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

$189,000

2 Beds ⋅ 1 Baths ⋅ 7144015 MLS

This 2 bedroom, 1 bath home is in a fantastic location with plenty of space both inside and out. The oversized living room overlooks the very large backyard, giving you plenty of room to spread out. A cement pad is already in place, making it a great start for you to add your own garage in the future. The bathroom offers plenty of space, and both bedrooms are generously sized. You will also love the cute front porch, a perfect spot to enjoy some fresh air without worrying about the bugs! The basement provides additional space to grow into or simply use for great storage. Newer windows, furnace, and central air add even more value to this home.

623 E Howard Street, Winona

Listing courtesy of Keller Williams Premier Realty.

$210,000

3 Beds ⋅ 1 Baths ⋅ 7142289 MLS

Welcome home! This charming property offers 3 bedrooms plus an additional bonus room perfect for a home office, nursery, or flex space. The spacious primary bedroom features a huge walk-in closet, while the main floor offers convenient laundry and full bathroom. Enjoy peace of mind with a newer solid metal roof installed in 2025, along with a newer A/C and furnace. Relax on the inviting front porch or enjoy the privacy of the fenced in backyard. Additional features include a one stall garage and plenty of functional living space throughout. A wonderful opportunity to make this home your own!

569 W Wabasha Street, Winona

Listing courtesy of Keller Williams Premier Realty.

$255,000

3 Beds ⋅ 2 Baths ⋅ 7144240 MLS

Welcome home! This beautifully updated 3-bedroom, 1.5-bath home offers comfortable living with the convenience of thoughtful updates throughout. Brought completely down to the studs in 2019, this home has been fully renovated. The home offers a fresh, move-in-ready feel while maintaining a welcoming sense of home. The main floor features an open floor plan, with the primary bedroom and laundry, making everyday living easy and efficient. Outside, enjoy a nicely landscaped yard that provides a great space for relaxing, entertaining, or enjoying the seasons. Located in walking distance to almost everything St. Charles has to offer. This home is ready for its next chapter!

237 W 14th Street, Saint Charles

Listing courtesy of Edina Realty, Inc..

$299,900

3 Beds ⋅ 2 Baths ⋅ 7129240 MLS

Embrace tranquility and boundless nature just outside Rollingstone. Set on 5+ acres of private wooded land, this country property is an absolute dream for anyone seeking a serene lifestyle away from the city. Arrive just in time for fall and soak in the sweeping, picturesque countryside views as the leaves begin to change. Perfect for outdoor enthusiasts, wildlife watchers, or anyone craving space and seclusion. Key updates include a brand-new septic system installed in 2024.

18599 Horse Shoe Road, Rollingstone

Listing courtesy of Coldwell Banker Realty.

$175,000

2 Beds ⋅ 1 Baths ⋅ 7143829 MLS

Great opportunity to build some quick equity! This 2 bedroom, 1 bathroom home offers everything conveniently located on one level, along with a 1 stall attached garage. Bring your cosmetic ideas and make this home your own. The large fenced backyard provides plenty of room to enjoy the outdoors. Conveniently located within walking distance to several schools and the walking paths. A great option for a first time buyer, downsizing, or anyone looking for an affordable home with potential!

687 W Belleview Street, Winona

Listing courtesy of Keller Williams Premier Realty.

$220,000

5 Beds ⋅ 2 Baths ⋅ 7143190 MLS

A rare opportunity with incredible flexibility and income potential! This property offers a unique setup with 4 bedrooms and 1 bathroom throughout the main level and basement, plus a separate upper-level efficiency unit with its own small kitchen, bathroom, and private entrance. The possibilities are truly endless—live comfortably in the main home while renting the upper unit for additional income, create a great setup for multi-generational living, or utilize the property as a full investment. The home currently has a rental certificate, adding even more appeal for investors looking for an income-producing property. Whether you're an owner-occupant looking to offset your housing costs or an investor looking to maximize rental potential, this property offers the flexibility and opportunity to make it your own. Come take a look and see the possibilities!

423 W Mark Street, Winona

Listing courtesy of RE/MAX Advantage Plus.

$449,900

4 Beds ⋅ 3 Baths ⋅ 7126794 MLS

Welcome to 1908 Country View Dr in St. Charles! Built in 2007, this spacious ranch-style home offers 3512 square feet of finished living space, 4 bedrooms, and 3 bathrooms, all set on a large lot with plenty of room to enjoy. The open-concept design creates an inviting flow between the main living spaces, making everyday living and entertaining comfortable and easy. With four bedrooms and generous finished space, there’s room for everyone to spread out, work from home, entertain, or simply enjoy the comforts of home. The 1,015-square-foot heated and finished garage is truly a standout feature. The garage includes a dedicated woodworking shop—perfect for the hobbyist, craftsman, or anyone who needs a little extra space for projects and hobbies. Outside, the large lot offers plenty of room to relax, play, garden, or enjoy the outdoors. If you’ve been looking for a spacious ranch home with an open layout, oversized heated garage, dedicated workshop, and room to grow, 1908 Country View Dr is one you won’t want to miss!

1908 Country View Drive, Saint Charles

Listing courtesy of Edina Realty, Inc..

$220,000

3 Beds ⋅ 2 Baths ⋅ 7142018 MLS

Charming Ranch Home on a Spacious Half-Acre Lot! Welcome home to this inviting 3-bedroom, 2-bathroom ranch-style home, ideally situated on a generous half-acre lot. Offering comfortable living spaces and plenty of room to enjoy the outdoors, this property has something for everyone. Step inside to find new flooring throughout most of the home, creating a fresh and updated feel. The home offers three bedrooms, two bathrooms, and a private home office—perfect for working from home or creating a dedicated study or hobby space. The lower level adds even more living space with a comfortable family room, ideal for movie nights, entertaining, or relaxing with family and friends. A large laundry room provides excellent storage and functionality. Outside, enjoy the expansive half-acre lot featuring a large vegetable garden in the backyard, offering plenty of space for gardening and outdoor activities. The new backyard deck provides the perfect spot for morning coffee, summer gatherings, or simply enjoying the peaceful surroundings.

4618 W 5th Street, Winona

Listing courtesy of Edina Realty, Inc..

$357,000

3 Beds ⋅ 4 Baths ⋅ 7141876 MLS

Enjoy beautiful golf course views and all the space you've been looking for at 100 Benson Drive in Lewiston! Nestled along the Lewiston Golf Course, this inviting 3-bedroom, 4-bath home (2 full, 2 half) offers a spacious layout designed for both everyday living and entertaining. The main level features generous gathering spaces filled with natural light, while the upper level offers three comfortable bedrooms, including a spacious primary suite. Downstairs, the fully finished lower level provides even more living space with a large family room that's perfect for movie nights, game days, a home gym, or play area. Whether you're hosting friends on the deck, relaxing with a morning coffee overlooking the course, or enjoying a quiet evening at home, this property offers the perfect balance of comfort and location. Recent improvements provide added peace of mind and include fresh interior paint throughout, updated hardware and fixtures, new cordless blinds, refreshed landscaping, freshly stained decks, a replaced A/C condenser, professionally serviced furnace and fireplace, professionally cleaned carpets, and an epoxy-coated garage floor. If you've been searching for a move-in ready home in one of Lewiston's most desirable neighborhoods, this is one you won't want to miss.

100 Benson Drive, Lewiston

Listing courtesy of Real Broker, LLC..

$145,000

3 Beds ⋅ 1 Baths ⋅ 7134077 MLS

Perfect starter home or a great addition to your rental portfolio, conveniently located just a few blocks from the college. This home features an open floor plan, three bedrooms, and a sunny front porch. Current rental certificate expires in 2027 and allows for 5 unrelated occupants. A great opportunity in a convenient Winona location!

577 W Sanborn Street, Winona

Listing courtesy of Real Broker, LLC..

$319,900

3 Beds ⋅ 2 Baths ⋅ 7140082 MLS

Historic Character, Timeless Charm & Peaceful Surroundings Welcome to a truly special 3-bedroom home where local history, distinctive craftsmanship, and comfortable living come together. An inviting open-concept main floor creates a wonderful flow for everyday living and entertaining, with a beautiful kitchen at the heart of the home, featuring ample storage and plenty of kitchen cabinetry. One of the home's most remarkable features is the one-of-a-kind fireplace crafted from two varieties of brick salvaged from the streets of 1800s Winona. Rich with local history and character, this exceptional architectural feature is a beautiful reminder of the community's past and a conversation piece unlike any other. Cozy up and keep warm by the gas fire, creating the perfect gathering spot on cool evenings. Adding even more character is a local stained-glass window, bringing beautiful color, artistry, and a unique sense of place into the home. Together, the historic brick fireplace and stained glass create an atmosphere filled with warmth, personality, and connection to Winona's heritage. The main floor underwent an extensive remodel in 2007, providing comfortable and functional living spaces while retaining the home's distinctive character. Main-floor laundry adds everyday convenience, while the two-car garage offers excellent parking and storage. Surrounded by mature trees, the property offers a peaceful and tranquil setting—an inviting place to enjoy quiet mornings, relax outdoors, or simply appreciate the beauty of the established landscape. The roof was replaced in 2021, providing an important recent update and added peace of mind. Historic details, thoughtful updates, abundant storage, mature trees, and a peaceful setting make this a truly distinctive Winona home—one with a story to tell and character you simply can't recreate.

106 Glendale Road, Winona

Listing courtesy of Real Broker, LLC..

$204,900

2 Beds ⋅ 1 Baths ⋅ 7139441 MLS

Affordable, move-in ready and maintenance free! 2+ bedroom home with an updated bath/laundry, full basement with high ceilings, plus a 2nd floor bath waiting for development! Great quiet neighborhood with a full lot and lots of yard space.

317 E Howard Street, Winona

Listing courtesy of Edina Realty, Inc..

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