Winona County Real Estate

county: Winona

Winona County is located in the southeastern corner of Minnesota, just a short drive away from the cities of La Crosse, WI and Rochester, MN. The county is known for its rolling hills, lush forests, and vast agricultural lands. It is a popular destination for outdoor recreation, including fishing, hunting, camping, and hiking.

The county seat of Winona is the city of Winona, which is home to a vibrant arts and culture scene, as well as a bustling downtown area. The city is also home to Winona State University, which provides a number of educational and cultural opportunities to the local community.

The county is also home to a number of small towns and rural communities, each with its own unique charm and character. The area is known for its rural beauty, and is a great place to settle down and raise a family. The county is also home to a number of lakes, including Lake Winona, which is a popular destination for fishing and water sports.

The area is also home to a number of local businesses, from small shops to large corporations. The county is home to a number of industries, including manufacturing, healthcare, and agriculture. The area also has a strong agricultural base, with a number of farms and ranches located throughout the county.

Overall, Winona County is a great place to live, work, and play. It offers a variety of recreational activities, a vibrant cultural scene, and plenty of employment opportunities. Whether you are looking for a place to settle down and raise a family, or just looking for a great place to visit, Winona County has something to offer.

Newest Listings in Winona County

$169,900

3 Beds ⋅ 1 Baths ⋅ 7120056 MLS

763 W Mark Street, Winona Is A Sleeping Beauty! You will LOVE the 3 Main Floor Bedrooms, Spacious Kitchen with Tiled Floors, Replaced Cabinetry & Countertops & Stainless Steel Appliances, Newly Stained & Painted Front Porch & Expansive Back Deck. The Backyard is Fully Fenced, offering privacy & safety for families, children & pets, plus open parking for 2+ vehicles! The Roof, Thermo Windows, Stainless Steel Appliances, Water Heater & Forced Air Furnace are all in good condition! The Main Floor also includes a separate Laundry Room with Washer & Dryer included in the sale. Special Bonus - The Fully Finished Upstairs offers 2 rooms which are perfect for many purposes: an office, hobby room, exercise room, den, storage, media/gaming, additional sleeping & storage galore! All exterior staining & painting will be completed the week of August 3rd, 2026. This property is Rental Certified. Come & Look Now!

763 W Mark Street, Winona

Listing courtesy of Jewson Realty.

$315,000

3 Beds ⋅ 2 Baths ⋅ 7120123 MLS

Immaculately maintained and nicely updated 3-4 Bedroom, 2 Bath Rambler in convenient West side location. Close to shopping, schools and restaurants! The 2-car attached garage features a newer 10'x20' workshop addition on the back. You are sure to enjoy the tranquil backyard green space, the manicured landscaping, and the new paver patio. The main level boasts 3 bedrooms, newer LVP flooring, and an updated kitchen with Stainless Steel appliances. The lower level is partially finished and has so many possibilities. You'll be sure to enjoy movie night in the massive family room. The bonus/game room can be turned into a 4th bedroom, and there is so much storage space. Updates include: the kitchen, SS appliances, windows, flooring, roof, vinyl siding, gutters, driveway, water heater, and radon mitigation system. This gem is ready for you to move right in and enjoy. Schedule your appt. before it's gone!

334 Oak Street, Winona

Listing courtesy of Real Broker, LLC..

$99,000

7118928 MLS

Imagine building your dream home where every day begins with breathtaking views of the Mississippi River and the stunning beauty of the Driftless Area. This incredible homesite offers the perfect opportunity to create a home that is uniquely yours while enjoying one of nature's most spectacular backdrops. Watch the seasons transform the landscape from your own backyard as bald eagles soar overhead, barges make their way up and down the river, and elegant cruise ships pass through the valley. Whether you're enjoying your morning coffee at sunrise or unwinding in the evening, the views are simply unforgettable. Don't miss this rare opportunity to own a piece of the Driftless Region and build the home you've always imagined. Contact the listing agent today for complete details and available information. **Please do not walk the property without your real estate agent. All showings must be accompanied by a licensed real estate agent.**

25579 Leeward Road, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$265,000

2 Beds ⋅ 2 Baths ⋅ 7119443 MLS

Affordable Opportunity in a Great Winona Neighborhood! Here’s your chance to own an affordable home in a desirable Winona neighborhood! This 2-bedroom, 2-bath home offers comfortable living today with the potential to easily create additional bedrooms as your needs change. Many important updates have already been completed over the years, including the kitchen, windows, roof, water heater, and driveway extension. Hardwood floors add character to the main level, while the finished lower-level family room provides extra space for entertaining, hobbies, or relaxing. Step outside to enjoy the fenced backyard with a deck—perfect for grilling, pets, or spending time outdoors. With its great location, functional layout, and room to make it your own, this home is an excellent opportunity for first-time buyers, downsizers, or anyone looking for an affordable place to call home.

1661 W 6th Street, Winona

Listing courtesy of Edina Realty, Inc..

$1,800,000

4 Beds ⋅ 3 Baths ⋅ 7108534 MLS

Positioned along the coveted main channel of the Mississippi River in Dresbach, Minnesota, this extraordinary custom residence was thoughtfully designed to embrace its remarkable setting while standing the test of time. Originally built in 2008 by Benson Construction, this estate is ingeniously structured so that every single riverfront room captures a panoramic, two-directional view of the water. Resting secretly on solid bedrock, this 4,500-square-foot home ensures absolutely no settling. This exceptional engineering combines with a striking exterior featuring natural stone, a Dryvit finish, and a distinctively curved steel roof. Inside, a dramatic 30-foot barrel ceiling frames a unique copper-door entry. The home features premium Brazilian Tigerwood flooring, a slate fireplace, and exquisite solid maple panel doors and millwork handcrafted by local Amish artisans. The layout offers 4 bedrooms, 2.5 bathrooms with luxury Kohler fixtures, and custom cabinetry in the library and master closets. A chef's kitchen boasts premium Diamond cherry cabinets, a Sub-Zero refrigerator/freezer, and a professional 6-burner Wolf cooktop and oven. Vehicles are housed in a deep 3-car garage finished with clean epoxy flooring. Outside, a composite circular deck overlooks approximately 110 feet of private shoreline with a private dock protected by a strategic wing dam. High-efficiency utilities feature luxurious heated hydronic concrete floors, off-peak energy electrical systems with Clearwater solar credits, a Moen Flo smart water monitor, and a reverse osmosis drinking system. The property includes landscaped butterfly gardens, low river traffic north of Dam 7, and local bike trail access. This is a residence defined not just by luxury, but by structural permanence and artistic excellence. Every element—from the raw, bedrock-anchored engineering to the meticulous Amish-crafted millwork—proves that no detail was overlooked and no compromise was made. To own this home is to inherit a masterclass in architectural integrity, offering an elite riverfront lifestyle built to endure for generations to come.

30960 Old Mill Road, Dresbach

Listing courtesy of Century 21 Affiliated.

$185,000

2 Beds ⋅ 2 Baths ⋅ 7118804 MLS

Welcome home to this well-maintained 2 bedroom, 2 bathroom ranch offering the convenience of one-level living with additional finished space in the basement! Whether you're looking for your first home, downsizing, or simply want a move-in ready property, this home checks all the boxes. Inside, you'll find beautiful hardwood floors in both bedrooms, an eat-in kitchen with appliances included, and a functional layout designed for comfortable everyday living. The finished lower level provides extra living space that could be used as a family room, hobby area, home office, or guest space. Outside, enjoy a spacious yard and a heated 2-car detached garage, giving you plenty of room for vehicles, storage, or projects year-round. The convenient Winona location puts you close to parks, schools, shopping, and everything the city has to offer. Don't miss your opportunity to make this charming home your own!

156 E Mark Street, Winona

Listing courtesy of Real Broker, LLC..

$510,000

5 Beds ⋅ 4 Baths ⋅ 7090573 MLS

Located on a quiet cul-de-sac, this spacious walkout two-story home sits on an impressive 1.47-acre wooded lot overlooking a pond. It offers 5 bedrooms, 4 bathrooms, and an attached 3-stall garage. Inside, you’ll find an inviting main living area with a fireplace, an open kitchen and dining space, custom-style cabinetry, main-floor laundry, a walk-in closet, and a finished walkout lower level. Enjoy the peaceful, private backyard setting from the deck or welcoming front porch. With numerous recent updates and a completed pre-inspection, this home is ready to enjoy with added peace of mind.

239 Willow Court, Saint Charles

Listing courtesy of Edina Realty, Inc..

$225,000

7117877 MLS

Completely renovated from top to bottom, this downtown Lewiston commercial property offers the perfect blend of modern updates and future potential. The building has undergone an extensive transformation, giving the next owner the confidence of major improvements already being completed. Brand-new electrical system with a 200-amp service and three-phase power to the building. New rubber roof for long-term durability and low maintenance. 40 inches of blown-in insulation in the attic for exceptional energy efficiency. New subfloor throughout, new front windows and exterior trim, enhancing the building's curb appeal and natural light. This property has endless potential!

80 E Main Street, Lewiston

Listing courtesy of Loam Commercial Real Estate.

$75,000

7117837 MLS

If you've ever dreamed of building your own home, this is your chance. This stunning lot is located in Rollingstone, MN surrounded by the beautiful bluffs. Imagine designing a space just for you, in a peaceful small town with parks, a school, walking trails, biking trails and ponds to fish or watch the wildlife. There is much to offer including a small town cafe and a local museum. You get all of these attractions just 10 minutes from the west end of Winona. These lots are ready—to—build with all the amenities, including city water and sewer, electric, two internet providers, and natural gas. All assessments are paid as well. Don 't miss your chance of building your own home!

210 Sweetwater Drive, Rollingstone

Listing courtesy of Edina Realty, Inc..

$539,900

6 Beds ⋅ 3 Baths ⋅ 7116367 MLS

Must see this stunning 6 bed 3 bath home located in one of the most desirable areas of Winona, ample space for entertaining and enjoying, some features include hardwood floors, large en suite, newer appliances, nice 3 car garage with basement access, fireplace, large kitchen, solid stone counters, great backyard, and more. Call today!

1850 Garvin Heights Road, Winona

Listing courtesy of Coffee House Real Estate LLC.

$950,000

5 Beds ⋅ 3 Baths ⋅ 7116381 MLS

Stunning oppurtunity awaiting, former industrial plant with plenty of power, multiple wells, sitting on 13 acres, high end finishes in office/potential residential space, spray foam, geo thermal, wood land, sitting on pavement with room to expand or enjoy, this is a one of a kind property and the potential is just waiting! Call today before it gets away.

23671 County Road 37, Saint Charles

Listing courtesy of Coffee House Real Estate LLC.

$549,900

3 Beds ⋅ 2 Baths ⋅ 7114286 MLS

Every detail of this thoughtfully designed 2024-built home has been carefully considered, from the elegant under-cabinet lighting to the high-end appliances and luxurious hard surface kitchen countertops that create a stunning and functional kitchen. The fully insulated garage already has water installed, is prepped for a future furnace with the necessary hookups in place, and is prewired for an electric vehicle charger, making it easy to create a comfortable, functional, year-round workspace. Step outside to the nearly 200-square-foot covered deck and soak in the breathtaking bluff views overlooking the scenic Driftless Valley. Built with quality and longevity in mind, this home showcases exceptional craftsmanship, premium finishes, and thoughtful design throughout. The partially finished lower level provides outstanding potential, already roughed in for two additional bedrooms, partially finished bathroom and a spacious family room while still offering abundant storage space. Whether you're looking for room to grow or simply appreciate superior construction and attention to detail, this home is sure to impress. Located in the charming community of Rollingstone, you'll enjoy the tranquility of small-town living while being just minutes from Winona. Combining quality construction, upscale finishes, and spectacular views, this remarkable 2024-built home truly has it all. Welcome home!

166 Rimrock Road, Rollingstone

Listing courtesy of Real Broker, LLC..

Start Your Search

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of the Regional Multiple Listing Service of Minnesota. Real estate listings held by brokerage firms other this firm are marked with the Broker Reciprocity logo. Information Deemed Reliable But Not Guaranteed. Property locations as displayed on any map are best approximations only and exact locations should be independently verified.

Listing data © 2026 Regional Multiple Listing Service of Minnesota. All rights reserved. By searching, you agree to the EULA.