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$1,950,000
3 Beds 3 Baths 220228333 MLS
Welcome to Red's Cabin, an original homestead on Howard Prairie Lake, never before offered for sale. Held by the family since 1889, this 9.12-acre lakefront estate spans five generations. Built in 2008 to honor that legacy, the 2,907 SF, 3 bed, 3 bath home showcases custom juniper woodwork, exposed timber, vaulted ceilings, a dramatic stone fireplace and an upstairs loft/game room. Offered fully furnished, the home is on-grid with security panels for all main-level windows. A balcony off the bunk room overlooks an impressive permitted pond fed by a year-round spring-fed stream you can hear from the house. A covered outdoor fireplace sits streamside, joined by a bocce court and detached garage. The estate includes 4.1 acres of water rights, adding to its rare combination of water, recreation and mountain setting. Gated with direct access to public lands, Howard Prairie Lake and the shoreline trail, this is a rare opportunity to own a generational Southern Oregon legacy property.

3665 Hyatt Prairie Road, Ashland

$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

$950,000
3 Beds 4 Baths 220228020 MLS
Set on more than 37 private acres in the Siskiyou Mountains, this property offers space, privacy minutes from Ashland and the Rogue Valley. Mt. Ashland Ski Area, Emigrant Lake and the Pacific Crest Trail are nearby, putting Southern Oregon recreation close at hand. The main residence features soaring wood-clad ceilings, exposed beams, expansive windows and a stone fireplace. The open great room flows into a gourmet kitchen with cabinetry, full-size refrigerator and freezer, double ovens and island. A media room, geothermal heating and cooling, and hard-wired generator add comfort and peace of mind. A detached four-car garage provides spaces, while the auxiliary building offers an open area, kitchen, full bath and three-car garage--ideal for a studio, workshop, recreation or guest space. A loft studio, greenhouse, gardens, water storage, creek, rock outcroppings and wildlife complete this Southern Oregon retreat.

5831 Old Highway 99 S, Ashland

$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

$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

$1,625,000
5 Beds 4 Baths 220227302 MLS
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

$965,000
220227186 MLS
Ten, six, or four-unit investment opportunity in Ashland's Hillview Condominiums near Scenic Park and Asante Ashland. Seller-carried financing available at ~3.99% AFR with 50% down, interest-only payments, with balloon due in three years. Each unit ranges from 1,034 to 1,174 SqFt with two bedrooms, one full bath, open living and dining space, high ceilings, in-unit laundry, kitchen with granite counters and all appliances included, dedicated parking, storage, and access to landscaped common areas. Ground-level units with fully fenced private backyards and poured concrete patios. Current gross monthly income is $15,730 across all ten units following rent increases effective August 1st, 2026. Stable tenancy averaging four-plus years, room for further rent growth, and association-maintained exterior building components including roofs, siding, paint, and landscaping. Complete investment analysis, rent roll, association documents, and due diligence materials available upon request.

240 Grant Street, Ashland

$1,395,000
220227184 MLS
Ten, six, or four-unit investment opportunity in Ashland's Hillview Condominiums near Scenic Park and Asante Ashland. Seller-carried financing available at ~3.99% AFR with 50% down, interest-only payments, with balloon due in three years. Each unit ranges from 1,034 to 1,174 SqFt with two bedrooms, one full bath, open living and dining space, high ceilings, in-unit laundry, kitchen with granite counters and all appliances included, dedicated parking, storage, and access to landscaped common areas. Ground-level units with fully fenced private backyards and poured concrete patios. Current gross monthly income is $15,730 across all ten units following rent increases effective August 1st, 2026. Stable tenancy averaging four-plus years, room for further rent growth, and association-maintained exterior building components including roofs, siding, paint, and landscaping. Complete investment analysis, rent roll, association documents, and due diligence materials available upon request.

254 Grant Street, Ashland

$2,800,000
3 Beds 6 Baths 220226424 MLS
Dana Campbell Vineyards is a legacy wine business offering multiple avenues for growth with unparalleled proximity to Ashland's renowned cultural amenities. Seller-carried financing available. Elegantly remodeled tasting room residence with three guest suites ideal for boutique hospitality, panoramic valley views, great room with service bar and gas fireplace, catering kitchen, break room, ADA-compliant bathrooms. Expansive paver patio, outdoor speakers, gas fire pit, composite deck and pergola with retractable awning, bocce ball court, and rose garden. State-of-the-art cold storage facility or potential winery building with glycol cooling system, fully irrigated acreage with southern exposure, over 13,000 established vines of eight estate-grown varietals producing 2,200 cases per year, seven additional acres ready for planting, wind turbine, frost fan, and all essential equipment included for turnkey tasting room operations. Inquire for additional details of untapped revenue streams!

1320 N Mountain Avenue, Ashland

$325,000
2 Beds 2 Baths 220225960 MLS
Upgraded and move-in-ready single-level end-unit townhome located near the Ashland Family YMCA and future site of 5.52-acre East Main Park! Fresh interior paint, all-new low-pile berber wool carpets, and new roof to be installed early August 2026. Entry with skylight and hall coat closet, bamboo flooring, kitchen with custom maple cabinets, granite counters, solar tube, and stainless appliances including Fisher & Paykel refrigerator. Open dining area and vaulted living room with sliding glass door to covered patio and fully-fenced private backyard with composite deck. Primary with dual closets and full ensuite bathroom with solid surface vanity, maple cabinets, solar tube, and tub shower. Full guest bath with matching amenities, guest bedroom with closet, laundry area with Speed Queen washer and dryer, and one-car garage. Association dues of $265 per month cover all exterior maintenance - including roof, siding, paint, front landscaping, and common areas. Inquire for details!

241 Clay Street, Ashland

$739,000
4 Beds 2 Baths 220225773 MLS
Experience contemporary Northwest living in this one-of-a-kind 4 bed, 2 bath w/elevated views & beautiful natural surroundings. Adventure awaits just outside your door w/convenient access to miles of hiking & biking trails. Thoughtfully designed w/versatile living & dining areas to accommodate every occasion. Vaulted great room featuring a gas fireplace w/tile surround & a wall of windows. Well-appointed kitchen showcasing white painted cabinetry, leathered granite countertops, tile backsplash & large pantry. The primary suite is a true private retreat w/direct access to a secluded deck w/hot tub, luxurious ensuite & oversized dual closets. Enjoy year-round outdoor living from the expansive terrace w/both covered and open-air spaces. The perfect setting to relax or entertain while taking in the stunning mountain views. Mature, landscaped grounds w/raised garden beds plus a 2-car garage complemented by an adjacent covered area. Ideal for additional parking or versatile storage!

1000 Ivy Lane, Ashland

$1,650,000
4 Beds 4 Baths 220225369 MLS
First time on the market for this one-of-a-kind custom ICF-built home with breathtaking panoramic views! This 4 bed, 3.5 bath, 4,972 sqft home offers a main-level office, multiple large storage rooms, and plenty of space for entertaining. The upper level features a spacious primary suite with a private balcony, plus (2) additional bedrooms and a bonus loft (not included in storage). The lower level is ideal for multigenerational living with a large entertainment area, wet bar, bedroom, bathroom, and bonus office/storage space. Situated on 14.78 acres, (house on 1 acre), 13.8 acres currently in hay production, with rare dedicated unlimited TID irrigation. Propane has been plumbed both interior and exterior to add a fireplace or connect your BBQ if desired. Also includes an approx. 1,500 sqft detached shop, barn with (6) 12x12 stalls, riding arena, plus (2) full RV hookups and 50-amp available at the barn, and endless opportunities for horses, livestock, or hobby farming.

40 Ashland Acres Road, Ashland

$595,000
3 Beds 3 Baths 220224168 MLS
Welcome to this stunning 1993-built home on a private .29-acre lot. Dramatic floor-to-ceiling windows flood the front rooms with natural light and frame the gorgeous scenery. The main floor features 2 bedrooms, including a large primary suite and walk-in closet, a main-level office/3rd bedroom with built in Murphy bed, 2 full baths, a cozy den, a sunroom, a huge front living room with vaulted ceilings and separate dining space. The eat-in kitchen offers plentiful storage in a serene setting overlooking the hills. The basement has an additional room with a craft room already set up to be a photographer's dark room with ventilation, a sink, and a half bath. Outside is a terraced backyard with gazebo and a huge half wrap around deck all providing spectacular views. Complete with an attached 2-car garage. A Newer roof, washer, dryer, dishwasher, and Air conditioning unit all installed/replaces in 2023 and 2024. Minutes from hiking trails, parks, schools, and shopping! Move in ready.

1536 Pinecrest Terrace, Ashland

$699,000
3 Beds 3 Baths 220223512 MLS
Gorgeous home, priced to sell!!! Perched above the boulevard in an upscale neighborhood of high-end homes, this picturesque property offers the perfect blend of luxury and nature. Located just steps from the scenic hiking trails of Hald-Strawberry Park, less than 1 mile from Lithia Park, OSF, and the best restaurants and shops in Ashland. The main level welcomes you with beautiful views out of every window, solid oak hardwood floors, and a living room with a classic brick fireplace and French doors leading to a lovely deck. The fully renovated kitchen stuns with premium travertine tile flooring, stunning Brazilian quartzite counters, and stainless steel appliances. There's more to love upstairs- gorgeous views, a spacious primary suite, a light and bright guest room, and a flexible 3rd bedroom that easily doubles as a home office, featuring built-in shelving and a charming window seat. Solar. EV charging. Garage workshop space and so much more! Home appraised at 815k. Instant equity!

215 Piedmont Drive, Ashland

$779,000
4 Beds 4 Baths 220223301 MLS
Custom view home with charming detached guest cottage located just above downtown between Lithia Park and the Ashland Public Library. Main level great room with vaulted double-height ceiling, walls of windows, reclaimed clear-grain fir trim, solid-core doors, refinished oak floors, kitchen with composite dining bar, tile counters and backsplash, cabinets with solid wood interiors and custom pull-outs, dining room with glass door to view deck with gas BBQ hookup, bedroom with closet and full ensuite bath, and pantry with washer and dryer. Upper level primary with skylights, hanging closet, French doors to private balcony, and full ensuite bath with jetted tub. Versatile lower guest suite or family room with French doors to paver patio, full bathroom with oversized shower, storage cellar with stainless utility sink, and one-car garage. Detached cottage with permitted kitchen, living area, full bathroom, loft bedroom, and private gated entrance from Terrace Street. Inquire for details!

307 Hillcrest Street, Ashland

$949,808
3 Beds 3 Baths 220223070 MLS
Tranquil & pristine Mountain oasis on over 121 acres with a campground, marketable timber, Greenhouse, stream w/waterfall, springs and amazing scenic views of Mt Shasta & Pilot Rock. Amazing main home w/tile entry & stained-glass w/3 bedrooms, 2.5 baths, 2145 SQ FT with open beam vaulted ceilings in the great rm w/ huge stone staircase. Kitchen w/granite counters, tile floors opens to dining & great rm loft area. 2 primary suites overlooking the deck and creek. The other primary suite has a door to lg covered deck. Detached 2 car garage. Off grid secluded unpermitted cabin by waterfall and campground. Woodshed w/Japanese architectural elements, on-site fire suppression. Next to Forest Lands w/private hiking trails; Pacific Trail, wildlife, berries and mushroom hunting. Enjoy unobstructed star gazing, snow shoeing, sledding and more just 20 minutes from downtown Ashland. Owner will carry with $500,000 Down, 6.5% for 3-5 years w/Sellers' approval of Buyer. Last house before the Lodge.

500 Mt Ashland Ski Road, Ashland

$850,000
3 Beds 3 Baths 220221511 MLS
Refined country view home on serene private acreage just 10 minutes from downtown Ashland. Recent upgrades include all new cement board lap siding, updated HVAC, and architectural shingle roof with solar array. Main level with 2,375 SqFt of living area, solid oak hardwood flooring, vaulted wood-paneled ceilings, three sets of sliding glass doors to redwood deck with infrared sauna and hot tub, great room with propane fireplace, formal dining, kitchen with leathered granite and quartz counters, stainless appliances including double ovens and induction cooktop, spacious primary with walk-in closet and full ensuite bath, two guest bedrooms, full guest bath, laundry room, and two-car garage. Upper-level office or fourth bedroom. Paved driveway, ample parking, mature plantings, grass lawns, full metal fencing around home, lower view deck with pergola, stone pathways, patio, and pond. Forest management by Lomakatsi. Access via Frank Hill Road or McKenzie Canyon Rd. Inquire for details!

1601 Frank Hill Road, Ashland

$2,500,000
5 Beds 7 Baths 220220624 MLS
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

$935,000
3 Beds 3 Baths 220220668 MLS
Quality custom view home in a private natural setting above the boulevard, just six minutes to Ashland's downtown plaza. Abundant natural light and airflow with operable wood-wrapped casement windows, high vaulted ceilings, solid core doors, and unique architectural view corridors throughout. Great room with solid Brazilian cherry flooring, gas fireplace, formal dining with built-in buffet, French doors to wrap-around view deck, kitchen with granite dining counter and stainless appliances, open family and informal dining room, powder room, laundry with utility sink, and two-car garage. Step-down primary suite with French doors to private balcony, walk-in closet, full ensuite bathroom with travertine double vanity, jetted tub, shower, and water closet. Upper loft with mountain views and stairwell skylights. Two lower-level guest bedrooms, full bath with tub shower, den, and French doors to pebbled concrete patio and organic garden. Newer HVAC and exterior paint. Inquire for details!

602 Ashland Street, Ashland

$2,250,000
220220428 MLS
Ten, six, or four-unit investment opportunity in Ashland's Hillview Condominiums near Scenic Park and Asante Ashland. Seller-carried financing available at ~3.99% AFR with 50% down, interest-only payments, with balloon due in three years. Each unit ranges from 1,034 to 1,174 SqFt with two bedrooms, one full bath, open living and dining space, high ceilings, in-unit laundry, kitchen with granite counters and all appliances included, dedicated parking, storage, and access to landscaped common areas. Ground-level units with fully fenced private backyards and poured concrete patios. Current gross monthly income is $15,730 across all ten units following rent increases effective August 1st, 2026. Stable tenancy averaging four-plus years, room for further rent growth, and association-maintained exterior building components including roofs, siding, paint, and landscaping. Complete investment analysis, rent roll, association documents, and due diligence materials available upon request.

230 Grant Street, Ashland

$2,195,000
4 Beds 4 Baths 220219782 MLS
Located just outside Ashland, this property offers a rare blend of natural beauty, water, quality improvements, and convenience. The custom built home is thoughtfully positioned to capture expansive views across the surrounding valley and toward distant mountains. This elevated country estate draws from a Northwest lodge aesthetic, offering welcoming living spaces, a spacious multilevel layout and a seamless indoor outdoor connection with expansive outdoor living spaces. A picturesque stretch of Neil Creek framed by mature trees adds character and tranquility. Gently rolling topography, lush pasture, and water rights support a variety of Ag uses. A recently constructed 5,000 SF barn complements the property and offers outstanding flexibility for equipment, hobbies, or recreational use. Ideal as a homestead or simply an elegant place to enjoy connection to the outdoors, this is a property that captures the essence of Southern Oregon living while remaining just minutes from Ashland.

5293 Highway 66, Ashland

$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

$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

$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

$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

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

The data relating to real estate for sale on this web site comes in part from the Internet Data Display (IDX) of the Southern Oregon Multiple Listing Service. Real estate listings held by brokerage firms other than our company are marked with the IDX logo and detailed information about them includes the name of the listing brokers. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information subject to change and should be independently verified. Listing content is copyright © 2018 SOMLS, Medford, Oregon. Last updated: