Ashland Homes with Tudor Style

Welcome to Ashland, Oregon—a charming city nestled in the heart of Jackson County, renowned for its vibrant arts scene, stunning landscapes, and a rich tapestry of culture. Known primarily as the home of the Oregon Shakespeare Festival, Ashland boasts a unique blend of small-town charm and big-city amenities. With its picturesque streets lined with quaint shops, exceptional dining options, and lush parks, it’s no wonder that residents and visitors alike fall in love with this enchanting locale.

One of the architectural gems you’ll discover in Ashland is the Tudor-style home, a design that beautifully marries elegance and warmth. Characterized by its steeply pitched gable roofs, decorative half-timbering, and charming stonework, Tudor homes evoke a sense of timeless sophistication. These residences often feature inviting nooks, spacious living areas, and intricate woodwork that reflect a bygone era of craftsmanship.

Living in a Tudor-style home in Ashland means more than just enjoying its aesthetic appeal; it’s about embracing a lifestyle enriched by the community’s artistic spirit and natural beauty. Imagine cozying up by a fireplace on a chilly evening or hosting friends in a beautifully landscaped garden. With access to nearby hiking trails, cultural events, and the stunning scenery of the Rogue Valley, your Tudor home will serve as a perfect sanctuary.

Whether you’re seeking a family abode or a serene retreat, Ashland’s Tudor-style homes offer a unique opportunity to experience the best of Oregon living. Come explore this vibrant city and discover your dream home today!

Newest Ashland Homes with Tudor Style

$319,900

3 Beds ⋅ 2 Baths ⋅ 220223687 MLS

Affordable Ashland living in desirable Tudor Heights! This spacious 3-bedroom, 1.5-bath condo offers 1,392 sqaure feet of comfortable living space with mountain and territorial views from a private upper-corner location. The main level features a bright living room with a 60s style fireplace, kitchen, half bath, and flexible den perfect for a home office, guest space, or potential 4th bedroom! Upstairs you'll find three bedrooms, a full bath, and laundry area. Recent improvements include new carpet and a new water heater. Enjoy a private patio, detached carport, and additional storage. Conveniently located near downtown Ashland, Lithia Park, restaurants, shopping, and the hospital. HOA covers water, sewer, trash, landscaping, exterior maintenance, and exterior insurance for easy, low-maintenance living!

495 Chestnut Street 24 Unit 24, Ashland

$215,000

2 Beds ⋅ 2 Baths ⋅ 220219913 MLS

Charming Ashland Condo in Prime Location! Conveniently situated near restaurants, shopping, medical facilities, & scenic hiking trails in beautiful Lithia Park, this inviting 2-bedroom, 1.5-bathroom condo offers both comfort & accessibility. Tucked toward the back of the desirable Tudor Heights Complex, updated w/ newer carpet, LVP flooring & exterior paint. The main level features a kitchen w/ refrigerator, range/oven, & microwave, plus a convenient half-bathroom. Living room opens to a covered back patio, perfect for enjoying your morning coffee. Upstairs, you'll find 2 bedrooms--one w/ a private balcony ideal for relaxation, the other w/ a walk-in closet & easterly mountain views. Full bathroom w/ a dual sink vanity & tub/shower combination. The HOA provides many amenities, including a covered assigned parking space w/ storage closet, water, sewer, garbage, roof maintenance, exterior upkeep, & common areas. Don't miss your opportunity to start enjoying the Southern Oregon Lifestyle!

495 Chestnut Street 19 Unit 19, Ashland

$230,000

2 Beds ⋅ 2 Baths ⋅ 220218166 MLS

Back on market due to buyer financing/economic changes. Home is priced aggressively for a quick sale. Rare opportunity for affordable, low-maintenance living near the heart of Ashland. This charming two-bedroom townhouse is the perfect fit for those seeking an uncluttered lifestyle, as the HOA handles all groundskeeping and full exterior maintenance. Ideally situated in a quiet neighborhood, you are just a short distance from Ashland's vibrant downtown. Inside, the home is equipped with high-efficiency mini-splits for year-round climate control and comfort. The thoughtful layout includes one bedroom featuring a beautiful view of the mountains, and the second with a private balcony. Off the living area is a private fenced covered patio, providing intimate spaces for outdoor relaxation. Added conveniences include dedicated covered parking and private storage. Combining price, position, and ease of ownership, this home is a standout offering.

495 Chestnut Street 23 Unit 23, 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: