Winona County Homes under $400,000

Welcome to Winona County, Minnesota, a hidden gem nestled along the banks of the Mississippi River. Known for its stunning natural beauty and rich history, Winona offers a vibrant community atmosphere combined with a wealth of outdoor activities. Whether you're an outdoor enthusiast, a history buff, or simply seeking a peaceful retreat, Winona has something for everyone.

One of the highlights of Winona County is its charming downtown area, brimming with unique shops, delightful cafes, and cultural landmarks. The Winona County Historical Society and the Great River Shakespeare Festival are just a couple of the local treasures that showcase the area’s vibrant arts scene. For nature lovers, the breathtaking bluffs and scenic parks, such as Garvin Heights Park and the beautiful Riverside Park, provide ample opportunities for hiking, biking, and enjoying the stunning views of the Mississippi River.

If you're considering making Winona your home, you'll be pleased to know that there are a variety of homes available for under $400,000. From cozy single-family homes to modern townhouses, the real estate market here offers something for every taste and budget. Many properties boast beautiful yards, easy access to local amenities, and proximity to schools, making it an ideal place for families and individuals alike.

With its friendly community, rich culture, and affordable housing options, Winona County is not just a place to live; it’s a place to thrive. Come explore what makes Winona a wonderful place to call home!

Newest Winona County Homes under $400,000

$375,000

4 Beds ⋅ 3 Baths ⋅ 7150180 MLS

Golf Course Views & Wooded Privacy in St. Charles! Enjoy a setting that offers the best of both worlds at 1618 Park Dr with beautiful views of the St. Charles Golf Course from the front deck and a peaceful, private wooded backdrop from the back deck. This 4-bedroom, 3-bathroom home with a 3-car garage has been lovingly owned by the same family since it was built in 1992 and is ready for its next chapter. Inside, you’ll find a spacious layout with plenty of room to make the home your own. The home has been well cared for over the years and is ready for a fresh coat of paint and your personal touches to bring your vision to life. Whether you're looking for space for your family, room to entertain, or simply a home in a beautiful St. Charles location, this property offers plenty of possibilities.

1618 Park Road, Saint Charles

Listing courtesy of Edina Realty, Inc..

$230,000

4 Beds ⋅ 2 Baths ⋅ 7155269 MLS

Discover the potential of this 1965 raised ranch home, offering 4 bedrooms, 2 bathrooms, and a 2-car tuck-under garage. The main floor features a comfortable living room plus a bonus family room with a woodburning fireplace, providing plenty of space to relax and entertain. Ample storage throughout and an oversized city lot add to the home’s appeal. New carpet provides a fresh start, while the property is ready for some tender loving care to bring out its full potential. A great opportunity for someone looking to make this home their own!

1659 Edgewood Road, Winona

Listing courtesy of Edina Realty, Inc..

$265,000

3 Beds ⋅ 2 Baths ⋅ 7154657 MLS

Enjoy the space, privacy, and convenience of this 3-bedroom, 2-bath ranch in Dakota! Set on a .311-acre partially fenced lot backing to woods, this home offers a peaceful setting with easy interstate access to both La Crosse and Winona. The main level features convenient laundry, comfortable living spaces, and access to a deck overlooking the spacious backyard. The finished lower level adds valuable living and entertaining space, giving you room to spread out. A 2-car garage features an overhead pass-through door to the backyard—perfect for lawn equipment, toys, or projects. Even better, a new well and septic system are currently being installed, offering added peace of mind for the next owner. Country-like surroundings with commuter convenience!

460 Center Street, Dakota

Listing courtesy of @properties La Crosse.

$265,000

4 Beds ⋅ 3 Baths ⋅ 7153676 MLS

Turn-key and truly hard to match in Winona, this duplex delivers the kind of condition and rental history investors dream about. The main unit offers 3 bedrooms and 2 bathrooms across the first floor and finished basement, giving tenants plenty of space and a comfortable layout. The upper unit features 1 bedroom and 1 bathroom, perfect for steady, reliable rental income. The exterior has been updated with vinyl siding just two years ago, providing great curb appeal and low-maintenance durability. Outside, you’ll find a partially fenced backyard that’s surprisingly spacious—ideal for tenants who value outdoor living. A detached 1-car garage adds even more value, whether used for storage or rented out for additional income. With its strong rental history, modern exterior, and appealing outdoor space, it will be tough to find another duplex in Winona this clean, this cared-for, and this ready to go from day one. Seller is a real estate agent licensed MN & WI. 24-hour notice needed to tour

421 E Sanborn Street, Winona

Listing courtesy of Edina Realty, Inc..

$179,900

3 Beds ⋅ 2 Baths ⋅ 7154183 MLS

This move-in ready, turnkey home is a great opportunity for first-time homebuyers or those looking for a rental investment property. This 3-bedroom, 1.5-bath home offers comfortable living space along with a number of improvements, including a newer roof, a refreshed kitchen with newer appliances, and an updated bathroom. Additional improvements include newer garage siding and exterior doors. One of the home's inviting features is the 3-season porch, providing a cozy spot to enjoy your morning coffee, relax with a good book, or take in the changing seasons. Conveniently located in town next to the aquatic center, this affordable property offers easy access to recreation and local amenities. With its practical layout, desirable features, and move-in-ready condition, this home is ready for its next owner or investor.

