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$828,000
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
$215,000
2 Beds ⋅ 2 Baths ⋅ 220219913 MLS
Charming Ashland Condo in Prime Location! Conveniently situated near restaurants, shopping, medical facilities, & scenic hiking trails in beautiful Lithia Park, this inviting 2-bedroom, 1.5-bathroom condo offers both comfort & accessibility. Tucked toward the back of the desirable Tudor Heights Complex, updated w/ newer carpet, LVP flooring & exterior paint. The main level features a kitchen w/ refrigerator, range/oven, & microwave, plus a convenient half-bathroom. Living room opens to a covered back patio, perfect for enjoying your morning coffee. Upstairs, you'll find 2 bedrooms--one w/ a private balcony ideal for relaxation, the other w/ a walk-in closet & easterly mountain views. Full bathroom w/ a dual sink vanity & tub/shower combination. The HOA provides many amenities, including a covered assigned parking space w/ storage closet, water, sewer, garbage, roof maintenance, exterior upkeep, & common areas. Don't miss your opportunity to start enjoying the Southern Oregon Lifestyle!

495 Chestnut Street 19 Unit 19, 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
$399,000
2 Beds ⋅ 2 Baths ⋅ 220219247 MLS
Centrally located townhome for sale in highly desired community in Ashland, Oregon. The HOA fees covers landscaping, community pool, garbage & water. Stepping into this home, one is immediately greeted with a bright living space & large picture windows overlooking the beautifully landscaped community open space. A bedroom and spacious bathroom also sit on the main floor. Downstairs is another bedroom with a large walk-in closet and ample storage in the basement. Separately deeded 1 car garage also included.

55 W Hersey Street, Ashland
$475,000
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
$339,000
2 Beds ⋅ 2 Baths ⋅ 220218449 MLS
Enjoy affordable living in Ashland in this charming 2-bedroom, 1.5-bath townhome offering 1,140 sq ft of comfortable space. This clean, move-in-ready home features all-new carpeting and fresh interior paint throughout. The electric range is brand new, AC only a couple years old, plus some new bathroom fixtures. The inviting living room includes a cozy fireplace, perfect for relaxing evenings. One bedroom offers a unique loft area, ideal for a reading nook, meditation area or extra storage with a mini-split for added cooling comfort. There's a balcony overlooking the enclosed patio, perfect for container gardening. Includes a single car garage. This is a small complex with common green spaces for residents to enjoy. Conveniently located just minutes from downtown Ashland's shops, dining, and entertainment, as well as the natural beauty of Lithia Park. The HOA fees of $250 a month.

153 E Hersey Street, Ashland
$749,000
4 Beds ⋅ 3 Baths ⋅ 220218224 MLS
Welcome to Billings Ranch, one of Ashland's most desirable communities. This stylish 3,184 sq ft, 4 bed, 3 bath home blends comfort and functionality with standout spaces for spring and summer entertaining. Upon entry you are greeted with a sweeping spiral staircase and 20-ft vaulted ceilings that create a grand open atmosphere. The main level offers a spacious living room, a dedicated dining area, and a beautifully appointed kitchen with two gas stoves, granite countertops, and ample prep space making it perfect for gatherings. Enjoy warm-weather living on the private back patio with a built-in gas firepit and grapevine-covered pergola, ideal for outdoor dining, relaxing evenings, and hosting year-round. A main-level bedroom, full bath and den complete the comfort of the downstairs. Upstairs, are three additional bedrooms, including a luxurious primary suite with its own gas fireplace, a spa-like ensuite bathroom with a jetted tub and a generous walk-in closet.

692 Vansant Street, 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
$230,000
2 Beds ⋅ 2 Baths ⋅ 220218166 MLS
Back on market due to buyer financing/economic changes. Home is priced aggressively for a quick sale. Rare opportunity for affordable, low-maintenance living near the heart of Ashland. This charming two-bedroom townhouse is the perfect fit for those seeking an uncluttered lifestyle, as the HOA handles all groundskeeping and full exterior maintenance. Ideally situated in a quiet neighborhood, you are just a short distance from Ashland's vibrant downtown. Inside, the home is equipped with high-efficiency mini-splits for year-round climate control and comfort. The thoughtful layout includes one bedroom featuring a beautiful view of the mountains, and the second with a private balcony. Off the living area is a private fenced covered patio, providing intimate spaces for outdoor relaxation. Added conveniences include dedicated covered parking and private storage. Combining price, position, and ease of ownership, this home is a standout offering.

495 Chestnut Street 23 Unit 23, 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
$379,900
3 Beds ⋅ 3 Baths ⋅ 220217759 MLS
Nicely updated 2000-built Ashland townhome, offering 1,388 square feet of comfortable, two-level living. Hardwood floors, a cozy gas fireplace and attractive finishes create a warm, inviting feeling throughout. The well-designed kitchen includes gas range, great cabinetry, good built-in storage, an attached eating area, and an open layout to the living spaces--ideal for relaxed living. The home has three bedrooms, two full baths and convenient powder room with pedestal sink. Enjoy lovely views in this active friendly community, a covered porch with plenty of sitting area, a small front and side garden plots for your plantings, a one-car garage and one separate assigned parking space. The professionally managed HOA offers low dues of just $75 a month. Excellent access to schools, shopping, transit and Ashland's renowned amenities--this well priced property is perfect for a starter home, rental investment, or part-time getaway. Stop by for a look!

827 Blackberry Lane, Ashland
$2,500,000
220217226 MLS
Located in the vibrant core of Ashland, 145 E Main Street presents a rare opportunity to own a historic, income-producing commercial asset in one of Oregon's most desirable downtown districts. Built in 1905, this classic property blends timeless character with strong investment fundamentals, currently delivering a 6% cap rate. The building offers 3,960 sq ft of commercial/retail space, presently occupied by professional office users and a popular locally owned restaurant that benefits from excellent downtown foot traffic. In addition, the property includes 2,920 sq ft of parking or warehouse storage space, currently leased as income-generating parking spaces--an increasingly valuable amenity in downtown Ashland. Positioned along E. Main St in the heart of the city's dining, shopping, and cultural corridor, this property provides investors with stable tenancy, multiple revenue streams, and long-term upside in a highly sought-after market. And 1 block from the Shakespeare Festival!

145 E Main Street, Ashland
$1,350,000
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. Seller carry option available with a considerable down.

8612 OR-66, 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
$950,000
3 Beds ⋅ 3 Baths ⋅ 220216742 MLS
This view property will not disappoint. Perfect wood window placement throughout takes in the surrounding mountain & valley views. Open floor plan w/ formal/informal dining & living, creates ample spaces for entertaining. Vaulted living room w/ slate tile flooring & a corner woodburning fireplace. Roomy kitchen w/ plenty of storage, granite counters & slider access to the large outdoor deck & integrated paneled Thermador refrigerator. Primary bedroom on the main floor is situated perfectly to take in the city views from the private deck. It also has walk-in closet, soaking tub & separate tile shower. One other bedroom & full bathroom located on the main floor. Downstairs is perfect for overflow guests, w/ its own living room, full bath, bedroom & an office space. Each level has its own 2 car attached garage. Mature, easy-care landscaping on this large lot w/ great privacy provided from the city owned lot below, which gives a rural atmosphere to the back yard while being close to town.

290 Skycrest Drive, 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
$725,000
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, a walk-in tile shower, separate soaking tub, dual vanities, and walk-in closet. The galley kitchen offers granite countertops, custom cabinetry, and quality appliances. The property also includes a detached sauna/private office - ideal for remote work or wellness, plus an EV-equipped 2-car garage, certified wood stove, and tankless water heater. Walkable to Lithia Park, the Oregon Shakespeare Festival, and downtown Ashland. At $267.43/sqft, priced below comparable 2026 Ashland sales. 1 yr home warranty included with the sale of an acceptable offer.

211 Glenview Drive, Ashland
$760,000
220216441 MLS
Versatile commercial building in the heart of downtown Ashland - surrounded by retail and restaurants, within one block of the Oregon Shakespeare Festival! Eight tenant suites with an established mix of professional and personal services, restaurant, and hair salon. Main level features a 55' x 10' breezeway to Will Dodge Way, three individual suites, and one common area bathroom. Upper level with five additional suites, full commercial kitchen, two additional shared bathrooms, and storage closets. High-traffic location with excellent visibility and ample public parking directly across Lithia Way. Recent appraisal of income and comparable sales with market value opinion available. Inquire with agents to access additional documentation and details!

116 Lithia Way, Ashland
$539,000
4 Beds ⋅ 3 Baths ⋅ 220216358 MLS
Set on a private corner lot above the boulevard, this 4-bedroom, 2.5-bath home offers a versatile layout designed to accommodate a variety of lifestyles. Thoughtful modifications were made to support full-time care, including wheelchair accessibility to the main and lower levels and upgraded electrical features, while still maintaining a warm, inviting feel throughout. The main level includes the galley-style kitchen, living area, half bath, and garage access. A short flight up leads to three bedrooms and an updated bath with jetted tub and added storage. Downstairs, the spacious primary suite features a large accessible custom bath with Corian surround. Whether you're seeking enhanced accessibility, multigenerational living options, or simply a well-maintained, move-in ready home with flexible space, this property offers comfort and adaptability.

1059 Terra Avenue, Ashland
$795,000
4 Beds ⋅ 3 Baths ⋅ 220215978 MLS
Welcome to this stunning Ashland sanctuary, where spectacular Rogue Valley views greet you the moment you step out of your front door. Nestled in one of the area's most desirable locations, this amazing property captures the magic of Ashland living. Inside, the home is incredibly warm and inviting, bathed in an abundance of natural light streaming through generous windows that seamlessly connect the tranquil indoors with the breathtaking landscape outside. Whether you are sipping your morning coffee while watching the sunrise paint the hills, or winding down after a day, enjoy downtown Ashland's vibrant arts scene and world-class theater, this residence offers an unparalleled lifestyle. The expansive vistas provide a daily reminder of the natural beauty that makes this region so beautiful. This is more than just a house; it is a retreat designed for peaceful living. Come experience the unforgettable views for yourself in a stunningly crafted home! Your Ashland dream awaits!

500 Lakota Way, Ashland
$379,900
3 Beds ⋅ 3 Baths ⋅ 220215743 MLS
Turnkey, energy-efficient, and beautifully updated. This townhome stands out with a 3-year-old roof with a 50-year warranty, owned solar, and a hybrid water heater for long-term savings and peace of mind. Inside, you'll find new flooring, granite countertops, refreshed cabinetry, stainless steel appliances, upgraded insulation, and mini-splits in the living room and all three bedrooms for year-round comfort. The spacious primary suite features dual closets and a private bath. A half bath, pantry, and laundry area add convenience. Step onto the newly built cedar deck overlooking peaceful wetlands. One-car garage with coated concrete floor. HOA covers yard care for easy living. Move-in ready and built for comfort. Some photos are virtually staged for illustrative purposes.

144 Crocker Street, Ashland
$735,000
3 Beds ⋅ 3 Baths ⋅ 220215130 MLS
Built - 2007 Craftsman Ranch -Style Home 3,488 sq ft that sits on level 13.63 acres useable beautiful land with (2,500 sq ft shop w/12x12 rolling doors ,14ft ceilings.3/4 plywood sheeting, 220 wired throughout, #3 rebar spaced throughout a concrete foundation w/ Green snap lock roof uniformed to match Home. Property features open meadows, mature timber, and a large, serene pond -- ideal for horses and outdoor living. Includes deeded access to Pinehurst Airstrip, enhancing equity and uniqueness. Located within the Cascade-Siskiyou National Monument, just 8 miles from Hyatt Lake and near Pinehurst School, this one-of-a-kind investment and lifestyle property is poised to gain equity and never lose it -- truly exceptional in Southern Oregon's most desirable areas that sits 24 miles on the outskirts of Ashland that takes only 38 min drive time to Ashland. Perfect location! Beautiful lifestyle.

15922 Green Springs 66 Highway, Ashland
$499,000
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
$379,000
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
$499,000
3 Beds ⋅ 3 Baths ⋅ 220214699 MLS
Light-filled & well-maintained 2-story home in the desirable Oak Knoll Meadows, ideally located on a landscaped corner lot w/ mountain views. This inviting 3-bed, 2.5-bath home features a spacious great room w/vaulted ceiling, expansive windows & a gas fireplace. The sunny kitchen & dining area overlook the great room, ideal for everyday living & entertaining. A main-level primary suite offers a peaceful retreat w/dual vanities, walk-in closet, & shower. Upstairs, open landing overlooks the living space, while 2-guest bedrooms & a full bath provide room for family, guests, or home office. Additional highlights include separate laundry rm, 2-car garage w/ yard access & spacious deck for outdoor entertaining. Community open space, trails, & guest parking. Convenient to the YMCA, schools, shopping, golf course, and local wineries, this move-in-ready home delivers comfort & ease.

1087 Oak Knoll Drive, Ashland
$3,250,000
4 Beds ⋅ 6 Baths ⋅ 220214637 MLS
Paradox Vineyard Estate is uniquely defined by elements of water, air, the natural light and beauty of the Rogue Valley, and a resounding commitment to environmental stewardship. Award-winning architecture and landscape design implemented by reputable local contractors with the highest caliber of building materials certified through LEED, Energy Star, and Green Globes. Senses are captivated by a soaring skylight galleria spanning through the home, four open-air water courts with columnar basalt fountains, and stunning panoramic mountain views. Tranquil and private outdoor spaces with mature plantings and ornamental trees encircle the home, including an in-ground spa and lap pool. Vineyard operations are professionally managed for continued turn-key production of organic grapes acclaimed by local and regional winemakers. Close-in rural community of high-end estates located within five miles of Ashland's downtown plaza. Inquire for additional details and documentation!

786 Pompadour Drive, Ashland
$489,000
3 Beds ⋅ 3 Baths ⋅ 220214291 MLS
Beautifully maintained and truly move-in ready, this home delivers space, comfort, and an easy sense of flow. The layout simply works. Everyday life unfolds naturally here, from cooking and gathering in the generous kitchen and dining areas to relaxing in the comfortable living spaces. Storage is abundant, making it easy to stay organized without sacrificing warmth. The sellers have maintained and upgraded the home over time, and that care is evident throughout. Enjoy open views of the green space and creek from the back patio or the primary bedroom balcony. The yard is intentionally low maintenance, with a few garden beds ready for homegrown vegetables or flowers. Tucked into a quiet, often overlooked Ashland neighborhood, this is a place where neighbors are friendly and considerate, offering a welcoming atmosphere and a home that feels easy to live in from day one.

267 Meadow Drive, Ashland
$1,650,000
5 Beds ⋅ 5 Baths ⋅ 220214060 MLS
Known as 309 and 311 Granite Street, this exceptional estate overlooks Lithia Park on nearly six private acres, blending European elegance with a tranquil forest setting. Mature trees, stone paths, patios, and water features create rare seclusion just minutes from downtown Ashland, the Oregon Shakespeare Festival, and the historic Plaza. Vaulted ceilings, fine woodwork, stained glass, and expansive windows fill the interiors with warm, old-world character and natural light. The main home centers on an open great room with a dramatic rock fireplace, flowing to an informal dining area and oversized kitchen, with additional living spaces for entertaining or everyday life. The primary residence offers 4,479 sq ft plus 2,364 sq ft of flexible ground-level space. A second residence adds 844 sq ft, a 1,153 sq ft multi-purpose room, and carport-about 8,840 sq ft total. Near Mt. Ashland, Crater Lake, Britt Festival, and Rogue Valley wineries, this is a rare architectural retreat of tranquility

309 Granite Street, Ashland
$1,795,000
4 Beds ⋅ 3 Baths ⋅ 220213243 MLS
5 magazine quality acres, masterfully landscaped with expansive emerald, green lawns, mature trees, ponds & waterfalls create the perfect setting, built with enduring quality. The walls are solid 4x6 Canadian Western Red Cedar, offering style & durability. Large open-floor plan is perfect for gatherings. Earthy materials feature Saltillo tile flooring, rich cherry custom cabinetry, Milgard wood-cased windows, & vaulted, beamed ceilings add substance & style. Upper-level primary has a private deck overlooking the estate style grounds & mountains. Guest house features dual porches, carport, & sits beside one of five waterfalls. A 22' x 44' greenhouse with raised cedar beds. Nearly a mile of crushed granite paths wind through the landscape. 3-car garage, full RV hook-ups, & a 20'x45' shop. A true paradise. Main home is 3/2, guest home is 1/1.

4896 Highway 66, Ashland
$1,249,000
8 Beds ⋅ 9 Baths ⋅ 220212846 MLS
Just blocks from downtown, this historic gem blends charm and flexibility. Original fir floors, built-ins, high ceilings, and abundant natural light pair with modern updates. Enjoy the welcoming lawn, pollinator garden, and large covered front porch. The main level offers spacious living and dining areas, kitchen, half bath, and generous entry spaces. A 1-bedroom apartment with interior and private exterior access--includes a kitchen, laundry and full bathroom--a separate additional en-suite bedroom with exterior entry adds versatility. Upstairs are four lovely en-suite bedrooms, one with a balcony, all with updated Renewal by Andersen windows and balcony door. A detached 704 sq ft, 2 bedroom, 1.5 bath, single level cottage with its own address and electric meter provides added flexibility or income potential. With six paved off-street parking spaces, sheds, on-street parking, and alley access, this property offers exceptional possibilities for multi-generational living or investors.

451 N Main Street, 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: