Jackson Homes with Guest Quarters Exterior features

Welcome to Jackson County, Oregon, a hidden gem nestled in the heart of the Pacific Northwest. Known for its stunning landscapes, vibrant culture, and outdoor recreational opportunities, Jackson County is a place where nature meets community. With the majestic Cascade Mountains to the east and the picturesque Rogue River winding through its heart, this county offers a perfect blend of adventure and tranquility. Whether you're exploring the charming streets of Ashland, savoring local wines in Medford, or hiking in the breathtaking Crater Lake National Park, Jackson County is a haven for those who appreciate the beauty of nature and the warmth of small-town living.

When it comes to real estate in Jackson County, homes with guest quarters are particularly appealing. Imagine the possibilities of having a dedicated space for family, friends, or even rental opportunities right on your property. These homes often feature separate entrances, ensuring privacy while maintaining a sense of togetherness. With exterior features that may include beautifully landscaped gardens, spacious patios, and outdoor entertainment areas, these properties are designed for both relaxation and socializing.

Whether you’re hosting weekend gatherings or providing a cozy retreat for visitors, homes with guest quarters offer flexibility and comfort. In Jackson County, you can find a variety of styles and sizes, from charming cottages to sprawling estates, all set against the backdrop of Oregon's stunning natural beauty. Discover your dream home in Jackson County, where the spirit of community and the allure of nature come together seamlessly.

Newest Jackson Homes with Guest Quarters Exterior features

$1,675,000

3 Beds ⋅ 4 Baths ⋅ 317835913 MLS

Privately gated and gracefully set on 5 acres in the heart of Southern Oregon wine country, this extraordinary estate blends timeless craftsmanship, architectural elegance, and the rare luxury of a privately owned 250-vine vineyard. Constructed at a cost exceeding $2 million, the residence was thoughtfully designed to reflect enduring quality and sophisticated living at every turn. A striking custom stone exterior, crowned by an authentic 100-year slate roof, creates a commanding first impression, while the roofline was intentionally crafted to mirror the surrounding mountain vistas. Inside, soaring ceilings, rich custom woodwork, and polished vein-cut travertine flooring create an atmosphere of refined warmth and understated grandeur. Designed for both elevated entertaining and everyday comfort, the chef’s kitchen features premium appliances, exquisite custom cabinetry, expansive gathering spaces, and a fully appointed butler’s pantry. Walls of windows frame serene mountain views, inviting the beauty of the outdoors into the home’s luxurious interior. The primary retreat offers a true spa-inspired experience with dual private bathrooms and separate custom closets, creating a level of comfort and privacy rarely found. A separate VIP guest suite or executive office provides exceptional flexibility for extended stays, multigenerational living, or private accommodations. Beyond the residence, the estate unfolds into a lifestyle property unlike any other — complete with a producing 250-vine vineyard, manicured grounds, and a peaceful sense of seclusion just minutes from modern conveniences. Every detail reflects intentional design, uncompromising materials, and a vision of luxury meant to endure for generations. This is more than a home — it is a legacy estate to be experienced in person to be fully appreciated. One seller is a licensed OR Realtor.

727 EARHART RD, Rogue River

$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

$773,500

3 Beds ⋅ 2 Baths ⋅ 551231731 MLS

Back On No Fault to Home Welcome to your private Southern Oregon retreat With Large Pond and two Garages! A True Gardeners Paradise For a Fraction - Nestled in the scenic hills of Eagle Point, this stunning Zoned ( EFU ), with a Large Pond, 3 bedroom, 2 full bath, 1 half bath home offers 2,344 square feet of thoughtfully designed living space on a massive 15.63-acre parcel The Largest at this price range — the perfect blend of comfort, functionality, and wide-open opportunity. Step inside to discover spacious living areas filled with natural light, ideal for both everyday living and entertaining. The layout flows beautifully, offering generous bedrooms, a well-appointed primary suite, and ample room for gatherings or quiet evenings at home. Step out onto the patio and take in what truly sets this property apart — Pearched over the descending valley of Eagle Point. Surrounded by mature trees and natural beauty, you’ll enjoy breathtaking sunsets, peaceful mornings, and the serenity that only Southern Oregon can provide. This expansive 15.63-acre property is perfect for horses, hobby farming, recreation, or future expansion. With usable land and room to grow, the possibilities are endless. Car enthusiasts, hobbyists, or those needing extra storage will appreciate the rare bonus of two separate 2-car garages, providing abundant space for vehicles, equipment, or workshop needs. Whether you’re seeking privacy, room to expand, or a property priced to sell fast with incredible upside, 120 Hammel Rd delivers exceptional value in a highly desirable area. Nature Space Opportunity. Schedule your private tour today before this rare Eagle Point acreage is gone. Key Points : Hunter Fiber Optics , Trash Compactor , Instant Hot H2o Tap, Green house , Pond With Kayaks , Irrigated Fields , Tree House , Paved Driveway & Pad , Garden shed , Covered Parking , wild Plum Trees, Updated Granite and Hardwood floors , Two fire places Gas / Pellet, Hot Tub, Motivated Seller, ADU Possible

120 HAMMEL RD, Eagle Point

$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

$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

$2,985,000

2 Beds ⋅ 2 Baths ⋅ 24066691 MLS

Wooldridge Creek Winery, including Crush Pad Creamery, is situated on 23 acres of land which includes 7 acre vineyard. This property, offered for sale for the first time in 47 years, is located 16 miles southeast of Grants Pass. It is sited on a gently descending hillside overlooking the beautiful Applegate Valley. The vineyard, established in 1978, is one of the five original post prohibition vineyards of the Rogue Basin. In addition to the turn-key operation of the winery and the creamery, the sale can include a lease on the adjacent 46 acres of vines planted in twelve varietals. Wooldridge Creek is the only combined winery and creamery in the Northwest.In addition to bulk and keg wines, Wooldridge Creek's case production is currently limited to 5,000 cases per year for the wine club and tasting room. However, the winery has the capacity to produce up to 31,500 cases annually. A hoist and hopper system are in place to allow for the transition from hand to mechanical harvesting, if preferred.The sale includes five winery and creamery buildings, a log home currently used as a short-term vacation rental and a studio apartment above a three-car garage. The tasting room is open daily from 11 a.m. to 5 p.m. Drop by and experience all that is Wooldridge Creek.

818 SLAGLE CREEK RD, Grants Pass

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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: