Winona County Homes under $750,000

Welcome to Winona County, Minnesota—a hidden gem nestled along the banks of the majestic Mississippi River. Known for its stunning bluffs, vibrant history, and a strong sense of community, Winona is the perfect blend of small-town charm and modern convenience. With a rich cultural scene, including art galleries, theaters, and the renowned Great River Shakespeare Festival, there’s always something to engage your senses and spark your creativity.

For those looking to call this enchanting area home, Winona County offers a variety of homes under $750,000, making it an attractive option for families, retirees, and first-time buyers alike. From cozy single-family homes in friendly neighborhoods to charming historic properties that reflect the county's rich heritage, you’ll find a diverse selection of residences that cater to all lifestyles and budgets.

Imagine waking up to the breathtaking views of the bluffs, enjoying leisurely strolls along the riverfront, or exploring the scenic trails that wind through lush parks. Winona County not only provides an idyllic backdrop for everyday life but also boasts excellent schools, healthcare facilities, and a thriving local economy.

Whether you’re seeking a peaceful retreat or an active lifestyle filled with outdoor adventures, Winona County has it all. With homes available under $750,000, your dream of living in this beautiful area is within reach. Come discover what makes Winona County a wonderful place to live, work, and play—your perfect home awaits!

Newest Winona County Homes under $750,000

$315,000

3 Beds ⋅ 2 Baths ⋅ 7157876 MLS

Welcome to 114 E. Wilmar Street in Rollingstone! Tucked away in a quiet neighborhood, this inviting 3-bedroom, 2-bath split-level home offers a wonderful combination of comfort, space, and functionality. Enjoy the convenience of main-floor laundry and a beautiful three-season porch, perfect for relaxing and enjoying the outdoors. The spacious lower-level family room features a cozy gas fireplace, creating an ideal space for entertaining or unwinding, along with additional room for a potential fourth bedroom. Recent updates include a new furnace in 2025. Step outside to enjoy the deck and spacious oversized two-car garage, offering plenty of room for vehicles and storage. A fantastic opportunity to enjoy small-town living in a peaceful neighborhood!

114 E Wilmar Street, Rollingstone

Listing courtesy of Edina Realty, Inc..

$469,900

3 Beds ⋅ 2 Baths ⋅ 7157491 MLS

Beautiful log home complemented by a durable metal roof nestled on 4 scenic acres in a picturesque location. This charming three-bedroom, 2 bath home features a spacious kitchen and inviting living room, with the primary bedroom conveniently located on the main level and offering a walk-in closet. The lower level provides a spacious family room along with two additional bedrooms, offering plenty of room for family and guests. Enjoy the convenience of a two-car attached garage, plus a separate 12’ x 18’ shed for additional storage. Surrounded by nature and offering privacy and beautiful views, this property provides the perfect combination of rustic charm, comfort, and acreage. Professional photos will be added 10/15/26.

22544 Windy Point Road, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$499,900

3 Beds ⋅ 2 Baths ⋅ 7158017 MLS

Country living at its best on 12 acres across from Cedar Valley Golf Course! This 3-bedroom, 2-bath ranch home features fresh paint, new carpeting, and a beautiful sunroom overlooking the valley. Gather around the gas fireplace and enjoy a space that’s wired for surround sound. The partially finished basement offers a blank canvas for whatever you envision next. A two-car attached garage plus a two-car detached garage with a storage loft provide plenty of room for vehicles, hobbies, and all your gear. Enjoy the space and views of country living, just 15 minutes from Winona.

