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$735,000
3 Beds 3 Baths 220228500 MLS
Impeccable views and quality updated home is ready to go! Step outside directly onto hiking trails and return to this tranquil turn-key home on the end of a dead end street! Ample parking and covered space for storage of all ski gear and all your toys, make this home a year round gem to come home to after a long day of adventure! Only 30 mins from Mt Ashland from the front door! Fully updated bathrooms, kitchen and backyard make this home completely turn-key! The expansive primary suite features a sauna, walk-in closet and private wrap-around deck. Impeccable views with an open floorplan provide ample opportunities for hosting. This rare gem of views, storage and quality upgrades is one you won't want to miss!

1750 Crestview Drive, Ashland

Listing courtesy of John L. Scott Medford.

$1,000,000
3 Beds 4 Baths 220228495 MLS
Live the best of Ashland in this iconic re-built Victorian, blending timeless charm with tasteful modern updates. Just steps from restaurants, cafés, Cabaret Theatre, and a couple blocks from OSF, it feels private while offering true downtown living. Stone-surround wood-burning fireplace with redwood mantel and beautiful fir floors welcome you in. Formal dining and covered screened patio feature mountain views. Kitchen boasts Neolith quartz counters, copper farmhouse sink, induction cooktop, smart refrigerator, double ovens, skylight, and breakfast peninsula. 2 primary suites--one on each level--offer tiled baths, glass-enclosed showers, quartz vanities, and soaking tub upstairs. Terraced low-maintenance landscaping, automated irrigation, private patios, ample off-street parking, and a backup generator add convenience. Ally access to detached 2-car garage and studio apartment above with full kitchen, bath, and large balcony--perfect for guests, rental income, or flexible living.

364 Hargadine Street, Ashland

Listing courtesy of John L. Scott Ashland.

$874,000
3 Beds 2 Baths 220228466 MLS
Under construction for mid-December 2026 completion, this architecturally inspired midcentury home sits off-street on a private flag lot in an established neighborhood with mature trees. Vertical-grain cedar and stucco meet clean lines and covered porches. This 3-bed, 2-bath home is light and bright with clerestory windows, 8 ft doors, and vaulted ceilings. The kitchen's large island with eating bar opens to the great room, where a fireplace with a built-in bench-and-mantel sits by a wall of windows. The primary suite offers a roll-in shower, double vanity, and walk-in closet. A rare pass-through garage links the driveway and rear alley; drive straight through in either direction. No HOA. Built by Suncrest Homes, an Ashland builder with 35+ years of experience, this Earth Advantage home is energy-efficient and exceeds code. Ask about a promo 5.125% rate with the builder's lender. Listing broker is related to the owners of Suncrest Homes, one of whom is a licensed OR real estate broker.

901 Hillview Drive, Ashland

Listing courtesy of Gateway Real Estate.

$625,000
4 Beds 2 Baths 220228422 MLS
Perched above downtown Ashland on a quiet street, this spacious 4-bedroom, 2-bath home offers privacy, proximity to town, and commands beautiful valley and mountain views. The open, light-filled floor plan centers around a vaulted great room and offers 2,176 square feet of flexible living space, including additional office and family rooms easily convertible to sleeping space on both levels. Step onto the expansive deck to dine outdoors, entertain, or simply enjoy the ever-changing scenery. A sauna provides a relaxing retreat, while ample storage and an attached garage add everyday convenience. Set on nearly a quarter-acre with mature fruit trees and room to garden, the property is just blocks from Lithia Park, the Ashland Plaza, dining, shopping, and the Oregon Shakespeare Festival. This is an exceptional opportunity to enjoy space, scenery, and an enviable location close to the heart of Ashland.

264 Alta Avenue, Ashland

Listing courtesy of Millen Property Group.

$642,000
2 Beds 1 Baths 220228381 MLS
The Hamaker-Taylor House, thoughtfully reimagined for modern living while preserving its Historic charm. Designed by notable architect Carlos Delgado, this 1889 cottage features a brand-new luxury kitchen with a beautiful sunroom/breakfast nook, new bathroom, updated windows, HVAC, plumbing, electrical, and roof (2026). Professionally landscaped and hardscaped front and back yards create inviting spaces for outdoor entertaining. An expansive covered front porch welcomes you home, while two bright bedrooms and beautiful Pergo flooring add warmth throughout. The full basement offers a unique art studio with lighting, hot/cold running water, and raised storage areas. Just three doors from Lithia Park, enjoy the sounds of the bandshell from your own porch. Minutes to OSF, the Plaza, and downtown Ashland. A rare opportunity to own a piece of Ashland history with modern luxury.

63 Nutley Street, Ashland

Listing courtesy of Windermere Van Vleet & Assoc..

$799,000
3 Beds 3 Baths 220228361 MLS
Rare, period Craftsman in Ashland's Railroad District, extensively remodeled while retaining wonderful original character. The 1,492 sq ft single-level main home features a deep covered front porch, built-in cabinetry, box beam ceilings and a river rock fireplace. Bright office with glass doors can also serve as a 3rd bedroom. The updated light-filled kitchen features all new appliances, induction cooking and abundant storage. The primary suite is an oasis with a beautifully updated bathroom featuring soaking tub, walk-in shower and heated floors. Private landscaped yard with mature trees, a water feature and wonderful outdoor living spaces. A detached 480 sq ft building offers additional flex space with bathroom, kitchenette and storage, plus alley access. 1,972 sq ft between the two buildings, just blocks to downtown, restaurants and bike path, this is the quintessential Ashland dream!

762 B Street, Ashland

Listing courtesy of Full Circle Real Estate.

$399,000
2 Beds 2 Baths 220228254 MLS
Peaceful country living opportunity on 6.65 acres nestled amongst the madrones, not far from downtown Ashland! The custom primary residence offers 2 beds/2 baths with a stonework entryway, pine paneling and cabinetry in the kitchen, a cozy wood stove, large windows, a metal roof, and an attached garage. A versatile bonus room adapts to a creative workshop, office, or extra bedroom. Outside, a spacious deck and flat yard lead to an impressive shop built from steel shipping containers, offering a large open workspace with a professional-grade engine hoist, ample storage, and hydraulic hangar-style doors. Down the hill, a quaint cabin in the woods offers multigenerational living, income potential, or home office space, with a full kitchen, bath, and sleeping loft. Outdoor lovers will appreciate the unbeatable access to Mt. Ashland and the Pacific Crest Trail.

5010 Old Highway 99 S, Ashland

Listing courtesy of John L. Scott Ashland.

$1,000
220228218 MLS
End of Irrigation Ditch. Neither the brokers, brokerage, or Jackson County warrants, nor can verify property condition, description, fixtures, permits, hazardous substances, zoning, history of illegal activity, or tax history. No guarantee of access, no sign. ''As Is'' sale. Listing brokerage does not accept bids or offers on Jackson County Taxation's behalf for these properties. There will be one public, in-person, oral auction per year held at the County Courthouse, 10 S Oakdale Ave, Medford, OR 97501, in the Auditorium, located on the first floor of the main building. Auction date is: OCTOBER 12, 2026 @ 10 AM. Brokers and brokerage do not represent the date or process, Buyer to verify process and date for accuracy.

Tolman Cr Road, Ashland

Listing courtesy of Coldwell Banker Professional Group.

$675,000
3 Beds 3 Baths 220228159 MLS
HYATT PINES RETREAT! Escape to this beautiful year-round mountain sanctuary on 7.76 ac. Tranquil setting & backing to BLM land. Mostly level, nicely treed & surrounded by exceptional homes & towering pines. Across from Hyatt Lake & near Howard Prairie Lake, outdoor adventure is at your doorstep--hiking, swimming, boating, camping, fishing, skiing & more! The home features a striking metal roof, fiber-cement siding, & wood casement windows. Cozy living room w/pellet stove. Main-level primary suite offers deck access, walk-in closet, ensuite bath with walk-in shower. 2nd main-level bedroom across from guest bathroom. Upstairs includes 3rd bedroom, loft, full bath & large bonus room (~23'x16') not included in the 1,912sf. Numerous updates include roof/siding/windows, kitchen, flooring, baths, doors, furnace, water heater. Four outbuildings include two large sheds, well house & garden shed. HOA $500/yr for road maintenance/winterization. Rare blend of privacy, recreation & mountain living!

7696 Hyatt Prairie, Ashland

Listing courtesy of John L. Scott Medford.

$99,000
220227198 MLS
Rare opportunity to own +/-12.16 acres in the Ashland area near Neil Creek Road with wooded hillside terrain, oak, madrone, pine, animal trails, and potential valley and Emigrant Lake views from portions of the property. The land has strong recreational appeal and a quiet, tucked-away feel once on site. Jackson County records show WR zoning, and County Planning has indicated a dwelling application may be possible through applicable land-use review; no dwelling approval is currently in place. No confirmed legal access, well, septic, or power service. Property is being marketed as-is, with all access, zoning, utilities, water, septic, dwelling potential, and intended use to be verified by buyer. A unique Ashland-area landholding for a buyer with vision, patience, and a willingness to complete their own due diligence.

Neil Creek Road 800 Unit 800, Ashland

Listing courtesy of Whitetail Properties Real Esta.

$699,000
3 Beds 3 Baths 220228031 MLS
Wake up to some of the finest south-facing mountain and valley views the Rogue Valley offers, from a rare 15-acre homestead in the sought-after Pompadour neighborhood, minutes from downtown Ashland. The land carries 13.5 acres of Talent Irrigation District (TID) water rights, plus a 20,000-gallon irrigation pond, a greenhouse, a yurt, and a clean barn with a loft and stalls. The property is fenced, with everything needed to restore it to a fully working farm. The main home offers a 3-bed/3-bath open-plan layout with vaulted ceilings, a beautiful kitchen, multiple fireplaces, hardwood floors, and a bonus room, with a two-family setup option. A detached 2-car garage with extra living space rounds it out. The home and grounds have deferred maintenance, and the price reflects the work required to restore it, including an ATT septic system, irrigation repairs, and a bridge over the irrigation ditch to reach the lower 5 acres. Cash or an FHA 203(k) rehab loan preferred.

320 Gaerky Creek Road, Ashland

Listing courtesy of Gateway Real Estate.

$700,000
220227922 MLS
Thoroughly updated duplex located above the boulevard within an eight-minute walk to the Ashland Public Library. Extensively renovated from 2019 to 2022 with over $240,000 in documented improvements - including new Daikin mini-splits, double-pane vinyl windows and shutters, LVP flooring, new baseboards and trim, lighting, bathroom fixtures and hardware, appliances, interior and exterior paint. Each unit includes a wood-burning fireplace with stacked-stone surround and wood mantle, two or three bedrooms with closets, one-and-a-half or two full bathrooms, private fenced backyards, and alley access to separate one-car garages. Professionally landscaped grounds with mature plantings, fig and mimosa trees, boulder-lined paths, drip irrigation, and gravel patios with corten steel edging. Excellent rental history with room for growth. Inquire for details!

373 Iowa Street, Ashland

Listing courtesy of John L. Scott Ashland.

$469,000
3 Beds 3 Baths 220227869 MLS
Well-located, well-built and lovingly maintained, this easy-care home offers comfort, convenience and no HOA! The 3-bedroom, 2.5-bath home was thoughtfully customized during construction with view balcony, open concept design, tile flooring throughout, central vacuum and a covered patio. A wall of windows featuring beautiful mountain views creates loads of natural light throughout the open living room, kitchen and dining room. A bedroom or office and full bath are conveniently located on the main level. Upstairs, the spacious primary suite is a true retreat, with lovely open sitting area, walk-in closet plus an additional closet and primary bathroom. The lower level features a double garage. A finished bonus room accessed through the garage makes a third bedroom, hobby room, or office etc. Also downstairs is laundry, half bath and extra storage. All appliances are included. Enjoy the front view balcony or rear covered patio overlooking the private, fenced yard. Easy living awaits!

262 Sheridan Street, Ashland

Listing courtesy of Millen Property Group.

$899,900
2 Beds 2 Baths 220227845 MLS
Location, character, and potential come together in this one-of-a-kind property situated on a generous 0.22-acre lot just steps from iconic Lithia Park. From the moment you enter, you'll be greeted by an abundance of warmth and sunshine, with natural light flooding both the living room and primary bedroom. The home boasts a unique personality, blending a cozy, rustic cabin vibe, with a flexible bonus space ready for your imagination ideal for a creative art studio, office, yoga room, or guest area. In the heart of the home, the kitchen features durable Corian countertops and a charming built-in breakfast nook, perfect for morning coffee. Relax on the covered front porch overlooking a well-maintained front yard equipped with an automatic sprinkler system. Enjoy your own a private courtyard with a detached single-car garage for parking or extra storage. Whether you're seeking a serene sanctuary or a property with endless possibilities in an unbeatable location, this gem is a must-see!

119 Granite Street, Ashland

Listing courtesy of eXp Realty, LLC.

$745,000
3 Beds 3 Baths 220227832 MLS
Delightful and lovingly maintained 3-bedroom, 2.5-bath home nestled in a desirable neighborhood with minimal through traffic. This inviting property features a covered front porch entry, an open great room- dining area designed for comfortable living and entertaining, a convenient guest bath, and a bright, sunny kitchen with a breakfast nook, abundant natural light, and direct access to a covered outdoor living space. The main-level primary ensuite offers privacy and convenience with direct access to the backyard patio. Eco-friendly bamboo and cork flooring add warmth and character, while the spacious second-floor bonus room provides flexible space for a home office, media room, playroom, or guest retreat. Enjoy beautiful landscapes, mountain views, and a private fenced backyard with a covered patio overlooking a serene common area. Complete with an attached two-car garage and situated in a wonderful neighborhood, this home offers comfort, privacy, and easy living.

527 Sutton Place, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

$895,000
3 Beds 3 Baths 220227806 MLS
Just steps from historic Lithia Park, this special property sits in one of Ashland's most desirable neighborhoods. Offering over 3,000 sq ft on .63 acres, this private home blends timeless character, mid-century charm and flexibility. The main level features two bedrooms, a full bath, an oversized living room with wood-burning fireplace, kitchen and dining area. The lower level offers a den with adjoining bonus room-ideal as an office, gym, media room or studio-plus laundry and a brand-new full bath with tile floors and shower. A separate, self-contained living space has its own living room, full kitchen, full bath and bedroom-ideal for guests, extended family, or potential ADU use. Recent upgrades include a new roof (2026), ducted HVAC heat-pump system, and a mini-split for the additional living space, all within two years. Outside, enjoy privacy, decks, lawn, water feature, circular driveway and carport with storage, plus easy access to Ashland's world class trail system. Tour today!

152 Strawberry Lane, Ashland

Listing courtesy of Cascade Hasson Sotheby's International Realty.

$127,500
220227699 MLS
Wooded acreage on hillside. Neither the brokers, brokerage, or Jackson County warrants, nor can verify property condition, description, fixtures, permits, hazardous substances, zoning, history of illegal activity, or tax history. No guarantee of access, no sign. ''As Is'' sale. Listing brokerage does not accept bids or offers on Jackson County Taxation's behalf for these properties. There will be one public, in-person, oral auction per year held at the County Courthouse, 10 S Oakdale Ave, Medford, OR 97501, in the Auditorium, located on the first floor of the main building. Auction date is: OCTOBER 12, 2026 @ 10 AM. Brokers and brokerage do not represent the date or process, Buyer to verify process and date for accuracy.

Timberlake Drive, Ashland

Listing courtesy of Coldwell Banker Professional Group.

