Winona Homes under $250,000

Welcome to Winona, Minnesota – a picturesque city nestled along the banks of the Mississippi River, known for its stunning bluffs, vibrant arts scene, and rich history. With a population of around 27,000 residents, Winona offers a charming small-town atmosphere while providing all the amenities of a larger city. The area is renowned for its scenic beauty, featuring lush parks, hiking trails, and the breathtaking views from Garvin Heights.

Winona is home to several educational institutions, including Winona State University, which contributes to the city's youthful energy and cultural vibrancy. The downtown area is alive with local shops, restaurants, and galleries, making it a delightful place to explore. The city also hosts numerous festivals and events throughout the year, fostering a strong sense of community among its residents.

For those looking to make Winona their home, there’s great news! The real estate market offers an array of charming homes priced under $250,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find a variety of options to suit your needs. From cozy bungalows to spacious single-family homes, these properties provide an excellent opportunity to invest in a welcoming community without breaking the bank.

Winona’s affordable housing market, combined with its stunning natural surroundings and vibrant culture, makes it an ideal place to call home. Discover the charm of Winona, where your dream home awaits!

Newest Winona Homes under $250,000

$199,900

2 Beds ⋅ 1 Baths ⋅ 7160820 MLS

Welcome to 1414F McNally Drive, an end-unit 2-bedroom, 1-bath home with everything on one level. The cedar siding was freshly restained in September 2026, so the exterior is ready to go. As an end unit, you get open views on one side instead of neighbors. Inside, new and updated windows brighten the kitchen, dining, and living areas. Electric baseboard heat is the primary heat source, and two newly added mini-split units give you flexible heating and efficient cooling when you want them, so you’re comfortable in every season. The monthly fee covers snow removal, lawn care, and access to the community pool. That means no shoveling, no mowing, and a place to cool off in July. It’s a good fit for first-time buyers, downsizers, or anyone who wants a simpler routine. Schedule your showing today.

1414F Mcnally Drive, Winona

Listing courtesy of Keller Williams Premier Realty.

$240,000

4 Beds ⋅ 3 Baths ⋅ 7160119 MLS

Welcome home to this spacious 4-bedroom, 3-bathroom property offering plenty of room to live, relax, and entertain! Enjoy the added versatility of a finished basement featuring a bonus family room, perfect for movie nights, gatherings, or extra living space. The oversized, finished 1,000-square-foot, 3-car garage provides exceptional room for vehicles, storage, hobbies, and more. A newer roof, offering added peace of mind. With generous living space, valuable updates, and an impressive garage, this home is ready to meet a variety of needs and lifestyles! This home is also rental certified for up to a family of 9.

1101 E Wabasha Street, Winona

Listing courtesy of Edina Realty, Inc..

$240,000

4 Beds ⋅ 2 Baths ⋅ 7159794 MLS

Welcome to this charming 4-bedroom, 2-bath home filled with character, warmth, and an exceptional amount of updates throughout! Beautiful wood floors, vaulted ceilings, and exposed wood beams create a wonderful blend of charm and architectural appeal. The inviting living room features a cozy wood-burning stove, while the updated kitchen and bathrooms offer modern conveniences. The practical and functional floor plan includes two bedrooms on the main level and two additional bedrooms upstairs, providing flexibility for a variety of living arrangements. Enjoy relaxing on the welcoming front porch or the wonderful wraparound back porch overlooking the fenced backyard. The extensive improvements to this home are truly impressive, including drywall throughout, replacement windows, updated siding and insulation, electrical and lighting updates, refinished wood floors, updated kitchen and bathrooms, a dual-zone gas forced-air heating system, new water service to the street, and so much more! Conveniently located directly across from Cotter High School, this home offers an incredible combination of timeless character, thoughtful improvements, and everyday functionality. So much has already been done for you in this charming home! Not used as a rental but home is rental certified.

1120 W Broadway Street, Winona

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..

$209,900

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.

$174,500

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.

$229,900

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.

$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.

$209,999

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.

$139,000

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..

$230,000

8 Beds ⋅ 2 Baths ⋅ 7134006 MLS

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.

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Winona Homes under $250,000

Newest Winona Homes under $250,000

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