Refine Search
Sort by
421 E Sanborn Street, Winona
$265,000
4 Beds ⋅ 3 Baths ⋅ 7153676 MLS
Turn-key and truly hard to match in Winona, this duplex delivers the kind of condition and rental history investors dream about. The main unit offers 3 bedrooms and 2 bathrooms across the first floor and finished basement, giving tenants plenty of space and a comfortable layout. The upper unit features 1 bedroom and 1 bathroom, perfect for steady, reliable rental income. The exterior has been updated with vinyl siding just two years ago, providing great curb appeal and low-maintenance durability. Outside, you’ll find a partially fenced backyard that’s surprisingly spacious—ideal for tenants who value outdoor living. A detached 1-car garage adds even more value, whether used for storage or rented out for additional income. With its strong rental history, modern exterior, and appealing outdoor space, it will be tough to find another duplex in Winona this clean, this cared-for, and this ready to go from day one. Seller is a real estate agent licensed MN & WI. 24-hour notice needed to tour

421 E Sanborn Street, Winona

Listing courtesy of Edina Realty, Inc..

825 W 5th Street, Winona
$179,900
3 Beds ⋅ 2 Baths ⋅ 7154183 MLS
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.

928 W Mark Street, Winona
$289,000
3 Beds ⋅ 3 Baths ⋅ 7154307 MLS
Welcome to 928 W Mark Street, ideally located in a fabulous Winona neighborhood within walking distance of Lake Winona and area schools! Built in 1942, this spacious 3-bedroom, 3-bath home offers wonderful character, generous room sizes, and plenty of opportunity to make it your own. The main level features a spacious living room with a gas fireplace, a large kitchen with a unique indoor grill, and a charming den highlighted by a beautiful bow window. Upstairs, you’ll find three generously sized bedrooms, including a primary suite with a private bath and two closets. Wood flooring is visible in the closets, offering the possibility of additional wood floors beneath some of the carpeting. The lower level provides even more living space with a family room and workshop area. An attached 2-car garage, spacious yard, and garden shed complete the property. With its desirable location, classic features, and great potential for personalized updates, this is a wonderful opportunity to make this home your own!

928 W Mark Street, Winona

Listing courtesy of Edina Realty, Inc..

376 W Sanborn Street, Winona
$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.

357 Valley Oaks Drive, Winona
$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..

Winona
$275,000
3 Beds ⋅ 2 Baths ⋅ 7151416 MLS
A rare opportunity in one of the most sought-after neighborhoods. This well-loved home offered for the first time in nearly 50 years on a beautifully landscaped property that reflects decades of care and pride. Enjoy true main-floor living with a comfortable, functional layout suited for everyday ease. The backyard is a standout space, offering privacy, mature landscaping, and plenty of room to relax or entertain. The deck and patio feature ambient lighting, creating a warm, inviting atmosphere for evening gatherings. The home is also equipped with gutter guards for low maintenance exterior care and a fuII-house generator, providing peace of mind and uninterrupted comfort year-round. Nestled in a quiet, established neighborhood known for its charm and community feel, this property combines timeless appeal with practical upgrades. Homes like this rarely come to market so don't miss your chance to make it yours.

Winona

Listing courtesy of Edina Realty, Inc..

42902 Kipp Drive, Winona
$1,795,000
4 Beds ⋅ 4 Baths ⋅ 7151214 MLS
Set on 38.38 private acres bordering 3,000+ acres of Great River Bluffs State Park, this 4,300 SF home was designed to make the landscape part of everyday life. Walls of windows capture sweeping bluff-country views, sunrises, sunsets, moonrises & star-filled skies. A 26-ft vaulted great room anchors the home, complemented by handcrafted cabinetry, site-finished hardwood, quartzite, soapstone & marble. The kitchen features Thermador & Bosch appliances and a walk-in pantry. With 4 BR, 3.5 BA, gym/guest suite, office, loft & expansion potential, the home adapts beautifully to everyday life and entertaining. Enjoy sunrise & sunset porches, decks, fire pit, hiking & XC skiing access, wildlife viewing, hunting, berries & a substantial peony garden. A 1,700 SF garage/workshop offers exceptional space for vehicles, hobbies & storage. Private and peaceful, with easy I-90 access and convenient to La Crosse, Winona & Rochester. Some properties have to be experienced. This is one of them.

42902 Kipp Drive, Winona

Listing courtesy of La Crosse By Owner, LLC.

109 Debi Lei Drive, Winona
$1,100,000
7151103 MLS
RARE 7.88 ACRE COMMERCIAL/ASSEMBLY OPPORTUNITY!! This property offers approx. 6,615 sq ft of building space situated on a generous 7.88-acre parcel. The property provides a unique opportunity for an organization, business, investor, or owner-user seeking substantial acreage with an existing large building. The expansive grounds offer plenty of room for parking, outdoor activities, expansion, or future development possibilities, subject to applicable zoning and approvals. The existing building provides a spacious footprint that can potentially accommodate a variety of uses or be adapted to meet the needs of the new owner. Conveniently located in Winona with easy access to the surrounding community, this is an exceptional opportunity to acquire a sizable property with flexibility & potential. Properties offering this combination of acreage & building space are rarely available. BRING YOUR VISION AND EXPLORE THE POSSIBILITIES! This listing includes 2 parcels - 323207873 & 324630440

109 Debi Lei Drive, Winona

Listing courtesy of Real Broker, LLC..

51 W Sarnia Street, Winona
$795,000
5 Beds ⋅ 5 Baths ⋅ 7150411 MLS
Commanding one of Winona's most coveted settings, this distinguished 1930 English Tudor blends timeless architectural presence with refined modern comfort. Set on three city lots beside 4 city-owned tennis courts, the residence captures sweeping views of Lake Winona, the Bandshell, Veteran's Park, and Sugarloaf-- an exceptional backdrop for everyday living and elegant entertaining. The all brick exterior showcases intricate masonry, Biesanz stone accents, a classic tile roof, and leaded glass windows that speak to the home's enduring craftsmanship and curb appeal. An automatic underground lawn sprinkling system help maintain the beauty of the landscaping and flower gardens with effortless ease. Inside, 5 bedrooms and 5 bathrooms are complimented by original hardwood floors, 9-foot main level ceilings, beautifully textured plaster walls, crown molding, generous room proportions and abundant storage throughout. Thoughtful updates include a quartz-appointed kitchen, custom tiled bathrooms, and a Biesanz stone upper terrace walk replaced in late fall 2025--enhance the home while preserving its character. With a stone wood-burning fireplace on each level and nearly three decades of meticulous care, this rare Tudor offer a "move-in ready" sanctuary of warmth, stature, and lasting elegance.

51 W Sarnia Street, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

51 E 3rd Street, Winona
$339,900
7148746 MLS
BUSINESS-ONLY SALE; real property/building is not included is sale. Hearts Desire - A Winona Icon Ready for New Ownership. Hearts Desire is a beloved Winona business with 43 years of history, now offered for sale as a turnkey opportunity. A true Winona icon, the store has built a loyal customer base and offers an eclectic mix of merchandise that gives it a unique personality and broad appeal. Located in central downtown Winona, Hearts Desire is a memorable stop for both locals and visitors, including cruise passengers traveling along the Mississippi River. The store features a wide variety of inventory, including: * Clothing and accessories * Greeting cards * Pots and pans * Paintings and artwork * School supplies * Toys * Soups and dips in many varieties * Crafts and craft supplies * Memorabilia and unique gift items * Hats and caps for all ages * Seasonal decorations and more! Winona is a beautiful, vibrant community with two four-year universities and a vocational college, providing a diverse population of students, families, professionals, and visitors. The city's downtown location and Mississippi River setting offer numerous opportunities for continued growth and community engagement. The current owner is willing to stay on and assist the new owner with the transition, providing valuable knowledge of the business, inventory, customers, and day-to-day operations. After 43 years, Hearts Desire is ready for its next chapter. This is an opportunity to take over an established, well-known downtown business and continue its legacy in the Winona community.

51 E 3rd Street, Winona

Listing courtesy of Elcor Realty of Rochester Inc..

25098 County Road 9, Winona
$829,000
4 Beds ⋅ 3 Baths ⋅ 7145333 MLS
This beautifully updated home is situated on 9.6 scenic acres, offering the perfect blend of modern comfort, space, and country serenity. The interior has been completely updated/remodeled, featuring four bedrooms, three bathrooms, with all new flooring, paint, trim, and doors throughout. The kitchen has been completely remodeled with new cabinetry, flooring, and beautiful hard-surface countertops, as well as a large 10 x 4 hard surface island. The lower level provides additional living space with a comfortable family room and a versatile flex room, currently being used as a music room. Bathrooms have been updated/remodeled also and a new electrical panel was installed. Major exterior improvements include a brand-new septic system, brand-new siding, roof, gutters, and garage doors, providing peace of mind for years to come. The spacious two-car attached garage offers convenient everyday access, while the additional 36’ x 24’ detached heated garage (with a loft) provides exceptional space for hobbies, projects, storage, or a home business. With extensive updates inside and out and nearly 10 acres of land (with trails), this move-in-ready property offers an incredible opportunity to enjoy modern living with plenty of room to spread out. Located directly across from the Cedar Valley Golf Course, you'll enjoy stunning views and the opportunity to hit the links anytime. Just minutes from both Winona and LaCrosse, this property gives you the best of both worlds -- country living with easy access to city amenities.

25098 County Road 9, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

423 W Mark Street, Winona
$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.

106 Glendale Road, Winona
$299,900
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..

65 E Broadway Street, Winona
$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..

689 E Lake Boulevard, Winona
$255,000
3 Beds ⋅ 2 Baths ⋅ 7134711 MLS
Welcome to this well-cared-for 3-bedroom, 2-bath home on Lake Boulevard, where year-round views of Lake Winona take center stage. Large living room windows bring the beautiful lake scenery inside and create a welcoming space to relax and enjoy the changing seasons. The home features new windows throughout, new laminate flooring, and spacious bedrooms with plenty of room for family, guests or a home office. An attached tuck-under garage adds everyday convenience, while the private backyard provides a great setting for gathering with friends, enjoying the outdoors or simply taking in the peaceful surroundings. A standout feature for hobbyists, mechanics or anyone needing extra space is the detached 18' x 26' garage in the backyard, offering plenty of room for a workshop, projects, storage or recreational equipment. With its combination of lake views, updates, outdoor space and exceptional garage setup, this Winona home offers a lifestyle that is hard to duplicate.

689 E Lake Boulevard, Winona

Listing courtesy of Re/Max Results.

351 E Sanborn Street, Winona
$255,000
3 Beds ⋅ 2 Baths ⋅ 7130964 MLS
Welcome to this inviting 3-bedroom, 2-bath home offering a comfortable layout and a convenient location close to parks, schools, downtown, shopping and dining. The spacious front porch provides a welcoming entrance and a great place to relax. The main level features a spacious dining room, eat-in kitchen with ample cabinet space, main-floor bedroom, full bathroom and convenient main-floor laundry, along with a back porch. Upstairs you’ll find two additional bedrooms and a second bathroom. Outside, enjoy a partially fenced yard, large deck and one-car garage. Additional highlights include plenty of storage throughout, forced-air heat, central air and all appliances included. A comfortable home with a functional layout in a convenient Winona location!

351 E Sanborn Street, Winona

Listing courtesy of Edina Realty, Inc..

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.