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1100 Cantrall Road, Jacksonville
$519,000
3 Beds ⋅ 2 Baths ⋅ 220217326 MLS
Completely remodeled home in the heart of desirable Applegate Valley! With a new roof, new windows throughout, exterior & interior paint, HVAC, flooring, and lighting fixtures throughout, this home is truly move in ready and worry-free. Step inside the front door and you will be greeted with an open floor plan and abundant natural light. The kitchen is a culinary dream with quartz counters, custom cabinets, and top-notch stainless steel appliances - including a range / oven and microwave w/convection oven. The spacious primary bedroom offers a new vanity in the bathroom and the laundry room and guest bath feature custom cabinets. With wooded views out every window, you'll be surrounded by the beauty of nature. The wood stove with stone surround brings a cozy vibe and the Trex deck is the perfect spot to enjoy your morning coffee. Only 1 mile to gorgeous Cantrall Buckley Park and the Applegate River and a 30 minute drive to Medford make this location ideal.

1100 Cantrall Road, Jacksonville

Sterling Creek Road, Jacksonville
$275,000
220216972 MLS
Build your dream home on this exceptional 13.24-acre residential property just outside the Jacksonville city limits. Located only five minutes from downtown Jacksonville, this rare offering combines privacy, convenience, and natural beauty in the foothills of Southern Oregon. The gently sloping terrain provides a highly usable and buildable layout with an approved homesite, making it ideal for a custom residence or private retreat. Set within a classic oak savannah, the property is dotted with mature oak trees and offers the opportunity to create a truly park-like setting. With ample space for outdoor living, recreation, and future improvements, this is a rare chance to own a large, buildable parcel so close to Jacksonville's shops, dining, and charm. A perfect canvas to bring your vision to life.

Sterling Creek Road, Jacksonville

615 Tumbleweed Trail, 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. 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

1379 Humbug Creek Road, Jacksonville
$185,000
220212650 MLS
Green House Removal next week !! Recent Well test 10gpm + Incredible views from this serene and buildable 22.63 acres in coveted Applegate Valley! Tucked away from main road, this amazing property offers peaceful surroundings, abundance of wildlife, and a fair quality gravel road. Surrounded by vineyards, farms, and million dollar homes, this special property offers gated access to insure privacy. Currently has 2700 sf greenhouse with fans. Owner willing to have greenhouse removed with acceptable offer. Property was acquired via Deed-In-Lieu of Foreclosure, and current owner has no knowledge of property details. Road is shared by only 1 neighbor. Land is a mixture of flat and sloped terrain. See attached documents for Easement, County Records, Soil and Aerial Maps. Not a drive by, need appointment to show.

1379 Humbug Creek Road, Jacksonville

440 N Fourth Street 104 Unit 104, Jacksonville
$399,999
3 Beds ⋅ 2 Baths ⋅ 220210806 MLS
Experience refined living in one of Southern Oregon's most desired communities—Jacksonville Towne Square. This turn-key 3-bedroom, 2-bath Condo offers elegant design and modern comfort, all listed under $500,000. The spacious, modern kitchen features granite countertops and an open layout ideal for entertaining. The expansive primary suite is a true retreat, boasting three closets, a luxurious soaking tub, and a separate shower. Enjoy beautiful views and the convenience of being just moments from downtown Jacksonville's charming shops, fine dining, the BRITT Festival, and all this historic town has to offer. This could be the perfect location to call home, or invest as shortterm, or long term rental. Make sure this one is on your list for tour. Buyer's to do their own due diligence.

440 N Fourth Street 104 Unit 104, Jacksonville

939 Beaver Creek Road, Jacksonville
$540,000
4 Beds ⋅ 3 Baths ⋅ 220207842 MLS
Live Among the Wildlife in this Forest Retreat! A rare combination of peaceful wilderness & modern comfort. Custom home nestled on 6 forested acres bordering expansive public lands. Watch deer families wander through the yard & enjoy a unique ''treehouse'' perspective, where your main living spaces sit among the treetops. Designed across 3 thoughtfully planned levels, the home's main floor offers elevated living w/ serene forest views. Spacious living & dining areas open to a beautiful chef's kitchen w/ large pantry for storage. The half bath & three access points to the wraparound deck make indoor-outdoor living effortless. Cathedral-style covered deck w/ ramp access is a great outdoor sanctuary. Upstairs are 3 inviting bedrooms, one w/ private deck & direct access to bathroom. Finished daylight basement provides flexibility w/ a large bonus room, additional bedroom, full bath & laundry room w/ laundry chute from upper level. Privacy, tranquility & a true connection w/ nature.

939 Beaver Creek Road, Jacksonville

321 Pair A Dice Ranch Road, Jacksonville
$3,995,000
4 Beds ⋅ 6 Baths ⋅ 220203312 MLS
Experience exceptional luxury, privacy and space in Jacksonville, Oregon. Set on 5 private, park-like acres with sweeping mountain and city-light views, this Mediterranean-inspired estate offers nearly 10,000 sq ft, 4 primary suites, 6 baths, soaring ceilings and 8 fireplaces. A chef's kitchen, private wine cellar, home theater and fitness rooms elevate everyday living and entertaining. French doors open to expansive outdoor gathering spaces, a Pebble Tec pool and spa, and panoramic views. A private lower level offers flexible space for guests, extended family or recreation, while a detached guest casita adds privacy and versatility. The impressive 12-car garage accommodates automobile collections, storage and hobbies. Enjoy Southern Oregon wine country minutes from historic Jacksonville, Britt Music & Arts Festival and wineries, with convenient access to Ashland, Rogue Valley International-Medford Airport and private aviation services. A luxurious retreat for gracious living.

321 Pair A Dice Ranch Road, Jacksonville

540 E California Street, Jacksonville
$978,000
6 Beds ⋅ 5 Baths ⋅ 220189849 MLS
LOCATION....LOCATION...LOCATION!! Brand new roofs have been recently installed on both properties and the historic Reames House is now Move in Ready! This one of a kind property is an incredibly rare find and just a short walk to downtown Jacksonville. This quaint little town is home to incredible restaurants, unique boutiques and the iconic Britt Music and Arts festival. Once a popular bed and breakfast, this property is rich with history and has been beautifully restored to accomodate a large two family set-up or can continue as a thriving BNB. A standout feature of this property is the separate tax lot that hosts the versatile Carriage House. A charming space that offers endless possibilities. In the past it too was enjoyed as a BNB. Today, it can easily be converted into a guest suite, art studio, or home office. Surrounded by lush gardens, a variety of fruit trees, and a peaceful patio. Don't miss out on this amazing opportunity to own a piece of Jacksonville History!

540 E California Street, Jacksonville

11777 Highway 238, Jacksonville
$8,500,000
4 Beds ⋅ 3 Baths ⋅ 220180676 MLS
Welcome to Red Lily, one of the most acclaimed vineyards in the Applegate Valley. This 255-acre property boasts strong water rights, breathtaking river frontage, a state-of-the-art winery, vineyard, and expanses of quality irrigated land for agricultural expansion, plus an iconic and well-trafficked wine-tasting venue. With its well-established reputation and a wealth of infrastructure, Red Lily provides an excellent canvas for developing a hospitality focus with events such as destination weddings, as well as on-site accommodations like bed and breakfast and cabin rentals. This rare gem offers an unparalleled setting with 4,000 feet of Applegate River frontage and convenient access to incredible outdoor activities. Nestled atop a secluded knoll is the main residence—a quintessential American cedar shingle-style home boasting over 4,000 SF of living space. The second home is a delightful farmhouse that has been thoughtfully updated. Owner terms may be available, call for details.

11777 Highway 238, Jacksonville

11777 Highway 238, 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

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:

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