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$1,350,000
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, 3 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
$630,000
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
$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
$1,200,000
5 Beds ⋅ 3 Baths ⋅ 220224554 MLS ⋅ 4,768 SqFt. ⋅ 219,106 Sqft. Lot ⋅ 5.03 Acres
One-of-a-kind Southern Oregon retreat just minutes from Ashland! A remarkable property offering a rare blend of privacy, craftsmanship and income potential in a private park-like setting with mature trees. This custom-built 5 bedroom home showcases soaring ceilings, walls of windows with views of Emigrant Lake/Grizzly Peak, large breakfast nook, custom pine log features/dramatic curved staircase, hardwood floors, granite/travertine countertops, floor-to-ceiling fireplace, large 3rd floor bonus wing, 1900+ sq. ft. wraparound cedar deck, workshop, charming playhouse and covered carport. The 1st floor ADU currently operates as a successful AirBNB with 2 bedrooms, beautiful kitchenette, granite countertops, stunning tile bathroom, ADA access, private driveway and entrance, for use as continued rental income or separate multigenerational family living. A former homesite offers additional potential. Rarely does a property combine this level of quiet privacy, quality and versatility.

4567 Old Highway 99 S, Ashland
$799,000
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
$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
$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
$900,000
5 Beds ⋅ 4 Baths ⋅ 220221548 MLS ⋅ 5,200 SqFt. ⋅ 477,417 Sqft. Lot ⋅ 10.96 Acres
2 HOMES AND A GUEST STUDIO/COTTAGE!!! 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. Must see to appreciate!

2909 Dead Indian Memorial Road, Ashland
$745,000
5 Beds ⋅ 3 Baths ⋅ 220221903 MLS ⋅ 3,060 SqFt. ⋅ 9,583 Sqft. Lot ⋅ 0.22 Acres
For Statistical Purposes Only.

1555 Windsor Street, Ashland
$794,000
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
$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
$4,500,000
5 Beds ⋅ 6 Baths ⋅ 220220674 MLS ⋅ 6,396 SqFt. ⋅ 151,588 Sqft. Lot ⋅ 3.48 Acres
Set on 3.48 private acres just 500 ft from Lithia Park and within a 1/2 mile of downtown Ashland, 237 Granite is a rare, legacy estate inspired by the timeless design principles of Greene & Greene Architects. Showcasing over 5,700 sq ft of refined living, this 5-bedroom, 5.5-bath residence embodies the essence of The Arts and Crafts Movement with exceptional craftsmanship, rich walnut flooring throughout, and a seamless connection to its natural surroundings. The grounds are a destination unto themselves--featuring a solar-heated pool, tranquil Japanese gardens with tea house, two waterfalls, a koi pond, and direct access to nearby hiking trails. Main level living w/ 871 sq ft primary wing, private caretaker quarters, and a separate 676 sq ft guest cottage with 1 bed, 1 bath, 2-car garage--offering flexibility for guests or extended living. ''The Gamble House'' of Ashland, this is the largest private estate of its kind in such close proximity to the cultural and natural heart of Ashland.

237 Granite Street, 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
$585,000
5 Beds ⋅ 3 Baths ⋅ 220219281 MLS ⋅ 1,973 SqFt. ⋅ 8,712 Sqft. Lot ⋅ 0.2 Acres
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
$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
$900,000
5 Beds ⋅ 3 Baths ⋅ 220214907 MLS ⋅ 2,146 SqFt. ⋅ 11,761 Sqft. Lot ⋅ 0.27 Acres
Comp Only - this information is for statistical purposes only. Centrally located sanctuary-like home, detached 400 SF guest addition with kitchenette and full bath, and exquisitely landscaped corner lot. Pride of ownership!

1595 Peachey Road, 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
$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
$1,250,000
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
$1,175,000
5 Beds ⋅ 5 Baths ⋅ 220209198 MLS ⋅ 3,207 SqFt. ⋅ 13,503 Sqft. Lot ⋅ 0.31 Acres
Welcome to an exceptional opportunity in Ashland, where comfort and flexible living come together. This rare property offers two single-level homes on one lot, each with lovely views of the East Hills and just minutes from downtown Ashland. The 2025 built main home features 2,019 sq ft, 3 bedrooms, and 2.5 baths with an open, light-filled design ideal for everyday living and entertaining. The custom island kitchen flows into a spacious vaulted great room anchored by a floor-to-ceiling fireplace. The primary suite is a retreat with a spa-like bath, soaking tub, walk-in shower, and skylight. While the great room extends living outdoors to a tongue-and-groove covered patio and landscaped, fenced yard. The second home offers 1,188 sq ft, 2 bedrooms, and 2 baths with an extensive remodel and all-new systems—ideal for guests, extended family, or rental income. Located in Ash Meadows, a new four-lot subdivision, this is a truly unique Ashland offering.

224 Alicia Street, Ashland
$845,000
5 Beds ⋅ 3 Baths ⋅ 220209677 MLS ⋅ 2,842 SqFt. ⋅ 9,147 Sqft. Lot ⋅ 0.21 Acres
In this 5 bedroom, + flex bonus room space, daylight ranch, every inch has been thoughtfully redesigned and renovated. Nestled in the trees of Roca Canyon above SOU and minutes from Downtown Ashland. Enter the main living area through the solid mahogany pivot door. The open floor plan is anchored by the restored white oak flooring, flooded with light and features a vaulted ceiling and sleek 2-sided fireplace. The designer kitchen includes a BOSCH appliance package with 36'' induction range, solid wood soft-close custom cabinetry and floating shelves and plenty of storage. The primary suite with mountain views and two guest bedrooms and an additional bathroom complete this level. Downstairs, discover a large den/theater/playroom with fireplace, stylish dry bar with beverage fridge, laundry area, and two massive bedrooms with walk-ins. Step outside to the energy efficient lagoon bottom pool. Enjoy the backyard oasis with large deck, zero-maintenance turf and full fencing for privac

704 Elkader Street, Ashland
$1,130,000
5 Beds ⋅ 4 Baths ⋅ 220207890 MLS ⋅ 3,656 SqFt. ⋅ 13,503 Sqft. Lot ⋅ 0.31 Acres
Welcome to this beautifully updated 5-bed, 3.5-bath home in one of Ashland's most desirable neighborhoods, just minutes from downtown. Thoughtfully designed across three levels, it blends generous living with intimate, inviting spaces. The main floor features a vaulted living room with fireplace and stunning territorial views, a true chef's kitchen with abundant storage and Bosch double oven, range. In addition, an elegant dining room, ½ bath and oversized two-car garage. Upstairs offers two spacious bedrooms and bathroom, plus the primary suite with serene views and spa-like en suite with heated tile floors. Opening onto a large backyard; the versatile lower level, with lounge/ bonus room, full bath, bedroom, and 5th bedroom/ office, could easily be self-contained and perfect for multi-generational living, guests, or an expansive work from home/ art studio space. Lovingly maintained, this home radiates warmth, quality, and charm, ready for its next chapter.

225 Sunnyview Drive, Ashland
$599,900
5 Beds ⋅ 3 Baths ⋅ 220207098 MLS ⋅ 2,388 SqFt. ⋅ 232,610 Sqft. Lot ⋅ 5.34 Acres
Serene retreat tucked into the trees, just minutes from downtown Ashland. This beautiful 5 bedroom, 3 bath home with separate living area downstairs, sits on over 5 acres with a Koi pond, fruit trees, and lake and mountain views, offering the perfect blend of privacy and convenience. With vaulted ceilings, large view windows, an open-concept floor plan, the home is filled with natural light and peaceful forest views. Enjoy main floor primary, multiple view decks, office, sunroom with sauna, large kitchen pantry, separate living area downstairs with kitchenette, living area, 2 bedrooms, bathroom. Owner upgrades: generator, roof, 2 car garage with shop, Koi pond, covered patio with fire pit, new water heater, solar panels, mini-split, furnace, outdoor lighting. Whether you're entertaining or relaxing in nature, this home offers a rare lifestyle opportunity. Don't miss the oversized garage and bonus shop.

