Riddle Homes for Sale

Welcome to Riddle, Oregon – a hidden gem nestled in the heart of Douglas County, where the charm of small-town living meets the beauty of the Pacific Northwest. With its breathtaking landscapes, friendly community, and a rich tapestry of outdoor adventures, Riddle offers a serene lifestyle that’s hard to resist.

Riddle is surrounded by lush forests and rolling hills, making it a paradise for nature enthusiasts. Whether you enjoy hiking, fishing, or simply soaking in the stunning views, the area provides an abundance of recreational opportunities. The nearby Umpqua River is perfect for kayaking and fishing, while the scenic trails invite you to explore the great outdoors.

The town itself boasts a close-knit community where neighbors become friends, and local shops and eateries showcase the warmth of small-town hospitality. Residents enjoy a slower pace of life, with the charm of historic buildings and the vibrant spirit of local events that bring everyone together.

For those considering a move, Riddle offers an array of homes for sale that cater to various lifestyles and budgets. From cozy single-family homes to spacious properties with sprawling yards, there’s something for everyone. Imagine waking up to the sounds of nature, sipping your morning coffee on a sunlit porch, and enjoying the tranquility that Riddle has to offer.

Whether you’re looking to settle down or find a peaceful retreat, Riddle, Oregon, invites you to explore its homes for sale and discover the perfect place to call home. Embrace the simplicity and beauty of life in this charming town – your dream home awaits!

Newest Riddle Homes for Sale

$350,000

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

$509,000

3 Beds ⋅ 2 Baths ⋅ 221026271 MLS

Nestled among the trees on five private acres in Riddle, this distinctive 3-bedroom, 2.5-bath home with a versatile flex room offers the peace and seclusion of country living while remaining conveniently accessible. Beautiful territorial and mountain views and a wooded setting create a wonderful sense of privacy.Step inside to an impressive great room featuring soaring vaulted ceilings, walls of windows and a dramatic floor-to-ceiling stone hearth & pellet stove—the perfect centerpiece for cozy evenings at home. Abundant natural light and views of the surrounding landscape bring the outdoors in. The spacious kitchen offers extensive cabinetry, stone countertops and generous workspace, while the flex room provides options for a home office, media room, gym or hobby space.The primary suite features a spacious ensuite with dual sinks, jetted soaking tub, separate tiled shower and large walk-in closet with built-in storage. Two additional bedrooms, another full bath, half bath, dedicated laundry and abundant storage add functionality.Outside, an expansive deck overlooking the trees and surrounding hills creates an inviting space for outdoor dining, entertaining or simply enjoying the peaceful setting. A two-car garage and plenty of additional parking provide room for vehicles, guests and more.A unique property offering acreage, privacy, views and versatile living. Just minutes from I-5.

1265 EVERGREEN RIDGE RD, Riddle

$290,000

3 Beds ⋅ 2 Baths ⋅ 579075438 MLS

Seller says make offer-New Price!, let's get you into your new home! All NEW remodeled home at discounted price! New Roof, new electric including panel, upgraded plumbing, appx 90% new drywall, new paint in/out; new flooring; new drywall, new dual pane/vinyl frame windows; upper bedrooms new heat; all new kitchen package-gas range/oven, dishwasher, garbage disposal, lg stainless sink, refrigerator, new storage cabinet that functions as pantry, new stainless range hood; rebuilt access landings; new vapor barrier; new ducting in crawlspace; All new main level bath, remodeled upper bath; new ceiling fans in most rooms. Throw in mud room that could dbl as office. Under stair storage w/motion light, new exterior lights. This home may be 99% new but the charm of the original build still remains- gingerbread architecture in/out. Locating home in front 1/3 of property gives you a backyard to enjoy, with room for 2 car garage and/or off street parking and still have room for yard. County/City maintained alley is easement to benefit the properties for access. Sale includes home warranty! Ask for amenities for additional extensive info! Located in a quiet small community you are only about 6 minutes to Canyonville, 5 min to I-5 north or south for additional amenities, recreation, medical and dental. At this low price this is a definite must see if you want to live in a nearly new home at a very competitive price, with potential for help from Seller or lender!

222 W 1ST AVE, Riddle

$330,000

4 Beds ⋅ 2 Baths ⋅ 611217303 MLS

Welcome to this spacious 4-bedroom, 2-bath home in the heart of Riddle! Offering 2,232 square feet of living space, this well-maintained home features a functional floor plan with generous room sizes and plenty of storage and built-ins throughout. Upstairs you'll find the large primary suite, along with two additional guest bedrooms with built-ins in every room. Both bathrooms include a walk-in shower and separate tub. The main level features a large living room and a downstairs bedroom, perfect for an office or guests, and a thoughtfully designed kitchen featuring a pantry and plenty of space for everyday living and entertaining. The fully fenced yard provides privacy and room to relax, entertain or garden, while the covered patio creates the perfect space for year-round outdoor enjoyment. This home also offers a two-car garage with plenty of extra parking for an RV, boat, or just extra parking for guests. Conveniently located near schools, parks, and local amenities, this property offers the perfect blend of comfort, space, and small-town living. Don't miss the opportunity to make this wonderful home your own.

212 PARK ST, Riddle

$775,000

4 Beds ⋅ 2 Baths ⋅ 203722712 MLS

Escape to your own private 7.22-acre retreat with gated entry, beautiful valley views, private beach and direct access to Cow Creek. This updated 4-bedroom, 2-bath home is surrounded by two irrigated pastures, mature woodland, and an incredible orchard featuring 70+ fruit and nut trees, berries, grapes, asparagus, and raised garden beds with drip irrigation. A spacious greenhouse, barn with hot and cold water, multiple outbuildings, chicken coop, RV hookup, and fenced pastures make this property ideal for hobby farming, homesteading, or simply enjoying peaceful country living. The detached garage includes a fully furnished 1-bedroom apartment with its own electric meter, full kitchen, laundry, covered deck, and ductless heating and cooling—perfect for guests or multi-generational living. Additional features include domestic and irrigation water rights from Cow Creek, a domestic water filtration and UV system, a 500-gallon propane system with tankless water heater, a 12kW backup generator, EV charging, and a new roof installed in 2025. A rare opportunity to enjoy privacy, self-sufficiency, and the beauty of Southern Oregon.

220 Faver DR, Riddle

$649,000

2 Beds ⋅ 2 Baths ⋅ 258104904 MLS

Nestled along the banks of Cow Creek, this off grid private 23-acre retreat offers the perfect blend of modern comfort and natural beauty. Built in 2019, this custom single-level home features 2 bedrooms, 2 bathrooms, vaulted ceilings, luxury vinyl plank flooring, granite countertops, and a cozy wood stove. Large windows and sliding doors invite the outdoors in, showcasing peaceful views of the river, mountains, and surrounding woods. Enjoy year-round relaxation from the covered deck overlooking the property's park-like setting. The gated acreage includes a detached garage, RV parking, workshop, garden area, outbuildings, and ample space for recreation, hobbies, or a self-sufficient lifestyle. Additional features include a mini-split heating and cooling system, tankless water heater, private water source, and high-speed internet availability. Conveniently located with paved road access while offering exceptional privacy and direct Cow Creek frontage. A rare opportunity to own a scenic Southern Oregon getaway. Approved for the addition of 10 campsites on the property.

4696 COW CREEK RD, Riddle

$590,000

3 Beds ⋅ 2 Baths ⋅ 648289917 MLS

A ONE-OF-A-KIND SOUTHERN OREGON RETREAT! Set on 1.38 peaceful acres, 1631 Glenbrook Loop Rd offers the perfect blend of privacy, space, character, and incredible amenities. With a sparkling in-ground gunite pool, large shop, RV parking, multiple outbuildings, and over 2,900 sq ft of functional living space, this property is designed for enjoying every season of life.Step inside and discover a home filled with character and personality, featuring beautiful crown molding, hardwood floors, fireplaces, built-ins, and unique details you simply don't find in newer construction. Specialized roll-out beds, ventilated produce shelving, and thoughtful touches throughout add charm and functionality without sacrificing comfort. The spacious kitchen offers abundant cabinetry, pantry storage, double ovens, and plenty of room to gather with family and friends.The finished attic and basement areas provide even more flexibility for guest space, hobbies, home offices, storage, recreation, or multigenerational living. Multiple gathering spaces make this home ideal for both everyday living and entertaining. Then step outside and discover what makes this property truly special. The private backyard oasis features a beautiful in-ground gunite pool, expansive patio areas, and mature landscaping, creating the perfect setting for summer entertaining or relaxing at home. The 1.38 acres give you room to spread out, while the large shop, RV parking, covered storage, and multiple outbuildings provide plenty of space for vehicles, equipment, hobbies, projects, and recreational toys. Space, privacy, a pool, a shop, acreage, and character—all in one incredible property. Connected to city water and offering the feel of a private country retreat, 1631 Glenbrook Loop Rd is a rare opportunity to enjoy a property that truly has it all. Come see the possibilities and fall in love with this unique Southern Oregon retreat!

1631 GLENBROOK LOOP RD, Riddle

$1,650,000

2 Beds ⋅ 3 Baths ⋅ 647409474 MLS

Experience elevated country living at 1757 Riddle Bypass—an exceptional 42.48-acre estate offering luxury, privacy, and versatility. This stunning 3,884 sq ft custom cedar home showcases impeccable craftsmanship with rich woodwork, hardwood floors, soaring beamed ceilings, and an open-concept design filled with natural light.The gourmet kitchen is designed for both function and style, featuring granite countertops, a large island, and an eating bar—perfect for entertaining. The home also includes a spacious finished daylight basement offering incredible flexibility for additional bedrooms, a game room, or multi-generational living.Step outside to take in breathtaking panoramic views of the surrounding mountains and valley from the expansive deck with vaulted cedar ceilings—an ideal space to relax or host gatherings.This property is fully equipped for a variety of lifestyles and uses. Highlights include a 1,440 sq ft garage complete with a walk-in cooler, a 60x80 shop zoned light industrial with 3-phase power, engineered for a crane, and a half bath—perfect for business or hobby use. The land features an orchard with deer fencing, a designated fenced garden area, and four full RV hookups.Additional features include a built-in 9x9 safe for added security. Whether you’re seeking a private retreat, working property, or multi-use estate, this one-of-a-kind offering delivers unmatched potential in a beautiful rural setting.Call today for your private tour of this extraordinary property!

1757 RIDDLE BY PASS RD, Riddle

$419,900

3 Beds ⋅ 2 Baths ⋅ 428246472 MLS

Could be last chance to get this wonderful property under market value- no issues other than unusual market! Beautifully maintained mini hobby farm at an incredible value. Last escrow did not close not fault of home. Previous hardship approval in past. Located just 2 miles from Canyonville in the peaceful community of Riddle, this exceptional 4.48-acre property offers the perfect blend of country living, modern upgrades,& breathtaking views. Full property well maintained, ready to impress from the moment you arrive. The upgraded 3-bed/2-bath stick-built home is truly move-in ready. Enjoy expansive views from nearly every window, spacious covered deck for year-round outdoor living, an inviting open floor plan designed for comfort and functionality. The kitchen features abundant cabinetry, an eat-at breakfast bar, with propane range- ideal for everyday living. The spacious living room showcases stunning views; professionally installed, highly efficient pellet stove w/ thermostat, providing economical, dependable heat—even while you're away. A separate laundry rm, generous primary w/en-suite, + 2 addl. roomy bdrms complete the home's comfortable layout. Outside, you'll find everything needed for your hobby farm or recreational lifestyle. Property is fenced/cross-fenced, includes dog run; versatile barn currently used as a shop with attached carports and workshop with room for 3 stalls. Lg covered metal RV hut with power/dump hookup, storage shed, and an upgraded chicken coop. The gently sloping to level acreage offers usable pasture, fire-defensible landscaping, whole house surge protection and much more! Schedule your showing now or call for more info while it is still available at this low price!

375 JORDAN CREEK RD, Riddle

$475,000

3 Beds ⋅ 2 Baths ⋅ 727657933 MLS

Seller is offering to contribute for buyers interest rate buy down!! Seller is offering to contribute towards buyers closing costs!! Almost 5 Acres outside of Riddle Oregon! NEW EVERYTHING!! This completely remodeled stick built home with 3-bedroom 2-bathroom home offers 2349 sqft of beautifully updated living space, featuring brand-new flooring, fixtures and finishes throughout. The spacious open floor plan flows seamlessly, creating a bright and inviting atmosphere. An office space provides the perfect spot for remote work, while the laundry room adds everyday convenience. The extra bonus room can easily serve as a fourth bedroom, hobby area, or organized storage. Enjoy the outdoors on the expansive covered deck, perfect for entertaining, or relax on the private decks off both bedrooms to soak in the peaceful scenery. With plenty of room for gardening, recreation, or even small animals, this property offers a perfect blend of modern comfort and country charm—ready for you to move in and make it your own.

181 OAK HOLLOW LN, Riddle

$675,000

3 Beds ⋅ 2 Baths ⋅ 403982759 MLS

This beautiful log home features soaring ceilings and large windows, along with French doors that open to a spacious wrap-around deck, providing stunning views of the creek and surrounding mountains. The property is very private, secluded, and gated. The open concept design is perfect for entertaining guests. A massive rock fireplace will keep you warm on cool winter evenings. Conveniently located one mile from I-5, and easy access to 7 Feather Casino and Resort, which offers entertainment and a variety of dining options. The home boasts approximately 700-800 feet of pristine Cow Creek frontage, ideal for swimming and fishing for salmon, bass, and trout. Additionally, there is a bonus room off the garage with a fish cleaning station. The property includes water rights for both irrigation and domestic use.There are four large shops with dimensions of 24x60, 24x12, 36x24, and 36X34 with matted stalls for animals. This one-of-a-kind home is sure to impress, so be sure to schedule your viewing today! The prior sale failure was not due to the home or property.

1138 YOKUM RD, Riddle

$394,900

2 Beds ⋅ 1 Baths ⋅ 345088697 MLS

Charming Riddle Farm! 1922 Water rights! Approximately 1,500ft of Cow Creek frontage. Farmhouse has had some updating and features two bedrooms and one bath. Large oversized room upstairs not in sq. footage. Newer greenhouses for all your growing needs or start a small farming business. Pellet stove is certified. Public water. Septic system. RV parking. Showing by appointment only!

4359 CANYONVILLE RIDDLE RD, Riddle

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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.