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24020 CTY  RD 17, Winona
$2,550,000
3 Beds ⋅ 4 Baths ⋅ 7069381 MLS
Welcome to paradise, located in the Pleasant Valley minutes outside Winona. This estate has many amazing qualities. Enter the estate on a fully paved driveway with an arched wrought iron entrance and custom concrete bridge, which passes over the teaming stream. The paved drive bordered by white picket fences leads to a concrete circle driveway entrance to the house. The 5,000+ square foot house is a 3-bedroom 4-bath, 2+ car heated and finished garage, open style executive walkout rambler. The entire house spares no detail and has been very well taken care of. Enjoy the large main floor master suite, with a large walk-in closet, and overlooks the pool and trout stream. Solid surface counters are in the kitchen and throughout the house. Main floor and lower floor laundry rooms. 3-season east and south-facing sunroom for a quiet place to take in the beautiful bluff country. Generous living room, family room, storage, abundant custom oak cabinets throughout, and a unique sit-down bar in the lower level. There is a sprawling custom concrete space with an in-ground pool and a custom-built pool pavilion that includes a kitchen and bathroom. The 36’x48’ horse barn has 3 stalls, a tack room, and an open area for managing the horses. There is a very large remodeled dairy barn, which has hand-hewn timber beams along with finished and heated workshop spaces. The 50’x70’ outbuilding has both cold storage and finished heated spaces. The 50’ x 80’ cold storage machine shed provides space to house farm equipment and supplies. The 140 acres of land includes 1/2 mile of private Pleasant Valley Creek, which has an abundance of trout, springs which feed two ponds, 40 acres of fenced and gated rotational grazing grounds, well-maintained trails through the property, valuable mature timber, 40 acres of tillable land, clover and alfalfa food plots for deer and turkey hunting, and 4 permanent enclosed hunting blinds. There is a custom-built trapper’s cabin which has bunks, heat, and a front porch where one can retreat to get away from it all. 1 mile from the 18-hole Bridges Golf Course and restaurant. Minutes to Lake Winona, where there are miles of paved biking and running trails, downtown Winona, and the Mississippi River.

24020 CTY RD 17, Winona

Listing courtesy of Bluff Country Properties,LLC..

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.

414 Dacota Street, Winona
$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.

225 Oak Leaf Drive, Winona
$479,000
4 Beds ⋅ 4 Baths ⋅ 7137124 MLS
Welcome to this spacious 4-bedroom, 3+ bathroom home located in the desirable Valley Oaks neighborhood! This home offers plenty of space along with features that make it comfortable for both everyday living and entertaining. Cozy up around the wood-burning fireplace or step outside onto the large back deck, offering a great space to relax, entertain, and enjoy the outdoors. The primary bedroom features its own full private bathroom and closet, while the additional bedrooms and bathrooms provide plenty of flexibility throughout the home. A 3-car attached garage offers excellent space for vehicles, storage, and more. Out front, the covered porch and porch swing create an inviting spot to sit back and enjoy the neighborhood. With 4 bedrooms, 3+ bathrooms, a large deck, wood-burning fireplace, 3-car garage, and a great Valley Oaks location, this home has plenty to offer.

225 Oak Leaf Drive, Winona

Listing courtesy of Richard L. Jacobson Real Estate.

24141 Homer Valley Road, Winona
$450,000
2 Beds ⋅ 1 Baths ⋅ 7069283 MLS
Escape to your own private retreat in the scenic bluff country of Winona, MN. This charming rustic log home, built with beautiful Montana pine, sits at the end of a quiet road on 27 acres, offering seclusion, privacy, and peaceful surroundings. This cozy 2-bedroom, 1-bath lodge is perfect as a personal getaway or a basecamp for outdoor adventure. Enjoy nearby hiking and camping, with plenty of space to explore and experience the natural beauty surrounding the property. Relax and unwind on the inviting covered front porch, where you can take in the fresh air, wooded views, and tranquil setting. Whether you're looking for a quiet escape or a place to reconnect with nature, this Private wilderness-style property delivers.

24141 Homer Valley Road, Winona

Listing courtesy of Keller Williams Premier Realty.

2197 Clinton Drive, Winona
$439,900
4 Beds ⋅ 3 Baths ⋅ 7160918 MLS
Welcome to desirable Valley View Estates! Lovingly cared for by the same owner since it was built in 1979, this exceptionally well-maintained 4-bedroom, 3-bath rambler is situated on a beautiful ¾-acre lot in one of the area’s most sought-after neighborhoods! The inviting main level features spacious living and dining areas, a cozy fireplace, three bedrooms, and two bathrooms. The fantastic walkout lower level offers an expansive family room complete with a pool table and second fireplace, an additional bedroom, and bathroom. Step outside to enjoy the beautiful backyard, offering plenty of space for relaxation and entertaining. The extensive list of improvements reflects decades of meticulous care, including a new roof in 2025, central air in 2024, furnace in 2022, Marvin replacement windows, and updated front porch and rear deck featuring maintenance-free decking and aluminum railings. A rare opportunity to own a truly cherished, one-owner home in an exceptional neighborhood!

2197 Clinton Drive, Winona

Listing courtesy of Edina Realty, Inc..

23216 Highway 43, Winona
$429,900
4 Beds ⋅ 2 Baths ⋅ 7130781 MLS
Want to be close to town and the interstate while still enjoying space and privacy? This could be just the place for you! Situated just off Highway 43 on a little over 2 acres, this beautifully updated home offers the perfect blend of convenience and country living. Step inside to an inviting open-concept kitchen, dining, and living area featuring beautiful cabinetry, JennAir appliances, and a cozy gas fireplace. Large windows capture peaceful views from both the front and back of the home. With four bedrooms, two baths, and an attached two-car garage, there’s plenty of room to spread out. Need even more space? You’ll love the impressive 36x48 pole shed—perfect for all your toys, hobbies, storage, or workshop needs. Updated, spacious, private, and conveniently located—this property has so much to offer!

23216 Highway 43, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

42671 Lisa Lane, Winona
$369,900
3 Beds ⋅ 2 Baths ⋅ 7161315 MLS
Enjoy privacy and nature on this peaceful tree lined lot with ranch style home offering 3-4 bedrooms and 2 full baths and bonus additional 3 car garage/workshop. The main level features 3 bedrooms, a spacious kitchen with abundant cabinetry, and a living room with a gas fireplace. A large three-season room overlooks the private backyard. The finished walkout lower level adds a family room, fourth bedroom, full bath, laundry room, ample closet and storage space, and a hobby room with convenient pullout shelves. Parking and workspace are plentiful with an attached 2 car garage and a detached 3.5 car garage featuring one heated stall and a metal roof. Price includes new flooring in lower level and living room. Schedule your showing today!

42671 Lisa Lane, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

8270 E Main Street, Winona
$339,900
4 Beds ⋅ 2 Baths ⋅ 7135485 MLS
Whether you want to have your business right at home or need plenty of storage space, this is the one, just minutes from Winona. This home is booming with character and waiting for you to add your touches. With four generous bedrooms, two bathrooms, an updated kitchen with new appliances, large dining & living rooms, attached one car garage, a partially finished basement for additional living space, you have plenty of room for the whole family. The vast backyard has an oasis with a large deck, established garden, plenty of green space and a creek providing stunning views and trout fishing. Additional storage is available in the climate controlled detached garage as well as the large shop that is already setup for a taxidermy business but could easily be used for another business or storage. A parking area next to the shop is perfect for additional off-street parking for additional vehicles or customers. Come see the endless possibilities and opportunities this home offers before it's too late!

8270 E Main Street, Winona

Listing courtesy of RE/MAX Advantage Plus.

334 Oak Street, Winona
$310,000
3 Beds ⋅ 2 Baths ⋅ 7120123 MLS
Immaculately maintained and nicely updated 3-4 Bedroom, 2 Bath Rambler in convenient West side location. Close to shopping, schools and restaurants! The 2-car attached garage features a newer 10'x20' workshop addition on the back. You are sure to enjoy the tranquil backyard green space, the manicured landscaping, and the new paver patio. The main level boasts 3 bedrooms, newer LVP flooring, and an updated kitchen with Stainless Steel appliances. The lower level is partially finished and has so many possibilities. You'll be sure to enjoy movie night in the massive family room. The bonus/game room can be turned into a 4th bedroom, and there is so much storage space. Updates include: the kitchen, SS appliances, windows, flooring, roof, vinyl siding, gutters, driveway, water heater, and radon mitigation system. This gem is ready for you to move right in and enjoy. Schedule your appt. before it's gone!

334 Oak Street, Winona

Listing courtesy of Real Broker, LLC..

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.

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..

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..

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..

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..

1880 W 5th Street, Winona
$249,900
3 Beds ⋅ 2 Baths ⋅ 7146537 MLS
Welcome to this inviting 3 bedroom, 2 bath home offering plenty of space, storage, and versatility! The main level features a larger living room and dining area, creating a comfortable space for everyday living and entertaining along with one bedroom or possible office space. Upstairs, you'll find two bedrooms, with either one offering the flexibility to serve as a home office, hobby room, or guest space. The basement provides even more room to spread out, including a spacious laundry room with additional workshop space, a nice-sized storage area, a family room, and an office area with the potential to become another bedroom with the addition of an egress window. Outside, enjoy the oversized backyard with a 6-foot vinyl fence surrounding approximately 75% of the yard, providing privacy and space for pets, gardening, or gatherings. Included is a sandpoint well, which is used for outside water usage only. A convenient 11x13 patio offers a great spot for relaxing or entertaining. The impressive 22x32, 2+ car garage provides plenty of room for vehicles, boats, or projects, while the 25x19 carport with vaulted ceiling adds even more covered parking or entertaining options. A new roof and siding add to the home's curb appeal and peace of mind. Conveniently located close to numerous stores, restaurants, and everyday amenities, this property offers a great location you've been looking for! Don't miss your chance...CALL FOR AN APPOINTMENT TODAY!

1880 W 5th Street, Winona

Listing courtesy of Keller Williams Premier Realty.

1120 W Broadway Street, Winona
$240,000
4 Beds ⋅ 2 Baths ⋅ 7159794 MLS
Welcome to this charming 4-bedroom, 2-bath home filled with character, warmth, and an exceptional amount of updates throughout! Beautiful wood floors, vaulted ceilings, and exposed wood beams create a wonderful blend of charm and architectural appeal. The inviting living room features a cozy wood-burning stove, while the updated kitchen and bathrooms offer modern conveniences. The practical and functional floor plan includes two bedrooms on the main level and two additional bedrooms upstairs, providing flexibility for a variety of living arrangements. Enjoy relaxing on the welcoming front porch or the wonderful wraparound back porch overlooking the fenced backyard. The extensive improvements to this home are truly impressive, including drywall throughout, replacement windows, updated siding and insulation, electrical and lighting updates, refinished wood floors, updated kitchen and bathrooms, a dual-zone gas forced-air heating system, new water service to the street, and so much more! Conveniently located directly across from Cotter High School, this home offers an incredible combination of timeless character, thoughtful improvements, and everyday functionality. So much has already been done for you in this charming home! Not used as a rental but home is rental certified.

1120 W Broadway Street, Winona

Listing courtesy of Edina Realty, Inc..

86 Knopp Valley Drive, Winona
$229,900
2 Beds ⋅ 2 Baths ⋅ 7106945 MLS
Welcome home to easy one-level living in this beautifully designed end-unit townhome! Offering 2 bedrooms, 2 bathrooms, and a spacious 2-car garage, this home features an open-concept floor plan with soaring vaulted ceilings and an abundance of natural light. The inviting living room is highlighted by a cozy gas fireplace, creating the perfect space to relax or entertain. The well-appointed kitchen flows seamlessly into the dining and living areas, while the private deck offers a peaceful place to enjoy your morning coffee or unwind at the end of the day. With its bright interior, thoughtful layout, and low-maintenance lifestyle, this move-in ready home is one you won't want to miss!

86 Knopp Valley Drive, Winona

Listing courtesy of Coldwell Banker River Valley, REALTORS.

25066 Gull Lane, Winona
$225,000
2 Beds ⋅ 1 Baths ⋅ 7082689 MLS
Rare opportunity to own your own slice of Mississippi River frontage! Whether you’re looking for a peaceful weekend getaway, investment opportunity, or the perfect location to build your future dream home, this property offers endless possibilities. Enjoy the beauty of river living with breathtaking views, wildlife, fishing, boating, and quiet evenings surrounded by nature. Conveniently located just minutes from Winona and La Crosse, you get the privacy and serenity of the river without sacrificing convenience. The existing 2 bedroom, 1 bath cabin/cottage offers charm and potential while you plan your next chapter. Properties with this setting and opportunity do not come along often come experience everything river life has to offer.

25066 Gull Lane, Winona

Listing courtesy of RE/MAX Results.

4618 W 5th Street, Winona
$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..

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.

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