899 Timberlake Drive, Ashland
$4,100,000
5 Beds ⋅ 5 Baths ⋅ 220206087 MLS ⋅ 5,002 SqFt. ⋅ 1,912,719 Sqft. Lot ⋅ 43.91 Acres
A private retreat setting where nature meets luxurious living. The 5BR/5BA Contemporary home captures the Siskiyou mtn range at every turn. The main level offers floor to ceiling windows, hardwood floors, living & dining room & Chef's kitchen appointed w/ island, wet bar, pantry, double ovens, wolf stove & more! Upstairs the main bedroom suite is an oasis unto itself w/views, decking & spa. A second primary suite, 2 add'l bedrooms/bath & laundry room w/abundant storage are downstairs. Each room has custom finishes & exquisite views to ensure a lifestyle of privacy & relaxation. Outside you're met w/soothing soundscape of a tiered cascading creek, lagoon waterfall style pool, cabana area, outdoor kitchen & bath, for ease of entertaining. Equestrian, livestock or agricultural enthusiasts will delight w/the endless possibilities. Fruit trees, garden beds, greenhouses, chicken coop & workout room complete this singular estate. 1BD/1BA guest apartment is a bonus to this luxe property.

1440 E Nevada Street, Ashland
$680,000
5 Beds ⋅ 4 Baths ⋅ 220201242 MLS ⋅ 2,677 SqFt. ⋅ 911,275 Sqft. Lot ⋅ 20.92 Acres
Enjoy breathtaking views of Emigrant Lake and surrounding mountains from this custom 5BR/4BA home set on 20 EFU-zoned acres, just 15 minutes from downtown Ashland. The versatile floor plan boasts a main-level primary suite, vaulted ceilings, solid oak floors, and a cozy wood stove. The sunlit kitchen with granite countertops flows into the formal dining room and vaulted living room with walls of windows. A separate-entrance lower level offers ideal multi-generational living. This home offers energy-efficient living; a strong producing well with filtration system (buyer to do their own due-diligence), and a ''smart'' 3-zone HVAC system. Additional improvements include an 85-gallon water heater, dual septic systems, a metal roof, fresh interior and exterior paint, and durable concrete composite siding. Unwind on the screened porch or expansive decks and feel like you're in your own private retreat!

1957 Old Greensprings Highway, Ashland
$1,051,326
5 Beds ⋅ 4 Baths ⋅ 220200333 MLS ⋅ 4,560 SqFt. ⋅ 14,810 Sqft. Lot ⋅ 0.34 Acres
Unique opportunity to own a private 4,560' compound, walking distance to downtown Ashland. The building is divided into two units: 394 Hersey, a two story 3,124' 3 bed/2 bath with a bonus room and garage, and 396 Hersey, a 1,436' ADA accessible 2 bed/2 bath with it's own parking and entrance. The main home opens up to 23' ceilings and a spiral staircase. The large living room provides abundant space for entertaining, and substantial natural light. The dining room features large columns and a Murano chandelier. In the kitchen, you will find a gas range, double ovens, and a pantry. Upstairs is the primary suite, complete with mountain views, a private balcony, spacious bathroom, closet, and bonus room. In the second unit, you will find Brazilian Cherry floors throughout, and a custom kitchen with granite countertops. E-1 zoning allows for flexible use between residential and business purposes. Short term rental use is permitted with conditional use permit. Please see 3D tours attached.

394 - 396 E Hersey Street, Ashland
$1,421,000
5 Beds ⋅ 4 Baths ⋅ 220199475 MLS ⋅ 3,635 SqFt. ⋅ 435,600 Sqft. Lot ⋅ 10 Acres
Seller financing considered! Searching for a stunning estate w/ a park-like setting that's only mins away from Downtown Ashland & I5? This Earth Advantage tri-level Suncrest home features 5 bedrms, 3.5 bathrms, 3635 sq ft, 10 acres, open floor plan, chef's kitchen (large island, top end appliances, granite countertops, ample cabinetry), stunning views of the valley & Grizzly Peak, main level primary suite, detached 2 car garage, in ground hot tub, fenced garden area (fruit trees & raised garden beds), brand new wrap-around deck, & solar system! Primary suite is large w/ 2 walk-in closets, walk-in shower, dual vanities, & a luxury stand-a-lone tub. Upstairs features 2 large bedrms that share a full bathrm. Lower-level features 2 bedrms, 1 full bathrm, family rm, & finished storage rm w/ built in safe. Property borders an extensive trail network (Ordson-Todd trailhead is steps away) that leads to Mt Ashland & Lithia Park!

2208 Lupine Drive, Ashland
$893,000
5 Beds ⋅ 4 Baths ⋅ 220199100 MLS ⋅ 3,913 SqFt. ⋅ 466,527 Sqft. Lot ⋅ 10.71 Acres
Spacious view home on 10 acres, 10 minutes from Ashland's Plaza! Enjoy panoramic views of Mount Ashland, fields & vineyards from the single-level, open floor plan home. Five generous bedrooms & three full baths in the main house comfortably accommodate a large family or lots of guests. A charming cottage with bedroom, loft & full bath adds space for living or work. Imagine hosting holiday gatherings: the sunny dining room fits a table big enough for feasts. The large open kitchen lets the chef prepare meals with ease, while guests relax at the breakfast bar or in the sunny family room. When you're done socializing, escape to your private primary suite, in its own wing. TID irrigation offers many options. Enjoy existing gardens, fruit trees & low-maintenance hayfields with income potential, or create your dream mini-farm or horse property! Main house reroofed in 2025; cottage in 2022. Furnishings available outside escrow to make this a truly turnkey retreat or full-time home.

100 Ashland Acres Street, Ashland
$694,900
5 Beds ⋅ 4 Baths ⋅ 220198776 MLS ⋅ 4,648 SqFt. ⋅ 24,829 Sqft. Lot ⋅ 0.5700000000000001 Acres
Fantastic cul de sac location in Ashland. This 5 bedroom 3.5 bathroom home offers tons of possibilities with an open and bright floor plan with the primary suite on the main level that offers deck access, a huge walk in closet and primary bathroom complete with double vanities and more. Large bedrooms and living areas with a bonus space on the lower level. This property has so much to offer. Bring your ideas and make this place shine again! U.S. Bank NA may have financing options available.

460 Sunshine Circle, Ashland
$795,000
5 Beds ⋅ 3 Baths ⋅ 220198367 MLS ⋅ 3,945 SqFt. ⋅ 10,890 Sqft. Lot ⋅ 0.25 Acres
Nestled in a pristine neighborhood, this spacious 3,945 SF home is thoughtfully designed for multigenerational living. With double-attached garages on both levels, it offers the perfect blend of space and privacy. Step inside the wide entry with warm hardwood floors leading to a light-filled gracious living room with wall of windows and breathtaking mountain views, a gas fireplace, and built-in bookcases. The open dining room shares the stunning vistas and flows seamlessly into a chef's kitchen with a large dining bar, island with gas cooktop, built-in buffet, and ample storage. The primary suite is a serene retreat with a spa-like bath, jetted tub, tile shower, dual vanities, and a large walk-in closet. Two additional bedrooms and a guest bath complete the main level. Downstairs, a very spacious family room, two bedrooms, full bath, and kitchenette provide added flexibility. Enjoy expansive decks on both levels, perfect for outdoor relaxation, & a low-maintenance yard for easy living

510 Guthrie Street, 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: