Winona County Homes under $250,000

Welcome to Winona County, Minnesota, a picturesque gem nestled along the banks of the majestic Mississippi River. Known for its vibrant history, stunning natural landscapes, and a tight-knit community, Winona offers a unique blend of small-town charm and modern conveniences. With its rich cultural heritage, you’ll find a variety of local festivals, art galleries, and historical sites that celebrate the area’s past while embracing the future.

For those looking to make Winona County their home, you’ll be delighted to discover a range of affordable housing options under $250,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, there’s something for everyone. From cozy single-family homes with spacious yards to charming townhouses with modern amenities, the real estate market here is diverse and inviting.

Imagine sipping your morning coffee on a sunlit porch or hosting gatherings in a backyard surrounded by the natural beauty that Winona is known for. With excellent schools, ample parks, and recreational activities, this county is perfect for families and outdoor enthusiasts alike.

Winona County’s real estate market offers not just homes, but a lifestyle enriched with community spirit and outdoor adventures. With homes priced under $250,000, now is the perfect time to explore the possibilities and find your dream home in this enchanting part of Minnesota. Come and experience the warmth and beauty of Winona County—your new home awaits!

Newest Winona County Homes under $250,000

$230,000

ACTIVE Status ⋅ 4 Beds ⋅ 2 Baths ⋅ 7155269 MLS ⋅ 1,614 SqFt.

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..

$179,900

ACTIVE Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 7154183 MLS ⋅ 1,028 SqFt.

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.

$219,900

ACTIVE Status ⋅ 5 Beds ⋅ 2 Baths ⋅ 7153362 MLS ⋅ 1,477 SqFt.

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

ACTIVE Status ⋅ 1 Beds ⋅ 1 Baths ⋅ 7152392 MLS ⋅ 646 SqFt.

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.

$179,900

ACTIVE Status ⋅ 3 Beds ⋅ 1 Baths ⋅ 7151085 MLS ⋅ 1,855 SqFt.

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

ACTIVE Status ⋅ 5 Beds ⋅ 2 Baths ⋅ 7150338 MLS ⋅ 1,900 SqFt.

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.

$235,000

ACTIVE Status ⋅ 4 Beds ⋅ 2 Baths ⋅ 7144777 MLS ⋅ 2,808 SqFt.

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.

$189,000

ACTIVE Status ⋅ 2 Beds ⋅ 1 Baths ⋅ 7144015 MLS ⋅ 1,020 SqFt.

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.

$209,999

ACTIVE Status ⋅ 5 Beds ⋅ 2 Baths ⋅ 7143190 MLS ⋅ 1,400 SqFt.

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.

$139,000

ACTIVE Status ⋅ 3 Beds ⋅ 1 Baths ⋅ 7134077 MLS ⋅ 980 SqFt.

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..

$230,000

ACTIVE Status ⋅ 8 Beds ⋅ 2 Baths ⋅ 7134006 MLS ⋅ 2,300 SqFt.

Great opportunity to own a well-located duplex in Winona featuring two units, each with 4 bedrooms and 1 bathroom. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this property offers excellent flexibility. The two-unit setup offers the potential for strong rental income while giving an owner-occupant the opportunity to offset their housing costs. Conveniently located near downtown Winona and just blocks from WSU, this property is an attractive option for both investors and owner-occupants

159 E King Street, Winona

Listing courtesy of Keller Williams Premier Realty.

$225,000

ACTIVE Status ⋅ 4 Beds ⋅ 2 Baths ⋅ 7130625 MLS ⋅ 1,200 SqFt.

First time on the market and truly one of a kind! This fun and whimsical property offers amazing views, beautiful established perennials and features you simply don't find every day. The main home has 3 bedrooms, a full bathroom, laundry tucked into a butler's pantry and 2 rooms with incredible views. The basement offers tons of storage. Outside, enjoy one of the most unique screened porches you will ever see, plus what is believed to be Winona Trolley #9, ready to become a garden shed or she shed. The lower level home includes a separate 1 bedroom living space with a kitchen, bathroom and laundry, perfect for guests, extended living or a mother in law suite. It could also offer potential for conversion to a garage. A truly special property!

149 E Lake Boulevard, Winona

Listing courtesy of Keller Williams Premier Realty.

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.