Ashland Homes with Traditional Style

Welcome to Ashland, Oregon—a picturesque city nestled in the heart of Jackson County, renowned for its vibrant arts scene, stunning landscapes, and a welcoming community spirit. With a population that embraces both residents and visitors alike, Ashland is famous for its annual Oregon Shakespeare Festival, charming downtown area, and an array of outdoor recreational opportunities. From hiking in the breathtaking Siskiyou Mountains to enjoying a leisurely stroll through Lithia Park, the city's natural beauty is simply unparalleled.

When it comes to finding your dream home in Ashland, you’ll discover a delightful selection of traditional-style residences that perfectly capture the essence of classic American architecture. These homes often feature elegant details such as gabled roofs, spacious front porches, and warm, inviting interiors that exude character and charm. With their timeless appeal, traditional-style homes in Ashland provide the perfect backdrop for creating lasting memories with family and friends.

The community of Ashland is not only about stunning homes but also about fostering connections. Neighborhoods are often lined with mature trees and lush gardens, creating a serene environment that invites relaxation and camaraderie. Whether you’re sipping coffee on your porch or exploring the local farmer’s market, you’ll find that Ashland offers a lifestyle filled with warmth and community spirit.

If you’re ready to make Ashland your home, let us guide you through the enchanting world of traditional-style homes. Experience the harmony of nature, culture, and community that makes Ashland a truly exceptional place to live. Your dream home awaits!

Newest Ashland Homes with Traditional Style

$739,000

4 Beds ⋅ 3 Baths ⋅ 220225931 MLS

Located just minutes from downtown, this impressive 2,596 sq. ft., 4-bedroom, 3-bathroom home features striking curb appeal and breathtaking views of Grizzly Peak. The bright interior boasts hardwood floors, formal and informal dining, and a spacious kitchen with solid-surface counters. Soaring ceilings frame the great room, which opens to an expansive deck overlooking a tiered backyard complete with garden boxes, a potting shed, and storage shed. Highlights include a main-level vaulted primary suite with a jetted tub and walk-in closet, a flexible upper-level bonus room with skylights, and carpeted guest bedrooms. Modern upgrades feature a new heat pump with advanced UV filtration, an electric vehicle charger, and an oversized attached garage with workshop space plus dedicated RV parking.

960 Oak Street, Ashland

$1,350,000

5 Beds ⋅ 6 Baths ⋅ 220225703 MLS

Live the Southern Oregon Dream! Welcome to an extraordinary Ashland estate where breathtaking views of Mount Ashland, the Cascades, downtown Ashland, and surrounding vineyards create a spectacular backdrop. Nestled behind a private gated entrance on 5 acres, 3 TID irrigated, this custom-built 5 bedroom, 6 bath home offers luxury, privacy, and versatility. Whether you're seeking a peaceful retreat, a multigenerational home, or space to operate a home-based business, this property adapts to your lifestyle. The thoughtfully designed floor plan features TWO private suites with their own entrance, ideal for extended family, a professional office, or creative studio. Garden beds, fruit trees, space for horses, animals, a 28 GPM well, RV hookups w/220, abundant parking, just minutes from the Shakespeare Festival, galleries, wineries and award-winning restaurants. You'll enjoy the best of country living without sacrificing convenience. Luxury. Privacy. Self-sufficiency. Endless possibilities.

808 Pompadour Drive, Ashland

$589,000

3 Beds ⋅ 3 Baths ⋅ 220225252 MLS

Welcome home to this wonderful 3 bedroom 2.5 bath property in the delightful Oak Knoll Neighborhood! Upon arrival, the beautifully landscaped front yard welcomes you in. The main level is perfect for entertaining with an updated kitchen, separate dining room and living room, cozy wood-burning fireplace and family room that looks out over the seasonal creek and oak trees. Upstairs you will find the three bedrooms including the primary suite! With abundant square footage and a large private lot, this home is sure to delight. Recent update include HVAC system in (June 2026) new roof (2025), exterior paint (2025) and Timbertech deck (2024).

775 Oak Knoll Drive, Ashland

$795,000

3 Beds ⋅ 3 Baths ⋅ 220224946 MLS

Enjoy expansive views of the 9th fairway at Oak Knoll Golf Course, Grizzly Peak, and surrounding vineyards from this inviting 3-bedroom, 2.5-bath home. Located on a quiet cul-de-sac, the 1,995 sq.ft. residence offers peaceful golf course living with direct cart access. This well-maintained home features a new roof (January 2026), a large deck perfect for entertaining, and RV parking. Inside, you'll find both a living room and a spacious family room with an open vaulted ceiling, plus a kitchen with a new double oven and gas cooktop. The primary bedroom and bath are generous, with elegant cultured marble counters and shower surround. Additional highlights include HVAC with an advanced air scrubber filtration system and ADA accessibility. Ideal for those seeking a single-level lifestyle with stunning golf course and mountain views in a highly desirable Ashland location. A rare opportunity to own a golf-front home in one of Southern Oregon's most beautiful areas.

738 Fairway Court, Ashland

$650,000

3 Beds ⋅ 3 Baths ⋅ 220224225 MLS

Charming custom home with panoramic mountain views on a spacious and private 0.29-acre flag lot located above the boulevard within six minutes of Ashland's downtown plaza. All new low-pile berber wool carpets and fresh interior paint in 2026, new central AC system in 2019, and new roof c. 2016. Main level with solid oak hardwood floors, living room with bay window and gas fireplace, formal dining with French door to concrete paver patio with fire pit, kitchen with tiled counters and backsplash, powder room, laundry closet, and two-car garage with extensive built-in storage cabinets. Versatile upper level with two guest bedrooms, a very spacious primary suite with private office or nursery, two full ensuite bathrooms, and three sets of French doors to the backyard. Abundant natural light with Eastern exposure - dormer windows throughout. Established trees and hedges, mature plantings, and grass lawns with automated drip and sprinkler irrigation. Inquire for details!

430 Wiley Street, Ashland

$799,000

5 Beds ⋅ 2 Baths ⋅ 220223588 MLS

Offered for the first time in generations, this extraordinary fourth-generation Ashland treasure presents a rare opportunity. Own a piece of local history just steps away from world-renowned Lithia Park. This timeless two-story residence sits on beautifully landscaped .32 acre lot. It offers 5 bedrooms, 2 bathrooms, and a character that cannot be replicated. This home is rich in charm and architectural detail. It showcases the craftsmanship of a bygone era, while providing ample space for modern living. Enjoy peaceful mornings on the porch, stroll through Lithia Park, and easy access to downtown Ashland's theaters, galleries, restaurants, and cultural attractions. Homes of this caliber, location, and historical significance seldom become available. This is a once-in-a-generation opportunity to continue the legacy of one of Ashland's cherished homes.

143 Granite Street, Ashland

$400,000

2 Beds ⋅ 1 Baths ⋅ 220222433 MLS

Charming historic fixer-upper on a private 0.26-acre lot with mature trees and incredible pollinator garden featuring 70+ plant species, lovingly cultivated over 30 years. New roof in 2019, new fencing in 2012, and new central ducting with gas furnace in 2006. Living and dining with solid oak floors and glass door to front office. Kitchen with antique gas stove, butcher block and tile counters, operable casement bay windows, wood and glass display cabinets, double sink with updated hardware, under-sink water filtration, and new dishwasher in 2023. Spacious main-level bedroom with closet, full bathroom with clawfoot tub shower, and sitting room with stairs to vaulted upper bedroom with closet. Backyard with deck and hot tub, raised beds, perennials, detached garage shop with alley access, and excellent potential for ADU or second dwelling. Centrally located above the boulevard in the desirable Siskiyou-Hargadine District near Triangle Park. Bring your ideas and inquire for details!

324 Liberty Street, Ashland

$495,000

4 Beds ⋅ 3 Baths ⋅ 220221886 MLS

3 bed, 2 bath main home with an attached 1 bed, 1 bath studio featuring a separate entrance! You'll love this wonderful neighborhood just 3 blocks from Helman Elementary School, with easy access to the bike path, tennis courts, playground, dog park, and community gardens -- all just 1 mile from Ashland Plaza. This home sits on nearly a quarter of an acre so lots of space to entertain and garden. Incredible fenced rear yard with expansive lawn areas, apple, plum & apricot trees, raised garden beds & grape arbor, covered patio and views of Mt Ashland. Two car garage creates a large space for a workshop or all your outdoor gear.

374 Cambridge Street, Ashland

$794,000

5 Beds ⋅ 6 Baths ⋅ 220221349 MLS

71, 73 and 75 Wimer. Gorgeous updated including plumbing and electric vintage home w/charm remaining a few blocks to downtown Ashland. The main home has 3 bedrooms (2 with ensuite baths) the 3rd bedroom has an ensuite 1/2 bath. Formal living and dining and eat in large kitchen w/breakfast bar & nook. Granite countertops. Wood floors on main level & carpet on stairs & bdrms. The woodwork door trim is beautiful & probably original. Newer deck & A/C unit. Detached building (71 and 73 Wimer) are one level studio units with kitchens & baths. 73 Wimer has private deck. Main house is rented for $2375.00 p/month & tenant pays utilities except water. Studios have been rented for $1250.00 & $1350.00 per month with utilities included & they have a separate shared laundry facility. Unique property for owner occupied or income producing. Circular driveway for main home & 2 parking spaces in front for studios. Has been traveler accomodations in the past. Buyer to do own due diligence on u

75 Wimer Street, Ashland

$550,000

4 Beds ⋅ 2 Baths ⋅ 220221283 MLS

Charming historic home with 29+ years of improvements and stewardship. Updated electrical, HVAC, plumbing, sewer line, new roof, solar tubes, skylights, wood-wrapped casement windows, and decks. Wood flooring, vintage fixtures and hardware, period lighting, leaded-glass windows, and picture rail moldings. Spacious open living and dining area with wood stove and door to covered side-porch, kitchen with wood and glass-fronted display cabinets, laundry closet, two bedrooms, and full bathroom. Vaulted upper-level landing, wood-paneled bedroom with panoramic mountain views, full bathroom, and fourth bedroom with closet. Terraced grounds with mature trees, ornamental plantings, paver patio, meandering pathways, sunny fenced gardening areas, rustic garden shed, and renovated detached garage workshop. Property backs to 1.43-acre natural greenspace owned by the City of Ashland near Hald-Straberry Park; conveniently located within a half-mile of downtown. Inquire for details!

71 Scenic Drive, Ashland

$339,000

2 Beds ⋅ 2 Baths ⋅ 220218449 MLS

Enjoy affordable living in Ashland in this charming 2-bedroom, 1.5-bath townhome offering 1,140 sq ft of comfortable space. This clean, move-in-ready home features all-new carpeting and fresh interior paint throughout. The electric range is brand new, AC only a couple years old, plus some new bathroom fixtures. The inviting living room includes a cozy fireplace, perfect for relaxing evenings. One bedroom offers a unique loft area, ideal for a reading nook, meditation area or extra storage with a mini-split for added cooling comfort. There's a balcony overlooking the enclosed patio, perfect for container gardening. Includes a single car garage. This is a small complex with common green spaces for residents to enjoy. Conveniently located just minutes from downtown Ashland's shops, dining, and entertainment, as well as the natural beauty of Lithia Park. The HOA fees of $250 a month.

153 E Hersey Street, Ashland

$749,000

4 Beds ⋅ 3 Baths ⋅ 220218224 MLS

Welcome to Billings Ranch, one of Ashland's most desirable communities. This stylish 3,184 sq ft, 4 bed, 3 bath home blends comfort and functionality with standout spaces for spring and summer entertaining. Upon entry you are greeted with a sweeping spiral staircase and 20-ft vaulted ceilings that create a grand open atmosphere. The main level offers a spacious living room, a dedicated dining area, and a beautifully appointed kitchen with two gas stoves, granite countertops, and ample prep space making it perfect for gatherings. Enjoy warm-weather living on the private back patio with a built-in gas firepit and grapevine-covered pergola, ideal for outdoor dining, relaxing evenings, and hosting year-round. A main-level bedroom, full bath and den complete the comfort of the downstairs. Upstairs, are three additional bedrooms, including a luxurious primary suite with its own gas fireplace, a spa-like ensuite bathroom with a jetted tub and a generous walk-in closet.

692 Vansant Street, Ashland

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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: