Winchester Real Estate

Welcome to Winchester, Oregon—a hidden gem nestled in the picturesque Douglas County. This charming city, surrounded by the breathtaking landscapes of the Umpqua Valley, offers a unique blend of small-town warmth and outdoor adventure. With a population of just over 1,000 residents, Winchester boasts a close-knit community where neighbors become friends and local events bring everyone together.

Nature enthusiasts will find their paradise here, as Winchester is conveniently located near the stunning Umpqua River, perfect for fishing, kayaking, and leisurely strolls along the banks. The nearby Cascade Mountains provide endless opportunities for hiking, camping, and exploring the great outdoors. Whether you’re an avid adventurer or simply enjoy the tranquility of nature, Winchester caters to all.

The city is also home to a variety of local businesses, charming shops, and delightful eateries that showcase the region’s rich agricultural heritage. From farm-to-table restaurants featuring local produce to cozy cafes where you can sip your morning coffee, Winchester offers a taste of the good life.

Families will appreciate the strong sense of community and the quality of life that Winchester provides. With excellent schools and numerous parks, it’s a wonderful place to raise children and create lasting memories.

If you’re looking for a place that combines the beauty of nature with the warmth of a welcoming community, Winchester, Oregon is the perfect destination to call home. Explore the possibilities and discover why so many are choosing to make this enchanting city their own.

Newest Listings in Winchester

$465,000

4 Beds ⋅ 2 Baths ⋅ 404977959 MLS

Welcome to the exclusive Wild Fern community in Winchester, where quality craftsmanship, neighborhood amenities, and a beautiful natural setting come together. This meticulously maintained 4-bedroom, 2.5-bath home showcases custom woodworking, quality finishes, and an inviting floor plan designed for comfortable everyday living and entertaining.Step outside to multiple expansive decks overlooking a peaceful backyard where seasonal Winchester Creek meanders through the property, creating a picturesque setting for relaxing and entertaining. A dedicated BBQ area makes outdoor gatherings easy while the surrounding landscape provides a wonderful connection to nature.Wild Fern residents enjoy community amenities including a swimming pool, tennis courts, and basketball court, along with miles of paved neighborhood streets ideal for walking and enjoying the surroundings. The Winchester location offers the added benefit of city services while enjoying lower county property taxes.Conveniently located near Umpqua Community College, shopping, dining, schools, and Roseburg, with nearby hiking and outdoor recreation just minutes away. This exceptional home offers a rare combination of craftsmanship, comfort, community amenities, and natural beauty in one of Winchester's most desirable neighborhoods. Schedule your private showing today!

299 WILD FERN DR, Winchester

$530,000

3 Beds ⋅ 2 Baths ⋅ 636742962 MLS

Charming and ideally located at 849 N View Dr, this home offers a seamless blend of comfort, functionality, and convenience. The thoughtfully designed layout features 3 bedrooms and 2 bathrooms with inviting living spaces bathed in natural light, creating a warm and welcoming atmosphere. Enjoy a fenced yard, sprinkler system, RV parking, and a garage, perfect for both relaxation and practicality. Nestled in a peaceful setting, yet just minutes from shopping, dining, local amenities, and major commuter routes, it combines tranquility with accessibility. Set in a highly desirable neighborhood, this property is a fantastic opportunity for both homeowners and investors—don’t miss your chance!

849 NORTH VIEW DR, Winchester

$485,000

3 Beds ⋅ 2 Baths ⋅ 176433898 MLS

Welcome to this beautifully updated residence in one of Winchester's sought-after neighborhoods. Nestled on a quiet, dead-end street with a welcoming atmosphere, this home offers the perfect blend of comfort, style, and convenience. Filled with natural light from expansive windows, the thoughtfully designed floor plan features 3 spacious bedrooms, including a luxurious primary suite with a stunning walk-in closet complete with custom built-in storage and a dedicated vanity. Quartz countertops, tiled showers, and tasteful updates throughout create a fresh, modern feel. Designed for today's lifestyle, the home also offers a versatile bonus room with French doors—ideal as a home office or potential 4th bedroom—plus an additional flex space perfect for a family room, game room, or media room. The well-appointed kitchen features abundant cabinetry, two pantry/storage closets. The layout of the home and living spaces, make entertaining effortless. Additional storage includes a coat closet, oversized linen closet, utility/storage room, and generous cabinetry in the laundry room. Step outside to enjoy the spacious front and backyard, offering plenty of room for gatherings, play, or simply relaxing. The garage features an epoxy-coated floor, and the attached shop provides additional workspace with a bank of cabinets or the potential to convert into a covered carport. Large driveway that can easily fit 6 vehicles. Ideal location--less than five minutes from I-5, approx 10 minutes to Umpqua Community College, and less than 1 mile from the beautiful North Umpqua River, where swimming, rafting, kayaking, and fishing can be enjoyed all summer long. If you have been searching for a move-in-ready home in a peaceful, established neighborhood with room to entertain and an unbeatable location, this Winchester gem is one you won't want to miss! More photos coming soon. Agent is owner.

