Ashland Homes with Driveway Parking features

Welcome to Ashland, Oregon – a charming city nestled in the picturesque Rogue Valley, known for its stunning landscapes, vibrant arts scene, and a strong sense of community. With the majestic Siskiyou Mountains as a backdrop, Ashland offers a unique blend of outdoor adventures and cultural experiences. The city is perhaps best known for the Oregon Shakespeare Festival, drawing theater enthusiasts from around the globe. Beyond the stage, Ashland boasts an array of local shops, gourmet restaurants, and beautiful parks, making it a delightful place to call home.

When it comes to real estate, Ashland offers a variety of housing options, including homes that feature convenient driveway parking. Imagine returning to your cozy abode after a day of exploring the lush trails or enjoying a night out at one of the city’s renowned eateries, and easily parking right at your front door. These homes with driveway parking not only provide the convenience of easy access but also enhance your living experience in this vibrant community.

Whether you’re looking for a charming cottage, a spacious family home, or a modern retreat, Ashland’s real estate market has something to suit every taste and lifestyle. Embrace the beauty of Southern Oregon while enjoying the comforts of a home that meets your needs. Ashland is more than just a place to live; it’s a lifestyle filled with culture, nature, and connection. Discover your dream home in Ashland today and experience the magic of this enchanting city!

Newest Ashland Homes with Driveway Parking features

$350,000

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

$775,000

3 Beds ⋅ 2 Baths ⋅ 220225944 MLS

Welcome to this beautiful eco-frlendly home in Ashland's sought-after Beach Creek Community. This thoughtfully designed 3-bedroom, 2-bath home offers 1,538 sq. ft. of sustainable living with soaring vaulted ceilings, expansive windows providing lots of natural light wlth mountain views. Built by KDA Homes, this Earth Advantage Platinum-certified, Net Zero-rated home features owned solar panels, providing lower utility. costs. The modern open-concept floor plan features seamless lndoor--0utdoor living, granite countertops, custom tile work, quality craftsmanship throughout, and two private decks ideal for relaxing. Located in the heart of Ashland, just minutes from downtown shopping, dining, entertainment, and nearby parks, allowing you to fully enjoy everything Ashland has to offer.

1221 Kirk, Ashland

$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

$2,400,000

3 Beds ⋅ 2 Baths ⋅ 220225850 MLS

One of the Rogue Valley's premier estate settings, this extraordinary 164-acre Ashland offering is paired with a proposed luxury residence by Asher Homes. The single-level design offers 2,778 sq ft with 3 bedrooms, 2 baths, a 912 sq ft 3-car garage, and walls of glass framing mountain and valley views. Refined finishes include large-plank hardwood, custom built-ins, a stone fireplace, metal roofing, and covered outdoor living with built-in BBQ and fireplace. Designed to Earth Advantage Platinum standards, the home features high-efficiency HVAC, solar-ready infrastructure, EV charging, generator tie-in, and wildfire-conscious materials. The build package includes vertical construction and an infrastructure allowance for driveway, septic, well systems, power, propane, water storage, trenching, and utility connections. Land offers 2,220 feet of Cove Creek frontage, a 48 GPM well, and paved access. Plans and pricing subject to site conditions, permitting, selections, and builder approval.

312 Sky Ridge Road, Ashland

$1,450,000

220225791 MLS

One block from the Oregon Shakespeare Festival and downtown Ashland's restaurants, galleries, and cultural amenities, the McCall House B&B is a beautifully restored 1883 Italianate home offered for sale as a private residence. Currently operating as a boutique hotel, the property features ten historic guest rooms, including two detached private Carriage House suites, and may continue as a licensed hospitality business for a buyer who wishes to carry on that tradition. The C-1 zoning also opens the door to a variety of commercial uses, including a restaurant, office suites, or other business opportunities. Ten on-site parking spaces are included, a welcome convenience this close to the Ashland Plaza. This is a rare opportunity to own one of the city's most celebrated historic addresses. Due to the C-1 zoning, conventional 30-year financing is unavailable, and non-cash buyers are encouraged to confirm lending options before requesting an appointment. Please do not disturb guests.

153 Oak Street, Ashland

$1,450,000

10 Beds ⋅ 12 Baths ⋅ 220225786 MLS

153 Oak 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

$950,000

3 Beds ⋅ 3 Baths ⋅ 220225745 MLS

Tremendous 360 view on 5.75 flat white fenced acres & walking distance to Emigrant Lake. You have 3 acres of water rights on open EFU land, a 36'x36' barn with loft, a 14' RV bay door, workshop & attached office. Behind the barn is a single horse stall. To the side is a gazebo to enjoy those wonderful summer outside nights. This home is greeted by a paved & gated 800' driveway leading to a drive-through that takes you to the front entrance. Brand new wrap around porch greets you so you can sit in awe at the beauty of your surroundings or sit under your backyard gazebo and say, ''Do I really live here''? Perched on a small knoll, this 2,934 sq ft 4/3 home, has 2 bonus rooms, with open floor plan, large entertaining living room with woodstove insert fireplace & kitchen with abundant cabinets & island. Ten-foot ceilings provide ample sunlight for all occasions. The upstairs primary suite has a fireplace, en-suite bathroom with soaking tub & walk-in closet. Country comfort at its best.

5597 Highway 66, 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

$650,000

2 Beds ⋅ 1 Baths ⋅ 220225643 MLS

Opportunity to own an historic two bedroom, one bath, 1,233 square feet, 1925 Craftsman-style home Above the Boulevard with easy access to town and all the amenities Ashland has to offer. This gracious property has been lovingly maintained by its present owner for the last thirty-four years. From the welcoming and covered front porch to the spacious, light-filled interior everything about this property harkens back to a time when life was a little slower. This single-story home with a full basement sits on a level .3 acre lot with a duplex that backs to the alley. Properties like this don't often come on the market. Home is located in ''The Siskiyou-Hargadine Historic District.'' Buyers are encouraged to do their own due diligence and check with the City Ashland regarding the legality of existing structures and possibilities for expansion.

363 Beach Street, Ashland

$695,000

4 Beds ⋅ 2 Baths ⋅ 220225640 MLS

Tucked away in one of Ashland's most sought-after neighborhoods, this exceptional property offers the rare feeling of a private nature retreat while remaining just minutes from the heart of the city. Surrounded by mature trees and abundant natural beauty, the home feels like a treehouse with beautiful views of the mountains that create a peaceful backdrop throughout the seasons. With access to a beautiful trail system, including the Ashland Ditch Trail, outdoor recreation begins right outside your door. Whether you're hiking, running, or simply enjoying a quiet walk, this location provides an unmatched connection to nature. The unique setting combines privacy, serenity, and convenience--offering a secluded escape without sacrificing easy access to downtown Ashland, local dining, shopping, parks, hospitals, and cultural attractions.

279 Alta Avenue, Ashland

$1,200,000

2 Beds ⋅ 3 Baths ⋅ 220225582 MLS

Experience refined living just one block from downtown Ashland in this custom-built 2012 luxury home designed for comfort and ease. Rich oak and red oak floors and cabinetry pair beautifully with custom metalwork and soaring wood-paneled ceilings in the great room. The chef's kitchen features a 6 burner Wolf cooktop, wall oven, speed oven, Sub Zero refrigerator, exposed edge granite countertops and custom pot racks. Spa inspired bathrooms include heated tile floors, dual vanities, tiled showers and abundant natural light, one with a soaking tub. An elevator and 36 inch doorways provide seamless accessibility throughout. The oversized finished two car garage offers space for a workshop, gym and storage with additional laundry, sink and gas heater. The private flagstone courtyard with gas BBQ, is perfect for relaxing and outdoor entertaining with lovely, low maintenance landscaping.

400 Allison Street, Ashland

Start Your Search

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: