Winchester Homes with Vineyard View

Welcome to the charming city of Winchester, Oregon, nestled in the heart of Douglas County. Known for its stunning natural beauty and rich agricultural heritage, Winchester is a delightful blend of small-town charm and vibrant community spirit. Surrounded by rolling hills and lush landscapes, this picturesque city offers a serene escape while being conveniently located near the bustling city of Roseburg.

One of the most enchanting features of Winchester is its breathtaking vineyard views. Imagine waking up to the sight of sprawling vineyards, where the sun casts a golden hue over the grapes, creating a picturesque backdrop for your daily life. Homes with vineyard views in Winchester are not just residences; they are a lifestyle choice, offering tranquility and the perfect setting for outdoor entertaining or quiet evenings with a glass of local wine.

Winchester is also known for its warm and welcoming community, where neighbors become friends and local events bring everyone together. The city boasts a variety of recreational activities, from hiking and biking trails to nearby rivers perfect for fishing and kayaking. The local farmers’ markets showcase the region's agricultural bounty, allowing residents to enjoy fresh produce and artisanal products right at their doorstep.

Whether you’re looking for a peaceful retreat or a vibrant community to call home, Winchester, Oregon, with its stunning homes featuring vineyard views, is the perfect place to plant your roots and embrace a life filled with beauty and connection. Come discover the allure of Winchester—where every day feels like a getaway!

Newest Winchester Homes with Vineyard View

$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

$99,900

24369491 MLS

This excavated lot offers incredible views of mountains, vineyards and stunning valleys. Don't miss your opportunity to build your dream home on this developed house pad in a highly desirable neighborhood in Winchester. Seller is a licensed home builder/ contractor and would be willing to provide services. Utilities are at the street.

233 WINCHESTER CREEK AVE, Winchester

Start Your Search

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.