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

166 Nob Hill Street, Ashland

Listing courtesy of Full Circle Real Estate.

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

593 Crowson Road, Ashland

Listing courtesy of John L. Scott Ashland.

1057 Oak Knoll Drive, Ashland
$575,000
3 Beds ⋅ 3 Baths ⋅ 220218209 MLS
The minute you enter this one level home you will say WOW! Gorgeous light & bright remodel w/prefinished hardwood floors, open living concept w/gourmet all new kitchen featuring island & room for bistro table w/chairs. Open floor plan including vaulted ceilings in living, kitchen & dining. Gas fireplace. Primary suite w/walk in closet, double sinks, amazing shower. A bonus sunroom/family room. 2 more good size bedrooms, 2nd full bath & one half bath. Dbl garage & large laundry room. Beautiful landscaping, covered back patio, side patio w/pavers. Low voltage lighting & drip watering system. Across the street from the Oak Knoll pond & HOA private trails for the neighborhood to enjoy. Just 3 blocks to golf course. Large shed for extra storage, workshop or your needs & subd. parking for visitors. Take your time to see all the details of this home & enjoy! Don't forget outdoor activities within 5 miles include golfing, camping, fishing, hiking and skiing is just 20 minutes away

1057 Oak Knoll Drive, Ashland

Listing courtesy of Absolute Realty.

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

852 Oak Street, Ashland

Listing courtesy of Millen Property Group.

128 S Mountain Avenue, Ashland
$855,000
220217221 MLS
Prime Investment & Development Opportunity in Ashland. Well-maintained duplex located close to downtown offering immediate cash flow and long-term upside potential. Both units are rented at $1,450 per month ($2,900 total), with tenants paying all utilities, keeping operating expenses low. Property has an excellent rental history and is professionally managed. Capital improvements include newer roof, vinyl windows, stainless appliances, gas log fireplace (rear unit), new water heater and additional updates. Situated on a large approx. 0.27-acre R-3 high-density zoned lot, creating exceptional future redevelopment potential. The City of Ashland Planning Department indicates a 5.4 base density factor with potential for up to 20 units. (buyer due diligence required). For development details contact Aaron Anderson or Nick Schubert at City of Ashland Planning Department.

128 S Mountain Avenue, Ashland

Listing courtesy of RE/MAX Integrity.

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

8612 OR-66, Ashland

Listing courtesy of John L. Scott Medford.

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

523 Strawberry Lane, Ashland

Listing courtesy of Gateway Real Estate.

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

50 Lowe Road, Ashland

Listing courtesy of Home Quest Realty.

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

211 Glenview Drive, Ashland

Listing courtesy of John L. Scott Medford.

2205 Ashland Street 210 Unit 210, Ashland
$325,000
1 Beds ⋅ 1 Baths ⋅ 220215889 MLS
This 1 br/1bath 2nd-floor corner condo greets you w/ sunlight pouring through generous windows, illuminating the inviting finishes that give the space its timeless, easy charm. Its open floor plan unfolds naturally, with the living area flowing into the kitchen with abundant counter space, ample storage, & brand-new appliances waiting to be used for the very first time. You'll love spending your mornings on your private balcony gazing out toward the Cascade Mountains as the light shifts across the peaks. Even workdays feel lighter here, thanks to a dedicated office nook that keeps productivity close to comfort. With its own dedicated laundry area & built-in storage, even the practical parts of life feel organized & beautifully tucked away. Perfectly located minutes from downtown Ashland, the Oregon Shakespeare Festival, shopping, dining, & scenic hiking/ biking trails -- with quick access to I-5 & just 30 minutes north of the California state line -- you're moments from everything!

2205 Ashland Street 210 Unit 210, Ashland

Listing courtesy of Bespoke Real Estate.

483 Strawberry Lane, Ashland
$435,000
220215800 MLS
Is this Ashland's best neighborhood? We certainly think so! This prime ½-acre lot, located in the desirable Strawberry Meadows Subdivision, is surrounded by stunning high-end homes. The gently rolling terrain is bordered by protected common areas to the west and south, offering added privacy and natural beauty. Lightly treed with expansive views of the Rogue Valley and surrounding mountain vistas, this property is a true gem. Just minutes above Ashland's vibrant plaza--home to charming shops, acclaimed restaurants, the renowned Shakespeare Festival, and picturesque Lithia Park--you'll enjoy the perfect balance of nature and culture. All city utilities are available, including public sewer, water, power, cable, and fiber optics. A well-managed homeowners association preserves the common areas and the character of the neighborhood, ensuring a lifestyle you'll love.

483 Strawberry Lane, Ashland

Listing courtesy of Windermere Van Vleet & Assoc..

4201 Highway 66, Ashland
$595,808
1 Beds ⋅ 1 Baths ⋅ 220215560 MLS
Rare opportunity to own 71.51 acres just right outside city limits of Ashland! LOCATION IS AMAZING!! Property consist of 2 additional tax lots. Super cute 2020 built MFG home w/vaulted ceilings & floor ceiling windows w/quartz counters & tile shower & lg wood deck. Near Emigrant Lake this property would be beautiful to build your dream home w/gated entry & gently sloping gravel road to the home w/incredible views of Cascade Mountains & Pilot rock. Creek frontage w/16.4 acres of water rights from Neil Creek. Trust has invested over $150,000 into the Creek management and rehab planting thousands of native plants. Gently sloping acreage w/pastures for horses or cattle or grape vines. 2 adjoining tax lots including. Priced to SELL! Buyer to do their own due diligence. Potential for maybe possibly another home site?

4201 Highway 66, Ashland

Listing courtesy of John L. Scott Medford.

220 Nutley Street, Ashland
$500,000
2 Beds ⋅ 2 Baths ⋅ 220215328 MLS
Stunning 2022 transformation of a classic 1920s single-level cottage situated on a spacious third-acre parcel, ideally located between Lithia Park and Hald-Strawberry Park and only moments from downtown Ashland. Comprehensive updates include new roof, foundation, windows, waterproof LVP flooring, full electrical rewire, modern plumbing, and new sewer line. The open kitchen showcases vaulted ceilings, butcher-block island, granite sink, marble backsplash, and a copper-accented range hood. Primary suite offers private deck access, designer lighting, and a spa-like bath with clawfoot tub. Vaulted living room flows to an expansive deck with mountain views. Versatile second bedroom/office, efficient mudroom laundry, and full guest bath complete the interior. Outside enjoy terraced landscaping, TID irrigation, fresh paving and multiple outbuildings. A rare opportunity in a prime Ashland location--contact today for more information!

220 Nutley Street, Ashland

Listing courtesy of John L Scott Ashland.

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

372 Glenn Street, Ashland

Listing courtesy of Full Circle Real Estate.

251 Granite Street, Ashland
$294,000
220214262 MLS
Exclusive Opportunity: Build Your Private Dream Home Directly Across from Ashland's Historic Lithia Park. Discover one of the last premier view parcels available on famous Granite Street, overlooking the park. Nestled in a luxury enclave with easy walkability to downtown, this expansive .65 acre lot offers 3-way views of Grizzly Peak, the Siskiyous, and Lithia Park (bonus: a peekaboo view of the Upper Duck Pond)! Unlike typical raw land, this site is meticulously prepared to fast-track your architectural vision. Premium infrastructure is already in place: a beautifully engineered retaining wall system, a fully paved private driveway, terraces, and City utilities at the building site. Step out your front door onto the Granite Street Trail or take a short stroll along Ashland Creek to the Shakespeare Festival, pickleball courts, and the historic Downtown Plaza's finest dining. Embrace the resort-feel luxury of this premium lot for your new home!

251 Granite Street, Ashland

Listing courtesy of John L. Scott Medford.

Ashland
$139,900
2 Beds ⋅ 1 Baths ⋅ 220212880 MLS
Welcome to your perfect Southern Oregon Retreat at 16170 Highway 66 in Ashland! This charming 2-bedroom, 1-bathroom single-wide home offers 840 square feet of comfortable living space on a generous .59-acre lot, providing the ideal blend of cozy functionality and outdoor potential. Whether you're seeking a peaceful vacation getaway just minutes from Ashland's renowned cultural attractions, wineries, and outdoor recreation, or looking for a smart investment property in one of Oregon's most desirable destinations, this well-proportioned home delivers exceptional value. The spacious lot offers room for gardening, outdoor entertaining, or simply enjoying the natural beauty of the Rogue Valley, while the efficient floor plan ensures easy maintenance and comfortable year-round living. Don't miss this rare opportunity to own an affordable piece of Ashland's lifestyle at an attractive price point!

Ashland

Listing courtesy of John L. Scott Medford.

451 N Main Street, 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

Listing courtesy of Full Circle Real Estate.

527 Chestnut Street, Ashland
$699,000
4 Beds ⋅ 4 Baths ⋅ 220212305 MLS
Freshly renovated turn of the century home set on over a third of an acre lot with views and gorgeous mature evergreens. Large covered wraparound front porch leads to the front facing living room w/ wood floors & picture windows allowing for an abundance of natural light. Spacious country kitchen has stainless steel appliances. There's a covered enclosed back porch style room w/ bathroom. There are two bedrooms, one of which is ensuite on the main level. Versatile upstairs space has a light filled landing, one bedroom suite and another huge space w/ great architectural features, views and a full bathroom. Plus, a detached oversized two car garage, lots of parking and a relatively level yard that has a ton of potential for gardening or future development. Just above the hospital and within the Health Care Services zoning district. This is a charming property awaiting the next owner to enjoy!

527 Chestnut Street, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

Dead Indian Memorial Road 1400 Unit 1400, Ashland
$210,000
220211332 MLS
Are you looking to construct the home of your dreams? If you're tired of searching unsuccessfully for a pre-built residence that suits your needs, consider building it yourself. We are proud to present this stunning 30-acre parcel located 8 miles from the beautiful city of Ashland, Oregon. From the top of the ridge, the views of Mt Ashland and the city below will take your breath away. Boasting varied topography, oak groves and cooler temperatures in the summer and above the fog during winter days, this spot is ideal for living off-the-grid without sacrificing proximity to great restaurants, shopping, cultural experiences like the Oregon Shakespeare Festival and more. Buyer due diligence recommended; applications for a homesite have already been submitted.

Dead Indian Memorial Road 1400 Unit 1400, Ashland

Listing courtesy of Oregon Adventure Realty.

16799 Highway 66, Ashland
$10,775,000
12 Beds ⋅ 10 Baths ⋅ 220210683 MLS
AUCTION: Bidder registration deadline: 1 December. Starting bids expected between $3.5M-$5.5M. Set amid pristine wilderness along the historic Green Springs Highway, New Frontier Ranch is a storied 958-acre legacy property where Old West heritage meets boundless possibility. Anchored by a 1910 farmhouse that once served as a stagecoach stop, the ranch unfolds across irrigated meadows, forests, creeks, and two reservoirs framed by views to Mount Shasta and Mount McLaughlin. A grand event hall, museum building, three log cabins, and a private campground create a ready foundation for hospitality, while a preserved ghost town adds a rare sense of discovery. Miles of trails invite hiking, horseback riding, and ATV adventures, with fishing and hunting close at hand. Grandfathered destination resort approvals open the door to a lodge, spa, weddings, retreats, and festivals, or a singular private wilderness estate.

16799 Highway 66, Ashland

Listing courtesy of Cascade Hasson Sotheby's International Realty.

774 Lisa Lane, Ashland
$850,000
4 Beds ⋅ 4 Baths ⋅ 220209966 MLS
Quality built contemporary home placed among the madrone and pine trees in the hills of beautiful Ashland OR. Versatile, user-friendly floor plan with many unique architectural features. The cozy living room w/ fireplace, kitchen and dining area surround a well-designed multi use pantry closet. Soaring open beam ceiling above leads to a wall of windows allowing for natural light and views of the trees and mountains afar. Two spacious decks to enjoy the natural setting. Main level has an artistically designed room with a spoke pattern beam ceiling, custom lighting, handcrafted shelving and a full bathroom. Lower level you will find a large spa primary bedroom suite w/ private patio, attached office/ reading room with access to the lower deck. Bathroom has double vanities, a soaking tub and radiant heat floors. Two additional bedrooms, a full bath and a laundry room are also on the lower level. Perfect for the outdoor enthusiast w/ hiking trails just a few feet from the front door.

774 Lisa Lane, Ashland

Listing courtesy of Ashland Homes Real Estate Inc..

420 Reiten Drive, Ashland
$2,900,000
3 Beds ⋅ 2 Baths ⋅ 220209913 MLS
Premier 36-Acre Cannabis Cultivation & Distribution Property - Ashland, Oregon. Rare opportunity to own a state-of-the-art Tier II cannabis cultivation & distribution facility on 36 acres near Emigrant Lake. This turnkey operation offers both scale & efficiency, featuring: Indoor Facility: 10,000 sq.ft. hydroponic grow, fully automated fertigation system capable of watering 3,200 plants in 30 minutes. Recently upgraded with 200 new 1,000-watt LED lights. Pre-wired for 3-phase power. Outdoor Grow: 20,000 sq.ft. setup with 500-plant capacity, also fully automated and plug-and-play ready. Storage & Infrastructure: 53' refrigerated unit for fresh frozen/cold storage, 4,120 sq.ft. barn & stg-bldgs. Human-detection infrared camera & alarm system provide full security. Residence: 2021 built, the 3-bed, 2-bath, 1,458 sq.ft. home includes a steel roof w/ lifetime warranty. Water Rights: Clayton Creek, Dunn & Talent Irrigation water rights included-an invaluable asset for long-term Success

420 Reiten Drive, Ashland

Listing courtesy of RE/MAX Integrity.

545 Ashland Creek Drive, Ashland
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 220209743 MLS
Private tranquility in the treetops 4 min. to downtown Ashland. Views of Lithia Park w/soothing sounds of Ashland Creek flowing. Style meets sophistication on this beautiful architecturally designed home w/over ½ acre. $400K in new updates in the last 2 years. Private gated courtyard entry. Hardwood floors throughout, tile bathrooms floors, over 100 windows to bring in abundant light & cement balconies w/copper railings w/unobstructed views. Many trails close by. New massive artisan river rock wood burning fireplace in great rm. Chef's kitchen w/built in refrigerator, 6 burner gas cook top, dbl ovens, wine refrigerator, granite counters w/lg island. Formal dining & breakfast rm. 3 bdrms + lg office/meditation rm; 2 bdrm en-suites; Primary w/2 walk in closets, quartz counters, glass sinks, steam shower, air jetted tub, water closet & private balcony. 4 car garage, 2nd courtyard patio off entry. Home allows for an abundance of natural light w/vaulted ceilings & skylights.

545 Ashland Creek Drive, Ashland

Listing courtesy of John L. Scott Medford.

Timberlake Drive 391E25 132 Unit 391E25 132, Ashland
$75,000
220208170 MLS
FANTASTIC new price! If privacy, quietness and views are what you are looking for, look no further This 5.38 wooded acreage with a seasonal ravine is a quick drive to downtown Ashland where one will find the world renown Shakespeare Theater, galleries, amazing restaurants, great shopping and the famous Lithia Park. Lot is large enough to give you the privacy wanted but one may be able feel a sense community nearby if that is what you are looking for. Buyer to verify. WR zoning would need to be changed to RR, rural residential, and home site approval needed to be obtained with the county. This to be verified by buyer doing their due diligence with Jackson County Planning or a local land use consultant. Take a drive by the property and give me a call! SELLER IS MOTIVATED! BRING ALL OFFERS....

Timberlake Drive 391E25 132 Unit 391E25 132, Ashland

Listing courtesy of Windermere Van Vleet & Associates.

1440 E Nevada Street, Ashland
$3,750,000
5 Beds ⋅ 5 Baths ⋅ 220206087 MLS
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

Listing courtesy of Ashland Homes Real Estate Inc..

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