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$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..

$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..

$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.

$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..

$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.

$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..

$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.

$499,900
6 Beds ⋅ 4 Baths ⋅ 7146036 MLS
Prepare to be wowed by this stunning six-bedroom, four-bath home filled with character, space, and incredible versatility! Soaring ceilings and a cozy fireplace create an impressive great room, while the spacious kitchen features solid-surface countertops and plenty of room to gather. The private primary suite is a true retreat with its own fireplace, heated floors, walk-in closet, and sliding door leading to the backyard. The upper-level attic offers exciting potential for a playroom, hangout space, home office, or whatever your heart desires. The lower level features a movie theater and a private living space with its own separate entrance, washer and dryer, furnace, air-conditioning unit, and water heater—perfect for rental income, guests, or extended living. The property is owner-occupied rental certified, offering an excellent opportunity for supplemental income. Outside, enjoy the fenced backyard and two-car detached garage—all in a convenient Winona location. This one-of-a-kind home truly has it all!

414 Dacota Street, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

$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..

$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..

$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..

$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.

$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..

$225,000
4 Beds ⋅ 2 Baths ⋅ 7130625 MLS
First time on the market and truly one of a kind! This fun and whimsical property offers amazing views, beautiful established perennials and features you simply don't find every day. The main home has 3 bedrooms, a full bathroom, laundry tucked into a butler's pantry and 2 rooms with incredible views. The basement offers tons of storage. Outside, enjoy one of the most unique screened porches you will ever see, plus what is believed to be Winona Trolley #9, ready to become a garden shed or she shed. The lower level home includes a separate 1 bedroom living space with a kitchen, bathroom and laundry, perfect for guests, extended living or a mother in law suite. It could also offer potential for conversion to a garage. A truly special property!

149 E Lake Boulevard, Winona

Listing courtesy of Keller Williams Premier Realty.

$265,000
3 Beds ⋅ 1 Baths ⋅ 7129489 MLS
Welcome to 34810 Old Homer Road, a cozy, cabin-like retreat situated just across from the Mississippi River! This charming three-bedroom, one-bath home offers comfortable one-level living with spacious bedrooms, a generous full bathroom, newer furnace and central air, and a warm, inviting feel throughout. What truly sets this property apart is the additional lot, offering an incredible opportunity to build your dream home while enjoying the existing home for yourself, guests, or future possibilities. The additional lot features a gazebo/entertainment area, creating a great spot to relax and gather with family and friends. Outside, you’ll also find a storage shed, an established garden area with apple trees, rhubarb and beautiful lilacs, plus a large deck offering plenty of outdoor living space and ready for a little TLC. With its unique setting, additional lot and fantastic location across from the Mississippi River, this property offers possibilities that are hard to find!

34810 Old Homer Road, Winona

Listing courtesy of Edina Realty, Inc..

$924,900
4 Beds ⋅ 5 Baths ⋅ 7128634 MLS
Rarely does a property offer this combination of space, privacy, recreation, and versatility. Situated on approximately 1.6 acres in the desirable Spring Brook/Cobblestone neighborhood, this impressive home offers nearly 5,900 sq. ft. of finished living space, 5 bedrooms, exceptional outdoor amenities, and an incredible six heated garage spaces. At the heart of the home is a beautifully designed kitchen with generous living and dining areas that flow effortlessly for everyday living and entertaining. The primary suite is a private retreat featuring its own fireplace, spa-inspired 5-piece bath, expansive walk-in closet, and adjoining bonus room—perfect for an office, fitness area, or quiet getaway. Upstairs are three additional spacious bedrooms, each with a walk-in closet, including two connected by a Jack-and-Jill bath and another with a private ensuite. The main level also features a dedicated office, laundry, multiple gathering spaces, and an inviting three-season room. The finished lower level adds even more flexibility with a spacious family room, wet bar, media room, 5th bedroom, bath, and abundant storage. Outside, enjoy the level backyard, patio with fire pit, and private Sport Court—ideal for basketball, pickleball, and year-round family fun. Two separate heated 3-car garages provide outstanding space for vehicles, recreational toys, hobbies, a workshop, and storage. A new septic system adds additional peace of mind. With its acreage, impressive square footage, recreational amenities, and unmatched garage space, 801 Spring Brook Drive offers a lifestyle and versatility that are truly hard to find.

801 Spring Brook Drive, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

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