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

$169,900

3 Beds ⋅ 1 Baths ⋅ 7120056 MLS

763 W Mark Street, Winona Is A Sleeping Beauty! You will LOVE the 3 Main Floor Bedrooms, Spacious Kitchen with Tiled Floors, Replaced Cabinetry & Countertops & Stainless Steel Appliances, Newly Stained & Painted Front Porch & Expansive Back Deck. The Backyard is Fully Fenced, offering privacy & safety for families, children & pets, plus open parking for 2+ vehicles! The Roof, Thermo Windows, Stainless Steel Appliances, Water Heater & Forced Air Furnace are all in good condition! The Main Floor also includes a separate Laundry Room with Washer & Dryer included in the sale. Special Bonus - The Fully Finished Upstairs offers 2 rooms which are perfect for many purposes: an office, hobby room, exercise room, den, storage, media/gaming, additional sleeping & storage galore! All exterior staining & painting will be completed the week of August 3rd, 2026. This property is Rental Certified. Come & Look Now!

763 W Mark Street, Winona

Listing courtesy of Jewson Realty.

$315,000

3 Beds ⋅ 2 Baths ⋅ 7120123 MLS

Immaculately maintained and nicely updated 3-4 Bedroom, 2 Bath Rambler in convenient West side location. Close to shopping, schools and restaurants! The 2-car attached garage features a newer 10'x20' workshop addition on the back. You are sure to enjoy the tranquil backyard green space, the manicured landscaping, and the new paver patio. The main level boasts 3 bedrooms, newer LVP flooring, and an updated kitchen with Stainless Steel appliances. The lower level is partially finished and has so many possibilities. You'll be sure to enjoy movie night in the massive family room. The bonus/game room can be turned into a 4th bedroom, and there is so much storage space. Updates include: the kitchen, SS appliances, windows, flooring, roof, vinyl siding, gutters, driveway, water heater, and radon mitigation system. This gem is ready for you to move right in and enjoy. Schedule your appt. before it's gone!

334 Oak Street, Winona

Listing courtesy of Real Broker, LLC..

$99,000

7118928 MLS

Imagine building your dream home where every day begins with breathtaking views of the Mississippi River and the stunning beauty of the Driftless Area. This incredible homesite offers the perfect opportunity to create a home that is uniquely yours while enjoying one of nature's most spectacular backdrops. Watch the seasons transform the landscape from your own backyard as bald eagles soar overhead, barges make their way up and down the river, and elegant cruise ships pass through the valley. Whether you're enjoying your morning coffee at sunrise or unwinding in the evening, the views are simply unforgettable. Don't miss this rare opportunity to own a piece of the Driftless Region and build the home you've always imagined. Contact the listing agent today for complete details and available information. **Please do not walk the property without your real estate agent. All showings must be accompanied by a licensed real estate agent.**

25579 Leeward Road, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$265,000

2 Beds ⋅ 2 Baths ⋅ 7119443 MLS

Affordable Opportunity in a Great Winona Neighborhood! Here’s your chance to own an affordable home in a desirable Winona neighborhood! This 2-bedroom, 2-bath home offers comfortable living today with the potential to easily create additional bedrooms as your needs change. Many important updates have already been completed over the years, including the kitchen, windows, roof, water heater, and driveway extension. Hardwood floors add character to the main level, while the finished lower-level family room provides extra space for entertaining, hobbies, or relaxing. Step outside to enjoy the fenced backyard with a deck—perfect for grilling, pets, or spending time outdoors. With its great location, functional layout, and room to make it your own, this home is an excellent opportunity for first-time buyers, downsizers, or anyone looking for an affordable place to call home.

1661 W 6th Street, Winona

Listing courtesy of Edina Realty, Inc..

$185,000

2 Beds ⋅ 2 Baths ⋅ 7118804 MLS

Welcome home to this well-maintained 2 bedroom, 2 bathroom ranch offering the convenience of one-level living with additional finished space in the basement! Whether you're looking for your first home, downsizing, or simply want a move-in ready property, this home checks all the boxes. Inside, you'll find beautiful hardwood floors in both bedrooms, an eat-in kitchen with appliances included, and a functional layout designed for comfortable everyday living. The finished lower level provides extra living space that could be used as a family room, hobby area, home office, or guest space. Outside, enjoy a spacious yard and a heated 2-car detached garage, giving you plenty of room for vehicles, storage, or projects year-round. The convenient Winona location puts you close to parks, schools, shopping, and everything the city has to offer. Don't miss your opportunity to make this charming home your own!

156 E Mark Street, Winona

Listing courtesy of Real Broker, LLC..

$539,900

6 Beds ⋅ 3 Baths ⋅ 7116367 MLS

Must see this stunning 6 bed 3 bath home located in one of the most desirable areas of Winona, ample space for entertaining and enjoying, some features include hardwood floors, large en suite, newer appliances, nice 3 car garage with basement access, fireplace, large kitchen, solid stone counters, great backyard, and more. Call today!

1850 Garvin Heights Road, Winona

Listing courtesy of Coffee House Real Estate LLC.

$495,000

5 Beds ⋅ 4 Baths ⋅ 7113201 MLS

Welcome to this spacious and beautifully updated 5-bedroom, 4-bathroom home offering over 4,000 square feet of thoughtfully designed living space on a desirable quarter-acre lot in WE Valley. Perfect for both everyday living and entertaining, this impressive home features two extra-large family rooms in addition to a formal living room, providing plenty of space for gatherings, relaxation, or recreation. Enjoy the convenience of two dining areas, three cozy gas fireplaces, and two laundry rooms. The expansive lower level boasts a large bar area with ample room for a pool table, game room, or additional dining space, making it an ideal entertainment hub. An oversized garage offers generous storage and parking, while the freshly painted interior and numerous recent updates give the home a fresh, move-in-ready feel. With its exceptional space, versatile layout, and desirable location, this WE Valley home is ready to welcome its next owners.

1555 48th Avenue, Winona

Listing courtesy of Edina Realty, Inc..

$409,000

4 Beds ⋅ 3 Baths ⋅ 7112622 MLS

Beautifully remodeled home located at the end of a quiet cul-de-sac. This property offers a country-like setting but is located just 10 minutes from downtown Winona. Outdoor enthusiasts will appreciate being close to a Holzinger Lodge trailhead, providing easy access to hiking, biking, walking, and all the natural beauty that makes Winona’s bluff country so special. This spacious home features four bedrooms and three bathrooms, including a primary suite on the main level. The open-concept floor plan centers around a large kitchen with pecan cabinetry, stainless steel appliances, brand new quartz countertops and backsplash and plenty of space for gathering and entertaining. Step out onto the composite deck and enjoy the privacy of a wooded backyard setting with view of the city during the winter months. The main level showcases refinished original hardwood floors and a striking two-sided Winona Stone fireplace that serves as a focal point between the living room and den/dining area. The newly remodeled walkout lower level offers two additional bedrooms, full bathroom, laundry room, and a spacious second family room featuring a TV area, fireplace, and walkout to patio. Extensive updates throughout the home provide both comfort and peace of mind, including Andersen windows, updated plumbing and electrical service with a 200-amp panel, newer roof and siding and fresh paint throughout. A large 8’ x 20’ storage shed with a concrete floor provides ample room for tools, equipment, and seasonal storage. This move-in-ready property combines exceptional updates, scenic views, outdoor recreation, and a highly desirable location into one remarkable home.

1260 Wincrest Drive, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$230,000

2 Beds ⋅ 3 Baths ⋅ 7111909 MLS

Welcome home to this spacious and inviting 2-bedroom, 3-bath residence conveniently located in the heart of Winona! With exceptionally large bedrooms, each featuring its own private bathroom, this home offers comfort, privacy, and a layout that's perfect for a variety of lifestyles. The oversized living room provides an ideal gathering space, while the generous dining room is ready for everything from holiday celebrations to everyday meals. The kitchen is designed with functionality in mind, offering abundant storage and enough space for a large family-sized table. You'll appreciate the convenience of laundry on both the main floor and in the basement, making daily chores easier no matter where you spend your time. Outside, the beautifully landscaped front yard comes alive with wildflowers and new tree seedlings planted in 2025 creating colorful curb appeal. The large, fenced backyard is perfect for entertaining, pets, or play, complete with a spacious deck and a garage-sized storage shed with plenty of room for lawn equipment, bikes, outdoor gear, and all your favorite toys. The property also offers 2-3 off-street parking spaces. Recent updates include Newer furnace (2020), New water heater (2024), New flooring in the primary bedroom (2026).

214 E Howard Street, Winona

Listing courtesy of Edina Realty, Inc..

$829,900

5 Beds ⋅ 5 Baths ⋅ 7110230 MLS

Backing up to a wooded city park and nearby Sugarloaf, this unique home sits on 2 1/2 acres of lush and verdant gardens. This oasis overlooks Lake Winona and beyond it much of Winona proper and the river. The pool house is made from the original stables on the property, and the hillside is dotted with trails to the gazebo, pickleball court and various seating areas. A koi pond and waterfall feature sit just beyond the kitchen and mere steps out the door is a wonderful patio and screen porch to enjoy whatever kind of day the weather brings. This home is expansive and in addition to the 5 bedrooms and 5 bathrooms includes design features you won't find elsewhere. A distinctive turret, a beautifully painted room with vaulted chapel-like ceilings and natural woodwork throughout are just some of the notable features. Outside a spacious detached garage has three individual stalls as well as unfinished updoor space that would make a great workshop, office space, or storage. Many new updates in this home, but some notable ones include: Custom blinds (2023), new boiler (2019), new water heater (2025), Tiled floor in family room (2025). The open kitchen is perfect for entertaining and features custom maple cabinets with exquisite detailing, a down-venting stove, double ovens, a walk-in pantry and a commercial sized fridge. The outdoor areas are not-to-be-missed too; outdoor speakers, expansive gardens, landscape lighting and more make this yard a show-stopper. The pool has many updates including a new liner and pump (2023), new filtration system (2024), new heater and light (2025) and new skimmer (2026).

53 W Lake Boulevard, Winona

Listing courtesy of Creek Realty.

$639,900

4 Beds ⋅ 4 Baths ⋅ 7111839 MLS

Hidden at the end of a quiet cul-de-sac, this remarkable cedar home offers the best of both worlds: a peaceful, wooded setting on 1.5 acres with the convenience of being just minutes from everything Winona has to offer. With over 4,700 finished square feet, there's room for everyone to spread out without ever feeling connected. Sunlight pours through walls of windows, highlighting the beautiful hardwood floors and stunning natural woodwork that make this home feel warm, inviting, and truly one of a kind. The main level was designed with gathering in mind. Whether you're hosting Thanksgiving dinner, cheering on your favorite team, or enjoying a quiet evening by the fire, you'll appreciate the spacious living areas connected by a gorgeous double-sided wood-burning fireplace. The kitchen offers everything a home chef could want, including a large center island, wall oven, cooktop, wine cooler, extensive cabinetry, and plenty of prep space. Choose between casual meals in the breakfast area or hosting friends and family in the formal dining room. Upstairs, you'll find four spacious bedrooms, including a private primary suite where you can wake up to peaceful views of nature. The ensuite features a jetted soaking tub, separate walk-in shower, and the perfect place to relax after a long day. Need even more room? The finished lower level offers endless possibilities with expansive recreation space, an additional sitting area, a ¾ bathroom, and generous storage. Whether you envision a game room, home gym, movie room, or guest retreat, the space is ready to fit your lifestyle. The pool table is negotiable with the sale. Step outside and you'll quickly understand what makes this property so special. The current owners have thoughtfully designed the landscape to showcase a variety of native Minnesota wildflowers, creating a yard that's as beautiful as it is intentional. From cheerful Black-eyed Susans to fragrant lavender hyssop and native peppermint, the gardens come alive in waves of color throughout the growing season while naturally attracting pollinators and helping create a more enjoyable outdoor space. Relax in the included hot tub, entertain on the deck or patio, or simply take in the peaceful views of mature trees and rolling green space. Every season brings something new to enjoy, and every window offers a view worth appreciating. Additional highlights include main floor laundry, zoned heating and cooling with two furnaces and two central air units, an oversized three-stall garage with more than 1,000 square feet of space, and a large turnaround driveway for guests. Homes like this rarely become available. If you've been searching for space, privacy, incredible craftsmanship, and a setting that feels like a retreat without sacrificing convenience, this home deserves a spot at the top of your list.

104 Forest Oak Court, Winona

Listing courtesy of Real Broker, LLC..

$264,900

5 Beds ⋅ 2 Baths ⋅ 7111039 MLS

Welcome to this well-maintained two-story duplex offering an excellent opportunity for both owner-occupants and investors. Featuring one upper unit and one lower unit, each residence has its own private laundry, creating convenience and eliminating shared common spaces. This property has seen numerous recent updates, including newer appliances, brand-new ovens in both units, a new laundry unit, fresh paint in the lower unit, and new siding and shutters completed in Fall 2025. Bright, sun-filled living spaces create a warm and inviting atmosphere in both units. Situated on a desirable corner lot in a great neighborhood, the property offers a large off-street parking area with plenty of room to add a spacious garage, if desired. An exterior storage shed provides additional storage for tenants or owners. With a proven rental history generating $2,400 per month, this duplex presents a fantastic investment opportunity while also serving as an ideal owner-occupied property with rental income to help offset your mortgage. Don't miss your chance to own this move-in-ready, income-producing property in a great location!

803 W 5th Street, Winona

Listing courtesy of Castle Realty, LLC.

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