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495 Chestnut Street 24 Unit 24, Ashland
$305,900
3 Beds ⋅ 2 Baths ⋅ 220223687 MLS
*Seller Motivated - will entertain all reasonable offers!* Affordable Ashland living in desirable Tudor Heights! This spacious 3-bedroom, 1.5-bath condo offers 1,392 sqaure feet of comfortable living space with mountain and territorial views from a private upper-corner location. The main level features a bright living room with a 60s style fireplace, kitchen, half bath, and flexible den perfect for a home office, guest space, or potential 4th bedroom! Upstairs you'll find three bedrooms, a full bath, and laundry area. Recent improvements include new carpet and a new water heater. Enjoy a private patio, detached carport, and additional storage. Conveniently located near downtown Ashland, Lithia Park, restaurants, shopping, and the hospital. HOA covers water, sewer, trash, landscaping, exterior maintenance, and exterior insurance for easy, low-maintenance living! Ownership occupancy only - no rental opportunities available at this time.

495 Chestnut Street 24 Unit 24, Ashland

Listing courtesy of eXp Realty, LLC.

590 Taylor Street, Ashland
$695,000
2 Beds ⋅ 3 Baths ⋅ 220223937 MLS
Beautifully Maintained Custom Ashland View Home! This property offers a blend of distinctive architecture and serene privacy with custom windows and natural beauty throughout. Step-down living room with gas fireplace, dining room has built-in shelving; house has engineered hardwood flooring and carpeted bedrooms; kitchen has newer 36'' gas range and built-in desk. Spacious ground-floor master bedroom, separate office that could be used as a guest bedroom, second upstairs bedroom, plus upstairs laundry room. View decks for indoor-outdoor living, mature landscaping and peaceful setting that includes patio, firepit, walking paths and fully fenced backyard. Quality upgrades include Karastan wool carpeting, newer roof, high-efficiency 2-stage HVAC, fresh interior paint, oversized garage with workshop/bonus area, central vac, 220v for EV charging and great storage throughout. Lovely hillside home on a quiet cul-de-sac just minutes from downtown with EZ access to Ashland's trail system.

590 Taylor Street, Ashland

Listing courtesy of John L Scott Ashland.

162 Crocker Street, Ashland
$375,000
3 Beds ⋅ 3 Baths ⋅ 220223627 MLS
Tucked into the desirable Chautauqua Trace neighborhood in Ashland, this well-maintained home was made for indoor-outdoor living. The real showstopper is the spacious private deck, accessed right off the dining area through a sliding glass door, creating an effortless flow from kitchen to open air. Picture slow morning coffee, summer dinners under the sky, and easy evenings hosting the people you love, all in your own peaceful retreat. Inside, easy-care laminate flooring runs throughout the main level, and the home offers three bedrooms and two and a half bathrooms with tiled baths that add both style and durability. The kitchen keeps everything within reach thanks to a large pantry. Beyond your doorstep, walking paths and open space invite you outside, while shopping and the YMCA sit just minutes away. Come experience it in person and picture yourself settling in.

162 Crocker Street, Ashland

Listing courtesy of John L Scott Ashland.

143 Granite Street, Ashland
$789,000
5 Beds ⋅ 2 Baths ⋅ 220223588 MLS
Offered for the first time in generations, this extraordinary fourth-generation Ashland treasure presents a rare opportunity. Own a piece of local history just steps away from world-renowned Lithia Park. This timeless two-story residence sits on beautifully landscaped .32 acre lot. It offers 5 bedrooms, 2 bathrooms, and a character that cannot be replicated. This home is rich in charm and architectural detail. It showcases the craftsmanship of a bygone era, while providing ample space for modern living. Enjoy peaceful mornings on the porch, stroll through Lithia Park, and easy access to downtown Ashland's theaters, galleries, restaurants, and cultural attractions. Homes of this caliber, location, and historical significance seldom become available. This is a once-in-a-generation opportunity to continue the legacy of one of Ashland's cherished homes.

143 Granite Street, Ashland

Listing courtesy of RE/MAX Platinum.

7979 Hyatt Prairie Road 42 Unit 42, Ashland
$229,000
2 Beds ⋅ 1 Baths ⋅ 220223508 MLS
The cabin of your dreams is waiting for you just 35 minutes from downtown Ashland at The Cabins at Hyatt Lake. Tucked into the trees near the shores of the Lake, this peaceful mountain getaway offers the kind of escape people search for and rarely find. With one of the larger and more desirable layouts, the added bump-out creates extra room to relax, gather, and enjoy every season. Vaulted wood ceilings, warm natural light, and a spacious open living area create an inviting place to unwind after a day on the lake, hiking nearby trails, or winter adventures in the snow. Step outside to the wraparound deck, enjoy coffee in the crisp mountain air, soak in the hot tub, and take in the quiet forest setting. Never used as a rental, this fully furnished retreat is truly turnkey. Main-level bedroom and bath, loft sleeping space above, and an oversized shared 2-car garage for boats, gear, and toys complete the package. Just a short walk to the lake and endless outdoor recreation year-round.

7979 Hyatt Prairie Road 42 Unit 42, Ashland

Listing courtesy of eXp Realty, LLC.

22494 Jefferson Road, Ashland
$2,140,000
5 Beds ⋅ 5 Baths ⋅ 220223401 MLS
Rare 203-acre Ashland estate with sweeping south-facing views offers a resort setting tucked away at the end of a mountain road. Completed in 2015, the 7,468 sq ft Craftsman residence was designed for beauty and function. The main level showcases two primary suites, two additional oversized bedrooms, expansive living and family rooms, and a gourmet kitchen. One walnut staircase leads to a private loft while a second stairway leads to a spacious upper level bonus room. The partially finished daylight basement has exterior and patio access. The original 1,812 sq ft home is now an amazing fully finished flex space, ideal for guests, office, studio, or recreation. Surrounded on three sides by the Siskiyou Cascade National Monument for vast recreational opportunities. The property offers pasture, wooded terrain, and creek frontage. This rare legacy estate delivers self sufficiency, seclusion, and unparalleled outdoor access while remaining within reach of Ashland's renowned amenities.

22494 Jefferson Road, Ashland

Listing courtesy of John L. Scott Medford.

457 Walnut Street, Ashland
$650,000
3 Beds ⋅ 4 Baths ⋅ 220223382 MLS
Enjoy exceptional privacy and beautiful views in this single-family retreat, nestled on a tree-lined 0.33-acre lot in one of Ashland's most desirable neighborhoods. A welcoming front deck leads to the 2,270 sq ft home featuring 3 bedrooms and 3 full bathrooms. The grand living room showcases expansive windows framing stunning trees, the valley and mountain views. The rear deck overlooks a professionally designed/built backyard with a charming gazebo. A versatile 336 sq ft house addition featuring a private half bath and a valley-view picture window is ideal for guests, a home office, or multi-generational living. The oversized 2-car garage provides ample storage and workspace. The garage backdoor leads to a custom Catio porch... Despite its peaceful and secluded setting, this home is conveniently located just minutes from downtown, the hospital, and Lithia Park, offering the perfect combination of tranquility and accessibility.

457 Walnut Street, Ashland

Listing courtesy of Gateway Real Estate.

820 Park Street, Ashland
$399,000
3 Beds ⋅ 3 Baths ⋅ 220222380 MLS
Exceptional end-unit townhome less than 1 mile from Southern Oregon University! Originally built as the developer's personal residence, this thoughtfully designed home offers approximately 30% more living space than other units in the community. Inside, you'll find rich Brazilian cherry hardwood floors, elegant Italian mosaic tile accents, new interior paint, and stainless-steel kitchen appliances. The spacious kitchen features granite countertops, abundant cabinetry, and a walk-in pantry, opening to a comfortable living area with a gas stove. The main level also includes a half bath, laundry area, and access to a private fenced patio with additional storage. Upstairs, the generous primary suite captures beautiful mountain views and offers a spa-inspired bath with dual sinks, soaking tub, walk-in shower, and two closets. A detached garage, deeded parking space, community pool, exterior maintenance, and landscaped common areas complete this outstanding property.

820 Park Street, Ashland

Listing courtesy of Windermere Van Vleet & Assoc..

1969 Colestin Road, Ashland
$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

Listing courtesy of Cascade Hasson Sotheby's International Realty.

75 Wimer Street, Ashland
$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

Listing courtesy of Absolute Realty.

8351 Dead Indian Memorial Road, 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

Listing courtesy of Gateway Real Estate.

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

Listing courtesy of John L. Scott Medford.

1020 Walker Avenue, Ashland
$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

Listing courtesy of Oregon Adventure Realty.

2000 Colestin Road, Ashland
$680,000
1 Beds ⋅ 1 Baths ⋅ 220220912 MLS
Beautiful Colestin property on 159 acres with 5 separate lots combined, seasonal creek running through this property, and amazing views. A must-see sanctuary on Colestin Road.

2000 Colestin Road, Ashland

Listing courtesy of John L. Scott Medford.

34 Scenic Drive, Ashland
$589,000
4 Beds ⋅ 3 Baths ⋅ 220220812 MLS
Timeless mid-century home just a block above Lithia Park and only a short jaunt to the plaza. Sitting in a quiet location with views, this home offers serenity while still being close in. Exposed beam ceilings on the lower level offers warmth and charm. A bank of picture windows in the living room allows one to take in the mountain views as well as overlooking the backyard. The kitchen opens to the spacious back deck which is perfect for entertaining and indoor/outdoor living. An oversized mudroom/pantry as well as an office nook round out the downstairs. Upstairs sit 4 bedrooms, including a spacious primary suite that opens to a private deck with views to take in the natural beauty. One bedroom with vaulted ceiling could be used as a media room or flex space. Outside, the yard is fully fenced and has garden beds and room to play. With a solar array and backup battery, this home is well-equipped. All of this is so close to town, Lithia Park and the incredible trail network of Ashland!

34 Scenic Drive, Ashland

Listing courtesy of Full Circle Real Estate.

495 Chestnut Street 1 Unit 1, Ashland
$240,000
2 Beds ⋅ 2 Baths ⋅ 220220712 MLS
If you are looking for the best views in Ashland's Tudor Heights, this is it. Positioned as the premier front unit, this condo offers a perspective no other home in the complex can match. Stay comfortable year-round with the rare addition of efficient ductless mini-splits for heating and cooling--a significant upgrade over the standard baseboard heat found in most units. The main level offers a seamless open layout that flows to your outdoor patio. Upstairs, both bedrooms provide unobstructed mountain views to the north and east, including a private balcony off the main suite--perfect for watching the sunrise. Whether you're walking to the Downtown Plaza for dinner or hiking through Lithia Park, everything is within reach. Enjoy the security and ease of a comprehensive HOA that handles exterior upkeep, allowing you to simply relax and enjoy the Southern Oregon scenery.

495 Chestnut Street 1 Unit 1, Ashland

Listing courtesy of Windermere Van Vleet & Associates.

7550 Hyatt Prairie Road, Ashland
$475,000
2 Beds ⋅ 2 Baths ⋅ 220220635 MLS
Attention investors!! If you're looking for a cozy getaway close to all the recreational activities Southern Oregon has to offer, this is the one for you! Currently an active short term rental and providing a strong return to the owners, this two-story charmer features 2 bedrooms plus loft area, 2 bathrooms, 1472 sq ft, 1.64 wooded acres, open floor plan, vaulted ceilings, hardwood flooring, metal roofing, attached 2 car garage, detached shop/garage, fenced yard, enclosed porch, certified woodstove, main level living, & much more! Living room, kitchen, and bedrooms are spacious as well! Can't go wrong with this property if you like to hike, fish, kayak, atv, bike, or simply enjoy a forested ambiance. Only seconds away from Hyatt Lake! This one won't last long on the market, so contact your agent today for a personal tour, before it's too late! No drive-by's allowed and this property is appt only.

7550 Hyatt Prairie Road, Ashland

Listing courtesy of John L. Scott Medford.

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

Listing courtesy of Redfin.

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

Listing courtesy of John L. Scott Medford.

430 Ashland Street, Ashland
$565,000
5 Beds ⋅ 3 Baths ⋅ 220219281 MLS
NEW PRICE!! Located above the Boulevard in one of Ashland's most sought-after neighborhoods, this 5-bedroom, 3-bath home offers the perfect blend of convenience and opportunity. Just minutes from downtown, local shops, restaurants, and hiking trails, the location is hard to beat. Inside, you'll find a functional layout with a cozy fireplace anchoring the main living space as well as original hardwood flooring. Updated solid wood interior doors throughout the home offer a touch of modern sophistication, while multiple sky lights allow for plenty of natural light. Outside, the lot provides plenty of room to garden, or reimagine the space to fit your vision. Whether you're looking for a solid investment property or a place to create your dream home, this one is full of potential.

430 Ashland Street, Ashland

Listing courtesy of Cascade Hasson Sotheby's International Realty.

166 Nob Hill Street, Ashland
$425,000
3 Beds ⋅ 2 Baths ⋅ 220218469 MLS
Builder/developer opportunity in one of Ashland's most sought-after neighborhoods. Exceptional redevelopment potential on a .35 acre corner lot just blocks from the Ashland Plaza. Elevated position captures sweeping mountain, city, and territorial views in an area of high-end homes. Existing structure is likely best suited for removal, creating a rare chance to build a stunning custom home on a large in-town lot or explore the potential for a lot split and development of two residences (buyer to complete all due diligence with the City of Ashland). Prime location near Lithia Park, OSF, and downtown amenities. Opportunities like this with size, views, and proximity to town are increasingly rare.

166 Nob Hill Street, Ashland

Listing courtesy of Full Circle Real Estate.

593 Crowson Road, Ashland
$735,000
3 Beds ⋅ 3 Baths ⋅ 220218220 MLS
Fully renovated home by Coleman Creek Construction with detached studio and garage on rare E-1 zoned acreage with development potential in city limits! Charming front porch and covered wrap-around patio, open-concept living area with double-height vaulted ceiling, kitchen with quartz dining counter, designer lighting, and stainless appliances including gas range oven. Main-level primary suite with skylights, glass door to back patio with retractable awning, and full ensuite bathroom with quartz vanity, deep soaking tub, and oversized shower with seamless glass and tile surround. Additional main-level bedroom and full guest bathroom with quartz vanity, stacked washer dryer, and tiled shower. Vaulted upper-level media room, office, or third bedroom. Detached studio with quartz dining counter, stainless appliances including electric range oven, full bathroom with quartz vanity, tub shower, washer dryer, plus two-car garage. Ample off-street boat or RV parking. Inquire for details!

593 Crowson Road, Ashland

Listing courtesy of John L. Scott Ashland.

852 Oak Street, Ashland
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 220217927 MLS
Platinum Earth Advantage home just minutes from downtown, offering 2,750 sq ft of thoughtfully designed 4BR, 3BA + office living space with stunning views of Grizzly Peak and the Cascades. This light-filled residence features 12' ceilings, expansive windows, quartz surfaces, designer lighting, and blonde wide-plank hardwood floors. The main level features two ensuite bedrooms, highlighted by a luxurious primary suite with radiant heated floors, dual shower system, and two walk-in closets. The chef's kitchen boasts an 11-ft island, double ovens, gas cooktop, beverage fridge, and walk-in pantry. Enjoy seamless indoor-outdoor living with an 8' slider to a spacious view deck. Lower level offers 2 bedrooms, office, second laundry, and potential for separate living. Professionally landscaped, private setting with detached 2-car garage, EV charging, and energy-efficient 2-zone HVAC system. Home designed by Vadim Agakhanov.

852 Oak Street, Ashland

Listing courtesy of Millen Property Group.

8612 OR-66, Ashland
$999,999
3 Beds ⋅ 4 Baths ⋅ 220217132 MLS
Stunning new contemporary home with mountain views on 20+ private acres! Interior highlights include natural hickory and maple hardwood floors and steps; porcelain tile in kitchen, bathrooms and great room, granite counter tops, washer and dryer in upstairs primary bedroom closet and connections for a second set up downstairs, windows wired for electric blinds or shades, beautiful stone fireplace all the way to the ceiling, all Dacor appliances. The exterior has stucco siding, and a metal roof on both the main house and detached garage. The oversized garage has enough space for 2 cars plus a shop area with ample lighting, EV charging outlet, and a heated full bathroom. The garage also has an attached 2 car carport. The covered patio boasts an outdoor fireplace and the upstairs balcony off of the primary bedroom is a perfect place to accommodate a hot tub and enjoy the views.

8612 OR-66, Ashland

Listing courtesy of John L. Scott Medford.

523 Strawberry Lane, Ashland
$995,000
5 Beds ⋅ 4 Baths ⋅ 220216782 MLS
Available for the first time, 2004-built custom home in Ashland's Strawberry Meadows. This 3,105 sq. ft. 5 bed/4 bath house sits on a private .46-acre lot bordering an oak-lined creek open space. Main level includes double-height entry with skylights, living room with wood-fire insert, dining room, well-planned kitchen with large pantry, and a primary suite with deck. Upper level offers four bedrooms, 3 with walk-in closets, and large family room with balcony overlooking the creek. Versatile layout accommodates expansive family life and home office space. Additional features include a 2-car garage, robust storage, an approx 200 sq ft finished bonus room not included in the square footage, and a generous patio off the dining/kitchen area with perennial gardens enclosed in a custom deer fence. Situated in a Firewise-certified neighborhood near Lithia Park with access to local hiking trails. This private and quiet property offers a rare opportunity for a special home in a coveted setting.

523 Strawberry Lane, Ashland

Listing courtesy of Gateway Real Estate.

50 Lowe Road, Ashland
$2,250,000
220216457 MLS
Prime investment opportunity in Ashland, Oregon! This 44-room motel is conveniently located just off the freeway at 50 Lowe Road, offering excellent visibility and accessibility for travelers. The property features beautiful mountain views and includes a well-maintained swimming pool, currently not open to the public, providing significant value-add potential. The property also includes a fully equipped restaurant space that is currently not in operation but offers the infrastructure needed to reopen or repurpose according to a new owner's vision. With its strategic location, existing amenities, and strong upside potential, this property presents an exceptional opportunity for investors or hospitality operators ready to bring new life and creativity to this motel.

50 Lowe Road, Ashland

Listing courtesy of Home Quest Realty.

211 Glenview Drive, Ashland
$625,000
4 Beds ⋅ 3 Baths ⋅ 220216451 MLS
Panoramic valley views, seconds from Downtown Ashland & Lithia Park - a rare combination of space, quality, and location. This 4-bedroom, 3-bath home offers 2,711 sqft on a private 0.26-acre lot. The vaulted living room features hardwood floors that continue throughout both levels, and nearly every room captures sweeping valley views. Two large decks extend the living space outdoors. The updated primary suite includes radiant floor heating, walk-in shower, soaking tub, and dual vanities. The galley kitchen offers granite countertops, custom cabinetry, and quality appliances. Detached sauna/private office, EV-equipped 2-car garage, wood stove, and tankless water heater. Shared private cul-de-sac with two neighbors - the approach is short and the privacy at the top is exceptional. Walkable to Lithia Park, the Oregon Shakespeare Festival, and downtown Ashland. Pre-inspection completed. 1-yr home warranty included. At $230.54 per sq ft, priced below comparable 2026 Ashland sales.

211 Glenview Drive, Ashland

Listing courtesy of John L. Scott Medford.

15922 Green Springs 66 Highway, Ashland
$735,000
3 Beds ⋅ 3 Baths ⋅ 220215130 MLS
Modern Airstrip Estate in Oregon's Green Springs Wilderness Usable land adjacent to BLM forest offers endless recreation--horseback riding, hiking, swimming, and paddleboarding. Enjoy rural privacy without sacrificing modern comfort or convenience: cable internet, reliable utilities, and strong cell service year-round--the perfect blend for today's lifestyle. Nestled along the scenic Green Springs Highway, this standout property includes deeded private access to Pinehurst Airstrip, ideal for aviation enthusiasts. Approx. 1,500 sq ft upstairs is perfect for a home office or creative studio. Shop 2,500.sq ft 347,500 estimate at 139.00 sq ft ,install/permit, 220 amp, box, 220 wiring foundation engineered, 12x 12 rolling door, 14 ft ceilings metal snap lock roof. Property sits on13.63 acres of usable land. Open Meadows, mature timber, large pond, with direct context inside the Cascade Siskiyou National Monument area. Seller finance, 3,488 sq ft Airstrip Estate, investment opportunity.

15922 Green Springs 66 Highway, Ashland

Listing courtesy of Rogue River Valley Realty.

369 Meadow Drive, Ashland
$450,000
3 Beds ⋅ 3 Baths ⋅ 220214909 MLS
Charming 3-bed, 2.5-bath home in a quiet Ashland neighborhood near shopping, the YMCA, and more. Enjoy peaceful countryside views and a year-round brook. The open layout features a cozy gas fireplace and a chef's kitchen with granite counters and a Bertazzoni six-burner range. The spacious primary suite includes a converted office/library space. Recent updates include new wood floors (2023), exterior paint (2022), updated carpet, expanded backyard, and reflashed windows. Move-in ready with quality upgrades throughout!

369 Meadow Drive, Ashland

Listing courtesy of Real Broker.

372 Glenn Street, Ashland
$350,000
2 Beds ⋅ 2 Baths ⋅ 220214714 MLS
Thoughtfully updated Glenn Vista Estates end-unit townhome offering comfort, privacy, and flexibility. The floor plan includes a bedroom and full bath on the main level, plus an additional bedroom and bath upstairs. The kitchen and bathrooms have been tastefully updated, with a skylight that fills the space with natural light. Other recent improvements include windows, roof, siding, and a newer HVAC system. The living room features a wood-burning fireplace, currently used with an electric insert, and opens to a front deck through a large sliding door, creating a seamless indoor-outdoor feel. The downstairs bedroom opens to a private, walled-in patio. As an end unit, the home enjoys added privacy and light, along with extra storage space in the garage. Community amenities include a pool and spa, all just minutes from downtown Ashland, as well as shopping, dining, and the Oregon Shakespeare Festival.

372 Glenn Street, Ashland

Listing courtesy of Full Circle Real Estate.

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