Winona Real Estate

Welcome to Winona, a charming city located in Winona County, Minnesota. Nestled in the picturesque Mississippi River Valley, Winona offers a unique blend of natural beauty, rich history, and vibrant community spirit.

Known as the "Island City," Winona is surrounded by the mighty Mississippi River on three sides, providing breathtaking views and a variety of recreational opportunities. Outdoor enthusiasts can explore the numerous hiking and biking trails, go fishing or boating on the river, or simply enjoy a picnic in one of the many parks.

Winona is also a city with a rich cultural heritage. It is home to the renowned Winona State University, which brings a youthful energy to the community. The city boasts a vibrant arts scene, with galleries, theaters, and music venues showcasing local talent. Don't miss the annual Great River Shakespeare Festival, a summer-long celebration of Shakespearean plays.

For history buffs, Winona offers a glimpse into its past through its well-preserved architecture and historic sites. The Winona County History Center provides a fascinating look into the region's history, while the Polish Cultural Institute and Museum celebrates the city's Polish heritage.

In addition to its natural beauty and cultural attractions, Winona boasts a thriving downtown area with a variety of shops, restaurants, and entertainment options. From boutique shopping to farm-to-table dining, there is something for everyone.

Whether you're looking to settle down, start a business, or just visit, Winona offers a warm and welcoming community with a small-town feel and big-city amenities. Come and experience the charm of Winona for yourself!

Newest Listings in Winona

$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.

$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.

$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..

$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..

$550,000

3 Beds ⋅ 3 Baths ⋅ 7139367 MLS

Very hard to find spacious 2,900 square foot 3-bedroom, 3 bath townhouse in a very private setting with wildlife abounding on all three sides! This property includes his and her offices/dens, 2 living rooms, main floor laundry, newer kitchen, custom stained glass, whole house surround sound plus a 4-car garage and a full basement just waiting for development.

68 Whispering Avenue, Winona

Listing courtesy of Edina Realty, Inc..

$329,900

3 Beds ⋅ 3 Baths ⋅ 7138119 MLS

This clean, well-maintained, move in ready home is a 3-bedroom, 2.5 bath and offers plenty of space and natural light. The large windows brighten the home, while the spacious primary bedroom provides a comfortable retreat. The lower level features a family room, storage room, and additional space to enjoy. A 2-car attached garage adds convenience, and the wooded backyard offers a peaceful setting.

1026 Glen Echo Road, Winona

Listing courtesy of RE/MAX Results.

$439,000

4 Beds ⋅ 3 Baths ⋅ 7136924 MLS

Prepare to be surprised by everything this spacious home has to offer! Step inside and you’ll find a warm, inviting interior featuring beautiful bamboo flooring and a fantastic kitchen with stainless steel appliances, solid-surface countertops and plenty of space for cooking and gathering. The sun-filled four-season room, cozy gas fireplace and inviting living spaces make this home wonderful for both everyday living and entertaining. Generously sized bedrooms include a primary suite with a private half bath, while the lower level offers incredible flexibility with a large family room, kitchenette, additional bedroom and ¾ bath—ideal for guests, extended family or multigenerational living, with potential for rental use, subject to City rental certification. Additional highlights include a newer roof, yard sprinkler system, an impressive four-car garage and an additional carport providing exceptional parking and storage. Conveniently located near downtown Winona, this exceptionally well-maintained home offers far more than meets the eye—space, versatility and thoughtful features you truly need to see in person to appreciate.

65 E Broadway Street, Winona

Listing courtesy of Edina Realty, Inc..

$339,900

4 Beds ⋅ 2 Baths ⋅ 7135485 MLS

Whether you want to have your business right at home or need plenty of storage space, this is the one, just minutes from Winona. This home is booming with character and waiting for you to add your touches. With four generous bedrooms, two bathrooms, an updated kitchen with new appliances, large dining & living rooms, attached one car garage, a partially finished basement for additional living space, you have plenty of room for the whole family. The vast backyard has an oasis with a large deck, established garden, plenty of green space and a creek providing stunning views and trout fishing. Additional storage is available in the climate controlled detached garage as well as the large shop that is already setup for a taxidermy business but could easily be used for another business or storage. A parking area next to the shop is perfect for additional off-street parking for additional vehicles or customers. Come see the endless possibilities and opportunities this home offers before it's too late!

8270 E Main Street, Winona

Listing courtesy of RE/MAX Advantage Plus.

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