Ashland, WI Homes for Sale under $500,000

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

Anthony Jennings Anthony Jennings & Crew Real Estate LLC

Completely Updated 3-Bed, 2-Bath Home on 5+ Acres with Insulated Freestanding Building This beautifully renovated home has been transformed inside and out. The owners have thoughtfully updated every room with fresh paint, modern fixtures, and newer appliances—creating a space that feels fresh, bright, and move-in ready. The home offers a smart and convenient layout with three bedrooms, two baths,

Kevin Porter Porter Realty LLC

Beautiful hardwood floors and leaded glass windows throughout this home. Currently set up as a duplex but could easily be converted into single family living. Large open rooms with high ceilings.

Jennifer Eng Coldwell Banker Realty - Ashland

Why live in the City when country living is only minutes away?! This five bedroom, 4 total bath is set on 5.13 picturesque acres. The attached and detached garages provide more-than-ample space for your vehicles, toys, hunting equipment or time working on a project.

Martin Hoglund By the Bay Realty

Welcome to this 3 bed, 2 bath home on historic MacArthur Avenue. The home sits within walking distance of Lake Superior, with easy access to biking and walking trails, schools, and the local hospital. The fenced yard and attached one-car garage add everyday convenience, while major updates in the last 10 years mean the home is ready for its next chapter.

A Giselle Smith eXp Realty, LLC- WI

1222 & 1218 Lakeshore Drive – Two Income-Producing Homes with Exceptional Potential Two well-performing rental properties are offered together for an unbeatable value. The eastern property (1218 Lakeshore Drive) is a freestanding 4-bedroom home with a solid basement and foundation, currently rented for $1,100/month with a consistent rental history. The western property (1222 Lakeshore Drive) has

Kevin Porter Porter Realty LLC

Beautifully maintained and thoughtfully updated, this bright two-story home showcases the craftsmanship of its era — 7-inch baseboards, craftsman-style window trim, natural finish hardwood doors, and 81⁄2-foot ceilings on the main level. Recently refinished maple floors greet you at the entry, where a large walk-in coat closet stands off the entry. A mullioned picture window anchors the living

Kevin Porter Porter Realty LLC

Charming Home with Upgrades and Expansive Outdoor Space! Welcome to this move-in ready home situated in a highly desirable neighborhood. The property features a fully enclosed, large fenced-in backyard with generous space to run, play, or garden. Storage is never an issue here—the property includes two separate garages plus a practical lean-to, offering massive space for vehicles, lawn equipment,

Jessica Nettleton By the Bay Realty

Completely Remodeled & Move-In Ready, 4 Bed, 2 Bath on a Corner Lot This one checks every box. A full remodel, done right, not just cosmetic. Brand-new LVP flooring runs through an open-concept layout, white shaker cabinets and recessed lighting give the kitchen a clean, modern feel, and every major mechanical system (plus all appliances) has been replaced. Fully permitted 2025-2026 remodel with

Heidi Hicks Visions First Realty, LLC

Beautiful downtown condo! New build in the historic Grand Opera House. This upper unit includes 2 bedrooms, 3 bath, oversized loft and walkout balcony with Lake Superior and downtown views. Each unit has its own private garage. Walk to the downtown shops, grocery store, lake walk, marina, or the Band Shell. Easy living at its finest.

Jay Emmert Coldwell Banker Realty - Ashland

Martin Hoglund By the Bay Realty

****Seller Financing Options Available**** Lake Superior luxury meets income potential! This beautifully remodeled 240 sq ft studio cabin offers an exceptional waterfront retreat on a private quarter-acre lot with approximate 60ft of private Lake Superior beachfront in Ashland, Wisconsin. Designed for comfort and style, everything you need. Kitchen, bathroom with shower, washer/dryer inside. This

Faith Mauritz Northland Real Estate Services

Enjoy the best of country living with the convenience of being just minutes from town. 3 bedroom, 1 bath bi-level home offers a comfortable layout with plenty of space for the whole family. The spacious lower level family room is perfect for entertaining, relaxing, or creating a recreational area. Outside you will appreciate the convenience of an attached garage plus a large detached garage

Jay Emmert Coldwell Banker Realty - Ashland

Thriving Dog Boarding, Training & Grooming Business with Home and Land in Ashland, WI 30995 US Highway 2, Ashland, WI 54806 Discover an exceptional opportunity to own a profitable, well-established pet care business with a loyal client base and consistent annual profits exceeding $100,000. Conveniently located on 9 scenic acres along Highway 2, this property offers both visibility and serenity —

Darcie Novak Thrive Realty - Duluth

Outstanding and RARE opportunity to own a condo with the shore of Lake Superior out your back door! Spectacular views and walk-out patio leads to a private sandy beach on the Chequamegon Bay. Beautiful interior includes a primary bedroom ensuite with lake views and luxurious soaking tub. Open concept living space allows the lake views to take center stage. Office/den with walk-in closet that can

Anthony Jennings Anthony Jennings & Crew Real E

Located in the heart of downtown Ashland, this 6-unit mixed-use investment opportunity offers strong rental income potential with historically solid occupancy in one of Northern Wisconsin’s most charming Lake Superior communities. The property features one commercial storefront on the main level along with five upper-level residential units, each offering 1 bedroom and 1 bathroom. Tenants pay

Aiden Bachand RE/MAX Results

Classic early-1900s two-story in the heart of Ashland, lovingly updated inside and out. A gorgeous wraparound porch — a recent addition — overlooks a quiet, tree-lined street anchored by a stunning mature maple, the perfect spot to visit with neighbors like times gone by. Inside, high ceilings and impeccable honey-toned hardwood floors set the tone. The added entryway offers backyard and garage

Kevin Porter Porter Realty LLC

Your opportunity to own one of the city's finest downtown condos! This upper unit includes 2 bedrooms, 3 bath, oversized loft and walkout balcony with Lake Superior and downtown views. Each unit has its own private garage. This building is the historic Grand Opera House originally built in 1893. Walk to the downtown shops, grocery store, lake walk, marina, or the Band Shell.

Jay Emmert Coldwell Banker Realty - Ashland

Spacious 2 bedrm home with attached garage, fenced in back yard, and usable basement! The front entrance is a solidly built ramp making access to the house easy. The original living rm more recently has been used as a craft space, and living rm use shifted to the wonderful 24'x28' addition in the back. That rm features high quality strand-woven bamboo flooring, a Lopi Woodstove, and a very nice

Jon Wheeler Blue Water Realty, LLC

Thriving Dog Boarding, Training & Grooming Business with Home and Land in Ashland, WI 30995 US Highway 2, Ashland, WI 54806 Discover an exceptional opportunity to own a profitable, well-established pet care business with a loyal client base and consistent annual profits exceeding $100,000. Conveniently located on 9 scenic acres along Highway 2, this property offers both visibility and serenity —

Darcie Novak Thrive Realty LLC