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2365 Eastside Road, Jacksonville
$1,149,000
4 Beds ⋅ 4 Baths ⋅ 220222432 MLS
Experience elevated mountain living on this breathtaking 9-acre estate at the base of Boaz Mountain. Designed with timeless lodge-inspired architecture, this 3,737 SF custom home captures luxury, warmth, and privacy at every turn. Towering vaulted ceilings, tile floors, handcrafted woodwork, and dramatic floor-to-ceiling windows create an unforgettable atmosphere filled with natural light and stunning views. The gourmet kitchen features quartz countertops, high-end appliances, oversized island, and walk-in pantry, opening seamlessly to expansive living and entertaining spaces. Resort-style outdoor living awaits with a heated in-ground pool with PebbleTec finish, outdoor kitchen, pool house, hot tub, 1,000+ SF deck, and beautifully curated grounds designed for unforgettable gatherings and peaceful evenings alike. Backing thousands of acres of public land, this is more than a home--it's a private Southern Oregon retreat built for luxury, adventure, and connection.

2365 Eastside Road, Jacksonville

13500 E Evans Creek Road, Rogue River
$930,000
4 Beds ⋅ 3 Baths ⋅ 220222158 MLS
Tucked away in the heart of Evans Valley, where Evans Creek and May Creek border the land, lies one of Southern Oregon's most treasured legacy waterfront ranches. Spanning 48.07 picturesque acres across two EFU tax lots with valuable water rights, this extraordinary estate feels straight from a storybook. Rolling pastures, mature trees, and open meadows create a breathtaking setting where elk return each spring to calve beneath wide Oregon skies. The stunning 3,406 sq. ft. custom home features soaring cathedral ceilings, dramatic timber accents, walls of windows, and an expansive wraparound porch perfectly designed to capture the sweeping views. The iconic restored 1940s red barn, admired for decades by photographers and locals alike, anchors the property alongside multiple outbuildings and livestock facilities. Completing the estate is a spacious 4-car garage with extensive built-in storage. A rare opportunity to own a timeless Southern Oregon waterfront sanctuary. Don't miss Video!

13500 E Evans Creek Road, Rogue River

3250 Annapolis Drive, Medford
$995,000
3 Beds ⋅ 3 Baths ⋅ 220221703 MLS
Priced to SELL! Panoramic valley views, single-level living & incredible shop space! Sweeping vistas stretch from Mt. Ashland to the Table Rocks and are visible from every primary living space. The vaulted great room and open kitchen offer open sightlines, easy flow and views at every turn. Three bedrooms include two en-suite bedrooms with private baths, plus a versatile office/flex room with its own closet--ideal for working from home, a nursery, hobby room or additional sleeping space. All everyday living is on one level. A 2-car attached garage plus oversized 3-car shop below with dedicated half bath provide five total garage spaces and exceptional room for vehicles, storage and projects. A rare combination of panoramic views, accessible single-level living and room for it all. Built 2017, finished 2018. VA Assumable loan at 3.875%.

3250 Annapolis Drive, Medford

4000 Little Applegate Road, Jacksonville
$1,025,000
4 Beds ⋅ 4 Baths ⋅ 220221529 MLS
Discover serenity on 4.58 acres in the heart of the Applegate Valley! 3,400 sq ft custom home offers 4 beds, 2.5 baths, separate in-law suite w/ private entrance. Enter into expansive, light-filled living with views of the Little Applegate River from nearly every room. Enjoy 14' ceilings & a stunning rock fireplace w/ Port Orford Cedar mantle in the Living Room. Chef's Kitchen, large island, granite counters, & breakfast nook flow seamlessly into the formal dining area & dedicated office. Primary suite is a luxurious escape w/ dual vanities, soaking tub, walk-in shower, & dual closets. On the opposite wing, find three bedrooms, w/ private entrance, ideal for family or guests. Relax on the wraparound porch, stroll through manicured landscaping, or unwind beside your private pond/water feature. Multiple seating areas along the river offer peaceful moments of reflection. Fenced pasture, irrigation system, detached 2,132 sq ft garage, w/three spacious rooms, HVAC, and limitless potential!

4000 Little Applegate Road, Jacksonville

312 Sky Ridge Road, Ashland
$899,000
220221479 MLS
312 Sky Ridge Road offers 164 acres in the hills above Ashland, combining privacy, natural beauty, and usable land in a premier Southern Oregon setting. Zoned EFU, the property features a blend of moderately sloping terrain, open ground, and native landscape ideal for recreation, investment, or an exceptional estate setting. Approximately 2,220 feet of Cove Creek frontage adds scenic beauty and recreational appeal. A strong 48 GPM well, per 2018 well log, provides an excellent water source for future improvements. A fully paved drive leads to the property, with plans underway for a custom luxury entrance designed to complement the scale and quality of the setting. Elevations ranging from approximately 2,120 to 2,520 feet capture panoramic views in nearly every direction, creating a remarkable sense of space and connection to the surrounding mountains and valleys. Conveniently located near Medford, outdoor recreation, public lands, and Southern Oregon amenities.

312 Sky Ridge Road, Ashland

254 Juanita Way, Jacksonville
$275,000
220221164 MLS
Location, location, location! Searching for an amazing view lot to build your dream home on that's close to Downtown Jacksonville as well? If so, this is the one for you! This rural lot is accessed through a private drive that is shared with million dollar plus homes and is ready to be built on! A few of the many features this property has to offer is a new well (cost $30k+), new well pump (cost $19k+), power is at the property line, RR-5 zoning provides homesite approval, septic approval, graded homesite pad, graveled driveway, & much more! Buyer(s) to perform their own due diligence pertaining to buildability of the property. Very rare opportunity to find buildable acreage within 5 mins from Downtown Jacksonville, so contact your agent today for a personal tour, before it's too late!

254 Juanita Way, Jacksonville

500 Ashland Loop Road, Ashland
$2,500,000
5 Beds ⋅ 7 Baths ⋅ 220220624 MLS
Discover this extraordinary Southern Oregon Luxury 2 acre estate perched above downtown Ashland w/views & incredible privacy. This custom built Pagnini home 5313 SQ FT, 5 bdrms, 5.5 bthms, 5 Car Garage + an additional 720 sq ft detached guest quarters. Grand entry, stunning wood floors, soaring ceilings, multiple fireplaces & walls of windows to take in the incredible views & abundant natural light. Gourmet kitchen w/quartz countertops, skylights & SS appliances w/double ovens. Main level primary suite w/ terrace access offers a soaking tub & steam shower. 2 upstairs guest suites both come complete w/private balcony & breakfast bar. Additionally this incredible home features a slate roof, sauna, elevator, a spacious office w/ en-suite + so much more. European-style terrace w/big natural boulders, fruit trees, a dog run, greenhouse, and manicured gardens along w/ abundant wildlife- no expense was spared on this remarkable Ashland retreat & it truly shows

500 Ashland Loop Road, Ashland

536 W La Strada Circle, Medford
$925,000
4 Beds ⋅ 4 Baths ⋅ 220220963 MLS
Gorgeous custom home with breathtaking views of the Rogue Valley and twinkling city lights. This beautifully upgraded home features soaring open beam ceilings, wood floors, alder cabinetry, quartz countertops, and open great-room living with a gas fireplace framed by a stunning rocked archway. The chef's kitchen offers a 5-burner gas range, island, wine cooler, and walk-in pantry, while the spacious covered deck off the kitchen is perfect for year-round outdoor dining, entertaining, or relaxing with the views. Main level includes the luxurious primary suite, office, and custom library with knotty alder built-ins and smart lighting. Downstairs features a fully finished lower-level expansion with 1,400+ SF of professional-grade gym space, private guest suite, and hidden-panel bonus room ideal for a theater, office, or speakeasy. Enjoy the pergola-covered Premium Signature Spa hot tub and beautifully landscaped backyard.

536 W La Strada Circle, Medford

5245 Pioneer, Medford
$575,000
3 Beds ⋅ 2 Baths ⋅ 220220971 MLS
Welcome to your own slice of Southern Oregon paradise! This spacious 3-bedroom, 2-bath home offers approximately 2,400 sq ft of living space on 5 beautiful acres with breathtaking panoramic views. The property features multiple barns, sheds, a 4-car carport, pasture space, and endless potential for hobby farming, animals, storage, or recreational use. Inside, you'll find an open layout with a large kitchen offering abundant cabinet storage, quartz countertops, and plenty of room for gathering and entertaining. The living room showcases a stunning stone fireplace that creates a warm and inviting atmosphere. Large sliding glass doors lead out to the porch where you can relax and take in the gorgeous surrounding scenery and sunsets. This older home is full of character, space, and opportunity for someone looking to create their dream rural retreat.

5245 Pioneer, Medford

22 Terra Linda Court, Eagle Point
$649,000
4 Beds ⋅ 4 Baths ⋅ 220220658 MLS
Versatile Craftsman in Eagle Point, over 3,000 sq ft, sweeping mountain views & room for everyone! The main level features vaulted ceilings, Alder doors, wood laminate flooring & spacious great room. The chef's kitchen offers granite counters, Knotty Alder cabinetry, stainless appliances, gas range, walk-in pantry, and large island. The main-level primary suite includes dual walk-in closets, double vanity & tiled walk-in shower with dual heads plus a second bedroom and full bath nearby. Upstairs offers additional bedroom with private bath and walk-in closet. The finished lower level has own entrance & driveway, bedroom, full bath, flexible living space & plumbing for future kitchenette--ideal for multi-generational living, guests or extended stays. Enjoy the wraparound covered deck, covered patio, and a nicely sized irrigated yard with plenty of room for pets, garden beds, entertaining, or simply enjoying the outdoors. Finished 3-car garage, RV parking, golf cart access, and NO HOA!

22 Terra Linda Court, Eagle Point

2244 Hillside Drive, Medford
$895,000
5 Beds ⋅ 5 Baths ⋅ 220220584 MLS
Perched in the desirable West Hills of Central Point, this exceptional property offers space, versatility, and breathtaking views from the expansive deck, on nearly an acre with irrigation. Enjoy sweeping panoramas of the Rogue Valley, Roxy Ann Peak, and Mount McLoughlin from your own backyard. The main 1570 sqft home features 3 bedrooms and 2 full and 1 half bathrooms with a comfortable, functional layout ideal for everyday living and entertaining. A separate 1200 sqft 2 bed, 1 bath guest home adds incredible flexibility for multi-generational living. Great well, plus 2000 gallon holding tank! The impressive RV garage is a true standout, offering ample space along with a workshop, den with wet bar, and half bath, perfect for hobbies, or a man cave! With room to spread out, stunning natural surroundings, and a prime location just minutes from town, this rare offering combines privacy, utility, and scenic beauty into one remarkable opportunity.

2244 Hillside Drive, Medford

381 Pinetop Terrace, Shady Cove
$539,000
3 Beds ⋅ 2 Baths ⋅ 220220352 MLS
Over 2,400-sq. ft. of comfortable living space in this versatile 3-bedroom, 2-bath home with a large bonus/game/multipurpose room that can easily serve as a 4th bedroom. Situated on a huge city lot in desirable Valley View Estates, this property offers breathtaking views with no HOA or fees. Connected to city water and sewer for convenience. The oversized 2-car garage includes an attached shop area, providing ample space for projects, storage, and all your toys, plus room for RV parking. Enjoy outdoor living and entertaining on expansive decks designed to capture the scenery. Tucked away on a private cul-de-sac in a sought-after Shady Cove neighborhood. Brand new roof installed April 2026, along with recent upgrades including interior and exterior paint, updated flooring, granite countertops, and more. Split floor plan features a spacious primary suite with soaking tub, separate shower, and walk-in closet. A must-tour!

381 Pinetop Terrace, Shady Cove

400 Coyote Run, Jacksonville
$1,477,000
2 Beds ⋅ 3 Baths ⋅ 220220012 MLS
Butterfly Hill is a LEED Silver certified, self-sustainable eco-luxury masterpiece in a gated community outside Jacksonville. This three-wing home delivers abundant sweeping views, open-concept living space & stunning folding glass doors which open directly to outdoors blending nature with the eco-luxury lifestyle. The kitchen stuns with a large tasking island, custom cabinetry, walk-in pantry and sleek cooking zone. Primary suite demands awe with a bank of windows facing the mountains & spa inspired bath. Flexible secondary suite is a perfect multi-use haven. 8-year-old Hügelkultur gardens, drought-tolerant native plantings, and a 15,000-gallon rainwater collection system supplies irrigation and dedicated fire suppression tank, solar power, KVA 20 generator and extensive fire hardening measures secure this home for years to come. Private hiking trails, wildlife, views and space without feeling endlessly remote.

400 Coyote Run, Jacksonville

374 Avalon Terrace, Eagle Point
$99,000
220219753 MLS
Panoramic valley views await on this premium .40-acre view lot in desirable Eagle Ridge Subdivision in Eagle Point, Oregon! Rare end-of-road location in a quiet cul-de-sac offers ultimate privacy and a peaceful setting, perfect for your custom-built dream home. One of the last available buildable lots at the end of Avalon Terrace, this spacious homesite showcases stunning mountain views, city lights, and breathtaking sunsets. City services available at the lot, CC&Rs in place with a minimum 1,700 sq ft home and NO HOA's! Bring your builder and house plans to create your ideal retreat. Conveniently located just minutes from the Eagle Point Golf Club, shopping, schools, and parks. Enjoy the perfect blend of privacy, luxury, and accessibility. Exceptional opportunity for new construction in a sought-after neighborhood!

374 Avalon Terrace, Eagle Point

575 Dogwood Way, Ashland
$769,000
4 Beds ⋅ 3 Baths ⋅ 220220097 MLS
It's the home you've dreamed of with astounding views of the valley and mountains from living and dining rooms and all four bedrooms! Designed by Jerry Toney it's been well cared for and improved over time with meaningful updates including terraced lawn with sundeck, two kitchen sinks, 16 (owned) solar panels and more! A large room on the first floor with built-in shelves is suitable for use as media, gym, or library. Garage has storage room plus workbench and sink. On the main level, vaulted ceilings and oversized windows running the length of the home create a spacious feeling that invites the valley below indoors. The primary suite boasts a walk-in closet/dressing area and a tiled bathroom complete with two-person soaking jacuzzi. The kitchen opens onto the main outside deck facilitating meals outside or barbecuing meals for inside. Throughout the home, custom western maple cabinetry and quality woodwork add warmth and character. Call your Realtor for a private showing today!

575 Dogwood Way, Ashland

Buckhorn Road 1000 Unit 1000, Ashland
$695,000
220219785 MLS
79.59-acre EFU property offering a rare combination of usable land, privacy, and natural beauty just 15 minutes from downtown Ashland. Approximately 50% prime pasture and 50% gently sloping forestland create a versatile setting for a variety of uses. Includes 29 acres of irrigated farmland with valuable 1888 water rights. Carter Creek, a tributary to Emigrant Creek, runs through the property, adding both character and a reliable water source. Ideal for a homesite, horse property, or recreational retreat with sweeping views of the Cascade Mountains and surrounding valleys. Just 5 minutes from Emigrant Lake with convenient backroad access to Mt. Ashland. Borders 120+ acres of BLM land with direct access to additional open space. Close to the Cascade-Siskiyou National Monument, offering miles of recreation and protected landscape. A unique opportunity to own a well-balanced Southern Oregon property with both usability and scenic appeal.

Buckhorn Road 1000 Unit 1000, Ashland

5293 Highway 66, Ashland
$2,195,000
4 Beds ⋅ 4 Baths ⋅ 220219782 MLS
Located just outside Ashland, this property offers a rare blend of natural beauty, water, quality improvements, and convenience. The custom built home is thoughtfully positioned to capture expansive views across the surrounding valley and toward distant mountains. This elevated country estate draws from a Northwest lodge aesthetic, offering welcoming living spaces, a spacious multilevel layout and a seamless indoor outdoor connection with expansive outdoor living spaces. A picturesque stretch of Neil Creek framed by mature trees adds character and tranquility. Gently rolling topography, lush pasture, and water rights support a variety of Ag uses. A recently constructed 5,000 SF barn complements the property and offers outstanding flexibility for equipment, hobbies, or recreational use. Ideal as a homestead or simply an elegant place to enjoy connection to the outdoors, this is a property that captures the essence of Southern Oregon living while remaining just minutes from Ashland.

5293 Highway 66, Ashland

17939 E Evans Creek Road, Rogue River
$548,000
1 Beds ⋅ 1 Baths ⋅ 220219173 MLS
You've been looking for land that's already done the work. This is it. Custom mountain chalet on 164.84 acres in the Klamath/Cascade range with breathtaking views, direct BLM access, and infrastructure serious growers and homesteaders spend years building. Rough-sawn wood exterior, standing-seam metal roof, open-concept interior with LVP floors, island cooktop, stainless range hood, and wood-burning stove. Outside: established hugelkultur raised beds, ventilated hoop greenhouse, 2.5-acre fenced homesite, and numerous fenced cultivation areas -- all on a fully irrigated Netafim drip system. A 12 GPM well backed by 40 acres of groundwater rights and 800-amp electrical service mean you're not compromising on water or power. Yurt, outbuildings, and shipping containers may convey. Extremely private. Deeply serene. Rich with wildlife. Southern Oregon living at its absolute finest -- without starting from scratch.

17939 E Evans Creek Road, Rogue River

3998 Little Applegate Road, Jacksonville
$2,150,000
4 Beds ⋅ 3 Baths ⋅ 220219078 MLS
Discover Belvoir Estate, an extraordinary French Country chateau on 25 private acres in Southern Oregon's Applegate Valley wine country. The home features soaring ceilings, expansive windows, panoramic views, refined finishes, Wolf and Sub-Zero appliances, and outdoor terraces perfect for relaxing or entertaining. The estate boasts 600+ feet of river frontage, open meadows, a historic barn, private guest house, and a sustainable organic garden, along with rare water rights dating to 1857. Enjoy temperate, fog-free winters just minutes from historic Jacksonville, local wineries, and dining, with an international airport 30 minutes away. Seller financing is available at favorable rates with a substantial down payment and approved terms, or sellers may consider a significant mortgage rate buydown credit. Experience a rare blend of timeless elegance, privacy, and natural beauty.

3998 Little Applegate Road, 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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