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709 ASH CREEK RD, Riddle
$365,000
3 Beds ⋅ 2 Baths ⋅ 734525790 MLS
Custom Cabin Creekside home featuring soaring knotty pine ceilings and beautiful wood flooring throughout. The inviting living area showcases a stunning river rock gas fireplace. The bright, functional kitchen offers, custome wood cabinets, stainless steel appliances, a center island, eating bar, and gas stove—perfect for everyday living and entertaining.The spacious primary suite features high ceilings, a walk-in closet, and a well-appointed ensuite WI custom tile shower with double sinks and ample storage.A large backyard deck extends the living space outdoors, providing the perfect setting for relaxing, entertaining, and enjoying the surrounding scenery. A spacious driveway provides ample parking for RVs, boats, and multiple vehicles. The property also features a garden area with raised beds, perfect for growing flowers, vegetables, or enjoying outdoor living. Behind the detached carport are two large additional storage units, offering excellent space for hobbies, equipment, or extra storage. One of the units includes a full bathroom and kitchenette area, providing added convenience and versatility for a variety of uses.A gorgeous year-round creek enhances the property's natural beauty, creating a peaceful and picturesque setting.Circular driveway with lots of parking.

709 ASH CREEK RD, Riddle

238 BALL LN, Riddle
$314,000
2 Beds ⋅ 2 Baths ⋅ 657165350 MLS
Discover your ideal hobby farm retreat on this expansive 2.47-acre flat, usable property! Fully fenced with an automated gate, this gem boasts stunning mountain views and seasonal Cow Creek, enhancing its picturesque charm. Perfect for horses and fulfilling all your hobby farm dreams, the land features numerous outbuildings, grape stands, five black walnut trees, two flourishing plum trees, a delightful apple tree, and a pear tree. The property also features new vinyl and chain-link fencing, a convenient dog yard located near the house, a sturdy reinforced bridge, a cozy chicken coop, various practical sheds, and a spacious carport/shop area equipped with a solid concrete floor and upgraded electrical systems. The beautifully updated home is equally impressive, featuring a new roof, double-pane windows, siding, and exterior paint all installed in 2019. Enjoy year-round comfort with a modern central air heat pump and upgraded windows. For ultimate peace of mind, a brand new high-end propane generator ensures uninterrupted power. Inside, the gorgeously remodeled kitchen shines, featuring a skylight, updated appliances, a double oven, sleek granite countertops, and beautiful custom soft-close cabinets. High-end waterproof luxury plank flooring flows seamlessly throughout. The guest bathroom features an easy-access walk-in tub, while the primary bedroom en-suite offers a luxurious remodel, complete with a spacious walk-in shower and a generous walk-in closet. With ample space for gardening and animals, the possibilities are truly endless. Don't miss this exceptional opportunity at all this value!

238 BALL LN, Riddle

3716 WEAVER RD, Riddle
$698,800
4 Beds ⋅ 3 Baths ⋅ 796431730 MLS
WOW! One-of-a-kind home completed in 2024 and set on 5.16 private acres, this custom-built property offers stunning river & mountain views and exceptional flexibility. Expansive windows and vaulted ceilings fill the home with natural light while framing the surrounding landscape. A bi-parting multi-slide door opens from the living area and kitchen to a spacious deck, creating seamless indoor-outdoor living. Designed for comfort and function, the home features knotty pine accents, a custom oversized rustic-style ceiling fan, kitchen display ledges, and integrated storage maximizing every square foot. Quartz countertops, stainless steel appliances, a spacious pantry, pellet stove, and a blend of luxury vinyl plank, tile, and carpet complete the open design. The floor plan includes two main-level bedrooms with a Jack-and-Jill bath w/ walk-in tile shower, while the upper-level primary suite offers a private bath and view deck. A fully equipped 1-bedroom apartment above the detached 2-car garage includes a full bath with marble counters, kitchenette, and dual refrigerators—ideal for multigenerational living, guests, or income potential. The large shop includes a full bath, pellet stove, 220V power, and washer/dryer hookups. Infrastructure includes brand-new septic, private well, Starlink internet, and a whole-house generator plug. Outside features RV parking and hookups, a private road to the bottom of the property, and an outdoor space prepped for a wood-fired pizza oven. A breezeway between home and garage provides covered parking with river views, while gas plumbing and hot tub hookups are in place. Entertain on the deck, or take in wildlife and the occasional passing train. Properties combining newer construction, acreage, river views, and multigenerational living are increasingly rare. With custom craftsmanship, flexible spaces, and thoughtful design throughout, this is truly a one-of-a-kind offering. Schedule your tour today!

3716 WEAVER RD, Riddle

1263 YOKUM RD, Riddle
$260,000
595297034 MLS
An exceptional opportunity to own 165 acres of Farm/Forest land at one of Douglas County's most unique river confluences—where Cow Creek meets the South Umpqua River near Riddle. This remarkable property offers approximately 2/3 mile of combined river and creek frontage, creating a rare blend of natural beauty, privacy, and recreational value. One of the property's standout features is a level, open area with excellent potential for a future homesite, hunting cabin, or tiny house retreat (subject to county approvals). Conveniently located near available utilities, this site offers an attractive balance of rural seclusion and practical accessibility.Currently enjoyed as a recreational retreat, the land provides outstanding fishing, wildlife viewing, hunting, and outdoor adventure. The property is home to abundant wildlife, including deer, bear, cougar, and bobcat, making it an ideal destination for sportsmen, outdoor enthusiasts, or those seeking a private escape. The extensive river and creek frontage offers peaceful settings, scenic views, and exceptional fish and wildlife habitat. With expansive acreage and Farm/Forest zoning, this property presents a wide range of possibilities, including timber management, agricultural pursuits, recreation, a private legacy property, or future development potential where permitted. Rarely does a property combine significant water frontage, sloped wooded acreage, a potential building site, nearby utilities, and such an exceptional location. Whether you're envisioning a weekend getaway, hunting basecamp, or a place to build your Oregon dream, this is a truly one-of-a-kind offering.

1263 YOKUM RD, Riddle

946 E 4TH AVE, Riddle
$270,000
3 Beds ⋅ 1 Baths ⋅ 114264188 MLS
Charming and move-in ready, this beautifully updated 3-bedroom, 1-bath home offers 816 square feet of comfortable living space with timeless character and modern updates. Original hardwood floors have been beautifully maintained, adding warmth and charm throughout the home.The updated galley kitchen features durable tile flooring, providing both style and functionality for everyday living. Thoughtful updates throughout make this home ready for its next owner to enjoy.Outside, you'll find exceptional storage and workspace, including an impressive 24' x 30' shop—perfect for hobbies, projects, parking, or extra storage. Two additional wood storage sheds (10' x 16' and 12' x 14') offer even more flexibility for tools, equipment, or seasonal items. Large driveway offers plenty of additional parking for rv or toysWhether you're looking for a cozy place to call home or a property with plenty of room for projects and storage, this well-maintained home is a must-see.

946 E 4TH AVE, Riddle

631 E 4TH AVE, Riddle
$292,637
4 Beds ⋅ 2 Baths ⋅ 205213801 MLS
Welcome to this delightful 4-bedroom, 2-bathroom home nestled in the peaceful town of Riddle, Oregon. This inviting property offers the perfect blend of comfort, functionality, and outdoor enjoyment—ideal for families, hobbyists, or anyone seeking a little extra room to breathe.Inside, you’ll find a quaint open floor plan that creates a seamless flow between the living, dining, and kitchen areas. Natural light fills the space, and the layout allows for both cozy gatherings and entertaining with ease. The kitchen opens into the main living area, creating an inviting central hub of the home.There are four well-sized bedrooms offering flexible space. Two full bathrooms provide convenience and privacy for everyone in the household.A major bonus is the converted garage, which now serves as additional living space—perfect for a family room, game room, home gym, or potential guest quarters. This added square footage brings flexibility and function to suit your lifestyle.Outdoors, this property truly shines. Enjoy the covered back patio, a peaceful spot for relaxing or hosting BBQs year-round. The fenced backyard features plenty of space for garden beds, ideal for growing your own vegetables, herbs, or flowers. For those with a green thumb or a passion for sustainability, this is a gardener’s dream.You’ll also find a dedicated workshop in the backyard—perfect for DIY projects, woodworking, or extra storage. Whether you’re a hobbyist or simply need a space to tinker and organize tools, this workshop is a fantastic addition.Call for your tour!

631 E 4TH AVE, Riddle

3450 SHOESTRING RD, Riddle
$550,000
4 Beds ⋅ 2 Baths ⋅ 182693375 MLS
Welcome to your dream country retreat where timeless charm meets modern luxury, this stunningly remodeled country estate offers the perfect blend of comfort, functionality, and natural beauty. Set on just over 3 flat, fully usable acres behind a secure gated entry, this property delivers exceptional privacy, seclusion, and breathtaking panoramic mountain views—plus creek frontage for a serene, picturesque setting. Inside, tasteful updates preserve the home’s original character while elevating everyday living. The main floor features a primary suite with a luxurious bathroom, offering a peaceful escape at the end of the day. The beautifully renovated kitchen boasts recessed lighting, ample cabinetry, and a seamless layout for both everyday meals and entertaining. Step down into the inviting living room, where log beams and a striking rock fireplace create a warm and rustic ambiance—perfect for cozy evenings with loved ones. Step outside to explore everything this incredible property has to offer: detached 2-car garage, HUGE shop for all your projects and storage needs, hay barn, pole barn, chicken coop, and tool shed—ideal for hobby farming or full-scale homesteading The land is fenced and flat, making it perfect for livestock, pets, gardening, or simply enjoying the expansive open space. After a day of country living, unwind in the covered hot tub area while soaking in the tranquil sounds of nature. Whether you’re looking for a private retreat, a working homestead, or the best of both worlds, this remarkable property delivers it all.

3450 SHOESTRING RD, Riddle

795 E ST, Riddle
$449,000
154695292 MLS
TWO HOMES FOR THE PRICE OF ONE! — A RARE RETREAT WITH EXCEPTIONAL VALUE!!BOM at no fault of the home. Nestled among serene mountain views and surrounded by fresh air, privacy, and natural beauty, this remarkable property offers an opportunity that is truly hard to find: two fully functional homes, each with its own character, comfort, and generous living space. Whether you’re seeking a multi-generational living setup, rental income potential, or simply room to spread out, this property delivers versatility without compromise.From the moment you arrive, the setting feels peaceful and inviting. Mature trees, open sky, and the quiet of nature create a sense of retreat, while thoughtful upgrades and abundant storage make everyday living effortless. Buyers are encouraged to conduct their own due diligence regarding all aspects of the property. While information is considered reliable, it is not guaranteed. Some furnishings in both homes may be negotiable. I have attached a outline on both living areas for your convince, just ask your Realtor to print you out a copy. Interior photos are mostly of the Pole Barn and just a couple of the front house. More photos will be added as soon as possible.

795 E ST, Riddle

215 E 2ND AVE, Riddle
$135,000
548243938 MLS
This is your opportunity to own two homes on one property!! Investors delight for rental cashflow or extended family home seekers! Centrally located in the heart of small-town Riddle just minutes from I5 and close to 7 Feathers Casino. Walking distance to elementary school, high school, post office, convenience store, bakery, etc. Each home is a 1 bedroom, 1 bathroom home- with individual power and water meters. Property is being sold as is. Neighborhood improvements (in construction) include a Riddle Activity Center: A comprehensive recreation and resiliency center in Southern Douglas County where community members will gather to improve their health, be active, have fun, and access essential services. Key program goals include Athletic courts, fitness center, indoor walking track, outdoor event spaces, concessions stand, emergency & disaster response, community and cultural enrichment, meeting & event rooms, community kitchen, dining hall, community theatre & music programs, community cafe, STEM events & programming, athletic tournaments, sporting events, childcare, pre-school, afterschool and summer programs, medical, dental and mental health care and more! Enjoy small town living at its finest while close to all the local amenities such a newer Grocery Outlet, Starbucks, Tractor Supply and new EV Charging station. Take advantage this rare dual-home opportunity—schedule your showing today!

215 E 2ND AVE, Riddle

247 OAK ST, Riddle
$260,000
3 Beds ⋅ 1 Baths ⋅ 623841764 MLS
Welcome to small-town living at its finest! This charming 3-bedroom, 1-bath home offers comfort, style, and functionality all in one inviting package. The beautifully remodeled kitchen is designed to fit today’s modern lifestyle, featuring updated finishes and a welcoming space perfect for cooking and gathering. The remodeled bathroom adds a fresh, updated feel, while the home’s heat and air conditioning provide year-round comfort. Outside, you’ll love the fenced backyard with beautiful landscaping, creating a peaceful setting for relaxing, entertaining, or gardening. A detached tool shed offers extra storage and workspace, and the one-car garage includes a built-in bench and cabinets for added convenience. With a gas furnace and thoughtful updates throughout, this cozy home is ready for you to move in and enjoy the charm of small-town living.

247 OAK ST, Riddle

5925 COW CREEK RD, Riddle
$482,000
1 Beds ⋅ 1 Baths ⋅ 667497605 MLS
Incredible off-grid opportunity on 143 acres outside of Riddle, OREGON! Enjoy approximately 1 mile of Cow Creek frontage—home to bass, steelhead, trout, and a rich variety of other aquatic wildlife. Multiple seasonal creeks, an old pond, and stunning natural swimming holes in Cow Creek make it perfect for outdoor recreations like kayaking, fishing, gold panning, or simply relaxing by the water. The land includes merchantable timber, multiple structures, and ample space for RVs, campsites, and a future homesite. Deer, Elk, your occasional friendly Bear and many other animals roam the forest around. This one-of-a-kind property also features a cozy 1-bedroom, 1-bath rustic caretaker’s cabin with spring water and a septic system already in place (though the conditions are unknown). Whether you’re looking for a private homestead, a recreational retreat, or a property with income potential, this expansive slice of southern Oregon offers endless possibilities. Off-grid living with pure beauty and privacy, yet just a short drive from amenities in Riddle, Canyonville, and Myrtle Creek. Don’t miss this unique chance to own a truly special piece of land on the beautiful Cow Creek River. Please do not disturb caretaker or wonder onto private property without permission. Buyer to do their due diligence on all aspects of the property.

5925 COW CREEK RD, Riddle

221 MAIN ST, Riddle
$506,000
4 Beds ⋅ 2 Baths ⋅ 203028965 MLS
Restored Victorian, .89 Acre Lot! Located in the charming small town of Riddle, this home has been extensively restored over the last 5 years and is in excellent condition inside and out. Move in Ready NOW! It is the historic John Bouseman Riddle House, built in 1894 by Mr Riddle, the town founder and successful entrepreneur in Southern Oregon. There are 3 very large outbuildings, including a 20x24 detached 2 car garage, 30x45 4 car garage/shop, and 18x45 RV garage! Park 6 cars and RV or boat. There is additional parking pad behind the shops and tons of parking in the driveway. Located on nearly 1 acre, the lot is level, fenced and fully usable. The views from nearly every window and the large porches overlook the hills and pastures of the Cow Creek Valley. 9'-4" ceilings on the main level, 9' ceilings upstairs, 4 big bedrooms with very large closets and 1 full bath are all upstairs. The Main level has the formal parlor, large dining room, kitchen with eating area, spacious den, full bath, laundry, and 8x11 Sunroom (not included in total SF). The large den on the main level has an attached bath and could be a primary bedroom (or 5th bedroom) on the Main level. There is also a cement basement, 13x19 and bone dry. The home boasts all the Queen Anne style of the era - large porches front and back, oval attic window, gingerbread trim, wood floors throughout, etc. Among the many upgrades: New HVAC system, Extensive Electrical and Plumbing Replacement, Sewer line, new paint inside & out (by LBP certified painter), Original Fir floors restored, new kitchen & appliances, bathroom remodels, extensive landscaping and property clearing & fencing, and so much more. It is so difficult to find a Victorian home restored, not remodeled. This property has potential as a Wedding Venue, Bed and Breakfast, Small Business home base, or just lovely small town home. Call to visit this charming, classic home today. Seller is Listing Agent

221 MAIN ST, Riddle

135 D ST, Riddle
$196,000
408803809 MLS
Unique opportunity to own a versatile church property in the heart of Riddle, Oregon. This offering includes two separate buildings with a large paved parking lot for convenient access and ample guest or congregation parking.Main Church Building: Thoughtfully designed with a traditional church layout, including a welcoming sanctuary space and private office. Ideal for worship services, community gatherings, or repurposing for other uses.Second Building: A spacious open-concept structure featuring two restrooms and a full kitchen, offering endless potential for events, classrooms, daycare, or multi-purpose ministry use.Whether you're looking to continue as a place of worship or transform the space for community, commercial, or residential purposes, this property offers flexibility and charm in a peaceful small-town setting.

135 D ST, Riddle

2100 BOYER RD, Riddle
$430,000
3 Beds ⋅ 1 Baths ⋅ 691373860 MLS
Escape to your own private retreat on 40 fully fenced acres with water rights, a charming 3-bedroom, 1.5-bath home, and a spacious shop perfect for hobbies, storage, or equipment. This beautiful property offers a blend of functionality and rural tranquility, ideal for those seeking space, privacy, and productivity.Enjoy the established orchard, ready to provide seasonal harvests, and plenty of room for livestock, gardening, or expanding your agricultural vision. The home features comfortable living spaces, practical updates, and country charm throughout.With water rights in place, you’ll have reliable access for irrigation and future projects. The property is fenced and cross-fenced, making it ready for animals or secure farming use. Whether you’re dreaming of a homestead, hobby farm, or simply a peaceful getaway, this property has it all. Beautiful lane creek flows through the property and there is merchantable timber throughout the 40 acres!

2100 BOYER RD, Riddle

3161 GLENBROOK LOOP RD, Riddle
$275,000
2 Beds ⋅ 1 Baths ⋅ 652390173 MLS
A Sweet and Simple ranch-style home on a gorgeous 1.35-acre parcel in a peaceful country setting. The living room features hardwood floors and a toasty wood stove insert with an attractive stone backdrop that brings character to the room. The large, open kitchen includes quality cabinets and a pleasant workspace. 2 Bedrooms plus a large family room that could be made into Primary suite, and the sunroom off of the primary bedroom make this a sizable home at this price! Out back, the covered deck and covered brick patio overlook a large level yard with mature trees and the neighboring pasture that stretches afar. Exterior improvements include a chicken coop, raised garden beds, a barn for animals, a greenhouse, and a separate workshop for projects or storage. This property is worth a look, so make your appointment today to see it!

3161 GLENBROOK LOOP RD, Riddle

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

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