Sisters Homes with Pickleball Community Features

Welcome to Sisters, Oregon—a charming town nestled in the heart of the Deschutes County, surrounded by the breathtaking beauty of the Cascade Mountains. Known for its rich history and vibrant arts scene, Sisters offers a unique blend of small-town warmth and outdoor adventure. With a population of just over 2,000, this picturesque community is a haven for those seeking a tranquil lifestyle with easy access to nature's playground.

One of the standout features of Sisters is its welcoming neighborhoods that cater to active lifestyles. For pickleball enthusiasts, the homes in this area often come equipped with community features that include dedicated pickleball courts. Imagine stepping out your front door and finding yourself on the court, ready to enjoy a game with neighbors or friends. This sport, known for its friendly competition and social environment, is a fantastic way to stay active while fostering connections within the community.

The real estate options in Sisters are as diverse as its residents, ranging from cozy cottages to modern family homes, all designed to enhance your living experience. Many properties are strategically located near parks and recreational areas, ensuring that outdoor activities like hiking, biking, and, of course, pickleball are just a stone's throw away.

Whether you’re drawn to the stunning landscapes, the vibrant community spirit, or the active lifestyle that Sisters offers, you’ll find that this town is the perfect place to call home. Discover your dream home in Sisters, where adventure and community come together seamlessly!

Newest Sisters Homes with Pickleball Community Features

$1,115,000

3 Beds ⋅ 4 Baths ⋅ 220226074 MLS

Enjoy single-level living in the desirable Aspen Lakes Golf Community with stunning fairway views and endless potential. This HUD-owned home is ideally situated on the golf course, offering a peaceful setting and an opportunity to create your dream home. The spacious floor plan is filled with natural light and captures beautiful views of the course from the main living areas. A separate guest quarters or mother-in-law unit, located just off the four-car garage, provides flexible space for extended family, guests, a private office, or hobbies. The oversized garages offers abundant room for vehicles, golf carts, and recreational gear. While the home does need repairs and updates, it presents an exceptional opportunity to build equity in one of Sisters' most sought-after golf communities. Just minutes from downtown Sisters, enjoy championship golf, mountain views, miles of recreation, and the relaxed Central Oregon lifestyle. HUD Home sold As-Is.

17084 Lady Caroline Drive, Sisters

Listing courtesy of RE/MAX Key Properties.

$1,749,900

4 Beds ⋅ 4 Baths ⋅ 220223064 MLS

Don't miss out; tucked into a pine canopy overlooking Aspen Lakes GC (pool/rec ctr) & Cascade Mtns; this contemporary craftsman home is a unicorn! Vaulted ceilings & enlarged windows offer natural light while framing the breathtaking surroundings. Main-level living, home offers 2 suites, + another bedroom (J&J bath), bunkroom, & theatre upstairs! Exquisite craftsmanship w/ wood beams, corner fireplace, & luxury LVP floors. Fully updated chef's kitchen, blending timeless style with modern functionality w/ premium finishes, abundant workspace, eating bar, & dining nook-all seamlessly connected to the open concept living & formal dining areas. Capture the golf course mtn. views w/ exceptional outdoor living w/ hot tub, water feature pond, and outdoor patio (fireplace & down heater). Front shade deck featuring covered entertaining spaces designed to take in the panoramic scenery. This remarkable property is complete with/ a 3-car garage w/ workshop & golf cart shed all on 1 private acr

16951 Lady Caroline Drive, Sisters

Listing courtesy of Stellar Realty Northwest.

$3,350,000

3 Beds ⋅ 4 Baths ⋅ 220223836 MLS

Discover one-of-a-kind living in this low energy, one-level, stepless smart home, completed in 2020 & designed as a legacy property. Set in the golden triangle on 19 low-to-no-maintenance acres w/direct public-land access, the estate offers panoramic sunrise and sunset views, unmatched privacy, & only minutes to Bend, Sisters, & Redmond. Designed for indoor-outdoor living, it features approx. 2,000 square feet of stamped concrete patios & decks, a timber-covered outdoor living area w/fireplace, BBQ area, & hot tub--ideal for entertaining or relaxing under the stars. The property includes an attached 1102 sq ft RV garage, 720 sq ft shop, guest house w/bedroom & loft, & a finished multi-purpose gathering room, 2 full RV hookups, dry-camp areas, walking paths w/scenic viewpoints, a labyrinth, pickleball, solar, & more. A rare retreat combining luxury, privacy, recreation, convenience, & it meets all defensible space requirements. This is a perfect full time, part time, or vacation home!

17771 Warrin Road, Sisters

Listing courtesy of Cascade Hasson SIR.

$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.

$729,000

2 Beds ⋅ 3 Baths ⋅ 220223685 MLS

One owner, custom built, meticulous condition, this Pine Meadow Village gem is the one you've been waiting for. 1,698 sq ft of open living with windows that pull in the mountain light, hardwood floors, and quartz countertops. The main level features a dedicated office or flex space with a full bath, perfect for guests or working from home. Upstairs, you'll find a second bedroom and the primary suite, which captures stunning mountain views. Three full baths total. Single car garage plus a covered porch for soaking in that Sisters air. Pine Meadow Village delivers the lifestyle: pool, hot tub, clubhouse, trails, and tennis/pickleball courts, all walking distance to downtown Sisters. Whether you're simplifying, investing, or planting roots in Central Oregon, this one is move-in ready and waiting for its next chapter.

446 S Cottonwood Street, Sisters

Listing courtesy of Coldwell Banker Mayfield Realty.

$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.

$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.

$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.

$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.

$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.

$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.

$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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