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161 Fourth Street, Ashland
$649,900
4 Beds ⋅ 2 Baths ⋅ 220228571 MLS ⋅ 1,698 SqFt. ⋅ 6,969 Sqft. Lot ⋅ 0.16 Acres
Two single-level homes on a spacious 0.16-acre lot with alley access in the heart of Ashland's Railroad District. Charming historic front home with covered porch, double-paned vinyl windows, original fir floors, high ceilings, picture rail moldings, dining with cast-iron gas stove, kitchen with glass-fronted display cabinets and butcher block counters, mudroom pantry with washer and dryer, primary bedroom with large walk-in closet, full bathroom with clawfoot tub shower, and guest bedroom with closet. Fully permitted second dwelling built in 1999 with front deck and covered entry, operable casement windows, oak hardwood flooring, spacious dining area and kitchen with wood cabinets, laundry closet, two bedrooms with closets, full bath with shower, and attached garage with second bay converted to workshop studio. New roofs, ductless mini-splits, and fully fenced private yards. Excellent investment opportunity and potential for short-term travelers' accommodations. Inquire for details!

161 Fourth Street, Ashland

1750 Crestview Drive, Ashland
$735,000
3 Beds ⋅ 3 Baths ⋅ 220228500 MLS ⋅ 2,103 SqFt. ⋅ 8,276 Sqft. Lot ⋅ 0.19 Acres
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

901 Hillview Drive, Ashland
$874,000
3 Beds ⋅ 2 Baths ⋅ 220228466 MLS ⋅ 1,656 SqFt. ⋅ 7,840 Sqft. Lot ⋅ 0.18 Acres
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

264 Alta Avenue, Ashland
$625,000
4 Beds ⋅ 2 Baths ⋅ 220228422 MLS ⋅ 2,176 SqFt. ⋅ 10,454 Sqft. Lot ⋅ 0.24 Acres
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

63 Nutley Street, Ashland
$599,000
2 Beds ⋅ 1 Baths ⋅ 220228381 MLS ⋅ 884 SqFt. ⋅ 4,791 Sqft. Lot ⋅ 0.11 Acres
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

145 Normal Avenue, Ashland
$1,035,000
3 Beds ⋅ 3 Baths ⋅ 220228353 MLS ⋅ 2,204 SqFt. ⋅ 43,560 Sqft. Lot ⋅ 1 Acres
Tucked at the end of a cul-de-sac, this distinctive single-level home offers the rare feeling of country living right in Ashland. Set on a private, fenced and irrigated acre, it was thoughtfully built with Logix ICF insulated walls, owned solar, radiant-heated floors and energy-efficient windows. Inside, warm wood ceilings, a dramatic skylit cupola, walls of windows and a large fireplace give the home character, while the spacious kitchen features abundant cabinetry and a generous granite island. A large studio/game room adds wonderful flexibility. Outdoors, expansive Trex decking connects to a screened gazebo, pergola and covered patio overlooking mature landscaping, a pond and waterfall, raised garden beds and fruit trees, with mountain and valley views beyond. Oversized 2-car garage, workshop/storage and RV/boat parking. Near the bike path, schools and Hunter Park--peaceful, private and wonderfully connected to town.

145 Normal Avenue, Ashland

3665 Hyatt Prairie Road, Ashland
$1,950,000
3 Beds ⋅ 3 Baths ⋅ 220228333 MLS ⋅ 2,907 SqFt. ⋅ 397,267 Sqft. Lot ⋅ 9.12 Acres
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

5010 Old Highway 99 S, Ashland
$399,000
2 Beds ⋅ 2 Baths ⋅ 220228254 MLS ⋅ 1,750 SqFt. ⋅ 289,674 Sqft. Lot ⋅ 6.65 Acres
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

7696 Hyatt Prairie, Ashland
$675,000
3 Beds ⋅ 3 Baths ⋅ 220228159 MLS ⋅ 1,912 SqFt. ⋅ 338,025 Sqft. Lot ⋅ 7.76 Acres
HYATT PINES RETREAT! Escape to this beautiful year-round mountain sanctuary on 7.76 ac. Tranquil setting backs to BLM land. Mostly level, nicely treed & surrounded by exceptional homes & towering pines in the 18-parcel community. 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 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 1,912sf. Numerous updates include roof, siding, windows, kitchen, flooring, baths, doors, furnace, water heater. Outbuildings: 2 large sheds, well house, garden shed. HOA $500/yr for road maintenance/winterization. Rare blend of privacy, recreation & mountain living!

