Jacksonville Homes with Vineyard View

Welcome to Jacksonville, Oregon – a charming historic town nestled in the heart of Jackson County. Known for its rich heritage and vibrant arts scene, Jacksonville offers a unique blend of small-town charm and modern amenities. As you stroll through its quaint streets, you’ll be captivated by beautifully preserved buildings that date back to the Gold Rush era, alongside a thriving community of local shops, galleries, and restaurants.

One of the most alluring features of Jacksonville is its stunning natural landscape. The town is surrounded by rolling hills and lush vineyards, making it a paradise for wine enthusiasts and outdoor lovers alike. Imagine waking up each morning to sweeping views of vineyards, with the lush greenery and rows of grapevines creating a picturesque backdrop for your daily life.

If you're looking for a home that offers both comfort and breathtaking scenery, Jacksonville's homes with vineyard views are a perfect choice. These properties not only provide a tranquil retreat but also allow you to indulge in the region's renowned wine culture. Picture yourself enjoying a glass of local Pinot Noir on your patio, while the sun sets over the vineyards, painting the sky in hues of orange and pink.

With its exceptional quality of life, rich cultural offerings, and stunning views, Jacksonville, Oregon, is more than just a place to live—it's a place to thrive. Whether you're seeking a cozy cottage or a spacious family home, Jacksonville’s vineyard view properties offer a unique opportunity to embrace the beauty and charm of this delightful town. Come discover your dream home in Jacksonville today!

Newest Jacksonville Homes with Vineyard View

$795,000

3 Beds ⋅ 3 Baths ⋅ 220224732 MLS

Nestled in the heart of Southern Oregon's premier wine country, and close to the historic town of Jacksonville, this property on 4.98 acres offers the perfect blend of rural charm and functional infrastructure. The property features a magnificent, classic wood barn set against a backdrop of mature landscape, sweeping valley and mountain views. The home boasts bright, inviting living spaces, a spacious upstairs primary suite, a light-filled sunroom, and a private entrance leading to 2 downstairs bedrooms, 1 full bathroom and studio. Enjoy unique access to the Applegate river, IRRIGATION WATER RIGHTS dated from 1876 and the natural beauty of the surroundings. Bring your horses or enjoy it as a peaceful country retreat. A true Applegate gem waiting for its next chapter.

7935 Upper Applegate Road, Jacksonville

$750,000

220218273 MLS

Tucked just outside the historic town of Jacksonville, this exceptional high-end 6.45-acre residential parcel offers privacy and showcases beautiful valley and mountain views. Accessed via a shared gated drive, the property has been improved for equestrian and rural living. Improvements include a 1,206 sq ft barn & adjacent riding arena. A fenced 1/3-acre Syrah vineyard, professionally installed, presents unique lifestyle or boutique agricultural potential. Enjoy direct access to the renowned Britt Woodlands Trail System, offering over 16 miles of hiking and biking trails right from your property. Served by a private well that last tested at 10.5 gpm, this property offers a rare opportunity to build your own dream estate in one of Southern Oregon's most desirable locations.

84 Placer Hill Drive, Jacksonville

$745,000

4 Beds ⋅ 3 Baths ⋅ 220217086 MLS

NEW PRICE! Own a piece of history! Located on a 1/3-acre lot near downtown Jacksonville's shops, restaurants, wineries, and music venues, this beautifully preserved C.R. Pursell log home was crafted from Douglas fir logs and blends timeless character with thoughtful updates. Highlights include the original stone fireplace built from rocks found on the property and an open floor plan connecting the living room, dining, and kitchen. The kitchen has custom cabinetry, stainless steel appliances, and the original cast iron sink. The main level also offers two bedrooms and a full bath. The primary bedroom upstairs is like a retreat. A finished basement provides a separate living space with its own entrance, laundry, bath, and bonus room--ideal for guests or rental potential. Enjoy mature landscaping and views from a spacious deck & the front porch. Plenty of off-street parking and a large garage/shop.

645 E California Street, Jacksonville

$849,000

3 Beds ⋅ 3 Baths ⋅ 220216793 MLS

Single-level custom home on acreage showcases dramatic views and architecture. Rare privacy in the midst of nature; yet home is close to Medford and historic Jacksonville and has high-speed cable internet. 14+ acres backed by BLM land at the end of a quiet country road. High-level view overlooking the Applegate Valley and mountains beyond. Possible seller-financing at below-market rate with 50% down, or lease-option. Home's design is inspired by Frank Lloyd Wright's principles, with sleek horizontal lines and a flowing open layout with prominent use of wood, stone, concrete and glass. Spacious high-ceilinged great room with clerestory, stone-finish fireplace and wall of patio doors. Luxurious primary suite boasts its own panoramic views, patio access, dedicated office, walk-in closet, and spa-like bathroom. Fire-resistant ICF construction. Zoned radiant heated floors, extensive cherry wood cabinetry, abundant storage, quality Pella windows, oversized garage, 400-amp electrical.

615 Tumbleweed Trail, 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

$8,500,000

4 Beds ⋅ 3 Baths ⋅ 23696912 MLS

Welcome to Red Lily Vineyards, one of the most acclaimed vineyards in the esteemed Applegate Valley of Southern Oregon. Renowned for its exceptional wines and captivating scenery, Red Lily Vineyards presents an alluring mix of established wine and agri-business with great opportunities for event and hospitality expansion. It's not just a business; it's a gateway to an extraordinary experience and a haven for those seeking a rare and sought-after investment and lifestyle opportunity. This 255-acre ranch and estate boasts strong water rights, breathtaking river frontage, a state-of-the-art winery, mature vineyards, and an expanses of quality irrigated land for vineyard and agricultural expansion plus perhaps the most iconic and well-trafficked wine tasting experience in Southern Oregon. Nestled atop a secluded knoll, commanding picturesque views of the Applegate Valley, is the main residence, a quintessential American cedar shingle-style home boasting over 4,000 square feet of living space. The second home, known as the winemaker's house, is a delightful farmhouse that has been thoughtfully updated. With its well-established reputation and a wealth of infrastructure, Red Lily provides an excellent platform for business expansion. This includes options for expanding vineyard and agri-business operations, developing a hospitality business with a focus on events such as destination weddings, as well as on-site accommodations like bed and breakfast and cabin rentals. An additional estate dwelling and farm-to-consumer sales are also relevant opportunities. This rare gem offers an unparalleled setting with 3,300 feet of Applegate River frontage and convenient access to incredible outdoor activities. The phenomenal location is a short commute from all the conveniences of Jacksonville and Medford and is centrally located within Southern Oregon. The offering is a hybrid sale that includes the business, brand, and real estate. Owner terms may be available. Thank you!

11777 Highway 238, Jacksonville

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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.

The data relating to real estate for sale on this web site comes in part from the Internet Data Display (IDX) of the Southern Oregon Multiple Listing Service. Real estate listings held by brokerage firms other than our company are marked with the IDX logo and detailed information about them includes the name of the listing brokers. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information subject to change and should be independently verified. Listing content is copyright © 2018 SOMLS, Medford, Oregon. Last updated: