are carefully sited to save 100's of pine trees & complement 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: Metal siding (fire/pest resistant); Solar & EV charger ready. 2-10 year Homebuyer Warranty included. Visit model home (631 N Sisters Woodlands Way). Open house Friday through Sunday from 12:00 to 4:00.

Sisters

504 W Sisters Park Drive Lot #102

3 Beds

2 Baths

1,519 Sq.Ft.

$787,000

MLS#: 220209675

Your dream home in Sisters is here! Nestled in the sought-after Saddlestone community, this beautiful property blends comfort and Northwest charm. The open-concept layout features a spacious kitchen flowing seamlessly into the dining and great room, completed with a cozy propane fireplace. The primary suite is conveniently located on the main level, offering an ensuite bath and walk-in closet. With three bedrooms, 2.5 baths, a dedicated office/flex space, and a generous two-car garage, this home offers both functionality and style. Relax on the deck under Central Oregon's starry skies and enjoy easy access to Sisters' shops, dining, trails, and events. Don't miss your chance to make this special home yours!

Sisters

1004 E Horse Back Trail

3 Beds

2 Baths

2,173 Sq.Ft.

$759,000

MLS#: 220201161

#220205923

Sisters

69856 Camp Polk Road

4 Beds

2 Baths

2,593 Sq.Ft.

$750,000

MLS#: 220205923

The Pinewood Cottage - Charming custom 3-bedroom, 2-bath Tudor-style home on a ½-acre lot bordering the Deschutes National Forest in Tollgate. This energy-efficient home offers year-round comfort—warm and inviting in winter, cool in summer. A beautiful central brick fireplace anchors the living space, adding character and a cozy focal point. The finished attic provides a versatile extra room perfect for an office, den, or reading room. Classic Tudor architecture, rich wood finishes, and thoughtful craftsmanship create a welcoming retreat surrounded by nature. Enjoy a spacious back deck for relaxing or entertaining, plus a detached two-car garage and separate storage shed. Tollgate amenities include a pool, tennis and pickleball courts, and miles of trails just outside your door. A perfect blend of charm, quality, and forest tranquility.

Sisters

14850 Schooner

3 Beds

2 Baths

1,781 Sq.Ft.

$745,000

MLS#: 220210763

New on site today

Home on .52 wooded acres w/ views of Central Oregon's stunning landscape. 3 bed, 2 bath home just minutes from Sisters w/ charming shops & dining, close to Black Butte Ranch & in Tollgate Community. 1 hour to Mt. Bachelor & 17 miles to Hoodoo for skiing. Lots of parking plus RV parking, room for toys & guests. Detached garage is set up as 400 sq ft insulated, heated studio for guests or office. Living room w/ vaulted ceiling. Kitchen/dining/family great room w/ lots of cabinetry & prep space, pantry, cook island & eat bar. Family room w/ wood burning stove & door to deck for dining. Primary suite w/ walk-in closet & private bath. 2 more bedrooms, guest bath & laundry area complete floorplan. HOA includes maintenance of common areas, pool, tennis/pickleball/basketball courts, playground & trails. From nearby Suttle Lake to endless recreation of the Cascade Mountains for hiking, fishing, paddleboarding and snow sports, this is Central Oregon living at its finest.

Sisters

69341 Silver Spur

3 Beds

2 Baths

1,837 Sq.Ft.

$725,000

MLS#: 220212648

Nestled on over half an acre in a quiet cul-de-sac, this home borders the Deschutes Trout Creek Conservation Area, offering privacy and nature at your doorstep. The three-bedroom, three-bathroom layout offers vaulted ceilings and a seamless blend of comfort and functionality.
The primary suite boasts a private second-story deck for a perfect outdoor retreat. With a two-car garage and a dedicated RV/boat garage which could also be used as a workshop, there is ample space for all your gear for outdoor adventures. The home includes a 20KW Kohler generator, gas fire stove, heat pump water heater, and new stainless steel appliances.
Located in the highly sought after Tollgate community with a saltwater pool, tennis/pickleball courts, basketball and volleyball courts, a recreational hall, BBQ area, paved walking paths, and trail access.
Don't miss this incredible opportunity! The reduced price reflects a discount for the buyer's potential upgrades to the upstairs area.

Sisters

69215 Martingale

3 Beds

3 Baths

1,960 Sq.Ft.

$720,000

MLS#: 220198766

Price reduced

2 Craftsman homes for price of one. Located in ClearPine Subdivision. Main home is 1372 sqft & ADU is 528 totaling 1900 sqft. Located down long driveway in rear of property where you will find main residence w/ two-car garage equipped w/ 30-amp power for RV. Both homes w/ open concept & equally spectacular. As you enter main house you will be greeted w/ expansive hallway. Main house w/ 2 ensuites at opposite ends of home w/ living area in center. Floor plan offers optimal privacy. ADU in front of property is 1 bedroom 1 bath w/ stackable W/D. Kitchen is full size w/ island making fully self-contained residence. Property is completely fenced w/ private yard for each home. Well cared for property w/ many upgrades has been owner occupied w/ solid rental history. Currently ADU is rented month to month. Close to local dining, shopping, Black Butte Ranch, Indian Ford Campground, Hoodoo Ski Resort less than 20 miles away & an hour to Mt. Bachelor Ski Resort.

Sisters

110 W Heising Drive

2 Beds

2 Baths

1,372 Sq.Ft.

$719,000

MLS#: 220211694

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

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