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16465 Suntree Lane, Sisters
$9,750,000
8 Beds ⋅ 9 Baths ⋅ 220203639 MLS
This is a testament to timeless grandeur. Nestled within Deschutes Land Trust's preserve, in the heart of Central Oregon, this remarkable 67 acre estate offers an enduring legacy that will be treasured for generations to come. The primary residence, spanning 5,050 sq ft, boasts three bedrooms, five bathrooms, and a chef's kitchen. Hand-carved hickory and heated stone floors exude warmth, while twenty-foot ceilings and expansive windows provide stunning views. The property features a private-access apartment suite, custom cabinetry, a heated three car garage, and manicured landscaping. Enjoy mountain vistas, an outdoor kitchen, and a fire feature in the courtyard, as well as direct access to private land for fishing and wildlife viewing. On this sprawling estate you will also find two other full residences. Home two is single story with 1,700 sq ft, 2 bed, 2 bath, and a two car garage. Home three is two story with 2,200 sq ft, 3 bed, 2 bath, and a 2 car garage.

16465 Suntree Lane, Sisters

Listing courtesy of Engel & Volkers Portland Rose City.

19100 Macalpine Loop, Bend
$8,750,000
5 Beds ⋅ 8 Baths ⋅ 220219311 MLS
Ten acres inside the gates of The Highlands at Broken Top, where Cascade mountain views frame every west-facing room & privacy is absolute. This estate was designed to host a life at full scale. A great room with vaulted timber beam ceilings & wood-burning fireplace opens to a main kitchen with onyx backlit backsplash & full prep kitchen. The main-level primary suite offers an infrared sauna, steam shower, fireplace, dual closets, & private patio, alongside three additional ensuite bedrooms, guest quarters, & a private office. The lower level adds a golf simulator, gym, and flex game room. Outside, a solar-heated saltwater pool & spa, outdoor kitchen, Alfa pizza oven, bocce court, gas firepits, & wood-burning fireplace with surround sound. The pool house with wet bar, & pass-through bar connects to heated RV/shop. Kitchen garden, greenhouse, & basketball court complete the grounds. Phil's Trail at the gate. One of a kind private homesites in The Highlands.

19100 Macalpine Loop, Bend

Listing courtesy of Cascade Hasson SIR.

65930 Mariposa Lane, Bend
$7,900,000
7 Beds ⋅ 9 Baths ⋅ 220204494 MLS
An architectural masterpiece in Bend's coveted Golden Triangle. Set on 9.77 private acres behind custom gates, this Northwest style estate by Norman Building & Design offers sweeping Cascade Mountain views. Walls of glass frame the high desert, anchored by a grand stone fireplace & massive beams. Chef's kitchen w/ slab granite & sculptural hood opens to dining & copper-topped wine bar. Steps lead down to a wine cellar & tasting room. Main-level primary suite w/new gas fireplace, spa bath & panoramic mountain views. Dramatic breezeway connects to a 2,095 SF guest house. Enclosed parking between both garages for 11 cars or 9+2 RVs. Expansive patios, fire pit, water feature & salt water hot tub under the stars. Well appointed main-level office with Mtn. views, exquisite wood finishes & timeless craftsmanship define this legacy estate--secluded yet minutes to downtown Bend. Only 25 min. Redmond Airport, Near golf, Mt Bachelor, equestrian estates & world class recreation.

65930 Mariposa Lane, Bend

Listing courtesy of Camerelle Real Estate LLC.

67480 Cloverdale Road, Bend
$6,999,000
6 Beds ⋅ 7 Baths ⋅ 220223667 MLS
Experience luxury country living on 25± acres between Bend & Sisters, Oregon. This exceptional equestrian estate offers breathtaking views of the Cascade Mountains, & surrounding countryside. The 9,075 square-foot custom home features 6 bedrooms, 6.5 bathrooms, soaring cedar ceilings, hardwood floors, a gourmet kitchen, library, office, game room, guest suite, & a private apartment for guests or staff. Outdoor amenities include a pool, hot tub, pool house with steam room & sauna, and beautifully landscaped grounds. Equestrian improvements are highlighted by a 170' x 90' indoor arena with stalls, tack rooms, paddocks, kitchen, full bath, & viewing loft. The property is fenced & cross-fenced, includes approximately 11 acres of irrigation, two RV hookups, & may qualify for approval to host up to eight weddings annually, subject to county requirements. A rare opportunity to own a premier Central Oregon equestrian & lifestyle property just minutes from recreation, dining & outdoor adventure

67480 Cloverdale Road, Bend

Listing courtesy of Hicks Team - Fay Ranches LLC.

18780 Macalpine Loop, Bend
$5,995,000
5 Beds ⋅ 6 Baths ⋅ 220205781 MLS
Discover luxury and tranquility on 10 acres in the gated Highlands community on Bend's Westside. This 5BD, 5.5BA custom estate spans 6,772 sq ft, and has been reimagined to blend mountain elegance with modern style. Vaulted ceilings, Montana mossy rock fireplace, and beam work add warmth and character. The chef's kitchen opens to light-filled living spaces with accordion doors for seamless indoor-outdoor flow. The main-level primary suite is an oasis, and upstairs offers guest suites, a media room, and bunk room. Enviable outdoor living features a pavilion with full kitchen, grills, pizza oven, MAK smoker, wet bar, firepit, and all-weather sound system. Enjoy year-round fun in the high-efficiency Modpool with a window to the Deschutes National Forest. A true all-ages playground with pickleball court, fenced play area, and access to Phil's Trail. Smart features include Control4, solar, EV charger, battery backup, and SPAN panel. A rare chance to own the pinnacle of High Desert living!

18780 Macalpine Loop, Bend

Listing courtesy of Cascade Hasson SIR.

17097 SW Lago Vista Drive, Powell Butte
$5,950,000
5 Beds ⋅ 7 Baths ⋅ 220209860 MLS
Among Central Oregon's most exceptional luxury estates, this newly constructed 2026 custom home in Brasada Ranch overlooks a private community lake with sweeping Cascade Mountain views and rare privacy bordering BLM land. Situated on 1.77 acres, the estate offers 15,108 total living sq ft, including a 13,201 sq ft main residence and separate casita. Designed for luxury living and entertaining, the home features 5 bedrooms, 7 bathrooms, expansive indoor-outdoor spaces, and multiple ensuite retreats. Approved plans and professional interior design selections are already in place, allowing the next owner to continue the vision or fully personalize the finishes. Enjoy access to world-class golf, dining, pools, fitness, horseback riding, trails, and resort amenities at Brasada Ranch.

17097 SW Lago Vista Drive, Powell Butte

Listing courtesy of High Desert Realty, LLC.

18883 Sutherland Court, Bend
$5,890,000
6 Beds ⋅ 9 Baths ⋅ 220202448 MLS
One of the most private & unique offerings in Highlands at Broken Top, this exceptional 10+ acre gated estate combines luxury living with the serenity of a park-like setting just minutes from Bend. Custom built by Norman Building & Design, the 9,197-sq. ft. residence showcases timeless craftsmanship, soaring ceilings, extensive stonework, custom cherry cabinetry, & walls of windows that capture the beauty of the surrounding landscape. Designed for both grand-scale entertaining & comfortable everyday living, the home offers multiple gathering spaces, a main-level primary suite, guest accommodations, & seamless indoor-outdoor living. Resort-style amenities include a pool, detached guest quarters, workshop & extensive garage space, EV charging, & room for collectors, hobbies, and recreation. Surrounded by natural beauty & adjacent to miles of recreation opportunities, this extraordinary estate offers a level of privacy, space, & flexibility rarely found in Bend.Seller financing available.

18883 Sutherland Court, Bend

Listing courtesy of John L Scott Bend.