339 PIONEER WAY, Winchester

$399,000

3 Beds ⋅ 2 Baths ⋅ 487961392 MLS

If you've been waiting for a home in Winchester with a great location and the chance to make it your own, this is one worth seeing. Just minutes from the North Umpqua River, Amacher Park, and I-5, you'll enjoy mountain views, a fenced backyard, and a new deck that's ready for summer evenings.The main level feels open and comfortable with a spacious living room, fireplace, and access to front and back decks. The primary suite is tucked away with vaulted ceilings, skylights, and a roomy tile bathroom, creating a quiet place to unwind. Downstairs adds even more flexibility with a family room warmed by a pellet stove, a half bath, laundry room with utility sink, and an oversized garage with plenty of storage.This home could use some fresh ideas and updating, but the location, layout, and setting make it an easy one to picture investing in. Bring your vision and build equity in a great neighborhood.

623 PIONEER WAY, Winchester

$489,500

4 Beds ⋅ 3 Baths ⋅ 271779634 MLS

Stunning custom built home in Winchester! Enjoy views of the North Umpqua River and bridge views from the large wrap-around deck. Inside features a grand great room, granite counters, an upgraded range, vinyl windows, new ductless HVAC, and built-in storage. Ideal for large or multi-family potential: downstairs offers extended living area, office, and play space. Outside, enjoy a huge yard with fruit trees, RV parking, and river access. Minutes to schools, shopping, and easy I-5 access. Schedule a tour today!

170 HURRICANE LN, Winchester

$599,900

4 Beds ⋅ 2 Baths ⋅ 277360378 MLS

This beautiful custom home is located in one of Douglas County's premier neighborhoods and there is no HOA! The all level lot is nearly 1/2 acre in size and boasts an amazing amount of parking. Bring your automobiles, RVs, boats, golf carts, trailers, or whatever you have, as there is room for all! The home's interior features a spacious kitchen with built in-oven and microwave, a downdraft gas range/oven, island, eating bar, dining nook, refrigerator with water and ice, disposal and tile flooring. The comfortable living room is centered around a classy gas fireplace and has a cathedral ceiling. The primary bedroom is good sized and has direct access to the back patio, (which would be a great place to install a hot tub), along with a bathroom with a walk-in shower, garden tub, double sink vanity and a walk-in closet. The den/office has 2 doors, with one being a french door. The family room makes a great spot to enjoy your favorite indoor activities. There is a formal dining room directly off the kitchen. The upper level is very unique and has two bedrooms. Enjoy the wonderful summer weather in the fully fenced expansive back and side yards, and on the covered patio on the rear of the home, which is accessible directly from the kitchen, making for great outdoor entertaining and living. In addition to all the parking in, and adjacent to the driveway, there is a lot of parking behind the gated fence on the right side of the home. Detached carport structure and storage shed are included. All this and low county taxes! If this sounds like a place you would enjoy calling yours, don't delay, call for a viewing appointment today!

251 MARTHA DR, Winchester

$490,000

4 Beds ⋅ 2 Baths ⋅ 152479269 MLS

Priced to sell and offering exceptional value in Winchester's sought-after Oak Valley Loop neighborhood! This beautifully maintained 4-bedroom, 2.5-bath home offers 2,581 square feet of thoughtfully designed living space, combining timeless finishes, everyday comfort, and room to grow.Step inside to soaring vaulted ceilings, rich bamboo flooring, and a warm natural gas fireplace that creates an inviting focal point in the main living area. The spacious main-level primary suite provides a private retreat, featuring a luxurious ensuite bath with a tiled walk-in shower, double vanity, relaxing jetted tub, and generous walk-in closet.Designed with both entertaining and daily living in mind, the kitchen showcases granite countertops, stainless steel appliances, under-cabinet lighting, a walk-in pantry, and an eating bar that seamlessly connects to the formal dining area. Step outside to the deck and enjoy effortless indoor-outdoor living, perfect for summer barbecues, morning coffee, or evening gatherings.Upstairs, a versatile bonus loft offers additional living space, while three generously sized bedrooms—each with its own walk-in closet—provide comfort and flexibility for family, guests, hobbies, or a home office.An extra-deep two-car garage, abundant storage throughout, fresh interior and exterior paint, and mature landscaping add to the home's appeal. The fully fenced backyard creates a private outdoor oasis, offering plenty of space to relax, garden, or play.With a Real Market Value of $593,570, this home presents an incredible opportunity to own in one of Winchester's most desirable neighborhoods. Conveniently located near schools, shopping, and recreation, 556 N View Drive delivers the perfect blend of space, quality, and value. Schedule your private tour today!

556 NORTH VIEW DR, Winchester

$489,000

3 Beds ⋅ 3 Baths ⋅ 668222765 MLS

Beautifully updated Winchester home with approximately $80K in recent upgrades, offering flexible living options and move-in ready comfort. This charming single-level home sits on a spacious level,lot features a fully remodeled kitchen, new fixtures throughout,new flooring throuout including hickory engineered harwood, remolded master suite, new laundry room, new ductless heating/cooling,new tankless H2o tank, and a cozy gas fireplace insert. Two bonus rooms connected by a breezeway provides an ideal office, hobby room, or flex space, or added storage room adds even more utility. The property includes a carport, ample driveway parking, and a separate garage with its own laundry. Above the garage is a fully furnished 1BD/1BA guest studio—perfect for extended family, guests, or potential rental income. The expansive fully fenced backyard offers room for gardening, play, or projects, complete with a workshop and greenhouse for year-round gardening. Additional improvements include a new roof installed in 2023 and fresh interior and exterior paint. This super-cute property offers privacy, versatility, and excellent multi-use living options in a peaceful Winchester setting. Truly move-in ready and charming.

335 PAGE RD, Winchester

$415,000

3 Beds ⋅ 2 Baths ⋅ 317509469 MLS

Top location in subdivision for view of the pond and greenbelt. Fenced with back deck. Common area tennis court, playground and walking trail. This lovely 2001 built home has vaulted ceilings, 3 bedrooms, 2 baths 1427 sq ft. Recently upgraded remodeled kitchen with breakfast nook, both baths totally remodeled, and flooring upgraded. Quartz countertops, new sink, newly painted interior. Great floor plan with spacious double garage. Sprinkler system. Seller will install new roof. Covered porch in back yard overlooking pond. Great outdoor space. Seller will replace the roof.

260 VILLAGE DR, Winchester

$34,500

733023484 MLS

Build your DREAM HOME on this gorgeous property in Winchester. ***Owner willing to carry contract*** Located in the desirable Page Road neighborhood, this vacant lot provides a peaceful and secluded retreat at the end of a quiet road. Enjoy stunning views of the mountains, North Umpqua River, Umpqua Community College, and vineyards, offering a picturesque backdrop from your future home. With a large 1/3 acre lot, this property presents endless possibilities to design and build your dream home tailored to your preferences and lifestyle. Embrace the Oregon dream with this serene property, offering a blend of natural beauty, tranquility, and proximity to urban conveniences. Close to medical facilities, shopping centers, and schools, ensuring easy access to essential amenities and services. Also enjoy proximity to recreational activities such as hiking, boating, fishing, and camping, providing opportunities for outdoor adventures right at your doorstep. Recent boundary survey on file.

214 GRAY SQUIRREL CT, Winchester

$999,000

4 Beds ⋅ 2 Baths ⋅ 786977472 MLS

Tucked away in one of Douglas County's most desirable neighborhoods, this stunning 19th century inspired custom Haynes-built home is a true showstopper. This 3,774 sq ft residence offers 4 bedrooms, 2.5 baths on a private, beautifully landscaped .63-acre lot.Step into a grand entry with soaring ceilings extending into the living and dining rooms, highlighted by 10-inch crown molding and hardwood floors with elegant mahogany inlay. The living room features a gas fireplace, while the family room offers a cozy wood stove. Decorative ornamental plaster adds timeless character to the living room and primary suite.The chef’s kitchen is designed for both function and style, featuring granite countertops, a large butcher block island with eating bar, gas cooktop, double ovens, custom built-in refrigerator, garden window, butler’s pantry, and additional pantry. Custom cabinetry throughout is inspired by Smallbone English design. The primary suite is a private retreat with French doors to its own deck, and a luxurious bath with Italian marble, jetted tub, and walk-in shower. A dedicated office showcases beautiful woodwork, hardwood floors, and built-ins.Outside, enjoy a large entertaining deck, gazebo, potting shed, and a peaceful seasonal creek. The exterior features reclaimed brick from the historic Umpqua Hotel, adding unique character.The impressive shop includes a 5-foot pit, loft “man cave,” and half bath—perfect for hobbies or storage. Community amenities include a swimming pool and tennis court.A rare blend of craftsmanship, history, and luxury—schedule your private tour today.

539 WILD FERN DR, Winchester

$165,000

24035561 MLS

Opportunity awaits in Winchester! Build your private dream home on this fantastic 1.26-acre lot, perfectly situated in the heart of Winchester. Zoned RS, this property offers a versatile canvas with gently sloping terrain (no steep grades), currently featuring open grass, blackberries, and scattered trees. Adding to its charm and history, the property includes the Original Amacher Barn, built in 1935. This wood-build barn with a metal roof half, wood floor and concrete slab was originally used by the Amacher family for caring for sheep. Today, it offers exciting possibilities—buyers must perform due diligence on potential options such as converting the barn into a barndominium, adding an ADU, or incorporating it alongside a brand-new dream home. With its generous size, the land also offers plenty of room for a garden, hobby farm, or space for animals, making it an ideal spot for those seeking a balance of history, lifestyle, and future potential. Conveniently located off Hurricane Lane. Must park by Oak Tree. DO NOT park at the barn entrance or in front of any gates. DO NOT enter the barn without being accompanied by a licensed real estate agent. Buyer to perform due diligence on all aspects of the property.

PIONEER WAY, Winchester

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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.