825 W 5th Street, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$269,900

4 Beds ⋅ 2 Baths ⋅ 7150762 MLS

A Classic Cape Cod design with deceptively large rooms throughout, 4 roomy bedrooms, a sweet lower-level family room, a front porch facing South that is enclosed giving you extra months of enjoyment. Tastefully, recently remolded kitchen, a whole house beaver system with a transferable warranty, 2 car garage and much more! A great property in a terrific location!

1022 Gilmore Avenue, Winona

Listing courtesy of Edina Realty, Inc..

$289,000

3 Beds ⋅ 3 Baths ⋅ 7154307 MLS

Welcome to 928 W Mark Street, ideally located in a fabulous Winona neighborhood within walking distance of Lake Winona and area schools! Built in 1942, this spacious 3-bedroom, 3-bath home offers wonderful character, generous room sizes, and plenty of opportunity to make it your own. The main level features a spacious living room with a gas fireplace, a large kitchen with a unique indoor grill, and a charming den highlighted by a beautiful bow window. Upstairs, you’ll find three generously sized bedrooms, including a primary suite with a private bath and two closets. Wood flooring is visible in the closets, offering the possibility of additional wood floors beneath some of the carpeting. The lower level provides even more living space with a family room and workshop area. An attached 2-car garage, spacious yard, and garden shed complete the property. With its desirable location, classic features, and great potential for personalized updates, this is a wonderful opportunity to make this home your own!

928 W Mark Street, Winona

Listing courtesy of Edina Realty, Inc..

$219,900

5 Beds ⋅ 2 Baths ⋅ 7153362 MLS

Spacious 5 bedroom/1.5 bath rental certified home is ready to be added to your portfolio! Home has been updated in many areas, newer upper full bath, updated kitchen/countertops, dishwasher and extensive drywall work throughout. Home has spacious living area, dining room and bedrooms, making this a great rental property or larger single-family home. Home has lots of original charm with hardwood flooring, large windows and some original doors/wood work. Conveniently located on the west end of Winona, close to colleges. Cotter, restaurants and shopping.

362 Cummings Street, Winona

Listing courtesy of Castle Realty, LLC.

$139,900

1 Beds ⋅ 1 Baths ⋅ 7152392 MLS

Welcome home to this charming 1-bedroom, 1-bath home! A great option for a first-time buyer or someone looking to downsize, this cozy home offers a comfortable and functional layout. Outside, you will find a large fenced-in backyard with plenty of room to relax, entertain, or enjoy time outdoors, plus a storage shed for added convenience. A cute home with a backyard you will love!

34 Lenox Street, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$275,000

3 Beds ⋅ 2 Baths ⋅ 7151416 MLS

A rare opportunity in one of the most sought-after neighborhoods. This well-loved home offered for the first time in nearly 50 years on a beautifully landscaped property that reflects decades of care and pride. Enjoy true main-floor living with a comfortable, functional layout suited for everyday ease. The backyard is a standout space, offering privacy, mature landscaping, and plenty of room to relax or entertain. The deck and patio feature ambient lighting, creating a warm, inviting atmosphere for evening gatherings. The home is also equipped with gutter guards for low maintenance exterior care and a fuII-house generator, providing peace of mind and uninterrupted comfort year-round. Nestled in a quiet, established neighborhood known for its charm and community feel, this property combines timeless appeal with practical upgrades. Homes like this rarely come to market so don't miss your chance to make it yours.

Winona

Listing courtesy of Edina Realty, Inc..

$179,900

3 Beds ⋅ 1 Baths ⋅ 7151085 MLS

Welcome home to this charming 3-bedroom, 1-bath home in Winona offering a great character, updates, and everyday convenience! Numerous improvements have already been completed, including a new roof in 2020, central air installed in 2021, and many newer windows. Inside, would appreciate the beautiful hardwood floors, french doors, spacious kitchen, and convenient main-floor bedroom and laundry. The functional layout offers comfortable living spaces with plenty of character throughout. Step outside to enjoy the fenced-in backyard, perfect for relaxing, entertaining, gardening, or pets. With many updates already completed, this home is ready for its new own. Schedule your showing today!

562 W 4th Street, Winona

Listing courtesy of RE/MAX Advantage Plus.

$265,000

3 Beds ⋅ 2 Baths ⋅ 7150898 MLS

Magical views of the main channel of the Mississippi River! Take in the beautiful sunrise every morning from inside your home or while relaxing on the front deck. Lovely ranch home with 3 bedrooms, 2 bathrooms and a 2 car garage. Large kitchen with an abundance of cabinet space that opens up to the spacious dining room. Living room with large picture window lets you enjoy the view of the river from inside. Cozy sun room off the back of the house leads to the back yard. Newer roof, siding and bathroom. Some windows have been replaced. Main floor laundry is a plus!

780 River Street, Dakota

Listing courtesy of Gerrard-Hoeschler.

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