Jackson Homes with Second Residence Exterior features

Welcome to Jackson County, Oregon, a picturesque gem nestled in the heart of the Pacific Northwest. Known for its stunning landscapes, vibrant culture, and a plethora of outdoor activities, Jackson County is a haven for nature lovers and those seeking a balanced lifestyle. With the majestic Cascade Mountains to the east and the lush Rogue River Valley to the west, residents enjoy breathtaking views and easy access to hiking, fishing, and skiing.

In Jackson County, the real estate market offers an exciting opportunity for those looking for homes with second residences. Imagine having a charming getaway right in your backyard! These homes typically feature exterior amenities that enhance your living experience, such as spacious decks for entertaining, beautifully landscaped gardens, and perhaps even a cozy guest cottage or studio. The versatility of these properties allows for a perfect blend of relaxation and functionality, whether you’re hosting family gatherings, enjoying a peaceful retreat, or generating rental income.

The communities within Jackson County, including Ashland, Medford, and Jacksonville, boast a rich history and a welcoming atmosphere. You’ll find a mix of arts, culture, and culinary delights, with local theaters, galleries, and farmers markets that reflect the area’s artistic spirit. Whether you’re exploring the historic streets of Ashland or indulging in the local wineries, Jackson County offers a vibrant lifestyle that makes it an ideal place to call home.

Discover the allure of Jackson County and the charm of homes with second residences—your dream escape awaits!

Newest Jackson Homes with Second Residence Exterior features

$1,585,000

3 Beds ⋅ 2 Baths ⋅ 667754935 MLS

A rare and enchanting commercial opportunity in the heart of Jacksonville, Oregon, Tiger Lily Inn & Venue Center is more than a property -- it is a destination. Steps from downtown shops, restaurants, wine country experiences, Britt Festival and the Historic Core, this curated venue blends storybook character, established event appeal, lodging potential and flexible commercial use. Known and loved as a boutique wedding and special-event venue, the property offers an intimate garden setting for weddings, reunions, retreats, private celebrations and unforgettable gatherings, with lush grounds, outdoor areas, guest accommodations and a bridal/flex studio. Historic Core commercial zoning may invite future possibilities such as boutique hospitality, wine tasting, culinary, wellness, private club, creative office/event use or additional improvements, subject to City approval and buyer due diligence. A distinctive Southern Oregon opportunity with beauty, brand identity and room for vision.

215 S 4TH ST, Jacksonville

$1,650,000

5 Beds ⋅ 3 Baths ⋅ 444414247 MLS

Addressed as 309 and 311 Granite Street, this exceptional estate is tucked above Lithia Park on nearly six private acres, blending timeless European elegance with the tranquility of a forested retreat. Surrounded by mature trees, stone pathways, outdoor patios, and serene water features, the property feels secluded and intentional, yet remains just minutes from downtown Ashland, the Oregon Shakespeare Festival, and the historic Ashland Plaza.Inside, the architecture immediately impresses with vaulted ceilings, dramatic wood craftsmanship, custom detailing, stained glass accents, and expansive windows that fill the home with natural light. Rich textures and thoughtful design elements create a warm, old-world atmosphere that is both grand and inviting.The main residence is centered around a generous open great room with a striking rock fireplace, flowing into an informal dining area and an oversized kitchen ideal for gathering. Multiple living spaces—including a formal dining room, den, and additional sitting rooms—allow flexibility for everyday living or entertaining on a larger scale.The primary residence offers 4,479 square feet, plus 2,364 square feet of flexible ground-level space. A second residence provides 844 square feet for guests or extended living, along with a separate 1,153 square foot multi-purpose room and carport. In total, the estate encompasses approximately 8,840 square feet of versatile living space.Ideally located near Mt. Ashland Ski Resort, Crater Lake National Park, the Britt Music & Arts Festival, and Rogue Valley wineries, this is a rare opportunity to own a private, architectural estate that seamlessly blends refined craftsmanship, natural beauty, and an exceptional cultural lifestyle.

309 GRANITE ST, Ashland

$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

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.

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: