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496 Beach Street, Ashland
$845,000
5 Beds ⋅ 6 Baths ⋅ 220230213 MLS ⋅ 3,647 SqFt. ⋅ 14,374 Sqft. Lot ⋅ 0.33 Acres
Gorgeously renovated Victorian blends historic charm with modern luxury in the heart of Ashland. R2 zoning offers versatile living: A gracious private residence, a home with Airbnb units, or a B&B with owner-occupied quarters. Once the beloved Midsummer Night's Dream B&B, it's now a private home with 2 vacation rentals in a stunning detached annex. The annex has produced income of up to $7500 a month in season. The main house (2375 SF) features hardwood floors, a lovely living room with fireplace, parlor/game room, formal dining room, chef's kitchen, laundry room, & small office. 3 luxurious suites are in the main home, with 2 more in the annex (1092 SF), each with a fireplace, spa bath, shower & a private deck. Expansive lush lawn areas with mature flowering trees & mountain views create a peaceful & picturesque setting. Unbeatable location near theaters, dining, & the magic that is Ashland. Off street parking. Inquire about purchase as turn-key operation with negotiated inclusions.

496 Beach Street, Ashland

425 W Nevada Street, Ashland
$839,000
5 Beds ⋅ 3 Baths ⋅ 220229842 MLS ⋅ 2,606 SqFt. ⋅ 6,098 Sqft. Lot ⋅ 0.14 Acres
Beautiful 2018 Craftsman home in Ashland's Billings Ranch neighborhood with 5 bedrooms and 2.5 baths, backing to open space with Cascade mountain and valley views. A covered porch opens to a bright foyer and main-level office or fifth bedroom behind French doors. The vaulted great room has view windows and stacked-stone fireplace, open to dining and a kitchen with white shaker cabinetry, pantry, breakfast bar, and smart convection gas double oven plus a third oven. The main-level primary suite has patio access, dual copper sinks, soaking tub, walk-in shower, and walk-in closet. Upstairs: second living room with built-in desk, a bedroom with a second walk-in closet, additional bedrooms, and a full bath. Washer and dryer stay. Outside: xeriscaped front, fenced backyard with firewise patio, fruit trees, grape vines, raised beds, garden shed, and 4-zone smart drip/sprinkler irrigation. Extra-deep 2-car garage with storage and workbench. Nearby wetland offers great bird watching!

425 W Nevada Street, Ashland

1650 Neil Creek Road, Ashland
$1,175,000
5 Beds ⋅ 4 Baths ⋅ 220229364 MLS ⋅ 3,270 SqFt. ⋅ 960,498 Sqft. Lot ⋅ 22.05 Acres
OWNER CARRY AVAILABLE! GOURMET KITCHEN. EMIGRANT LAKE VIEWS. 22 ACRES OF PRIVACY. This updated 5-bedroom, 3.5-bath home offers 3,270 sq ft on 22.05 acres. The gourmet kitchen features granite countertops and a stunning oversized island with 360-degree access for cooking and entertaining. Guest quarters and two separate laundry rooms provide flexibility. Updates include all-new doors and windows, a new roof, and new stucco with an imperfect smooth finish and upgraded cloth underneath designed to help reduce temperatures. A large garage with generous shop space accommodates vehicles, tools, and hobbies. The engineered greenhouse includes a concrete perimeter and separate power meter, with potential for shop conversion, subject to buyer due diligence. Level areas offer possibilities for future projects; buyers to verify permitted uses and development options. Enjoy beautiful lake views, exceptional privacy, and versatile spaces--with owner financing available to bring your vision to life!

1650 Neil Creek Road, Ashland

597 Henley Way, Ashland
$799,500
5 Beds ⋅ 3 Baths ⋅ 220229216 MLS ⋅ 2,394 SqFt. ⋅ 13,503 Sqft. Lot ⋅ 0.31 Acres
Lovely mid-century architectural design home set in a serene, treed setting, just a short stroll from downtown. Stunning 5-bd, 3-ba home w/ vaulted ceiling, exquisite solid walnut floor, bespoke walnut dining room screen. The kitchen is a chef's paradise featuring custom zebra wood cabs w/ pullout drawers, a pantry, Caesarstone counter, and a handcrafted concrete tile backsplash. The expansive living room w/ a gas stucco fireplace ready for an insert, zebra wood shelving all framed by breathtaking views of Grizzly Peak. The main level includes 3 bd & 2Ba with a large primary suite. The lower level with family room, another gas fireplace ready for an insert, 2 more bedrooms (one currently serving as an office), workout room with an outside entrance. All woodwork downstairs is crafted from Madrone, beautiful custom floating shelves and a tile bath on a private 0.31-acre cul-de-sac lot offers direct access to Ashland walking trails, providing a tranquil setting even quieter than camping.

597 Henley Way, Ashland

1068 E Main Street, Ashland
$1,250,000
5 Beds ⋅ 3 Baths ⋅ 220228921 MLS ⋅ 3,092 SqFt. ⋅ 11,761 Sqft. Lot ⋅ 0.27 Acres
Own a piece of Ashland's history with this incredible historical home, cherished by the same family for 100 years. Built in 1900, this 3,092 sq.ft. home offers 5 bedrooms and 3 full bathrooms and has been beautifully renovated for modern living while preserving its historic elegance. Original details include beautiful woodwork throughout, formal living and dining rooms, inglenook seating, wood flooring, original entry stairwell, and an original fireplace updated with a gas insert. The updated kitchen features custom cabinetry, granite countertops, a large island, and skylights. Updated bathrooms retain their vintage charm with claw-foot soaking tubs and gorgeous custom shower tile-work. The fully fenced property features gated entry, mature landscaping, and a large 2-car garage. Ideally located in the heart of Ashland, just minutes from downtown shopping, dining, entertainment, and nearby parks, making it easy to enjoy everything Ashland has to offer.

1068 E Main Street, Ashland

1058 Linda Avenue, Ashland
$599,000
5 Beds ⋅ 3 Baths ⋅ 220228065 MLS ⋅ 3,100 SqFt. ⋅ 10,018 Sqft. Lot ⋅ 0.23 Acres
Welcome home to this spacious 5 bedroom, 3 bath multigenerational home offering approximately 3,100 square feet of comfortable living space on a roomy .23-acre lot. Thoughtfully designed with two living rooms, there's plenty of room for gathering, relaxing, or creating separate spaces for extended family. A 2-car garage provides convenient parking and storage, while the covered back deck provides space to enjoy the tranquil backyard complete with a charming fish pond; perfect for enjoying your morning coffee or unwinding at the end of the day. Located in a quiet neighborhood just minutes from everything Ashland has to offer, you're less than 10 minutes from downtown Ashland, the Oregon Shakespeare Festival, and Emigrant Lake. Come experience the space, flexibility, and peaceful setting this special home has to offer!

1058 Linda Avenue, Ashland

364 Vista Street, Ashland
$1,275,000
5 Beds ⋅ 4 Baths ⋅ 220227353 MLS ⋅ 3,468 SqFt. ⋅ 14,810 Sqft. Lot ⋅ 0.34 Acres
Built in 1889 for hardware merchant George Eddings and later home to Ashland mayor D.B. Provost, the Eddings-Provost House has watched over the town from its hillside above the boulevard for 137 years. Designed by Col. James Norris, it is Queen Anne at its most confident: a veranda wrapping the northwest corner on spool-turned columns, hand-carved scallop shells set into the bay window frieze, and that same fan motif answered again inside on the stair. Ten-foot ceilings. Fir and mahogany throughout. Three fireplaces, one with a beveled-mirror overmantel. Stained glass, period fixtures, a third-floor loft under skylights. Four bedrooms, three baths, & rooms with real breathing room. A second tax lot holds a permitted 440 sq ft ADU, garage, & in-ground pool framed by terraced river-rock walls. Kitchen and baths await a new vision. Listed on the National Register in 1980, beside its 1889 twin, the Carter House. Rare, documented, & ready for its next family. Request historical information

364 Vista Street, Ashland

619 Elkader Street, Ashland
$1,625,000
5 Beds ⋅ 4 Baths ⋅ 220227302 MLS ⋅ 4,487 SqFt. ⋅ 15,246 Sqft. Lot ⋅ 0.35 Acres
This 4-bedroom home, plus a separate 1-bedroom accessory unit, is a standout on almost any block, thanks to its amazing use of space and unique contemporary design. The pitched metal roof, clean lines, and mix of materials really catch the eye. Inside, the main-floor primary bedroom suite boasts high windows in the dual-primary bath, while the expansive living/dining area off the kitchen is filled with built-ins that flow into the foyer-adjacent front office. The private, ''open horseshoe'' courtyard design brings natural light into the living room, dining room, kitchen, and primary bedroom. Plus, there's a fully self-contained private accessory residential unit with a full kitchen, one bedroom, and its own entrance.

619 Elkader Street, Ashland

55 Pompadour Drive, Ashland
$1,290,000
5 Beds ⋅ 6 Baths ⋅ 220227205 MLS ⋅ 5,974 SqFt. ⋅ 2,204,136 Sqft. Lot ⋅ 50.6 Acres
Tucked over the hill on more than 50 acres, this nearly 6,000 square foot estate delivers exceptional privacy and quiet seclusion, with amazing views of Grizzly Peak, minutes from downtown Ashland's shops, dining, and theaters. A long private drive sets the tone. Inside, two spacious primary suites, one lower and one upper, open the door to multigenerational living or a comfortable two family setup, joined by elegant formal and casual living spaces. Outside, a pool and hot tub are framed by expansive decks made for long summer evenings. The barn offers living quarters with a loft and workshop, ideal for guests, a studio, or a retreat. Solar adds year round efficiency, and the grounds are as thoughtfully appointed as the home, with mature oaks lining the drive and surrounding the residence. Beyond, the acreage opens to sweeping valley and mountain views. Rare privacy and refined living within easy reach of everything Ashland offers at a price that can't be beat!

55 Pompadour Drive, Ashland

485 Orchard Street, Ashland
$589,000
5 Beds ⋅ 4 Baths ⋅ 220227203 MLS ⋅ 2,487 SqFt. ⋅ 23,958 Sqft. Lot ⋅ 0.55 Acres
Over 1/2 Acre lot near historic Ashland Plaza! This 5 bedroom 4 bath home offers 2,487 sqft of living space set in a highly sought after neighborhood just minutes from shopping, dining and entertainment such as the Oregon Shakespeare Festival. The spacious floor plan provides plenty of room for everyday living, hosting and creating dedicated spaces for work, hobbies or relaxation. Two fireplaces add warmth and character, while the multiple sliding doors allow natural light to flood the living areas. One bathroom features an ADA accessible shower with floor to ceiling tile and custom stone, delivering both style and functionality. Outside, the beautifully landscaped lot offers an ideal setting for gardening or entertaining while providing convenient parking for multiple RVs, campers, trailers or boats. Don't wait, your next chapter starts here!

485 Orchard Street, Ashland

12300 Oregon 66, Ashland
$499,900
5 Beds ⋅ 3 Baths ⋅ 220226295 MLS ⋅ 2,404 SqFt. ⋅ 217,800 Sqft. Lot ⋅ 5 Acres
Escape to a private retreat on five level, wooded acres in the heart of the Highway 66 recreation corridor, just minutes from Howard Prairie, Hyatt Lake, and Lake of the Woods. This beautifully maintained, recently updated split-level home seamlessly blends comfort, privacy, and year-round adventure. A slate entry opens into a spacious living room featuring a bay window and a wood-burning stove insert. The home offers five bedrooms, three full baths, a formal dining area, and flexible living and family rooms--each with its own fireplace--plus a dedicated office or hobby space. The kitchen is equipped with granite countertops and tile flooring, ideal for casual meals or hosting guests. Set in a peaceful forest environment close to fishing, boating, hiking, mountain biking, and snowmobiling, this property is perfect as a primary residence, seasonal getaway, or investment property. Experience the quintessential Southern Oregon lifestyle in a serene, nature-filled setting.

12300 Oregon 66, Ashland

808 Pompadour Drive, Ashland
$1,299,000
5 Beds ⋅ 6 Baths ⋅ 220225703 MLS ⋅ 4,935 SqFt. ⋅ 217,800 Sqft. Lot ⋅ 5 Acres
Live the Southern Oregon Dream! Welcome to an extraordinary Ashland estate where breathtaking views of Mount Ashland, the Cascades, downtown Ashland, and surrounding vineyards create a spectacular backdrop. Nestled behind a private gated entrance on 5 acres, 1.6 TID irrigated, this custom-built 5 bedroom, 6 bath home offers luxury, privacy, and versatility. Whether you're seeking a peaceful retreat, a multigenerational home, or space to operate a home-based business, this property adapts to your lifestyle. The thoughtfully designed floor plan features TWO private suites with their own entrance, ideal for extended family, a professional office, or creative studio. Garden beds, fruit trees, space for horses, animals, a 28 GPM well, RV hookups w/220, abundant parking, just minutes from the Shakespeare Festival, galleries, wineries and award-winning restaurants. You'll enjoy the best of country living without sacrificing convenience. Luxury. Privacy. Self-sufficiency. Endless possibilities

808 Pompadour Drive, Ashland

591 Chestnut Street, Ashland
$645,000
5 Beds ⋅ 3 Baths ⋅ 220225471 MLS ⋅ 2,010 SqFt. ⋅ 7,840 Sqft. Lot ⋅ 0.18 Acres
Beautifully maintained 5-bedroom, 3-bathroom home offering the convenience of mostly single-level living in a desirable Ashland location less than one mile from downtown, Lithia Park, and the Oregon Shakespeare Festival. The thoughtfully designed floor plan features a spacious main-level primary suite and a private upper-level en suite bedroom with views, perfect for guests, multigenerational living, or a home office. The heart of the home is an incredible chef's kitchen with Brazilian cherry hardwood floors, leathered granite countertops, an oversized island with stylish pendant lighting above, double ovens, and wine refrigerator. Open-concept living spaces are filled with natural light and connect seamlessly to the partially covered patio and large, fully fenced backyard. Additional highlights include wide doorways, a dedicated laundry room, whole-house water filtration, generous storage, and a large walk-in closet. Call for a tour today!

591 Chestnut Street, Ashland

541 Fairview Street, Ashland
$996,000
5 Beds ⋅ 3 Baths ⋅ 220225227 MLS ⋅ 2,586 SqFt. ⋅ 6,969 Sqft. Lot ⋅ 0.16 Acres
Beautifully restored 1908 classic home located on a rare R2 zoned double lot just blocks from downtown Ashland's theatres, restaurants, galleries, and parks. MAIN RESIDENCE Featuring 3 bedrooms and 2 full baths, interior highlights include original fir floors, high ceilings, designer lighting, updated kitchen, pantry and abundant natural light throughout. Flexible layout supports guest space, office, or extended living arrangements. LOWER LEVEL Remodeled with separate entrance, kitchen, bedroom and full bathroom offering independent living space. Foundation of main home was updated in 1997 with central heat, air, electrical and plumbing systems. DETACHED COTTAGE Separate remodeled cottage with bedroom and bath ideal for additional flexible living needs, guest suite, or office. OUTDOOR FEATURES Mature landscaping with fenced yard, irrigation, water feature, dry sauna, spa, storage shed, and ample off street parking. ADDITIONAL HIGHLIGHTS R2 zoning ideal for income producing living.

541 Fairview Street, Ashland

4567 Old Highway 99 S, Ashland
$1,175,000
5 Beds ⋅ 3 Baths ⋅ 220224554 MLS ⋅ 4,918 SqFt. ⋅ 219,106 Sqft. Lot ⋅ 5.03 Acres
One of a kind Southern Oregon retreat just 15 minutes from downtown Ashland, offering privacy, exceptional craftsmanship, sweeping views & proven income in a peaceful park like setting. A true money maker, the fully permitted first floor 2 bedroom/ 1 bath ADU currently operates as a successful Airbnb, generating approximately $25,000 a year in net income, per seller. The custom one owner main home features soaring ceilings, walls of windows framing Emigrant Lake and Grizzly Peak, a dramatic curved staircase, custom pine log accents, hardwood floors, granite and travertine finishes, floor to ceiling fireplace, kitchen with breakfast nook, third floor bonus wing & over 1,900 sq. ft. of wraparound cedar decking. Also includes workshop, playhouse and covered carport. The Airbnb has its own private driveway and entrance, ADA access, kitchenette with granite counters and a custom bath, ideal for rental income, guests or multigenerational living.

4567 Old Highway 99 S, Ashland

143 Granite Street, Ashland
$789,000
5 Beds ⋅ 2 Baths ⋅ 220223588 MLS ⋅ 1,935 SqFt. ⋅ 13,939 Sqft. Lot ⋅ 0.32 Acres
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

22494 Jefferson Road, Ashland
$2,140,000
5 Beds ⋅ 5 Baths ⋅ 220223401 MLS ⋅ 7,468 SqFt. ⋅ 8,867,073 Sqft. Lot ⋅ 203.56 Acres
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

1105 Ivy Lane, Ashland
$607,500
5 Beds ⋅ 3 Baths ⋅ 220222389 MLS ⋅ 2,138 SqFt. ⋅ 11,325 Sqft. Lot ⋅ 0.26 Acres
Mid-century modern home built in 1971 with lovely mountain views and flexible living space. Enjoy gathering spaces and outdoor living from the expansive view deck overlooking the surrounding mountains. The home offers two spacious living areas, including one with a fireplace, along with kitchen, dining area, and office nook with views of Grizzly Peak. The main level features the primary suite, laundry hookups, a second bath, and an oversized second bedroom. Downstairs includes two additional bedrooms with separate exterior access, plus a second laundry area, offering flexibility for a variety of living arrangements. Above the oversized 2-car garage is a large bonus room ideal for guests, hobbies, or studio space.

1105 Ivy Lane, Ashland

75 Wimer Street, Ashland
$759,000
5 Beds ⋅ 6 Baths ⋅ 220221349 MLS ⋅ 1,616 SqFt. ⋅ 9,147 Sqft. Lot ⋅ 0.21 Acres
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

500 Ashland Loop Road, Ashland
$2,500,000
5 Beds ⋅ 7 Baths ⋅ 220220624 MLS ⋅ 6,033 SqFt. ⋅ 87,120 Sqft. Lot ⋅ 2 Acres
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

610 Orchard Street, Ashland
$900,000
5 Beds ⋅ 3 Baths ⋅ 220220148 MLS ⋅ 3,458 SqFt. ⋅ 22,651 Sqft. Lot ⋅ 0.52 Acres
Enchanting oasis property,½ acre of lush landscaping, abundant flora waterfalls and swimming pond with its own filtration system. Main house with large wrap around deck to take in the wonderful, secluded backyard and mountain views. Lots of skylights and space with high ceilings welcomes you to your relaxing living room with custom exotic wood built-in and rock fireplace. Large primary bedroom with views via 20 windows. Primary bathrooms includes steam shower. Just outside primary bedroom you can retreat onto a private covered deck with 1 yr old spa. 1 more bedroom on main floor then journey downstairs to 1 bedroom and additional bonus room. Solar system provide total electricity for entire main house. Also, a 3-car garage. A separate addressed 915 sq ft ADU with 2 bedrooms, 2 parking spots, fireplace, vaulted knotty pine ceilings, Corian countertops in bath and kitchen, tile & oak flooring with mahogany trim wood and its own private deck that is included for family or rental options

610 Orchard Street, Ashland

1625 Peachey Road, Ashland
$980,000
5 Beds ⋅ 4 Baths ⋅ 220220059 MLS ⋅ 2,595 SqFt. ⋅ 10,454 Sqft. Lot ⋅ 0.24 Acres
Gorgeous craftsman multi-generational living opportunity in one of Ashland's most desirable neighborhoods, just steps from parks, hiking trails, and hundreds of acres of public land. Immaculate landscaping and curb appeal create a striking first impression. A classic covered porch overlooks the front yard and a private park across the street. Step inside to vaulted ceilings and an open floor plan. Pristine oak flooring is complemented by modern cabinetry and a spacious kitchen island with quartz countertops, ideal for chefs and entertaining. Floor-to-ceiling sliding glass doors offer seamless indoor-outdoor living. Enjoy an expansive deck overlooking a serene backyard with pocket views of Grizzly Peak. The 350 Sq ft guest house is thoughtfully designed for convenient access while maintaining privacy with a dedicated fence, creating ideal separation between living spaces.

1625 Peachey Road, Ashland

430 Ashland Street, Ashland
$565,000
5 Beds ⋅ 3 Baths ⋅ 220219281 MLS ⋅ 1,973 SqFt. ⋅ 8,712 Sqft. Lot ⋅ 0.2 Acres
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

523 Strawberry Lane, Ashland
$995,000
5 Beds ⋅ 4 Baths ⋅ 220216782 MLS ⋅ 3,105 SqFt. ⋅ 20,037 Sqft. Lot ⋅ 0.46 Acres
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

309 Granite Street, Ashland
$1,650,000
5 Beds ⋅ 5 Baths ⋅ 220214060 MLS ⋅ 6,332 SqFt. ⋅ 258,746 Sqft. Lot ⋅ 5.94 Acres
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

2101 Dead Indian Memorial Road, Ashland
$785,000
5 Beds ⋅ 4 Baths ⋅ 220213217 MLS ⋅ 3,018 SqFt. ⋅ 218,235 Sqft. Lot ⋅ 5.01 Acres
Experience the ultimate Ashland lifestyle at this remarkable 5-acre estate, located just three miles from the Plaza yet below the snowline for year-round ease. This 3,370-sqft residence balances understated elegance with authentic country charm. The expansive interior boasts 5 beds and 3.5 bths, designed for flexibility. The main level offers three spacious bedrooms, a cozy family room, and a gourmet kitchen featuring granite surfaces, stainless appliances, and a sunlit breakfast nook. A distinct advantage is the private guest suite with a separate garage entrance, ideal for multi-generational living. Upstairs, retreat to the massive rec room or the private primary suite. Outside, the property shines as an equestrian paradise with irrigation, cross-fencing, and a 4-stall barn / detached shop with power. If you have been waiting for a property that truly has it all, this is it!

2101 Dead Indian Memorial Road, Ashland

500 Pompadour Drive, Ashland
$1,128,000
5 Beds ⋅ 5 Baths ⋅ 220210091 MLS ⋅ 3,566 SqFt. ⋅ 221,720 Sqft. Lot ⋅ 5.09 Acres
Incredibly desirable Ashland setting--private, quiet & close to town yet distinctly rural. On 5.09 acres with panoramic views of Mt. Ashland & the city, this 3566 sq ft 1985 home offers 5 bedrooms, 4.5 baths & two full primary suites, including a main-level retreat. The main floor features two sitting rooms with wood-burning fireplaces, a living room bar & a 2019 kitchen remodel with quartz leather-finish counters & painted cabinetry. Upstairs features two bedrooms with walk-in closets, a large bath & separate HVAC, plus a guest suite with a loft & window seat. Outdoor amenities: pool with Trex decking, gazebo, apple & plum trees, Gearky Creek, Talent Irrigation water & two workshops (50'x50' & 42'x36'). Other highlights: 2-car garage with workbench, wine cellar, auto generators, water softener, security system & abundant storage. Updates: roof, exterior paint, trellis, decking, railings, pool/spa (2018); HVAC (2019); blinds (2019); electrical/lighting (2018).

500 Pompadour Drive, Ashland

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. Last updated:

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