1500 Netarts Highway W, Tillamook
$5,850,000
3 Beds ⋅ 4 Baths ⋅ 220226137 MLS
Tillamook Bay Timber Retreat is 318± acres of merchantable timber and proven hunting ground on the Oregon Coast, anchored by a 6,650±-square-foot log lodge constructed from 24-inch timber harvested on-site. The three-level main residence with 3 bedrooms and 4 bathrooms features wall-to-wall windows framing 180+-degree views of the Pacific Ocean and Tillamook Bay, a two-story slate fireplace, and a residential elevator. A matching 3910± square foot, 3-bedroom, 2.5-bathroom additional home with an updated kitchen and granite counters sits alongside a six-bay heated shop with a vehicle lift, compressor reels, and a full bath. The property carries 251± acres of 45±-year-old standing timber valued at $3.8+ million, and provides habitat for Roosevelt Bull Elk and coastal Black-Tail Deer. This is a legacy-scale coastal holding for the buyer who demands timber income, trophy-class hunting, and generational privacy in a single asset. Seller financing available with timber reservation.

1500 Netarts Highway W, Tillamook

Listing courtesy of Fay Ranches, Inc..

7820 SE Amity Road, Amity
$5,750,000
4 Beds ⋅ 4 Baths ⋅ 220174703 MLS
Located in the heart of Oregon Wine Country, we proudly offer you Jubilee Vineyard;140 acres tucked away in the Eola-Amity Hills of the Willamette Valley.Eola-Amity Hills is an established and highly desired American Viticultural Area (AVA). A total of 32 acre of vines; Pinot Noir, Chardonnay, Gamay, Dolcetto grapes stretch across the hills of this property.The property of Jubilee Vineyard is made up of three separate tax lots encompassing mature forest, ponds and pastures offering additional opportunities to develop more vineyards. Overlooking the Amity Valley, a 5,140sqft, 4 bed, 3.5 bath craftsman style home sits on top of the vineyard Also offered at the lower part of the vineyard is a second 1664sqft ranch style home with 3 bedrooms and one full bath.This turnkey vineyard provides endless possibilities for wine enthusiasts and entrepreneurs.Don't miss your chance to embrace the vineyard lifestyle and become part of the respected wine making community of the Willamette Valley.

7820 SE Amity Road, Amity

Listing courtesy of Fay Ranches, Inc..

16305 N East Ochoco Highway, Prineville
$5,500,000
3 Beds ⋅ 3 Baths ⋅ 220223785 MLS
Discover the beauty and potential of this incredible 2,090-acre ranch featuring 180 acres of irrigation and Ochoco Creek running through the property. The centerpiece is a stunning 3,200 sq ft custom log home, complemented by a charming 1,966 sq ft cottage--ideal for guests or multi-generational living. Historic charm abounds with an early 1900s barn, chicken coop, multiple ponds, and natural springs. Bonus: 9.87 acres zoned RR1 (1-acre min) offers exciting future development potential. A rare opportunity to own a legacy property--schedule your private tour today!

16305 N East Ochoco Highway, Prineville

Listing courtesy of Cascade Hasson SIR.

63435 Palla Lane, Bend
$5,285,000
4 Beds ⋅ 5 Baths ⋅ 220225078 MLS
Some homes ask for attention. Harmony earns it quietly. Years from now, people won't remember the square footage or the finishes. They'll remember how this house felt. The quiet in the morning. Music drifting from another room. Light reflecting off the lake before dinner. Harmony was designed around those moments. Inspired by the enduring character of classic American lake houses, it draws from weathered wood, vintage records spinning in the background, and a relaxed, timeless aesthetic. Every room picks up where the last one leaves off. Light, views, and proportion repeat like familiar chords, creating a house that feels calm and balanced. Surrounded by mature pines in front, and backing to one of two lakes within Tanager, Harmony earned seven COBA Tour of Homes awards, including Best in Show. More importantly, it succeeds at something awards cannot measure. It makes people want to stay.

63435 Palla Lane, Bend

Listing courtesy of Cascade Hasson SIR.

56680 Lunar Drive, Bend
$4,987,000
5 Beds ⋅ 5 Baths ⋅ 220224796 MLS
Did you know there is a place where you can kayak, fish, float or boat the Deschutes river right from your own waterfront estate? Enjoy miles of boating or paddling from this legacy compound located just outside the resort area with no HOA & no CC&Rs. Yet you are an 11 minute bike ride to the resort village or the Sunriver Airport. This thoughtfully designed Frank Lloyd Wright inspired home offers timeless luxury and thoughtful design features, built for year round multi generational living with a commercial grade elevator. Close to the numerous restaurants, shops & golf, then come home to one of the finest riverfront compounds in the Bend Oregon area. Resting on two separate tax lots totaling 1.53 acres with over 200' of river frontage, it includes over 2400 sq ft of garage space, has designs & foundation in place for a 2nd 2200 sq ft guest house, all wrapped in sublime landscaping behind a gated entry. Be sure to watch the 2 minute video, ask for the link to the dedicated web page

56680 Lunar Drive, Bend

Listing courtesy of Bend Premier Real Estate LLC.

11500 NE Canyons Ranch, Terrebonne
$4,950,000
3 Beds ⋅ 6 Baths ⋅ 220222840 MLS
Featured on the cover of Build Magazine (May 2025) and as the Home Spotlight in Bend Magazine (Summer 2025), this 2024 estate is one of the newest custom homes in Ranch at the Canyons, offering luxury living with a modern organic aesthetic, smart home automation, designer lighting, and professional-grade appliances. Set on 6.5 private acres, walls of glass frame breathtaking views of Smith Rock, the Crooked River, and the Cascade Mountains. The home features a chef's kitchen, two private offices, a dedicated fitness room, guest casita, workshop, attached two-car garage, and a separate RV garage with 14-foot and 10-foot doors. The primary suite offers a steam shower and infrared sauna. A resort-style pool, multiple patios, and a courtyard fireplace complete the outdoor experience. Residents enjoy access to 1,700 acres of ranch land, trails, stocked ponds, equestrian facilities, pickleball and tennis courts, a clubhouse with fitness center and pool, and private Crooked River access.

11500 NE Canyons Ranch, Terrebonne

Listing courtesy of Cascade Hasson SIR.

11540 NE Canyons Ranch Drive, Terrebonne
$4,949,999
4 Beds ⋅ 6 Baths ⋅ 220198522 MLS
Perched above the Crooked River Canyon, this Ranch at the Canyons estate captures iconic views of Smith Rock, the River, and the Cascade Mountains. Stone + wood finishes add warmth, with hardwood floors, coffered ceilings, and custom built-ins. The heart of the home is a double-sided fireplace and chef's kitchen with Wolf/SubZero, 3 ovens, stone counters, oversized island, and banquette. The wet bar and seamless flow to the great room make entertaining effortless! The primary suite offers sweeping views and a spa-like bath, with a private junior suite and 2 additional ensuite bedrooms ideal for guests. Bonus room with wet bar and built-ins, plus an office with panoramic canyon and mountain views. Spacious mud/laundry room off the garage. Multiple outdoor seating areas invite you to relax and take in the surrounding landscape. Set on 12+ acres in a gated 1,700-acre community with 46 homesites, offering river access, equestrian facilities, clubhouse amenities, trails + more.

11540 NE Canyons Ranch Drive, Terrebonne

Listing courtesy of Avenir Realty.

13301 SW Seven Peaks Loop, Powell Butte
$4,875,000
3 Beds ⋅ 5 Baths ⋅ 220227833 MLS
Perched at one of Brasada Ranch's highest points, this home claims some of Central Oregon's most captivating views-a 240-degree sweep from Mt Jefferson across seven peaks of the Cascades to the Newberry Caldera, to the green Alfalfa farmland. Designed by Jim Rozewski and built by Palisade Homes, it sits close to the landscape without ever feeling exposed. Western Home Journal wrote that homes like this ''borrow the logic of an observatory, prioritizing outlook over enclosure.'' A staircase rises from the distinctive steel pivot entry door to the second-level great room wrapped in glass, timber beams overhead and a stone-and-steel fireplace at its heart. Built for entertaining, the kitchen opens through a servery window to a covered terrace with dining, seating, fireplace, and BBQ. Effortless from floor to floor, an elevator connects each level. Five outdoor living spaces dissolve the line between inside and out. Nothing here is accidental-this place, this view, impossible to replicate.

13301 SW Seven Peaks Loop, Powell Butte

Listing courtesy of Keller Williams Realty Central Oregon.

61410 Tam McArthur Loop, Bend
$4,490,000
4 Beds ⋅ 6 Baths ⋅ 220229076 MLS
Set within the coveted gated community of Broken Top, this Norman built, newer-construction single-level residence pairs contemporary design with exceptional livability and sweeping golf course views. Done to the nines with all the bells and whistles, the home offers 4 ensuite bedrooms, a dedicated office, second living room, and versatile bonus room ideal for a golf course simulator, gym, or media room. An oversized homesite provides rare space and privacy while the expansive outdoor living area features a built-in BBQ and overhead heaters for year-round entertaining. Spacious 4-car garage includes an EV charger. Inside, enjoy premium Thermador appliances, whole-home air filtration, and Cat 4 switches controlling lighting and blinds. Sophisticated finishes, generous gathering spaces, and seamless indoor-outdoor living create an exceptional retreat in one of Bend's most sought-after private communities.

61410 Tam McArthur Loop, Bend

Listing courtesy of The Agency Bend.

19167 Cartwright Court, Bend
$4,250,000
5 Beds ⋅ 7 Baths ⋅ 220223644 MLS
Overlooking Tetherow's prestigious Kidd's Corner with views of 4 fairways and situated across from the 3-acre neighborhood park in the highly sought after gated neighborhood, Tartan Druim is where you will find this impressive 6,504sf, light-filled home with detached casita. Capturing vast views throughout with features that comprise of a primary suite, guest suite, office, great room, gourmet kitchen, 2 powder rooms and mud room on the main level with 3 additional bedrooms, 2 bathrooms and 2 bonus rooms upstairs, and a 3 car garage. Graced w/high end finishes including a wood burning stone fireplace as a focal point in the great-room, built in bookshelves, wood beams, new carpet, fresh exterior paint and stain, and tons of fun touches. Kitchen amenities include an oversized island, ample storage, Dacor gas range, double ovens, Sub Zero fridge and beverage fridge. Outside enjoy the built in BBQ, gas firepit with seating area and sunken hot tub while taking in the panoramic views.

19167 Cartwright Court, Bend

Listing courtesy of Cascade Hasson SIR.

2451 Terri Drive, Medford
$4,250,000
6 Beds ⋅ 7 Baths ⋅ 220215329 MLS
Perched atop the peak of Mt. Baldy, this masterpiece occupies the most prestigious lot in Southern Oregon. Unparalleled 180-degree panorama, capturing the Rogue Valley from Table Rock to Mt. Ashland. This high-tech fortress of comfort blends security and self-sufficiency with resort-level opulence. The ''future-proof'' infrastructure includes a gravity-fed solar well with 4,000g of storage, a 26kW propane backup generator, and a 1,000g in-ground tank. An elevator connects three levels of luxury, highlighted by a main-level bifold window wall for seamless indoor-outdoor living. A 2BR/2BA guest suite with a full kitchen, while the connoisseur's lower level boasts a wine cellar, root cellar, sauna, and space for a gym or theater. A 40x16 heated pool and automated cover. 140 acres of adjoining BLM land. With a natural plateau ready additional structures. Just 10 miles from the airport.

2451 Terri Drive, Medford

Listing courtesy of eXp Realty, LLC.

4705 NE Wittmer, Prineville
$4,000,000
4 Beds ⋅ 4 Baths ⋅ 220223091 MLS
INCREDIBLE INVESTMENT OPPORTUNITY! Situated on 220 fenced & x-fenced ac, this 1-of-a-kind estate offers 10,000+ sqft of custom living space w/ breathtaking panoramic views in every direction. Ideal as a private retreat, luxury estate, or multi-generational property, the possibilities are endless. The home features 3 bd/ 4 ba, spacious floor plan, indoor pool, custom copper-finished bar & game room, 3-car garage, walk-in cooler & freezer, & expansive decks on both levels. The primary suite includes a fireplace & stunning views. ADA-friendly features include extra-wide hallways, stairlift, & wheelchair access to the pool area. A whole-home Generac generator provides peace of mind, while the 10+ person hot tub offers the perfect place to relax. Property amenities include 2 wells, an insulated shop w/ bathroom, woodstove, & 2 oversized roll-up doors. Horse trailer included. Ready for your vision. *Photos have AI furniture added.* Professional photos coming soon

4705 NE Wittmer, Prineville

Listing courtesy of Coldwell Banker Sun Country.

61594 Hosmer Lake Drive Lot 273 Unit Lot 273, Bend
$3,999,900
4 Beds ⋅ 5 Baths ⋅ 220217640 MLS
Welcome to an extraordinary collaboration between Fusion Home Builders and Jason Todd Home Design -- 5,000 square feet of refined luxury nestled within Tetherow, Bend's prestigious resort community. Fusion delivers unmatched craftsmanship and signature elegance, every detail of this home has been carefully considered. From the moment you open the door, soaring ceilings, abundant natural light, and a sense of privacy and sophistication set the tone. The main level showcases an open-concept kitchen flowing into generous dining and living spaces, anchored by an exceptional master suite, study, powder room, and abundant exterior hosting space. Two additional en-suite bedrooms, dedicated laundry, recreation room, fourth bedroom, full bath, and mudroom complete an interior where luxury and livability exist in perfect balance. The garage level includes a 2-car plus dedicated RV garage -- built for the Central Oregon lifestyle.

61594 Hosmer Lake Drive Lot 273 Unit Lot 273, Bend

Listing courtesy of eXp Realty, LLC.

61859 Hosmer Lake Drive Lot 374 Unit Lot 374, Bend
$3,999,000
4 Beds ⋅ 6 Baths ⋅ 220219257 MLS
The Legacy at Tetherow is a Curtis Homes flagship mountain modern residence set on nearly half an acre in one of Bend's most coveted golf and resort communities. Warm vertical wood siding, natural stone accents, timber beams, and low-slope metal roofs create a refined lodge presence, perched above the Cascade-Highland trail with open space at its back for privacy. A rare Tetherow feature: an HOA-approved fenced dog run, in a community that typically does not permit fencing. More than 5,100SF of heated living spans two levels. The main floor offers a vaulted great room with fireplace, a chef's kitchen with Wolf and Sub-Zero appliances and quartzite counters, a main-level primary suite with fireplace and spa bath, a second ensuite bedroom, den, and covered Trex balconies with BBQ and fire pit. Downstairs: rec room with wet bar, a glass enclosed gym with folding sliding doors, two more ensuite bedrooms, and a covered porch with hot tub and fire pit.

61859 Hosmer Lake Drive Lot 374 Unit Lot 374, Bend

Listing courtesy of Curtis Homes Realty.

59047 Old Lake Road, Christmas Valley
$3,999,000
5 Beds ⋅ 7 Baths ⋅ 220217220 MLS
In the middle of this desert oasis is a stunning, awe inspiring, welcoming home that sits in the middle of 288 acres. The property is bordered by 10s of thousands of acres of BLM land that provides endless recreational opportunities. Follow the rose bush lined driveway to the solid front door with sidelights and transom. View the expansive entry and vaulted ceiling with double stairways to the second floor. This home boasts travertine tile, slate, and hickory, Belizean rosewood, black walnut, and juniper hardwood inlaid flooring throughout the rooms. The kitchen is a cook's delight with the replica of an old wood cook stove and matching refrigerator, wall oven, warming oven, chef sink, plate rack, Lazy Susan, and appliance garage surrounded by hickory cabinets. Large rooms throughout. Comes with an incredible third floor apartment with French doors to balcony looking out over the grazing cattle in the pasture. Native rock accents. Quality materials. New exterior/interior paint/decks.

59047 Old Lake Road, Christmas Valley

Listing courtesy of RE/MAX Key Properties.

17945 Mountain View Road, Sisters
$3,999,000
4 Beds ⋅ 7 Baths ⋅ 220214782 MLS
Nestled in a breathtaking location, this timeless estate offers sweeping views of the majestic Cascade Mountains and Whychus Creek Canyon. Surrounded by luxurious gardens, the home stands in contrast to the low-maintenance high desert landscapes that dominate the nearly 40-acre property and the sparsely developed land around it. With European-inspired elegance, this estate boasts an array of exceptional features, including a lighted tennis court, three stunning rock fireplaces, and expansive aggregate patios--both covered and uncovered. Additional highlights include a heated dog kennel, solarium, sunroom, formal and informal dining spaces, and an oversized family room. The home offers four bedrooms, each with an ensuite bathroom, including a main floor primary suite with two full baths, separate closets, and a chef's kitchen with a large pantry. Enjoy the convenience of a three-car garage with ample attic storage for all your toys.

17945 Mountain View Road, Sisters

Listing courtesy of Ponderosa Properties.

321 Pair A Dice Ranch Road, Jacksonville
$3,995,000
4 Beds ⋅ 6 Baths ⋅ 220203312 MLS
A true masterpiece in Southern Oregon, 1st time, extraordinary Mediterranean estate captures sweeping views of the Jacksonville Mountains & glittering city lights. Set on 5 private park-like acres w/city water, ±5700 SQ FT of luxury on main level, ±3484 SQFT private lower level; ideal for entertaining, additional living/guest quarters & lg detached private guest Casita--designed & built by Mike Pagnini--showcases unmatched craftsmanship and timeless elegance. Highlights include 4 luxurious primary suites, 6 baths, a Pebble Tec pool & spa, guest casita, & a 12-car garage. Inside, grand living spaces feature soaring dome ceilings, 8 fireplaces, and French doors opening to stunning outdoor living areas. Chef's kitchen, wine cellar, theater, & fitness rooms complete the experience. Ideally located near Rogue Valley International-Medford Airport w/Million Air Medford for private jet access, & minutes from the Britt Music & Arts Festival, Oregon Shakespeare Festival, & renowned wineries.

321 Pair A Dice Ranch Road, Jacksonville

Listing courtesy of John L. Scott Medford.

62333 McClain Drive, Bend
$3,950,000
4 Beds ⋅ 6 Baths ⋅ 220227071 MLS
Welcome to your ultimate entertainer's paradise in the coveted Westgate Community! This custom-built masterpiece sits on 2.5 acres and was featured in the 2025 COBA Tour of Homes, winning accolades for Best Kitchen, Best Landscaping, & Best Value. With its modern design framed by stunning Cascade Mountain views, this home is truly spectacular. At its heart lies a jaw-dropping gourmet kitchen, complete with top-of-the-line Thermador appliances, perfect for culinary adventures. The main level features a luxurious primary suite with a spa-like bathroom, plus 2 additional bedrooms, each boasting private en-suites. Ascend to the expansive loft designed for function and fun, including a full bath, bedroom, and wet bar-ideal. Step outside to your private oasis with a underground heated 8'x44' MOD pool with fenced yard. Storage is easy with a rare 2,491 sq ft shop with 14' doors. This one-of-a-kind home perfectly blends luxury and everyday practicality, making it the quintessential retreat.

62333 McClain Drive, Bend

Listing courtesy of Cascade Hasson SIR.

29700 SW Mountain Road, West Linn
$3,850,000
5 Beds ⋅ 5 Baths ⋅ 220225322 MLS
OWNER/SELLER FINANCING AT 5%. Luxury horse property and equestrian estate for sale in West Linn, Oregon. Gated 24.24± acre EFU farm near Portland with 80'x120' indoor riding arena, 13 oversized and 7 standard stalls plus room for 7 more, 8,500± SF event venue barn, 4,646± SF main home, second 1,800± SF home, pool, tennis court, shop, 7 cross-fenced pastures and 60 acres of irrigation water rights. Turnkey income from arena lease, boarding, and childcare. Minutes to I-205, Wilsonville and Portland. Existing revenue streams include an approximately $4,000/month horse barn with arena lease, and $5,000/month childcare operation. OWNER FINANCING / SELLER FINANCING AVAILABLE AT 5% WITH SUBSTANTIAL DOWN. Luxury horse property for sale in West Linn, Oregon. This gated 24.24± acre equestrian estate in Clackamas County offers turnkey horse facilities, event venue potential, irrigation water rights, and established income, all minutes from Portland.

29700 SW Mountain Road, West Linn

Listing courtesy of Keller Williams Realty Mid-Willamette.

664 NW Powell Butte Loop, Bend
$3,800,000
4 Beds ⋅ 5 Baths ⋅ 220204557 MLS
Experience elevated living on Awbrey Butte w/ this sleek & modern masterpiece. Designed w/ elegance in mind, this stunning home showcases imported Italian marble flooring & custom RGB LED ceiling lights throughout. The great room features soaring ceilings, fireplace, & floor-to-ceiling windows that frame the easterly views. The gourmet kitchen is a showstopper—featuring a large island w/ breakfast bar, granite countertops, double oven, walk-in pantry, & high-end Café commercial appliances. The main level offers a luxurious primary suite w/heated bathroom floors, dual vanities, soaking tub, tile shower, & walk-in closet. Also on the main level: a private office & cozy den! Upstairs, enjoy a game room & dedicated home theater, 2 junior suites each w/ large walk-in closets & private balconies, plus an additional bed & bath. Enjoy 4th of July fireworks from the expansive front deck or entertain year-round on the covered back patio. Minutes to trails, parks, shops, and downtown Bend!

664 NW Powell Butte Loop, Bend

Listing courtesy of Cascade Hasson SIR.

20172 Soft Breeze Court, Bend
$3,799,000
4 Beds ⋅ 5 Baths ⋅ 220222292 MLS
Set along a coveted stretch of riverfront, this modern residence stands among Bend's most compelling offerings--where architecture and setting align with rare clarity. The home opens to a series of outdoor living spaces, fire features, and sweeping water views, creating a seamless connection to the landscape and rhythm shaped by river. Inside, a refined composition clean-lined detailing, and expansive glass draws in natural light while framing the outdoors with intention. The kitchen is designed for both elevated entertaining and daily ease, anchored by a natural stone island and a stainless steel appliance suite. A main-level primary suite offers a private retreat with a steam shower and patio Hot Tub access. Each additional bedroom in main house is en suite, complemented by an office, utility space, and triple-zoned HVAC. An attached apartment with its own garage bay adds flexibility. All of it, just moments from Bend's everyday conveniences--yet a setting that feels a world apart.

20172 Soft Breeze Court, Bend

Listing courtesy of Cascade Hasson SIR.

18880 Baker Road, Bend
$3,750,000
5 Beds ⋅ 3 Baths ⋅ 220221468 MLS
A riverfront sanctuary that comes to market once in a generation. Encompassing nearly three acres and 400 feet of low-bank frontage on the Deschutes River, this property represents one of the largest riverfront parcels in all of Bend - set along one of the Northwest's most iconic waterways, with a sweeping stretch of shoreline unlike anything else on the market. The River Home spans nearly 4,000 sq ft with multiple indoor and outdoor living spaces, a private primary wing, and a guest wing - all with unobstructed river views. Here, the Deschutes National Forest is your closest neighbor - and the cherished mountain town of Bend is just minutes away. Step from your back door to cast a line, host a gala, or watch the seasons change from the bank. Family weddings, holiday events, and legendary dinner parties have graced these grounds for years. As the current owners will tell you: no one ever turns down an invitation, and guests are reluctant to leave. It's hard to put a price on magic.

18880 Baker Road, Bend

Listing courtesy of Stellar Realty Northwest.

1440 E Nevada Street, Ashland
$3,750,000
5 Beds ⋅ 5 Baths ⋅ 220206087 MLS
A private retreat setting where nature meets luxurious living. The 5BR/5BA Contemporary home captures the Siskiyou mtn range at every turn. The main level offers floor to ceiling windows, hardwood floors, living & dining room & Chef's kitchen appointed w/ island, wet bar, pantry, double ovens, wolf stove & more! Upstairs the main bedroom suite is an oasis unto itself w/views, decking & spa. A second primary suite, 2 add'l bedrooms/bath & laundry room w/abundant storage are downstairs. Each room has custom finishes & exquisite views to ensure a lifestyle of privacy & relaxation. Outside you're met w/soothing soundscape of a tiered cascading creek, lagoon waterfall style pool, cabana area, outdoor kitchen & bath, for ease of entertaining. Equestrian, livestock or agricultural enthusiasts will delight w/the endless possibilities. Fruit trees, garden beds, greenhouses, chicken coop & workout room complete this singular estate. 1BD/1BA guest apartment is a bonus to this luxe property.

1440 E Nevada Street, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

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