Sisters Homes with Short Term Rentals Allowed Community Features

Welcome to Sisters, Oregon—a charming town nestled in the heart of Deschutes County, surrounded by the breathtaking Cascade Mountains. Known for its stunning natural beauty, Sisters offers a unique blend of small-town charm and outdoor adventure, making it a perfect destination for both residents and visitors. With a rich history rooted in the Old West, Sisters is renowned for its vibrant arts scene, cozy shops, and delightful eateries that reflect the spirit of the region.

One of the most appealing aspects of living in Sisters is the abundance of homes that allow short-term rentals. This feature not only provides homeowners with the opportunity to generate income but also invites visitors to experience the beauty of Sisters and its welcoming community. Imagine owning a charming cabin or a modern home where you can host guests seeking adventure in the nearby mountains, lakes, and forests. The potential for rental income is a significant draw for many homeowners, allowing you to enjoy the benefits of vacationing in your own serene retreat while sharing the magic of Sisters with others.

Community features in Sisters are designed to enhance the quality of life for residents. Enjoy access to beautiful parks, hiking trails, and local events that bring the community together. Whether you're sipping coffee at a local café, exploring the vibrant arts district, or engaging in outdoor activities like hiking, biking, or fishing, Sisters truly offers something for everyone. Embrace the opportunity to own a piece of this enchanting town and experience the perfect blend of adventure and tranquility that Sisters, Oregon has to offer!

Newest Sisters Homes with Short Term Rentals Allowed Community Features

$3,500,000

4 Beds ⋅ 5 Baths ⋅ 220225659 MLS

Set on approximately 79 private, forested acres bordering Deschutes National Forest, this custom home near Sisters, OR offers 6,366 sq ft, 4 bedrooms, and 4 baths. The great room's massive river rock fireplace, hand-forged ironwork, and cherry cabinetry set the tone, while the kitchen features Sub-Zero, Wolf, Dacor, and Miele appliances alongside a granite island and butler's pantry with wine fridge. Oak hardwood floors, a formal dining room with French glass doors, and a family room with a Jotul wood stove and Brazilian cherry floors add warmth throughout. The primary suite includes a marble trimmed fireplace, soaking tub, and glass-block shower; a downstairs guest suite and upstairs Jack-and-Jill bedroom offer flexible living. Outdoors, enjoy a private pond, flagstone patio, firepit, and an auto irrigation system supplied by a private well. A nearly 3200 sq ft detached garage/shop rounds out this rare forest retreat, minutes from Sisters and surrounded by developed Forest trails.

67376 Peterson Mill Road, Sisters

Listing courtesy of Ponderosa Properties.

$1,299,500

4 Beds ⋅ 3 Baths ⋅ 220224591 MLS

Stunning custom home with mountain views in Pine Meadow - walking distance to downtown Sisters. Quality construction and attention to detail are evident throughout: hardwood floors, wood beams, fireplace with stone hearth, heated tile bathroom floors, etc. The open-concept lower level connects the great room, dining area, and kitchen (featuring a generous island and beautiful cabinetry). A dedicated office, large laundry/mudroom, and oversized 2-car garage complete the downstairs layout. The upstairs master suite features a spa-like bathroom with 2 shower heads, a walk-in closet, plus a spacious covered deck with stunning mountain views. There are 3 guest bedrooms upstairs as well. The lot is exceptionally private, bordered by common area (and the irrigation pond/stream) on two sides - preserving those views. Exterior features include: wraparound front porch; back paver patio; built-in BBQ; fire-pit area. Brand new heat pump, freshly painted/stained, all furnishings negotiable!

751 S Redwood Street, Sisters

Listing courtesy of eXp Realty, LLC.

$498,000

3 Beds ⋅ 3 Baths ⋅ 220224477 MLS

Steps from Deschutes National Forest trails and minutes from downtown Sisters, this turnkey home offers a modern, lock-and-leave lifestyle. The bright, open-concept main floor features tall ceilings, luxury vinyl plank floors, and custom built-ins. A spacious kitchen boasts quartz countertops, ample cabinetry, and a large island flowing into the living and dining areas. A convenient half bath is on the main level. Upstairs, there are 3 spacious bedrooms: the private primary ensuite features a walk-in closet, separated from two flexible guest bedrooms/office spaces and a convenient laundry room. An attached two-car garage provides plenty of room for all your Central Oregon gear. Enjoy park views, HOA-maintained landscaping, and endless outdoor recreation right outside your front door. Perfect as a full-time residence or vacation retreat!

950 N Hindeman Avenue, Sisters

Listing courtesy of Avenir Realty.

$740,000

3 Beds ⋅ 2 Baths ⋅ 220223801 MLS

Set among the pines in one of Black Butte Ranch's most coveted locations, Country House Condo 63 enjoys a setting few properties can match. Positioned in a desirable second-row location with adjoining common area, the home overlooks Phalarope Lake, open meadows and the Three Sisters, Mount Washington and Broken Top beyond. Walls of windows on both levels fill the home with natural light and showcase the landscape from nearly every room. A main-level bedroom and full bath are complemented by two upstairs bedrooms connected by a Jack-and-Jill bath, including a bedroom with a walk-in closet and sitting area overlooking the mountain backdrop. Vaulted wood ceilings and warm architectural details reflect mountain lodge design. Offered fully furnished and moments from the Lodge area, Lakeside Bistro, pools, fitness center, pickleball courts and more. Whether envisioned as a private getaway, vacation home or investment opportunity, this retreat is ready to be enjoyed from day one.

12960 Hawks Beard CHC63 Unit CHC63, Sisters

Listing courtesy of Keller Williams Sunset Corridor.

$619,000

3 Beds ⋅ 2 Baths ⋅ 220223779 MLS

Located just a few short blocks to downtown Sisters, this lovely Cottonwood Condo has been tastefully updated and is ready for the next fortunate owner. The welcoming floor plan has a well appointed kitchen with solid surface counters, energy star appliances & hardwood flooring. Quality construction through out with solid wood windows and doors, paver patio and upstairs deck with views towards the Cascades. Comfortable living room on the main level with a flex room that can be used as a bedroom or office. Upstairs is a 2nd primary suite, 3rd bedroom & a bonus room with cozy fireplace and private deck. The detached two car garage has plenty of room for Central Oregon gear & two vehicles. Ease of living with more time to enjoy the outdoors & vibrant Sisters downtown out your front door. Community features include Firewise certification, pool, two tennis courts, paths, community center, park & much more. Don't miss this opportunity to secure one of only 5 Cottonwood condos built!

547 W Jefferson Avenue, Sisters

Listing courtesy of Cascade Hasson SIR.

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 220223615 MLS

If you've been waiting for the right Black Butte Ranch opportunity, this is it. Set on nearly half an acre, this fully furnished 3,482 sq ft retreat offers 4 bedrooms, 3 baths, multiple gathering spaces, soaring wood ceilings, exposed beams, and a stunning stone fireplace that has anchored decades of memories. Beautifully preserved with authentic Northwest character, it is ready to enjoy the day you close while leaving room to make it your own over time. Major investments are already complete, including a newer roof and a brand new $61,000 composite wraparound deck built for years of gathering under the pines. Imagine mornings with coffee on the deck, afternoons playing pickleball, golfing, or biking the trails, relaxing by the pool, evenings around the fireplace, and weekends spent making memories. Whether you're creating your own mountain retreat or taking advantage of Black Butte Ranch's full service rental program, this is the kind of place people return to year after year.

13800 Balsam Root, Sisters

Listing courtesy of Real Broker.

$499,000

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.

$655,000

2 Beds ⋅ 2 Baths ⋅ 220221764 MLS

Nestled in the desirable Tollgate community, this charming 2-bedroom, 2-bath home sits on a peaceful and level 0.68 acre parcel surrounded by the beauty of Central Oregon. Inside, you'll find vaulted ceilings, an open-concept layout, and a modern kitchen featuring granite countertops and stainless steel appliances. The kitchen flows seamlessly into the dining area and great room with a cozy wood stove. The main level includes a full bathroom and laundry room, while upstairs offers two bedrooms. an additional full bath and a versatile loft space. Enjoy Tollgate amenities including a clubhouse, a seasonal pool, pickleball court, tennis court, playground, park and walking trails.

69318 Lariat, Sisters

Listing courtesy of Stellar Realty Northwest.

$899,000

3 Beds ⋅ 2 Baths ⋅ 220220765 MLS

This sanctuary in the heart of Sisters, Oregon, is nestled within 19.4 acres of Ponderosa pines and has access to National Forest trails. Enjoy views of Black Butte and Mt. Jefferson as you wake and sip your morning coffee from the new wrap-around deck. Step inside the beautifully remodeled 1,793 SF 3-bedroom, 2-bath cabin with a bright, open interior featuring a great room and an office. New windows, hardwood and laminate flooring, tongue-and-groove wood ceilings accented by ambient lighting, and fresh paint inside and out. Enjoy your hobbies in the versatile 30'x40' shop with a 30'x16.5' RV bay and two insulated 22'x14' rooms -- perfect for a home office, game room, fitness studio, craft space, or more! The 2-car oversized garage has heated storage, dedicated wood storage, and a storage room. Plus a pump house/greenhouse combo for the gardening enthusiast. 9.4 of the total acres are in forest deferral for only $13 in taxes, totaling $2,006.80 for the entire property!

15020 Remuda Road, Sisters

Listing courtesy of Avenir Realty.

$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.

$515,000

2 Beds ⋅ 1 Baths ⋅ 220219264 MLS

If you've been dreaming of a getaway ''cabin in the woods'', your dream awaits in Sisters, OR. Private .65 acre setting offering quiet serenity. Relax on huge back deck where you're hidden from the world except for birds & wildlife. After your respite, cozy up to the woodburning fire or enjoy Tollgate community amenities: saltwater swim pool, pickleball/tennis, hiking/biking path easily accessible to US forest land yet oh-so-convenient to town. Lightly used as a second home. Could sleep 6 with two queens plus trundle - furnished! Includes newer GE stacked washer/dryer. Second deck off upstairs bedroom. Don't delay, call today!

69307 Scabbard, Sisters

Listing courtesy of Stellar Realty Northwest.

$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.

Start Your Search

The content relating to real estate for sale on this website comes in part form the MLS of Central Oregon. Real Estate listings held by Brokerages other than Selling Central Oregon, LLC are marked with the Reciprocity/IDX logo, and detailed information about these properties includes the name of the listing Brokerage. © MLS of Central Oregon (MLSCO). This content was last updated on . Some properties which appear for sale on this website may subsequently have sold or may no longer be available. All information provided is deemed reliable but is not guaranteed and should be independently verified. All content displayed on this website is restricted to personal, non-commercial use, and only for ascertaining information regarding real property for sale. The consumer will not copy, retransmit not redistribute any of the content from this website. The consumer is reminded that all listing content provided by automatic transmission by MLSCO is © MLS of Central Oregon (MLSCO).