Ashland County Real Estate

Ashland County Real Estate

Welcome to Ashland County, Wisconsin – a hidden gem nestled along the shores of Lake Superior, where natural beauty meets a rich cultural tapestry. Known for its stunning landscapes and vibrant communities, Ashland County is the perfect destination for those seeking adventure, tranquility, and a sense of belonging.

With its breathtaking vistas, Ashland County is a paradise for outdoor enthusiasts. Explore the vast Chequamegon National Forest, where miles of hiking trails wind through lush woodlands, offering opportunities for birdwatching, wildlife spotting, and unforgettable camping experiences. In the winter, the area transforms into a snowy wonderland, perfect for snowmobiling, cross-country skiing, and ice fishing on the pristine waters of the lake.

Beyond its natural allure, Ashland County boasts a charming downtown area filled with local shops, art galleries, and eateries that celebrate the region's unique heritage. Experience the warmth of the community at local events such as the annual Ashland County Fair or the Bayfield Apple Festival, where you can savor delicious local produce and crafts.

For those considering a move to this idyllic county, Ashland offers a variety of housing options, from cozy lakeside cottages to spacious family homes, all set against the backdrop of stunning landscapes. With a strong sense of community and a slower pace of life, Ashland County is not just a place to live; it’s a place to thrive.

Discover the beauty, charm, and opportunities that await you in Ashland County, Wisconsin – where every season brings new adventures and lasting memories.

Newest Listings in Ashland County

$495,500
ACTIVE Status ⋅ 3 Beds ⋅ 3 Baths ⋅ 7140309 MLS ⋅ 2,178 SqFt.
Discover the perfect blend of privacy, comfort, and Northwoods charm on 6.5 beautiful acres just 3 minutes from downtown LaPointe. Built in 2001, this well-maintained 3-bedroom, 3-bathroom home offers mostly main-floor living and plenty of space to enjoy the peaceful surroundings of Madeline Island. Natural hardwood floors, warm wood siding, and abundant windows create an inviting atmosphere throughout the home. The kitchen features a skylight that brings in natural light, while the bright sunroom provides a wonderful space to relax and take in views of the surrounding property. Gather around the wood-burning fireplace on cool evenings or step outside onto the newly constructed deck to enjoy the tranquility and privacy of the acreage. Outside, the property is beautifully established with mature maple and oak trees, a large garden, and ample room to explore and enjoy the outdoors. A pole building provides additional storage or workspace, while the attached two-stall insulated garage offers convenient year-round parking and storage. A brand-new furnace was installed in summer 2026, providing added peace of mind. With its combination of privacy, mature trees, usable acreage, comfortable living spaces, and convenient proximity to town, this property offers a rare opportunity to enjoy the best of Madeline Island living. Whether you're looking for a full-time residence, island getaway, or private retreat, this exceptional property is ready to welcome you home.

870 Middle Road, La Pointe

Listing courtesy of Timber Ghost Realty, LLC.

$549,900
ACTIVE Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 7139375 MLS
Rare opportunity to make history! Located just steps from Maslowski Beach this beautiful property has been a well-loved hallmark of Ashland for years. Nestled adjacent to Prentice Park on over 3.5+/- acres this stately brownstone building is “serving up” multiple possibilities for you. Renovations in progress have thoughtfully and masterfully brought a simply amazing list of updates including a renovated dining room with crystal chandeliers, professionally refinished hardwood floors, revealed brownstone, garage foundation, kitchen porch, remodeled kitchen, basement reconfiguration, and much more. This iconic landmark greets you with stately and unique marble pillars. The main floor consists of a Bar/Lounge, formal Dining Areas, Commercial Kitchen, and wrap-around porch with stunning Lake Superior views. Upstairs offers a host of options which include a newly remodeled bathroom, kitchenette, and space for a residence, offices or event space. Don’t miss out on the opportunity to add your name to Historic Property City of Ashland No 141.

315 Turner Road, Ashland

Listing courtesy of Anthony Jennings & Crew Real E.

$49,900
ACTIVE Status ⋅ 7138410 MLS
Three+/- acres of land across the road from Lake Superior on Madeline Island. Bring your camper and experience life on island time! A beautiful variety of trees fill this parcel just down the road from Islands End Forest and trails protected by The Madeline Island Wilderness Preserve. Experience the pristine majesty of this area. Close to Big Bay Town Park and State Park. This is a recreational lot that won't allow the construction of a home. Shown by appointment only.

36XX N Shore Road, La Pointe

Listing courtesy of Anthony Jennings & Crew Real E.

$49,900
ACTIVE Status ⋅ 7138357 MLS
Adjacent to Prentice Park with potential lake views! Just under two+/- acres this property overlooks Prentice Park and is just steps to Maslowski Beach. Enjoy privacy with the option of indulging in all the park and beach has to offer including artesian water and Lake Superior's pristine beauty. The adjoining property has excellent lake views. Adjoining the bike trail that meanders through the park this is a special piece of land that affords easy access through the park to the beaches of the Chequamegon Bay. Tree coverage offers seclusion from your neighbors and a very, spacious yard to enjoy. Nestle yourself into this natural area just minutes from Ashland's city center.

2821 Junction Road, Ashland

Listing courtesy of Anthony Jennings & Crew Real E.

$74,900
ACTIVE Status ⋅ 7137672 MLS
One and a half acres+/- on the corner of Copper Falls Drive and HWY 13. Incredible corner property just a mile and a half to Copper Falls State Park. Easy on/off graveled driveway, cleared areas, and wooded areas allow for the footprint you seek. A commercial venture would receive excellent exposure. If you choose a residential option you have just the right amount of seclusion and space to nestle inside the acreage. The City of Mellen is the key connection between Copper Falls State Park and the North Country Trail in the Chequamegon-Nicolet National Forest, and is approximately thirty minutes south of Lake Superior. Shown by appointment only.

8XX Copper Falls Dr, Mellen

Listing courtesy of Anthony Jennings & Crew Real E.

$23,900
ACTIVE Status ⋅ 7137627 MLS
Directly across the street from Lake Superior in the heart of Ashland! City water, electric, natural gas and sewer all available. Lake views and walking access to the lakefront trail that leads to beaches, marinas, parks and the artesian well. There is a small garage encroachment on the southeast corner of property - see Plat of Survey in associated docs. Access easement from Beaser Avenue.

1306 Lake Shore Drive W, Ashland

Listing courtesy of Anthony Jennings & Crew Real E.

$319,900
ACTIVE Status ⋅ 8 Beds ⋅ 6 Baths ⋅ 7127965 MLS ⋅ 5,824 SqFt.
Three suite building boasting modern updates with gorgeous vintage character intact! Two main levels and one upper level suite all featuring their own wow factor and unique character. One of the main level suites has been newly renovated from a former bar and is just stunning! Soaring ceilings with original tin overlay, a twenty foot long birch bar and two booths were beautifully restored that add incredible character. The comfortable layout and architectural details are so well thought out. The upper level suite offers a very spacious open concept layout with high ceilings, a primary ensuite, two more bedrooms and baths. All three units have their own dedicated laundry within the suite.Two-car detached garage and full basement offer plenty of storage and workspace. Set on an almost half acre+/- corner lot the partially fenced backyard has lovely greenspace for outdoor relaxing. Only a few blocks away from the beaches of Lake Superior and the quaint shops and restaurants of downtown Ashland. Live on site and lease out the other spaces long term or short term, this income property is one you’ll treasure!

116 14th Avenue E, Ashland

Listing courtesy of Anthony Jennings & Crew Real E.

$249,900
ACTIVE Status ⋅ 7114266 MLS
Reminiscent of a European bistro the Second Street Bistro offers a rich, warm atmosphere, wall of high backed booths, coveted corner window seat, and bar. Set on the corner of Second Street and Main Street just down from Lake Superior in the heart of Ashland this is the place that locals and visitors seek out for great fare and comfortable ambiance. The side courtyard offers a wonderful place for outdoor dining and gatherings. Signature entree recipes are included with the sale as well as training from the current owners if desired. A new roof, fresh paint, all new flooring, and high grade commercial kitchen flooring have been installed within the last five years. Convenient upper level office and full basement for storage complete this excellent opportunity!

201 Main Street E, Ashland

Listing courtesy of Anthony Jennings & Crew Real E.

$182,900
ACTIVE Status ⋅ 2 Beds ⋅ 3 Baths ⋅ 7114226 MLS
Bright & beautiful commercial space with a spacious, two-bedroom apartment upstairs. In the heart of Ashland's City Center this property offers incredible exposure for your business. A warm welcome includes soaring ceilings, bright Main Street views, generous reception area, office, conference room, and plenty of space for storage. The upper level two-bed apartment has some great wow factor with a primary bedroom ensuite including another room that would make a great walk-in closet, studio, or office space. Both units have the option of front and back entrances. A full basement offers even more storage and another half bath. Live onsite or rent out the apartment for extra income. Just one block from Lake Superior!

404 Main Street W, Ashland

Listing courtesy of Anthony Jennings & Crew Real E.

$149,900
ACTIVE Status ⋅ 1 Beds ⋅ 3 Baths ⋅ 7114195 MLS
The beacon of the Harbor Bar is guiding you to Ashland! With it's iconic historic facade this is your chance to own a commercial property and upper level apartment just a block away from Lake Superior. Incredible exposure on HWY 2 with off street parking the main level houses the bar, walk-in cooler, two restrooms, and back storage area. A nice two bedroom upper level apartment has a deck off the living space with Lake Superior views and a bright, enclosed sunporch off the back. Live on site or rent out the apartment for extra income. Continue the business or bring your ideas to this great property and location!

1222 Lake Shore Drive E, Ashland

Listing courtesy of Anthony Jennings & Crew Real E.

$374,900
ACTIVE Status ⋅ 7114168 MLS
PRIME LOCATION and just steps away from Lake Superior on HWY 2 in the middle of downtown Ashland! This is it! Just under a half acre+/- perched atop the lakefront trail with sweeping views of Chequamegon Bay. Catch the views and all the commuters. Bring your business ideas and create a space you and your clients easily access and look forward to coming to. The Bay View Pawn Shop is closing. Seller will consider land contract with acceptable down payment, sellers credit and approval.

421 Lake Shore Drive W, Ashland

Listing courtesy of Anthony Jennings & Crew Real E.

$2,750,000
ACTIVE Status ⋅ 7114105 MLS
Grand Commercial Space in the heart of Ashland! This stately building is a fully functional, thoughtfully designed, full service prior medical building, with proper wiring and a 23,570 sq. ft. floor plan designed for efficient patient servicing with public and private entrances. Twenty-seven exam rooms are available through four hallways, all accessible from the 3,200 sq. ft. lobby with multiple waiting areas and a bright community room. A 1000-amp cabinet by Siemens services eight electrical boxes and fire detection system. Facilities include an X-ray room, mammography, several nurses’ stations, nine bathrooms, and numerous offices. A very spacious central area behind the lobby reception offers a multitude of flex-use options. The possibilities are endless for the use of this property; clinic, spa, daycare, retail space, event space, office space - bring your vision! Close to one hundred parking spaces are ideal for customers and employees. Part of the building is leased and income producing. Leasing options are also available.

415 Ellis Avenue, Ashland

Listing courtesy of Anthony Jennings & Crew Real E.

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