7696 Hyatt Prairie, Ashland

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

1058 Linda Avenue, Ashland

320 Gaerky Creek Road, Ashland
$699,000
3 Beds ⋅ 3 Baths ⋅ 220228031 MLS ⋅ 3,356 SqFt. ⋅ 681,278 Sqft. Lot ⋅ 15.64 Acres
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.

320 Gaerky Creek Road, Ashland

5831 Old Highway 99 S, Ashland
$950,000
3 Beds ⋅ 4 Baths ⋅ 220228020 MLS ⋅ 2,953 SqFt. ⋅ 1,582,970 Sqft. Lot ⋅ 36.34 Acres
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

262 Sheridan Street, Ashland
$449,000
3 Beds ⋅ 3 Baths ⋅ 220227869 MLS ⋅ 2,062 SqFt. ⋅ 3,049 Sqft. Lot ⋅ 0.07 Acres
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

119 Granite Street, Ashland
$800,000
2 Beds ⋅ 2 Baths ⋅ 220227845 MLS ⋅ 2,955 SqFt. ⋅ 9,583 Sqft. Lot ⋅ 0.22 Acres
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

527 Sutton Place, Ashland
$745,000
3 Beds ⋅ 3 Baths ⋅ 220227832 MLS ⋅ 2,400 SqFt. ⋅ 6,098 Sqft. Lot ⋅ 0.14 Acres
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

152 Strawberry Lane, Ashland
$880,000
3 Beds ⋅ 3 Baths ⋅ 220227806 MLS ⋅ 3,004 SqFt. ⋅ 27,442 Sqft. Lot ⋅ 0.63 Acres
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

480 Mount Ashland Ski Road, Ashland
$995,000
3 Beds ⋅ 3 Baths ⋅ 220227627 MLS ⋅ 2,480 SqFt. ⋅ 2,360,952 Sqft. Lot ⋅ 54.2 Acres
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

2025 Green Meadows Way, Ashland
$595,000
3 Beds ⋅ 2 Baths ⋅ 220227602 MLS ⋅ 1,726 SqFt. ⋅ 9,583 Sqft. Lot ⋅ 0.22 Acres
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

2590 Siskiyou Highway, Ashland
$635,000
4 Beds ⋅ 2 Baths ⋅ 220227582 MLS ⋅ 2,120 SqFt. ⋅ 312,760 Sqft. Lot ⋅ 7.18 Acres
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

2140 Birchwood Lane, Ashland
$410,000
2 Beds ⋅ 2 Baths ⋅ 220227463 MLS ⋅ 1,359 SqFt. ⋅ 5,227 Sqft. Lot ⋅ 0.12 Acres
This inviting, move-in-ready home is filled with natural light and offers a functional, comfortable layout with fresh interior paint and upgraded blinds throughout. The living room features a cozy gas fireplace and flows seamlessly into the kitchen and dining area. Brand-new, high-end stainless appliances, a stylish backsplash behind the range, and a dedicated eating area complete the kitchen. The spacious primary suite offers a generous closet and ensuite bath with a walk-in shower. A second bedroom, additional full bathroom with a tub/shower combination, and conveniently located hall laundry closet add to the thoughtful layout. Step outside to a fully fenced, low-maintenance backyard featuring a concrete patio, southwest-facing exposure, and mature trees that provide beautiful filtered light and welcome shade. A beautifully landscaped front yard with a drip irrigation system and an attached two-car garage complete this truly charming home!

2140 Birchwood Lane, Ashland

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

619 Elkader Street, Ashland

2234 Dollarhide Way, Ashland
$439,920
2 Beds ⋅ 3 Baths ⋅ 220227296 MLS ⋅ 1,714 SqFt. ⋅ 2,178 Sqft. Lot ⋅ 0.05 Acres
Move-in ready and beautifully updated! The main level features new vinyl flooring (2025), LED lighting, and an electric fireplace for added ambiance. The kitchen offers an eating bar, dining area, and new dishwasher (2025). A half bath with pedestal sink and attached one-car garage complete the main level. Upstairs are 2 bedrooms, 2 full baths, new carpet (2026), a spacious landing ideal for an office or flex space, and a view deck with retractable awning. The primary suite includes a walk-in closet and ensuite bath with shower. Laundry closet includes washer & dryer. Major updates include new roof (2025), heating & A/C (2024), water heater (2024), exterior paint (2026), and new smoke/CO detectors (2026). Enjoy a private fenced backyard with patio, garden beds, views, and refreshed low-maintenance landscaping. Extensive updates and a functional floor plan make this home ready to enjoy!

2234 Dollarhide Way, Ashland

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

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