Jacksonville Homes with Guest Quarters Exterior features

Welcome to Jacksonville, Oregon—a charming gem nestled in the heart of Jackson County. This picturesque city is steeped in history, boasting a vibrant downtown area that reflects its Gold Rush origins. With its beautifully preserved buildings, Jacksonville offers a unique blend of old-world charm and modern amenities. Residents enjoy a delightful small-town atmosphere, enhanced by a thriving arts scene, local wineries, and an array of outdoor recreational opportunities. Whether you're exploring the scenic trails of nearby Table Rock or savoring the culinary delights at local eateries, Jacksonville is a community that embraces both nature and culture.

For those seeking a home that accommodates guests with style and comfort, Jacksonville’s real estate market features stunning properties with guest quarters. These homes often come equipped with separate living spaces, providing an ideal solution for hosting family and friends or even generating rental income. Imagine welcoming loved ones into a cozy suite complete with its own amenities, ensuring privacy while still being close to home.

Exterior features of these homes often include beautifully landscaped yards, spacious patios, and outdoor entertaining areas, perfect for enjoying the mild Oregon climate. With the backdrop of the stunning Siskiyou Mountains and the charming streets of Jacksonville, these properties offer a serene retreat for both residents and their guests.

Discover the perfect blend of history, community, and modern living in Jacksonville, Oregon, where your dream home with guest quarters awaits!

Newest Jacksonville Homes with Guest Quarters 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

$485,000

3 Beds ⋅ 2 Baths ⋅ 195284107 MLS

Head to the hills! Bucolic 2.48 acres, bordering BLM land and Poorman's Creek, part of the old Pearce Placer Goldmining Claim in George Black Gulch.Remodeled throughout with vaulted and beamed ceilings, second kitchen, open floor plan. RV parking with water, power and septic hook-up. Workshop, garage and cabin.

4539 HWY 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: