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$1,250,000
2 Beds 2 Baths 220222210 MLS
Rare opportunity to own 160 private acres on the outskirts of Ashland, offering extreme end-of-the-road seclusion, breathtaking panoramic views, and endless potential for recreation, hunting, and homesteading. Surrounded by nature and abundant wildlife, this remarkable mountain retreat delivers the peace and privacy that are increasingly difficult to find. Located just 30 minutes from Mt. Ashland and approximately 45 minutes to downtown Ashland, the property offers the perfect balance of remote living and convenient access to dining, culture, and outdoor adventure. The custom-built home features a stunning great room that truly must be experienced in person, with soaring ceilings, warm finishes, and walls of windows framing the surrounding landscape. A spacious primary suite, inviting guest accommodations, large barn, and substantial shop space make this property ideal as a full-time residence, legacy ranch, or unforgettable weekend mountain escape.

1969 Colestin Road, Ashland

$649,999
4 Beds 3 Baths 220222192 MLS
Tucked into the highly sought-after Little Applegate Valley, this exceptional Southern Oregon lifestyle estate offers a rare blend of privacy, natural beauty, recreation, and valuable water resources (Irrigation rights 1857 priority). There is an irrigated organic orchard and berries. This setting feels more like living in a private park than a traditional rural property, with mountain biking, hiking, and outdoor adventure accessible directly from Grouse Creek Road. Enjoy nearby fishing, boating, and paddling at Applegate Lake, while remaining just minutes from historic Jacksonville with its renowned dining, wineries, festivals, and vibrant community atmosphere. This is a 4 bedroom, 3 bathroom, open-concept home with soaring vaulted ceilings. With hardwood floors, tons of natural lighting, and a big kitchen, this home has everything you could need for your own private retreat. Sitting on 8+ acres of land, bordering BLM land, with incredible views, this property checks all the boxes

4046 Little Applegate Road, Jacksonville

$900,000
5 Beds 4 Baths 220221548 MLS
2 HOMES AND A GUEST STUDIO/COTTAGE ON 1 LOT!!! Just 3 miles from town, this exceptional 11-acre property sits on a sunny south-facing hillside with breathtaking views and endless possibilities. Ideal for a multi-generational family compound, rental income opportunity, homestead, or private retreat, this unique property offers an incredible combination of living space, infrastructure, and outdoor amenities. The 2,200 sq. ft. log home is filled with warmth and rustic charm, while the 1,800 sq. ft. second home includes a full basement for additional living or storage space. A separate 1,200 sq. ft. fenced studio/cottage provides excellent flexibility for guests, a home office, or a creative space. Additional improvements include two large septic systems, RV hookups with water and electricity, a separate laundry room, two tiny cabins, multiple storage buildings, root cellar with shop above, and a barn-style structure on the lower portion of the property with a newer roof.

2909 Dead Indian Memorial Road, Ashland

$669,900
220222128 MLS
Looking to increase your revenue? Don't miss this turnkey investment opportunity offered at $699,900 with a total gross rent of $75,156 and net income of $48,865. This property features a total of 5 units spread across two distinct buildings on a single .18-acre tax lot zoned SFR-10. The property has a total building space of 7,841 square feet. Don't let the age of this home scare you, the updates on both structures have been extensive. There is a two-story triplex with 3 units and a separate two-story duplex where each floor serves as its own individual unit; the buildings also feature separate power meters and their very own private laundry facility located onsite. Total gross rental income at a monthly rate for $6,263. The property is currently occupied aside from one unit on the triplex for your viewing purpose.

60 N Orange Street, Medford

$639,900
4 Beds 3 Baths 220221644 MLS
OPEN HOUSES this weekend! Sept 12 & 13, 12-2pm Priced $30K below recent appraised value with home inspection on file! This spacious 4-bedroom, 3.5-bath home is located in an established neighborhood in the North Medford School District and offers two living areas, a separate dining room, and an updated kitchen with Corian countertops and a gas range. All four bedrooms are upstairs, including a spacious primary suite. In addition to the attached 2-car garage and adjoining shop area, you'll find a large RV garage with dual roll-up doors, plus a separate heated and cooled RV/storage building with an additional room and bathroom. Out back, enjoy a private yard with a covered patio, room for BBQs and gatherings, gardening, or simply relaxing outdoors.

2769 Stonebrook Drive, Medford

$799,000
3 Beds 3 Baths 220222075 MLS
Exceptional 2026 new construction in the heart of historic Jacksonville, Or. Enjoy being just a short stroll from local favorites including the Britt Music & Arts Festival, trolley tours, wine tasting rooms, woodland trails, charming art boutiques, and fine dining. This beautifully designed home offers 3 spacious bedrooms, 2.5 bathrooms, and over 1,570 sq ft of living space filled with abundant natural light and an inviting open-concept layout. The gourmet kitchen features soft-close cabinetry, granite countertops, stainless steel appliances, and a convenient eating bar. The primary suite offers a relaxing retreat with a walk-in closet and a beautifully tiled walk-in shower. Additional highlights include luxury laminate flooring, a finished 1-car garage, an elegantly tiled guest bathroom, and a private driveway. Located within the historic district, this property also qualifies for short-term rental applications, creating a unique opportunity for both homeowners and investors.

205 N Oregon Street, Jacksonville

$1,395,000
5 Beds 4 Baths 220222059 MLS
Mid-century modern dream estate on a rare, private 1.92 acres within city limits! Don't miss this unique opportunity to enjoy the serenity & space of a rural retreat while living in one of East Medford's most desirable neighborhoods. 2 tax lots, each w/their own gated drive & entry. The main home is an architectural gem featuring 5 bedrooms & 3.5 baths. Thoughtfully designed w/large outdoor spaces, perched in the hills to capture stunning mountain, sunset, & city light views. Large floor-to-ceiling glass windows & large open spaces create an indoor/outdoor feel all 4 seasons. Resort-style amenities include a beautiful pool & hot tub, private tennis court, & breathtaking park-like grounds to create your own secluded sanctuary. The 2nd parcel features an additional 220 SF guest studio w/full bath, large 3-car shop/garage w/ attached RV garage thoughtfully configured to showcase this property as one large estate but offering exceptional flexibility & convenience.

50 Mariposa Terrace, Medford

$399,000
2 Beds 2 Baths 220222030 MLS
Escape to your own private mountain retreat. Nestled on 10 peaceful, forested acres, this authentic log home offers the perfect blend of rustic charm, privacy, and natural beauty. Surrounded by towering trees and abundant wildlife, this is the ideal place to unwind and reconnect with nature. The 1,025 sq. ft. home features 2 bedrooms, 1 full bath, a cozy main-level bedroom, and a spacious loft perfect for guests or additional living space. A newly built detached laundry room with a full bath adds extra convenience. The property also includes a large equipment barn, detached two-car carport, woodshed, and plenty of room to garden, explore, or simply relax. Fresh spring water supplies the home and helps keep the landscape green year-round. Whether you're looking for a full-time residence, weekend getaway, or peaceful escape, this special property captures the timeless appeal of authentic log home living.

836 Ulrich Road, Prospect

$965,000
7 Beds 5 Baths 220222015 MLS
Rare opportunity to own 2 residences plus a studio on one tax lot. Offers exceptional flexibility for multigenerational living, rental income, live-work, or guest accommodations. The 1,720 SF main residence was fully renovated in 2018, including a new poured foundation, and has 4 bedrooms, 2 baths, open living spaces, a kitchen with crisp white cabinets, subway tile backsplash & a main level bedroom. The main residence includes a double garage with a 480 SF upper-level studio with a full bath. A separate second 1,070 SF residence, built in 2018, offers stylish & charming single-level living with high ceilings, 2 bedrooms, 2 baths, & contemporary finishes. Situated in an established historic neighborhood with mature trees, the property has off-street parking, modern systems, and is close to Ashland's downtown. This R-2-zoned property features separate addresses & meters & allows for 2 Airbnb units with owner occupancy on premises. Request property offering details.

563 Rock Street, Ashland

$559,000
3 Beds 3 Baths 220221847 MLS
Escape to your private 10+ acre wilderness sanctuary! This grand log home perfectly blends rustic luxury with ultimate functionality. The property backs up to BLM land for unmatched privacy & boasts spectacular, views of the Cascade Mtns. Inside find breathtaking, open-beam vaulted ceilings and a warm, inviting living space centered around a brick-surrounded pellet stove. The highly versatile floor plan offers 2 spacious main-level bdrms. Upstairs, discover a privately tucked-away primary suite complete with an en-suite bath and flexible loft area. Large, functional kitchen features abundant storage, walk-in pantry, and an adjacent dedicated laundry room. The exterior features an oversized garage with built-in shop area, plus dedicated RV parking. Embrace outdoor living on the massive, 932 sq ft covered porch, perfect for morning coffee or sunset views. A dream property for hobbyists, outdoor enthusiasts and travelers alike!

275 Citadel Road, Trail

$574,500
2 Beds 2 Baths 220221786 MLS
Price reduced - sellers are motivated! Rogue River frontage at its best w/the ability to fish salmon & steelhead right from your own backyard. Enjoy an ever-changing backdrop of wildlife including deer, eagles, ospreys, otters, beavers & a variety of birds. This beautifully updated 2-bdrm, 2-bath MF home offers 1,512-sq. ft. of living space above a spacious double car garage w/shop area. Built in 1993, it features vaulted ceilings, gas fireplace, laminate flooring & a remodeled kitchen w/quartz countertops, new cabinets & skylight. Major upgrades include all new windows, new plumbing, new A/C (2024) & new irrigation pump (2025). Primary bath includes walk-in shower. Outdoor living shines w/extensive decking including 12x12-covered & 12x40-upper deck, lower patio, firepit, raised garden beds, fenced yard w/dog run, drought-tolerant landscaping, 2 sheds & room for boat/RV parking. 2-Car carport, blacktop driveway, private well, public sewer & .36-AC lot complete this riverfront retreat.

150 Castaline Place, Shady Cove

$890,000
5 Beds 3 Baths 220221779 MLS
Rare opportunity to own a premier estate in one of Medford's most sought-after locations! This stunning 5,563 sq ft home sits on 2.76 fully irrigated acres offering privacy, luxury, and functionality. The attached ADU with separate entrance and kitchenette provides flexible living or rental income potential. Entertain in style with your gorgeous in-ground pool, or head to the impressive 1,000 sq ft shop featuring 400-amp service, ideal for hobbyists, contractors, or car enthusiasts. The 1,800 sq ft barn and two fully fenced, irrigated pastures make this a turnkey equestrian or agricultural property. Two high-producing wells ensure abundant water supply year-round. Tucked away from the road for ultimate privacy, yet just minutes to town, shopping, and amenities. Every detail of this estate has been thoughtfully designed for those who demand the best in rural living without sacrificing convenience. Properties like 3600 Madrona Ln simply don't come available often!

3600 Madrona Lane, Medford

$1,450,000
4 Beds 3 Baths 220221600 MLS
Experience life on the banks of the Rogue River with approx. 140-ft of low-bank frontage on the famous ''Davis'' Salmon & Steelhead fishing hole--offering exceptional fly fishing, direct river access, and your own backyard raft/boat launch for days spent enjoying true riverfront living. Built in 2011 by Al Morris with exceptional quality and craftsmanship, this 2,727-sq. ft. custom home features 4-bedrooms, 2.5-baths, vaulted beamed ceilings, oak hardwood floors, a rock fireplace with built-ins, granite countertops, quality stainless appliances and formal dining. The primary suite captures peaceful river views and includes double vanity, roll-in shower, oversized closet & an outdoor spa. Full basement/garage has elevator, 4 roll-up doors, painted floors & swim spa room. A finished insulated shop/RV garage includes a pellet stove, propane furnace and ¾-bath. Gated 1.64-acre property with irrigation, mature redwoods, newer fencing, covered patio, and blacktop driveway.

38 Meadow Lane, Shady Cove

$535,000
4 Beds 3 Baths 220221520 MLS
Experience modern living in the desirable Rockland Place Subdivision. This four-bedroom, 2.5-bath home offers 1,890 square feet of thoughtfully designed space with an open-concept layout and quality finishes. The main-level primary suite features vaulted ceilings, a spacious walk-in closet, and a well-appointed bathroom with quartz counters and custom tile work. The kitchen is built for living and entertaining, featuring custom cabinetry, stainless steel appliances, quartz countertops, and a cozy gas fireplace that anchors the main living space. Upstairs, three additional bedrooms offer flexibility for guests, family, or a home office. Step outside to a covered patio, landscaped yard, and automatic sprinkler system, all within a fully fenced backyard designed for easy maintenance and outdoor enjoyment. Conveniently located near shopping, restaurants, and medical services, this home combines comfort, style, and practicality in one of the area's sought-after neighborhoods.

3775 Sidney Way, Medford

$759,000
5 Beds 6 Baths 220221349 MLS
71, 73 and 75 Wimer. Gorgeous updated including plumbing and electric vintage home w/charm remaining a few blocks to downtown Ashland. The main home has 3 bedrooms (2 with ensuite baths) the 3rd bedroom has an ensuite 1/2 bath. Formal living and dining and eat in large kitchen w/breakfast bar & nook. Granite countertops. Wood floors on main level & carpet on stairs & bdrms. The woodwork door trim is beautiful & probably original. Newer deck & A/C unit. Detached building (71 and 73 Wimer) are one level studio units with kitchens & baths. 73 Wimer has private deck. Main house is rented for $2375.00 p/month & tenant pays utilities except water. Studios have been rented for $1250.00 & $1350.00 per month with utilities included & they have a separate shared laundry facility. Unique property for owner occupied or income producing. Circular driveway for main home & 2 parking spaces in front for studios. Has been traveler accomodations in the past. Buyer to do own due diligence on u

75 Wimer Street, Ashland

$600,000
4 Beds 3 Baths 220221322 MLS
Discover this unique Medford, Oregon home! Nestled on a peaceful half-acre lot, this stunning 4-bedroom, 3-bathroom residence offers nearly 3,000 sq. ft. of comfortable living space with breathtaking elevated views of the surrounding hills. Step inside to a bright, open layout featuring a spacious island kitchen with expansive cabinetry, granite counters, stainless steel appliances, and a brand-new oven. The living room showcases panoramic views and a cozy gas fireplace insert. Two primary bedrooms (one on each level) provide flexibility and privacy, while the downstairs family room/game room is perfect for entertaining or relaxing. Outside, enjoy a large backyard ideal for play, gatherings, or letting pets run free. Hobbyists will love the 24x26 garage shop with its new garage door. Located in a wonderful neighborhood, you're just minutes from hiking and biking trails in the 1,740-acre Prescott Park on Roxy Ann Peak. A rare opportunity to own a view-rich retreat in Medford!

1568 Angelcrest Drive, Medford

$779,000
4 Beds 3 Baths 220221289 MLS
Set in a quiet cul-de-sac in the hills above Rogue River with sweeping panoramic views, this stunning estate has been designed for comfort, relaxation, and unforgettable entertainment. The home welcomes with an expansive open-concept layout filled with natural light and framed by picturesque mountain vistas from nearly every room. The stunning pool and entertainment area serve as the centerpiece of the property and include a pool-house upgraded with a custom covered patio with bar and gas grill, an indoor and outdoor shower, lavatory and sink, as well as a built-in stereo system and lighting features, all of which provide an experience rivaling a private resort. A custom water feature extends from the pool through the beautifully landscaped grounds, creating an atmosphere of tranquility and escape. Recent upgrades to the home include a new metal roof, new energy-efficient windows, new interior and exterior paint, and all new appliances. This is a home that will truly last a lifetime.

305 Woodville Way, Rogue River

$525,000
4 Beds 2 Baths 220221283 MLS
Charming historic home with 29+ years of improvements and stewardship. Updated electrical, HVAC, plumbing, sewer line, new roof, solar tubes, skylights, wood-wrapped casement windows, and decks. Wood flooring, vintage fixtures and hardware, period lighting, leaded-glass windows, and picture rail moldings. Spacious open living and dining area with wood stove and door to covered side-porch, kitchen with wood and glass-fronted display cabinets, laundry closet, two bedrooms, and full bathroom. Vaulted upper-level landing, wood-paneled bedroom with panoramic mountain views, full bathroom, and fourth bedroom with closet. Terraced grounds with mature trees, ornamental plantings, paver patio, meandering pathways, sunny fenced gardening areas, rustic garden shed, and renovated detached garage workshop. Property backs to 1.43-acre natural greenspace owned by the City of Ashland near Hald-Straberry Park; conveniently located within a half-mile of downtown. Inquire for details!

71 Scenic Drive, Ashland

$749,000
2 Beds 2 Baths 220221177 MLS
This sophisticated home combines high-end finishes & top-of-the-line infrastructure w/ stunning sunset views, a strong producing well w/ water rights, & a professional-scale solar array designed for complete self-sufficiency. Enjoy a grand layout featuring vaulted ceilings, wide plank engineered white oak floors, two wood stoves, and Knotty Alder solid core doors. Sliders lead to a brand new two-tiered deck, while the primary offers a free standing tub, marble shower, & a view balcony. This smart home provides seamless control over lighting, media, HVAC, etc via a central wireless hub. The firewise exterior includes a metal roof and fiber cement siding. A 28 solar panel array with 22,000KW storage is backed by two generators integrated for automatic operation. There's a heated barn with drive-through doors, two climate-controlled 40' shipping containers, & a storage shed. Newly completed in 2024 & 15min to town, this property is one of a kind. Inquire for a full features list.

8351 Dead Indian Memorial Road, Ashland

$340,000
3 Beds 3 Baths 220221172 MLS
One of only two end units still available! Welcome to Sunwood Addition in West Medford your opportunity to own a brand new townhome in a thoughtfully planned community. Sunwood Addition features beautifully designed townhomes offering 3 bedrooms, 2.5 bathrooms, and approximately 1,300 square feet of well planned living space with generous storage throughout. Enjoy open-concept living, abundant natural light, and quality finishes. The primary suite includes a spacious walk-in closet for added comfort and convenience. Ideally located near parks, schools, and local amenities, Sunwood Addition offers the perfect balance of style, comfort, and affordability. Photos are of the model unit. Broker is the builder/owner and has a financial stake in the sale of the units.

2032 Sunset Drive 1 Unit 1, Medford

$459,000
3 Beds 3 Baths 220221116 MLS
New in 2023, this 3 bed 2.5 baths 1419 sf. 2 story home functions with kitchen, dining, living and half bathroom down stairs while upstairs you will find the primary bedroom with its own balcony, laundry and additional bedrooms. The custom kitchen features stainless appliances with white farmhouse sink, eating bar, and pantry. The flooring is a mixture of solid surface and carpet throughout the home including the garage! Exceptional parking on and off site including what is behind luxury gates for cars, RV, or sports court and gates provide additional security. Enjoy the patio in the back for BBQ and quiet shade in the evenings. Two car garage with door openers and the home is close to all the amenities of town. Schedule an appointment today!

266 Reanna Way, Medford

$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

$975,000
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

$715,000
3 Beds 3 Baths 220221008 MLS
Back on the market through no fault of the property! Custom-built home on a private .69-acre lot in Ashland with breathtaking valley and mountain views. This versatile property offers a primary bedroom on the main level, vaulted ceilings, fireplace, built-ins, and spacious living areas designed for comfort and entertaining. Large kitchen with breakfast nook and abundant storage throughout. The primary suite features double sinks, separate shower, and a jetted soaking tub with its own hot water system. Downstairs includes a finished daylight basement with separate entrance and plumbing in place ideal for guest quarters, multi-generational living, or future mother-in-law suite potential. Enjoy the fenced garden with raised beds, TID irrigation water, oversized 2-car garage, easy-care landscaping, and a new roof installed in 2023. Rare blend of privacy, flexibility, and stunning views.

1020 Walker Avenue, Ashland

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: