Winona Homes for Sale

Welcome to Winona, a charming city located in Shannon County, Missouri. Known for its picturesque landscapes and friendly community, Winona offers a peaceful and serene environment for residents to call home.

If you are considering making Winona your new home, you'll be delighted to explore the diverse range of homes for sale in this area. Whether you are looking for a cozy bungalow, a spacious family home, or a tranquil retreat surrounded by nature, Winona has something to offer for everyone.

With a real estate market that caters to various preferences and budgets, finding your dream home in Winona is an exciting journey waiting to unfold. From modern amenities to traditional charm, the homes for sale in Winona showcase the unique character of this city and provide a comfortable living experience for residents.

Imagine waking up to the stunning views of the Ozark Mountains or enjoying a leisurely stroll in the vibrant neighborhoods of Winona. With a strong sense of community and an abundance of natural beauty, Winona is more than just a place to live – it's a place to thrive.

Discover the endless possibilities that Winona has to offer and find your perfect home in this idyllic city in Shannon County, Missouri. Let the warmth and hospitality of Winona welcome you to a new chapter in your life.

Newest Winona Homes for Sale

$529,900

3 Beds ⋅ 2 Baths ⋅ 60333294 MLS

Exceptional Ozark Retreat on 28+ Acres with Equestrian Barn, Trails, RV Hookups, Spring Creek & Breathtaking Views!Welcome to 20890 Thomas Lane, a truly special property where beautiful living spaces, exceptional outdoor amenities, and the natural beauty of the Missouri Ozarks come together in one remarkable setting. Situated on approximately 28.2 acres, this beautifully maintained 3-bedroom, 2-bath home offers privacy, comfort, incredible views, and an outdoor lifestyle that is hard to find. From the moment you arrive, you will notice the immaculate landscaping and the care that has gone into creating a beautiful, park-like setting. Thoughtfully designed paths wind throughout the property and lead you around the home and outdoor living areas, creating easy access while adding to the charm and character of the grounds. Multiple walk-around decks, many of which are covered, surround the home and provide an abundance of places to sit back, relax, entertain, and take in the spectacular views. From the decks, enjoy beautiful views across the meadow below the home, where the peaceful surroundings create the perfect backdrop for morning coffee, evening gatherings, or simply enjoying the quiet beauty of the Ozarks. The outdoor amenities continue throughout the acreage, making this property an incredible destination for those who love to explore and spend time outside. Trails have been thoughtfully cut throughout the property, offering opportunities to explore your own land by foot, 4-wheeler, or horseback. Bring your horses and enjoy trail riding right from home, or hop on the ATV and spend the day discovering the acreage. The property is designed to be enjoyed rather than simply looked at, with room to ride, explore, relax, entertain, and make lasting memories. At the front of the property, you'll discover one of its most unique and beautiful natural features--a live-running spring creek.

20890 Thomas Lane, Winona

$114,900

4 Beds ⋅ 3 Baths ⋅ 60332040 MLS

Large home for sale in Winona, Missouri. This is a 4 bedroom, 3 bath home with central heat and air + ventless wall heater, covered back deck, big yard, on a paved street just outside of town.

19507 J F Norton Parkway, Winona

$350,000

4 Beds ⋅ 3 Baths ⋅ 60331242 MLS

A rare opportunity to own 25 beautiful acres near Winona and Low Wassie, Missouri, adjoining Mark Twain National Forest and located within Missouri's designated Elk Zone. This established country property offers an all-brick four-bedroom, three-full-bath walkout basement home surrounded by beautiful grounds, mature landscaping, and abundant wildlife. The property features an impressive approximately two-acre stocked pond, providing excellent fishing, wildlife viewing, and a beautiful setting to enjoy the outdoors. The manicured yard is complemented by mature flowers and shrubbery, along with an established orchard featuring apple trees, pear trees, grapes, and a variety of other fruit-producing trees. Beyond the maintained grounds, the acreage offers excellent recreational potential with a mixture of open areas and wooded habitat. The property adjoins Mark Twain National Forest, providing immediate access to an enormous outdoor recreational resource. Located in the elk zone, elk have been known to be present on the property, along with an abundance of deer and other wildlife. The older all-brick home offers plenty of space with four bedrooms, three full baths, and a walkout basement. While the home reflects its era, it provides a solid base for a buyer looking for a comfortable residence with exceptional acreage and recreational amenities. Whether you're looking for a hunting property, small farm, recreational retreat, homestead, or simply a private place in the country, this property offers an uncommon combination of acreage, water, wildlife, established landscaping, fruit trees, and direct adjacency to Mark Twain National Forest.

8214 Cr 563, Winona

$450,000

4 Beds ⋅ 3 Baths ⋅ 60331240 MLS

A rare opportunity to own 53 beautiful acres near Winona and Low Wassie, Missouri, adjoining Mark Twain National Forest and located within Missouri's designated Elk Zone. This established country property offers an all-brick four-bedroom, three-full-bath walkout basement home surrounded by beautiful grounds, mature landscaping, and abundant wildlife. The property features an impressive approximately two-acre stocked pond, providing excellent fishing, wildlife viewing, and a beautiful setting to enjoy the outdoors. The manicured yard is complemented by mature flowers and shrubbery, along with an established orchard featuring apple trees, pear trees, grapes, and a variety of other fruit-producing trees. Beyond the maintained grounds, the acreage offers excellent recreational potential with a mixture of open areas and wooded habitat. The property adjoins Mark Twain National Forest, providing immediate access to an enormous outdoor recreational resource. Located in the elk zone, elk have been known to be present on the property, along with an abundance of deer and other wildlife. The older all-brick home offers plenty of space with four bedrooms, three full baths, and a walkout basement. While the home reflects its era, it provides a solid base for a buyer looking for a comfortable residence with exceptional acreage and recreational amenities. Whether you're looking for a hunting property, small farm, recreational retreat, homestead, or simply a private place in the country, this property offers an uncommon combination of acreage, water, wildlife, established landscaping, fruit trees, and direct adjacency to Mark Twain National Forest.

8214 Cr 563, Winona

$218,000

3 Beds ⋅ 2 Baths ⋅ 60330760 MLS

Rare opportunity to own a 3-bedroom, 2-bath home on 7 acres within the city limits of Winona, Missouri! This unique property offers the perfect combination of in-town convenience and country charm. Inside, you'll find beautiful original hardwood floors that add warmth and character throughout the home. Outside, a spacious 30' x 30' concrete block outbuilding provides endless possibilities for a workshop, storage, hobby space, or equipment. The level acreage offers excellent potential for future subdivision or development making this an attractive investment as well as a wonderful place to call home. Conveniently located less than 15 miles from the crystal-clear Current River and less than 15 miles from the renowned Cross Country Trail Rides in Eminence, you'll enjoy quick access to some of the Ozarks' finest floating, fishing, horseback riding, and outdoor recreation. Whether you're looking for a family home, investment property, or a place with room to grow, this one offers endless possibilities in a highly desirable location.

8028 Weaver Street, Winona

$289,900

5 Beds ⋅ 3 Baths ⋅ 60329125 MLS

Stunning 5-Bedroom, 3-Bath Multi-Generational Ozarks Retreat on 1.36 Acres! Located with convenient highway frontage in Winona, MO, this versatile 3,584 sq. ft. home offers the ultimate blend of space, custom character, and high-end living.The main floor welcomes you with a warm living room featuring a vaulted wood ceiling, a cozy propane fireplace and beautiful hardwood floors.. The kitchen is designed for easy entertaining with a kitchen island, stainless steal appliances, tiled countertops and a large kitchen island overlooking the massive dining room , supported by a large walk-in pantry. Retreat to the spacious main-floor master suite, complete with a private en suite bath and a walk-in closet. Step out onto the expansive, 450 sq. ft. back deck--the perfect spot for evening relaxation, cookouts, and enjoying your quiet acreage.Downstairs, discover a fully equipped, walk-out basement that serves as a completely independent living space! Featuring its own full kitchen (no appliances), living room, laundry/utility room, three (non-conforming) bedrooms, and a full bath, this layout is perfect for guest quarters, multi-generational families, or excellent rental income potential.Connected to city water and powered by Howell-Oregon Electric Cooperative, this home is as practical as it is beautiful. Better yet, you are situated right in the heart of the Ozarks' most iconic attractions--just minutes from Rocky Falls and a short 15-minute drive to Eminence, where you can access the Jack's Fork River, historic Alley Springs, and thousands of acres of public conservation land. And don't forget to go searching for the wild horses. Spacious, versatile, and located in an outdoor lover's paradise--schedule your private tour today!

9468 Mo-19, Winona

$194,900

3 Beds ⋅ 2 Baths ⋅ 60327911 MLS

Very nice brick home on a corner lot. New roof on home and storage building this year!This home features covered front porch, large living room with brick fireplace, open kitchen and dining room, 3 bedrooms, 2 baths, screened-in porch, oversized 1 car attached garage with lots of cabinets for storage. This home is in a great established neighborhood, property has a storage building out back, pretty yard with shade trees.

8737 Sapper Street, Winona

$170,000

3 Beds ⋅ 2 Baths ⋅ 60323336 MLS

Do not let the street view of this home and property fool you! This 3 bedroom/ 1 and 3/4 bath home (the primary bath has a shower but no tub) has mostly hardwood floors throughout this spacious living space with a HUGE fenced back yard to contain pets and children. Anderson windows!The yard sports a 1200 sq. ft. shop building with concrete floor and restroom with water heater and utility sink for the mechanic or craftsman in the family. There is a detached garage, storage building, and two double-space carports on the property. Owners states that there was a double-gate access to the property from the rear alley that has been fenced but could easily be opened up for vehicle access to the shop building. Pick your favorite colors for a fresh coat of paint to truly make this home 'yours.' All appliances and security camera system stay with the property.When your work-day or work-week is complete, you will be mere minutes from the Ozarks National Scenic Riverways - the FABULOUS AND BEAUTIFUL Current and Jacks Fork Rivers! The magnificent Jacks Fork River tourist town of Eminence is only 11 miles further north on Hwy. 19, Rocky Falls - one of Missouri's most unique geological features - is 11 miles to the NE, and the Current River is only 22 miles east at Van Buren - home of Big Spring - one of the largest springs in the U.S. and the world, with an average of approximately 286 MILLION gallons of water discharged daily into the Current River just a hop, skip, and jump downstream from Van Buren. Don't forget one of Missouri's most photographed sites - Alley Spring - or the ewild horses and elk in the area of Eminence and Peck Ranch!So whether it's the horse trail rides at Eminence, the wild horses, kayaks, canoes, fishing trips, or tourists of Eminence, or nature watching or hunting on Peck Ranch, Winona is in the middle of it all. If you travel a bit to the south, you will find the BEAUTIFUL Eleven Point River. The next chapter of you lives are wa

17150 3rd Street, Winona

$124,900

4 Beds ⋅ 2 Baths ⋅ 60322723 MLS

3/4 Bedroom, 2 Bath Home on Corner Lot in Winona, MissouriCharming and spacious home located within walking distance of Winona Schools. This property features original hardwood floors in several rooms, a large family room or optional fourth bedroom, central AC and propane heat, and a fireplace for added comfort. The screened front porch with handicap ramp, back patio, and large fenced backyard offer great outdoor living spaces.Additional highlights include a metal roof, stainless steel side-by-side refrigerator, stove, large utility room with a cellar, and a beautifully landscaped front yard with mature flowers. Situated on a fenced in corner lot. Just ten minutes from Rocky Falls, a beautiful natural rock-based spring and local swimming hole, and only fifteen minutes from the scenic Jacks Fork and Current Rivers, this location offers endless opportunities for floating, hiking, horseback riding, and exploring the breathtaking landscapes that make the Ozarks so beloved. $124,900 Outbuildings do not convey with property.

8286 Lockman Street, Winona

$63,900

3 Beds ⋅ 1 Baths ⋅ 60321406 MLS

Discover the potential in this 3-bedroom, 1-bathroom fixer-upper located in a quiet, low-traffic neighborhood in Winona, Missouri. Situated on a corner lot of nearly 1 acre, this property offers the kind of space and privacy that is hard to find within city limits.While the home needs some TLC to reach its full glory, it boasts solid bones and a functional layout, making it the perfect canvas for a DIY enthusiast, a first-time flipper, or an investor looking for a high-potential rental.

17187 Edgewood Road, Winona

$114,900

4 Beds ⋅ 1 Baths ⋅ 60319437 MLS

Charming in-town home situated on a desirable corner lot! This 4-bedroom, 1-bath property offers plenty of space and functionality. Enjoy a fully fenced yard--perfect for pets, kids, or outdoor entertaining. The property features a large carport for convenient covered parking, along with a versatile workshop and a greenhouse ideal for hobbies or gardening enthusiasts. A small unfinished basement provides excellent storage or can serve as a reliable storm shelter.Great opportunity for homeowners or investors--don't miss out on this well-rounded property with tons of potential!

8643 Sapper Street, Winona

$59,900

2 Beds ⋅ 1 Baths ⋅ 60315092 MLS

Charming 2-bedroom, 1-bath home with a functional layout and multiple living areas, offering plenty of potential for updates and personalization. The family room features a cozy fireplace, while the additional living space can be used for entertaining, a home office, or relaxation. Original features throughout give this home character and a solid foundation to build upon.Both bedrooms are well-sized and share a full bathroom, creating a practical and efficient floor plan. The large yard provides space for outdoor activities, gardening, or future enhancements.This property represents a great investment opportunity for buyers or investors looking to add value. With some updates and cosmetic improvements, it can be transformed into a comfortable, modern home or a solid rental property. Conveniently located and easy to show, this home is full of potential for the right buyer.

18119 Sallee Street, Winona

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