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1311 W 5th Street, Winona
$229,900
2 Beds ⋅ 2 Baths ⋅ 7158496 MLS
Super cut and cozy 2 bedroom 2 bathroom home in Winona. Open concept living with warm wood floors. New sink and faucet in the kitchen that features a breakfast bar, that opens up to the dining room and living room. Main level bathroom has a new vanity and sink. Lower level adds another family room, full bathroom, laundry and storage. Relaxing screened in porch overlooks the back yard. New light fixtures, new fenced in yard, new ceiling fans, new landscaping, new garage door opener and the list goes on!

1311 W 5th Street, Winona

Listing courtesy of Gerrard-Hoeschler.

114 E Wilmar Street, Rollingstone
$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..

1659 Edgewood Road, Winona
$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..

460 Center Street, Dakota
$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.

1022 Gilmore Avenue, Winona
$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..

362 Cummings Street, Winona
$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.

562 W 4th Street, Winona
$174,500
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.

780 River Street, Dakota
$265,000
3 Beds ⋅ 2 Baths ⋅ 7150898 MLS
Magical views of the main channel of the Mississippi River! Take in the beautiful sunrise every morning from inside your home or while relaxing on the front deck. Lovely ranch home with 3 bedrooms, 2 bathrooms and a 2 car garage. Large kitchen with an abundance of cabinet space that opens up to the spacious dining room. Living room with large picture window lets you enjoy the view of the river from inside. Cozy sun room off the back of the house leads to the back yard. Newer roof, siding and bathroom. Some windows have been replaced. Main floor laundry is a plus!

780 River Street, Dakota

Listing courtesy of Gerrard-Hoeschler.

468 Main Street, Winona
$237,000
5 Beds ⋅ 2 Baths ⋅ 7150338 MLS
Rare opportunity to own a 5 bedroom, 2 bathroom rental certified home located directly across from Winona State University! Same owner since 1995 and now on the market for the first time in over 30 years. Wood floors are found throughout the home, with some currently covered by carpet. Basement offers laundry and additional space. Carport in back plus additional off street parking. Furnace replaced in 2023. Great location for a student rental or investment property with a long history as a rental.

468 Main Street, Winona

Listing courtesy of Keller Williams Premier Realty.

1215 W Mark Street, Winona
$323,900
4 Beds ⋅ 2 Baths ⋅ 7150138 MLS
Spacious 4 bed, 2 bath rambler with large rooms throughout, ideal as an in-law scenario with upstairs independent from the downstairs. Let your imagination run with the possibilities that this property has to offer! Gorgeous hardwood floors, marble finishes throughout, beautiful wood finishes and walls. New vinyl siding, 3-year-old metal roof, quiet residential location - this one is ready to move in!

1215 W Mark Street, Winona

Listing courtesy of Edina Realty, Inc..

1223 W 5th Street, Winona
$235,000
4 Beds ⋅ 2 Baths ⋅ 7144777 MLS
3 Bedroom/2 bathroom located in the heart of Winona next too Jefferson Elementary School. Large 2.5 car garage, mostly fenced yard. Updates to kitchen/bathrooms, electrical and plumbing; finished basement. Large deck off of the kitchen and charming front porch! This is a great home for the price! Seller can accommodate a quick closing!

1223 W 5th Street, Winona

Listing courtesy of Century 21 Affiliated.

623 E Howard Street, Winona
$189,000
2 Beds ⋅ 1 Baths ⋅ 7144015 MLS
This 2 bedroom, 1 bath home is in a fantastic location with plenty of space both inside and out. The oversized living room overlooks the very large backyard, giving you plenty of room to spread out. A cement pad is already in place, making it a great start for you to add your own garage in the future. The bathroom offers plenty of space, and both bedrooms are generously sized. You will also love the cute front porch, a perfect spot to enjoy some fresh air without worrying about the bugs! The basement provides additional space to grow into or simply use for great storage. Newer windows, furnace, and central air add even more value to this home.

623 E Howard Street, Winona

Listing courtesy of Keller Williams Premier Realty.

18599 Horse Shoe Road, Rollingstone
$294,900
3 Beds ⋅ 2 Baths ⋅ 7129240 MLS
Buyer walked away but their loss is your gain! Embrace tranquility and boundless nature just outside Rollingstone. Set on 5+ acres of private wooded land, this country property is an absolute dream for anyone seeking a serene lifestyle away from the city. Arrive just in time for fall and soak in the sweeping, picturesque countryside views as the leaves begin to change. Perfect for outdoor enthusiasts, wildlife watchers, or anyone craving space and seclusion. Key updates include a brand-new septic system installed in 2024.

18599 Horse Shoe Road, Rollingstone

Listing courtesy of Coldwell Banker Realty.

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.

577 W Sanborn Street, Winona
$139,000
3 Beds ⋅ 1 Baths ⋅ 7134077 MLS
Perfect starter home or a great addition to your rental portfolio, conveniently located just a few blocks from the college. This home features an open floor plan, three bedrooms, and a sunny front porch. Current rental certificate expires in 2027 and allows for 5 unrelated occupants. A great opportunity in a convenient Winona location!

577 W Sanborn Street, Winona

Listing courtesy of Real Broker, LLC..

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..

1026 Glen Echo Road, Winona
$319,900
3 Beds ⋅ 3 Baths ⋅ 7138119 MLS
This clean, well-maintained, move in ready home is a 3-bedroom, 2.5 bath and offers plenty of space and natural light. The large windows brighten the home, while the spacious primary bedroom provides a comfortable retreat. The lower level features a family room, storage room, and additional space to enjoy. A 2-car attached garage adds convenience, and the wooded backyard offers a peaceful setting.

1026 Glen Echo Road, Winona

Listing courtesy of RE/MAX Results.

30 Tews Avenue, Lewiston
$293,000
3 Beds ⋅ 3 Baths ⋅ 7138264 MLS
Welcome to this inviting 3-bedroom home that has just had the exterior freshly painted offering comfortable main-level living in a wonderful, close-knit community. All 3 bedrooms are conveniently located on the main floor, including a spacious primary suite featuring a large window that fills the room with natural light and a lovely 3/4 bath with a walk-in shower. The nicely sized eat-in kitchen provides plenty of space for preparing everyday meals, while the beautiful dining room is ready for family dinners, holiday gatherings, and making memories. Patio sliders open from the dining area to the Trex deck, creating an ideal space for grilling, relaxing, and entertaining. Main-floor laundry, conveniently located near all the bedrooms, makes everyday living a breeze. The lower level offers even more room to spread out with an almost-finished family room, a convenient half bath, and a large open storage/recreation area with plenty of possibilities for your needs and hobbies. Step outside and enjoy a beautifully manicured lawn made easy with an irrigation system. With the park and golf course nearby, plus all the charm of small-town living, this home offers a wonderful opportunity to settle in, make yourself comfortable, and make it your own. Home is being sold As-Is. Sellers are providing a 1-year Home Warranty! Come see all that this Lewiston home has to offer!

30 Tews Avenue, Lewiston

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.

159 E King Street, Winona
$230,000
8 Beds ⋅ 2 Baths ⋅ 7134006 MLS
Great opportunity to own a well-located duplex in Winona featuring two units, each with 4 bedrooms and 1 bathroom. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this property offers excellent flexibility. The two-unit setup offers the potential for strong rental income while giving an owner-occupant the opportunity to offset their housing costs. Conveniently located near downtown Winona and just blocks from WSU, this property is an attractive option for both investors and owner-occupants

159 E King Street, Winona

Listing courtesy of Keller Williams Premier Realty.

27317 Fern Glen Road, Dakota
$350,000
3 Beds ⋅ 3 Baths ⋅ 7133707 MLS
Enjoy a stunning Mississippi River view from almost every room! After undergoing a full remodel & primary suite addition, this bright & spacious Dakota home is ready for new owners. The main floor features two bedrooms, tile bathroom, functional kitchen, two living spaces, and a sun room to fully take in the view. The whole upper level is a primary suite, complete with more river views, bathroom with dual vanity, soaking tub, tile shower, and large walk-in closet. Downstairs is an entertainer's paradise with built-in bar and room for games or a movie room. All this situated on a .86 acre lot with a brand new septic system for peace of mind. Buy now and enjoy the autumn colors from your front deck!

27317 Fern Glen Road, Dakota

Listing courtesy of Edina Realty, Inc..

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..

1103 Gilmore Avenue, Winona
$273,000
3 Beds ⋅ 2 Baths ⋅ 7129104 MLS
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
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.

34810 Old Homer Road, Winona
$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..

1943 Brownell Street, Saint Charles
$339,900
3 Beds ⋅ 2 Baths ⋅ 7129819 MLS
Move-in ready and thoughtfully updated, this 3-bedroom, 1.75-bath home offers comfortable single-level living with standout features throughout. The open main living area features in-floor heat, while the spacious kitchen offers white cabinetry, stainless steel appliances, a large center island, and pantry. A large family/bonus room added in 2025 provides an impressive second living space with vaulted ceilings and recessed lighting. Currently enjoyed as a home theater, the projector and screen are included with the sale. The primary suite features a walk-in closet and private 3/4 bath with a custom-tiled walk-in shower, while a second bedroom also offers a walk-in closet. Outside, enjoy a generous yard with a 6-foot privacy fence added in 2025 and an oversized attached two-car garage with abundant room for storage, hobbies, or projects. With single-level living, expanded living space, an oversized garage, and a private fenced yard, this home offers much more than meets the eye. Come see the space for yourself!

1943 Brownell Street, Saint Charles

Listing courtesy of Coffee House Real Estate LLC.

173 Sunrise Drive, Minnesota City
$275,000
3 Beds ⋅ 2 Baths ⋅ 7129374 MLS
Step into this move in ready, recently remodeled ranch style home in a quiet neighborhood just outside Winona where you won’t have to worry about city disturbances! At an estimated 1600 finished sq footage, this three bedroom, two bath house has plenty of living space, with an attached one car garage, and a fenced in backyard great for a small family, pets, or even rental property. The house underwent extensive remodeling in 2022, property was hooked up to city sewer and water service and inside the main floor received new hardwood flooring, windows, doors and trim, kitchen cabinets and counter tops, kitchen appliances, as well as bathroom vanity, toilet and tile. The now finished downstairs received completely new rooms with hardwood flooring, carpeted stairs, recessed lighting, doors and trim, washer and dryer, standing shower, vanity, toilet and tile, as well as dedicated water heater softener, furnace, and laundry closets to keep everything tucked away out of sight. Additionally, the roof had new hail strike proof shingles installed in 2025.

173 Sunrise Drive, Minnesota City

Listing courtesy of Beycome Brokerage Realty LLC.

419 E Broadway Street, Winona
$180,000
3 Beds ⋅ 1 Baths ⋅ 7127670 MLS
3 bedroom, 1 bath home with plenty of potential to make it your own! Wood floors run throughout the home, and the basement offers bonus space for a family room, office, hobby area, or whatever fits your needs. This home needs some TLC, but it’s a great opportunity to put in your own updates and build equity alongthe way. The 2 stall garage provides great storage, and the large deck is a nice spot to relax orentertain. Located right on the parade route and just a short distance from the local donught shop, close enough to smell them!

419 E Broadway Street, Winona

Listing courtesy of Keller Williams Premier Realty.

574 Wilson Street, Winona
$210,000
3 Beds ⋅ 1 Baths ⋅ 7122198 MLS
Welcome to this charming and nicely updated home on a desirable corner lot. Everything has been done for you, including a brand-new metal roof, a new HVAC system and newer flooring throughout. Best of all, this property is rental certified, making it an incredible find for both future homeowners and smart investors. Do not miss out on a turn-key property that combines modern comfort with a fantastic location.

574 Wilson Street, Winona

Listing courtesy of Edina Realty, Inc..

765 E Lake Boulevard, Winona
$299,900
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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