Winona Homes under $400,000

Welcome to Winona, Minnesota—a charming city nestled along the banks of the Mississippi River, known for its stunning natural beauty and vibrant community spirit. With a rich history that dates back to the 19th century, Winona is not just a place to live; it’s a place to thrive. The city boasts a unique blend of cultural attractions, outdoor adventures, and a welcoming atmosphere that makes it an ideal spot for families, young professionals, and retirees alike.

One of the most appealing aspects of Winona is its diverse housing market, particularly for those seeking homes under $400,000. Here, you’ll find a variety of options, from charming historic homes with character to modern constructions designed for today’s lifestyle. This affordability allows residents to enjoy the benefits of homeownership without breaking the bank.

Winona is also known for its excellent schools, parks, and recreational opportunities. Whether you’re hiking the scenic bluffs, exploring the historic downtown filled with boutique shops and local eateries, or enjoying a riverfront festival, there’s always something to do. The community is tight-knit, making it easy to connect with neighbors and build lasting friendships.

With its picturesque landscapes and a strong sense of community, Winona is more than just a place to live; it’s a place to call home. Explore the real estate opportunities available in this delightful city, and discover how you can make Winona your own without exceeding your budget. Your dream home is waiting!

Newest Winona Homes under $400,000

$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

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.

$237,000

5 Beds ⋅ 2 Baths ⋅ 7150338 MLS

Rare opportunity to own a 5 bedroom, 2 bathroom rental certified home located directly across from Winona State University! Same owner since 1995 and now on the market for the first time in over 30 years. Wood floors are found throughout the home, with some currently covered by carpet. Basement offers laundry and additional space. Carport in back plus additional off street parking. Furnace replaced in 2023. Great location for a student rental or investment property with a long history as a rental.

468 Main Street, Winona

Listing courtesy of Keller Williams Premier Realty.

$323,900

4 Beds ⋅ 2 Baths ⋅ 7150138 MLS

Spacious 4 bed, 2 bath rambler with large rooms throughout, ideal as an in-law scenario with upstairs independent from the downstairs. Let your imagination run with the possibilities that this property has to offer! Gorgeous hardwood floors, marble finishes throughout, beautiful wood finishes and walls. New vinyl siding, 3-year-old metal roof, quiet residential location - this one is ready to move in!

1215 W Mark Street, Winona

Listing courtesy of Edina Realty, Inc..

$235,000

4 Beds ⋅ 2 Baths ⋅ 7144777 MLS

3 Bedroom/2 bathroom located in the heart of Winona next too Jefferson Elementary School. Large 2.5 car garage, mostly fenced yard. Updates to kitchen/bathrooms, electrical and plumbing; finished basement. Large deck off of the kitchen and charming front porch! This is a great home for the price! Seller can accommodate a quick closing!

1223 W 5th Street, Winona

Listing courtesy of Century 21 Affiliated.

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.