25434 County Road 9, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$498,800

2 Beds ⋅ 3 Baths ⋅ 7157901 MLS

Welcome to desirable Knopp Valley, a 55+ community! This stunning 2025-built home features high-end finishes, exceptional craftsmanship, and thoughtful design throughout. Located within walking distance of Saint Mary’s University, where you can enjoy convenient access to sporting events, musical performances, lectures, and a variety of cultural and educational activities. This fantastic neighborhood also offers walking and biking trails, convenient access through the underground tunnel, pickleball and tennis courts, green space, and a playground just steps away. Step inside to discover a beautiful open-concept design with in-floor heat in both the home and garage. Designed for comfortable one-level living, the home features extra-wide hallways and doorways for added accessibility. The gorgeous primary suite includes a beautifully finished bath with a custom ceramic tile shower featuring dual showerheads, including a rainfall showerhead. The main level also offers convenient laundry and a dedicated office. Upstairs, the spacious loft features a family room, additional bedroom, and full bath, making it ideal for guests or extended family. Plans are already in place for a potential third bedroom and additional storage. A whole-house reverse osmosis system and low-maintenance construction add to the home's appeal. Outside, enjoy a privacy-fenced yard, professional landscaping, a sprinkler system, and an oversized, heated two-car garage. Move right in and enjoy the exceptional quality, comfort, and convenience this beautiful home has to offer! An added bonus—this home can also be purchased completely furnished, offering a truly turnkey opportunity!

54 Brickyard Lane, 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..

$265,000

3 Beds ⋅ 2 Baths ⋅ 7154657 MLS

Enjoy the space, privacy, and convenience of this 3-bedroom, 2-bath ranch in Dakota! Set on a .311-acre partially fenced lot backing to woods, this home offers a peaceful setting with easy interstate access to both La Crosse and Winona. The main level features convenient laundry, comfortable living spaces, and access to a deck overlooking the spacious backyard. The finished lower level adds valuable living and entertaining space, giving you room to spread out. A 2-car garage features an overhead pass-through door to the backyard—perfect for lawn equipment, toys, or projects. Even better, a new well and septic system are currently being installed, offering added peace of mind for the next owner. Country-like surroundings with commuter convenience!

460 Center Street, Dakota

Listing courtesy of @properties La Crosse.

$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..

$420,000

8 Beds ⋅ 3 Baths ⋅ 7153429 MLS

Prime Investment Opportunity! This charming two story triplex, offers a fantastic location just two blocks from Winona State University. The property combines historic character with numerous recent improvements, including a new roof, new siding in 2025, fresh interior paint, new carpeting, new plumbing, and a newly repaired deck. With 12 parking spaces, this property provides exceptional convenience for tenants and guests. Located close downtown, shopping, restaurants, walking and biking trails and beautiful lakes, location offers strong appeal for variety of prospective tenants. Whether you are looking to add to your portfolio or own a property in a highly convenient location, this triplex offers plenty of potential. Don't miss this opportunity to own a well-located property with significant updates and excellent access to the best of Winona.

376 W Sanborn Street, Winona

Listing courtesy of eXp Realty.

$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.

$515,000

3 Beds ⋅ 3 Baths ⋅ 7152701 MLS

Step inside to a bright, inviting floor plan engineered for effortless day-to-day living and entertaining. The main level boasts an open-concept kitchen that connects seamlessly to the primary living spaces, ensuring nobody is left out of the conversation. The finished square footage extends down into a versatile lower level, providing flexible bonus spaces that can easily adapt to a variety of needs—whether you require a home office, a fitness area, or a secondary media room

17 Richland Avenue, Saint Charles

Listing courtesy of Keller Williams Premier Realty.

$635,000

4 Beds ⋅ 3 Baths ⋅ 7152307 MLS

Welcome to this exceptional 4-bedroom, 3-bath home built in 2023 and located in the desirable Valley Oaks neighborhood! Offering over 3,300 finished square feet, this beautifully designed home combines modern style, spacious living and the convenience of main-level living. The impressive great room features a vaulted ceiling and modern gas fireplace and flows seamlessly into the dining area and gorgeous kitchen with quartz countertops, a large center island, upgraded cabinetry, black stainless steel appliances and a fantastic walk-in pantry. The main level features three bedrooms, including a beautiful primary suite with a tray ceiling, generous walk-in closet and spa-inspired bath with double vanities and a luxurious walk-in shower. Laundry and all essential living facilities are conveniently located on the main level. The finished lower level provides even more room to spread out with a spacious family room, fourth bedroom, full bath and dedicated office space, plus additional unfinished space for storage. Enjoy the heated screened-in deck, perfect for relaxing or entertaining throughout much of the year, along with an attached 3-car garage. With modern finishes throughout and no updating needed, this home is truly move-in ready. Best of all, the HOA takes care of lawn maintenance and snow removal, giving you more time to simply enjoy your home!

357 Valley Oaks Drive, 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.

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.