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22544 Windy Point Road, Winona
$469,900
COMING SOON Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 7157491 MLS ⋅ 1,786 SqFt.
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.

54 Brickyard Lane, Winona
$498,800
ACTIVE Status ⋅ 2 Beds ⋅ 3 Baths ⋅ 7157901 MLS ⋅ 1,902 SqFt.
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..

376 W Sanborn Street, Winona
$420,000
ACTIVE Status ⋅ 8 Beds ⋅ 3 Baths ⋅ 7153429 MLS ⋅ 3,742 SqFt.
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.

562 W 4th Street, Winona
$174,500
ACTIVE Status ⋅ 3 Beds ⋅ 1 Baths ⋅ 7151085 MLS ⋅ 1,855 SqFt.
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.

423 W Mark Street, Winona
$209,999
ACTIVE Status ⋅ 5 Beds ⋅ 2 Baths ⋅ 7143190 MLS ⋅ 1,400 SqFt.
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
ACTIVE Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 7140082 MLS ⋅ 1,584 SqFt.
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
ACTIVE Status ⋅ 4 Beds ⋅ 3 Baths ⋅ 7136924 MLS ⋅ 2,549 SqFt.
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
ACTIVE Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 7134711 MLS ⋅ 1,584 SqFt.
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
ACTIVE Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 7130964 MLS ⋅ 1,536 SqFt.
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..

1103 Gilmore Avenue, Winona
$273,000
ACTIVE Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 7129104 MLS ⋅ 1,481 SqFt.
Welcome home to this charming 3-bedroom, 2-bathroom home in a fantastic Winona location! Enjoy stunning views from the living room and primary bedroom, along with beautiful red oak hardwood floors in the main living and dining areas and two main-floor bedrooms. The hardwood floors were refinished in 2018, and the kitchen features a new laminate countertop installed in December 2024. The inviting living room includes a wood-burning fireplace insert, while the sunroom offers triple-pane windows filled with krypton gas for exceptional insulation and energy efficiency. The home also features solar panels in the backyard, and all appliances are less than six years old. The water line to the main was replaced in 2020. Step outside to enjoy nearby walking and biking paths connecting to the lakes, with hiking in the bluffs also close by. The library and downtown Winona are approximately 1.5 miles away. Add in wonderful location that puts outdoor recreation and local amenities within easy reach, and this home is one you won't want to miss.

1103 Gilmore Avenue, Winona

Listing courtesy of Pemberton RE.

149 E Lake Boulevard, Winona
$225,000
ACTIVE Status ⋅ 4 Beds ⋅ 2 Baths ⋅ 7130625 MLS ⋅ 1,200 SqFt.
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.

34810 Old Homer Road, Winona
$265,000
ACTIVE Status ⋅ 3 Beds ⋅ 1 Baths ⋅ 7129489 MLS ⋅ 1,439 SqFt.
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..

765 E Lake Boulevard, Winona
$299,900
ACTIVE Status ⋅ 4 Beds ⋅ 1 Baths ⋅ 7125858 MLS
The shop is the true standout. With 2,275 sq. ft. that have 16-foot ceilings, two 14-foot garage doors, three additional 8-foot garage doors, and a heated portion of the building, there is an incredible amount of room for vehicles, equipment, hobbies, storage, and a 1/4 bathroom. Finding this kind of substantial workspace on a property this close to everything Winona has to offer is exceptionally rare. A total of 3,601 insulated and heated, including an extra 560 sq. ft. not heated = total 4,161 sq. ft. The home offers the opportunity to make it your own and needs new flooring throughout, allowing the next owner to choose flooring that fits their style and vision. Adding even more value and peace of mind, the roofs on both the home and shop were put on in 2022. Outside, enjoy the incredible setting beneath Sugar Loaf and take in the views of Winona and the surrounding Driftless Area. With more than a half-acre of land, there is room to enjoy the property while still being conveniently located in town. If you've been looking for a property that combines a home, land, breathtaking views, and an exceptionally large shop in the heart of Winona, this is one you won't want to miss. The shop alone makes this property a rare find—and the location, acreage, and views make it even more special. WELCOME HOME!

765 E Lake Boulevard, Winona

Listing courtesy of Real Broker, LLC..

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