$5,000
220227696 MLS
Flat piece of land behind near Pac Power. Neither the brokers, brokerage, or Jackson County warrants, nor can verify property condition, description, fixtures, permits, hazardous substances, zoning, history of illegal activity, or tax history. No guarantee of access, no sign. ''As Is'' sale. Listing brokerage does not accept bids or offers on Jackson County Taxation's behalf for these properties. There will be one public, in-person, oral auction per year held at the County Courthouse, 10 S Oakdale Ave, Medford, OR 97501, in the Auditorium, located on the first floor of the main building. Auction date is: OCTOBER 12, 2026 @ 10 AM. Brokers and brokerage do not represent the date or process, Buyer to verify process and date for accuracy.

Maywood Way, Ashland

Listing courtesy of Coldwell Banker Professional Group.

$1,200
220227698 MLS
Small unbuildable parcel near Mt. Ashland. Neither the brokers, brokerage, or Jackson County warrants, nor can verify property condition, description, fixtures, permits, hazardous substances, zoning, history of illegal activity, or tax history. No guarantee of access, no sign. ''As Is'' sale. Listing brokerage does not accept bids or offers on Jackson County Taxation's behalf for these properties. There will be one public, in-person, oral auction per year held at the County Courthouse, 10 S Oakdale Ave, Medford, OR 97501, in the Auditorium, located on the first floor of the main building. Auction date is: OCTOBER 12, 2026 @ 10 AM. Brokers and brokerage do not represent the date or process, Buyer to verify process and date for accuracy.

Mt Ashland Ski Road, Ashland

Listing courtesy of Coldwell Banker Professional Group.

$27,000
220227687 MLS
Wooded acreage. Neither the brokers, brokerage, or Jackson County warrants, nor can verify property condition, description, fixtures, permits, hazardous substances, zoning, history of illegal activity, or tax history. No guarantee of access, no sign. ''As Is'' sale. Listing brokerage does not accept bids or offers on Jackson County Taxation's behalf for these properties. There will be one public, in-person, oral auction per year held at the County Courthouse, 10 S Oakdale Ave, Medford, OR 97501, in the Auditorium, located on the first floor of the main building. Auction date is: OCTOBER 12, 2026 @ 10 AM. Brokers and brokerage do not represent the date or process, Buyer to verify process and date for accuracy.

13103 Old Highway 99 S, Ashland

Listing courtesy of Coldwell Banker Professional Group.

$53,400
220227685 MLS
1977 456 sq ft cottage. 40 acres wooded. Neither the brokers, brokerage, or Jackson County warrants, nor can verify property condition, description, fixtures, permits, hazardous substances, zoning, history of illegal activity, or tax history. No guarantee of access, no sign. ''As Is'' sale. Listing brokerage does not accept bids or offers on Jackson County Taxation's behalf for these properties. There will be one public, in-person, oral auction per year held at the County Courthouse, 10 S Oakdale Ave, Medford, OR 97501, in the Auditorium, located on the first floor of the main building. Auction date is: OCTOBER 12, 2026 @ 10 AM. Brokers and brokerage do not represent the date or process, Buyer to verify process and date for accuracy.

13099 Old Hwy 99 S, Ashland

Listing courtesy of Coldwell Banker Professional Group.

$99,000
220227665 MLS
This 5.36-acre wooded lot near the end of Timberlake Drive offers privacy, tranquility and sweeping views from high above the valley floor. Just 6.5 miles from Ashland's vibrant downtown, the neighborhood's large parcels and scattered rural homes create a sense of space, with neighbors nearby but not too close. Enjoy expansive valley and mountain views as you watch sunrises and sunsets, listen to the birds, and relish the quiet of this peaceful setting. The lot has received homesite approval twice in the past, although both approvals have expired. Buyers should conduct their own due diligence with Jackson County Planning regarding homesite and development possibilities, as well as easements and utilities. Access is via Timberlake Drive, with an additional undeveloped access easement from Clayton Road. Enjoy acreage, views and solitude within easy reach of Ashland.

4334 Clayton Road, Ashland

Listing courtesy of Nestwell Real Estate.

$995,000
3 Beds 3 Baths 220227627 MLS
UNOBSTRUCTED VIEWS OF MT. SHASTA from the residence and not just somewhere on the property. Discover a rare mountain retreat, about 54± acres, where you can enjoy amazing privacy, peace, and stunning views of Mt. Shasta and Mt. McLoughlin without any obstructions. This unique lodge-style home boasts impressive massive post-and-beam construction and timeless design. The 3-bed, 2-bath home features an open great room w/floor-to-ceiling windows & breathtaking views. The expansive deck is perfect for sunsets, entertaining, & enjoying peaceful mountain life. A separate 1-bedroom guest cabin with its own deck and beautiful views adds extra privacy and flexibility. It's perfect as a main home, a luxurious second home, a family retreat, or a creative escape. You'll find it about 3 miles from Mt. Ashland Ski Area & 15 miles from the lively downtown Ashland. This is a truly unique chance to experience remarkable architecture, acreage, recreation, tranquility, and extraordinary natural beauty

480 Mount Ashland Ski Road, Ashland

Listing courtesy of Millen Property Group.

$800,000
4 Beds 2 Baths 220227619 MLS
Beautifully updated craftsman home on a spacious corner lot with alley access in Ashland's Railroad District - walking distance to the Co-Op, Oregon Shakespeare Festival, Noble Coffee, Chozu Spa, Peerless Restaurant, and downtown entertainment. New furnace, exterior paint, expanded deck, fencing, concrete driveway with remote-operated gate, automated landscape lighting and irrigation, interior fixtures and appliances. Original wood floors, picture rail molding, and five-panel doors with antique mortise hardware throughout. Spacious living room with abundant natural light, gas fireplace with slate hearth, formal dining, updated kitchen, laundry mudroom, full bath with tub shower, and two bedrooms with closets on main level, plus two bedrooms and full bath with tub shower on upper level. Basement workshop with resurfaced and epoxy-sealed concrete floor. Formerly renovated ''top-to-bottom'' with new roof, insulation, AC, sewer lateral, supply and drain lines. Inquire for details!

311 B Street, Ashland

Listing courtesy of John L. Scott Ashland.

$595,000
3 Beds 2 Baths 220227602 MLS
What an amazing home in this highly desirable neighborhood. You have the best curbside look on the block with low maintained manicured front and backyard. Close to the Oredson Todd Woods and surrounding Ashland trails. Featured with abundant living space for all to enjoy. A large living room with dining area, wood stove and open space that leads you to an additional enclosed sunroom to enjoy the abundant sunlight, crafts and comfortable summer evenings. Also, there is a great living room for additional entertainment. Hard wood, laminate & vinyl flooring. Both bathrooms have been recently remodeled. One bedroom has been used as an office with a long countertop working space. The primary bedroom also leads you out to a wonderful large deck. Rear deck is designed for BBQ's and entertainment. Come and enjoy this special backyard with views of the Cascades and Grizzley Peak. Just 3 miles from the Shakespeare Festival. TID water comes with this property.

2025 Green Meadows Way, Ashland

Listing courtesy of John L. Scott Ashland.

$669,000
4 Beds 2 Baths 220227582 MLS
This beautiful recently renovated ranch is home located just 15 minutes from Ashland. Step inside to hickory hardwood floors, an open floor plan and unobstructed million-dollar panoramic views of Emigrant Lake, Pompadour Bluff, Grizzly Peak and the Siskiyou Mountains. Several french doors offer an immersive indoor-outdoor living concept with an ample patio perfect for dining and BBQing. The fourth extra large bedroom is adjacent to a solarium that would make a fantastic hot tub space. This 7+ acre mini-ranch is fully fenced and gated, with an interior dog fence line that is approximately two acres. Irrigated with water rights from a spring source, the ample lawn space is a dream come true. This versatile property features offer multiple workshops, a greenhouse, a paved basketball court, two carports, plenty of parking for RVs, boats, trailers and so much more. This one wont last long!

2590 Siskiyou Highway, Ashland

Listing courtesy of Cascade Hasson Sotheby's International Realty.

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