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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..

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.

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..

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..

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.

34 Lenox Street, Winona
$139,900
1 Beds ⋅ 1 Baths ⋅ 7152392 MLS
Welcome home to this charming 1-bedroom, 1-bath home! A great option for a first-time buyer or someone looking to downsize, this cozy home offers a comfortable and functional layout. Outside, you will find a large fenced-in backyard with plenty of room to relax, entertain, or enjoy time outdoors, plus a storage shed for added convenience. A cute home with a backyard you will love!

34 Lenox Street, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

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..

562 W 4th Street, Winona
$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.

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.

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.

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.

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.

134 Fairfax Street, Winona
$225,000
3 Beds ⋅ 1 Baths ⋅ 7130345 MLS
Located near the golf course, this 3 bedroom home offers plenty of space and possibilities. All 3 bedrooms are on one level, with one currently being used as a laundry and storage room. Move the laundry to the basement and open up that room for additional living space. Wood floors add character throughout the home. The large eat in kitchen is great for everyday meals, while the basement offers a spacious family room plus plenty of storage. Lots of closet space throughout, along with a great front porch to enjoy. The 40 x 16 garage gives you room for vehicles, a workshop, or all your extra toys.

134 Fairfax Street, 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..

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..

152 Janet Marie Lane, Winona
$349,000
3 Beds ⋅ 3 Baths ⋅ 7124704 MLS
Immaculate townhome in quiet neighborhood. Easy main floor living with primary bedroom walk-in closet and private bathroom. Vaulted open kitchen with large breakfast bar/island and spacious living & dining room with fireplace that walks out to the deck overlooking woods. Lower level has family room that walks out to the patio, second and third bedrooms or office, full bath. Laundry and half bath on main level. Low monthly association fees.

152 Janet Marie Lane, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

37000 Krage Drive, Winona
$309,900
1 Beds ⋅ 1 Baths ⋅ 7123595 MLS
Escape to the peace and privacy of country living with this charming farmhouse situated on 6.7 scenic acres at the end of a quiet dead-end gravel driveway. Updated in 2014/2015, this inviting home blends modern comforts with much charm. The spacious kitchen serves as the heart of the home, featuring in-floorheat, a cozy pellet stove, and two convenient exterior doors providing easy access to either the welcoming front porch or the 16x16 backyard deck...perfect for enjoying your morning coffee or entertaining family and friends. The main floor also offers a comfortable living room filled with natural light, a full bathroom, and the convenience of main floor laundry. Upstairs, you'll find a generous bedroom complete with a relaxing sitting area, along with a large 13x16 storage room that offers excellent potential to be converted into an additional bedroom, office, or hobby space. Outside, the possibilities are endless with a sprawling yard surrounded by open countryside. The property includes a 24x25 garage/shed ideal for projects or extra storage, a spacious 26x40 machine shed for equipment or recreational vehicles, and a classic barn waiting for someone to restore it to its former glory. Brand new septic system in 2015. Whether you're dreaming of a hobby farm, gardening, raising animals, or simply enjoying the relaxing feel of rural life, this property offers the space, privacy, and versatility to make it your own. Don't miss this rare opportunity to own an updated country home with acreage and endless potential. Don't miss your chance...CALL FOR AN APPOINTMENT TODAY!

37000 Krage Drive, Winona

Listing courtesy of Keller Williams Premier Realty.

1304 Mcnally Drive Unit A, Winona
$349,900
3 Beds ⋅ 3 Baths ⋅ 7122511 MLS
Welcome home to this beautifully maintained 3-bedroom, 3-bathroom property offering generous living spaces, abundant storage, and a wonderful setting overlooking an open field. The spacious layout includes an inviting eat-in kitchen, a separate dining room, and large bedrooms designed with both comfort and functionality in mind. The primary suite features a large walk-in closet and a bathroom complete with a relaxing, jetted tub. You'll appreciate the convenience of the attached two-car garage and the additional living space provided by the enclosed three-season room. Step outside onto the rear deck and enjoy peaceful views with no backyard neighbors. With its thoughtful layout, spacious rooms, and meticulous upkeep, this home is ready for its next owners to move right in and enjoy.

1304 Mcnally Drive Unit A, Winona

Listing courtesy of Key Real Estate.

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