Winona Real Estate

Winona Real Estate

Welcome to Winona, Mississippi – a charming city nestled in the heart of Montgomery County. Known for its rich history and warm Southern hospitality, Winona offers a delightful blend of small-town charm and modern amenities, making it an ideal place to call home.

Founded in the late 19th century, Winona boasts a vibrant downtown area that reflects its historical roots. Stroll along the picturesque streets lined with quaint shops, local eateries, and historic buildings that tell the story of this lovely community. The city is also home to the famous Winona Country Club, where residents can enjoy a round of golf amidst stunning landscapes.

Nature enthusiasts will find plenty to love in Winona. The nearby Lake Montgomery offers serene views and recreational opportunities, including fishing, boating, and picnicking. The lush parks and walking trails throughout the city provide perfect spots for family outings or a peaceful evening walk.

Education is a priority in Winona, with access to quality schools and a strong sense of community involvement. Families will appreciate the safe neighborhoods and supportive environment that foster growth and development for children of all ages.

Culturally rich and community-oriented, Winona hosts various events throughout the year, including festivals, farmers' markets, and art shows, ensuring there’s always something happening in this vibrant city.

Whether you’re looking to settle down or simply explore, Winona, MS, offers the perfect blend of tranquility and excitement. Come discover why so many are proud to call this beautiful city their home!

Newest Listings in Winona

$199,900
3 Beds ⋅ 2 Baths ⋅ 11910926 MLS
Move-in ready and loaded with updates! This spacious 3-bedroom, 2-bath home offers approximately 1,716 square feet of comfortable living space in the desirable Pinehaven subdivision. The open-concept floor plan features a large living area that flows into the kitchen with granite countertops, stainless steel appliances, abundant cabinet space, and a generous laundry room. A separate den provides additional living space, making it ideal for a family room, home office, or playroom. The oversized primary suite includes a private bath with double vanities, granite countertops, and walk-in closets. Outside, you'll enjoy an attached two-car garage, concrete driveway, fenced backyard, and a convenient location close to schools, shopping, and everything Winona has to offer. This well-maintained home is truly move-in ready and offers the space, functionality, and updates today's buyers are looking for.

621 Middleton Rd, Winona

Listing courtesy of .

$275,000
3 Beds ⋅ 2 Baths ⋅ 11900009 MLS

106 Hampton St, Winona

Listing courtesy of .

$79,900
4 Beds ⋅ 2 Baths ⋅ 4156029 MLS
Carroll County Deer Camp Ready for Hunting Season! Located just minutes from Vaiden and Interstate 55, this 1± acre property offers the perfect setup for those who enjoy the outdoors. Whether you own hunting land nearby or are looking for a comfortable place to spend deer season, this property provides the ideal home base for making memories in the woods. Featuring 4 bedrooms and 1 bathroom, there is plenty of room for family, friends, and hunting buddies. After a day in the woods, relax on the beautiful deck or utilize the covered skinning rack, providing a convenient setup for cleaning game. Enjoy the peace and privacy of a country setting while still being conveniently located near town and Interstate 55. This property offers the perfect place to call home, a weekend getaway, or a ready-to-enjoy deer camp for those who love spending time outdoors. Mostly furnished and ready to enjoy, this Carroll County property is ready for the next season of memories.

1884 County Rd. 9, Winona

Listing courtesy of Buck Commander.

$59,000
3 Beds ⋅ 2 Baths ⋅ 11878468 MLS

585 North Mission Road, Winona

Listing courtesy of .

$379,000
4 Beds ⋅ 3 Baths ⋅ 11878446 MLS

322 Sawyer Road, Winona

Listing courtesy of .

$59,000
3 Beds ⋅ 2 Baths ⋅ 4155205 MLS
413 Fairground is a renovation project ready for customization. Situated on a double lot, this home was originally built in 1951. It has a double front entry. The front porch faces Fairground Street while the double carport and concrete drive face Jefferson Street. There is an additional concrete patio facing the second lot that offers a park-like setting. Key highlight — this home is walkable to the high school. Winona High School is literally 6 doors down. This home is actually walkable to the grocery store, convenient store, fitness center, hospital, pharmacy, coffee bar, and shopping. It would be possible to live here and have accessibility to the necessities and conveniences of local commerce without the need for transportation. You could live here without a car. The first half of this project has already been done for you. This home has been fully gutted down to the studs. Choose 413 Fairground — a canvas for creating a home of your own.

413 Fairground Street, Winona

Listing courtesy of Powers Properties.

$340,000
3 Beds ⋅ 2 Baths ⋅ 4153563 MLS
Welcome to 11 Rolling Green Circle — this expertly crafted and well planned 3-bedroom, 2-bath home in the desirable Rolling Green Estates community offers a thoughtfully designed split floor plan, one of the most sought-after home layouts because the quiet retreat of the primary suite is private and set apart from the secondary bedrooms and preserves the center of the home for family gathering and the kitchen is truly the heart of the home.***Step through richly stained double-entry doors with divided-light glass panels that provide picturesque views and invite natural light into the stunning foyer illuminated by upgraded slim pendant lighting featuring a hammered glass shade—a sophisticated focal point creating an elegant and inviting first impression.***Take time to notice how the hammered glass shade of the foyer pendant diffuses the light and casts an intricate pattern across the ceiling and walls. The blend of glow and shadows creates a soft, shimmering display that resembles delicate sunbursts or rippling reflections that mirror water on light. An exquisite entry experience awaits that feels airy, artistic and grand. You are sure to feel welcome upon arrival.***Your foyer sweeps into two gathering spaces—the formal dining room and the family room. The spacious family room features impressive 14+ foot vaulted ceilings that soar above the cozy gas-log fireplace with wood mantel. Above the wood mantel is a designated mounting area for a large-screen TV. Your family room is connected to the kitchen and the bright breakfast room that opens to the covered back porch making grilling and outdoor entertaining a delight.***The heart of the home is the well-appointed kitchen, offering abundant granite countertop space, center island perfect for prepping meals, built-in pantry cabinetry directly to the left of the stove, wraparound over-the-counter cabinetry with under-cabinet lighting, breakfast area for casual dining conveniently located near the custom-built corner coffee bar, and a generous stool-height bar that stretches along the sink-side of the kitchen and provides additional seating or a great place to serve charcuterie.***Your kitchen opens to two spaces—a separate formal dining room providing an ideal setting for hosting family and friends for meals and holidays and a dedicated office space designed with productivity in mind, featuring two workstations, built-in book cases, and a window adding light and cheer to the work-from-home or homework environment.***Your private primary suite serves as a relaxing retreat with a jetted soaking tub, walk-in shower, granite countertop with double vanity, vast mirrored wall with dressing-room lighting, his-and-her closets, and a dreamy sleep space that is graciously spacious.***Thoughtfully situated on the opposite side of the home are two additional bedrooms and a full hall bath conveniently located between both bedrooms and easily accessible for all, including guests.***Additional features to highlight include a generous laundry room with pantry storage, cabinets directly above the washer and dryer hookups, wall shelving, and space for a freezer or safe. The side-entry two-car garage has a nook for tools, a dedicated storage room, and conveniently located within the garage are built-in stairs that provide access to a partially floored attic—it sure is nice having a place to store your Christmas tree and holiday decorations until it's time to celebrate again.***Outdoor living at 11 Rolling Green Circle is just as fulfilling. Enjoy porch sitting or taking it easy in the swing on your expansive and welcoming front porch, unwind behind your privacy fence on the covered back porch looking out over the backyard listening to the waterfall trickle into the coy pond, sunbathe on the lounging deck and cool off with a dip in your above-ground pool, or rest in the shade of the awning and watch the water swirl.***Thoughtfully planned. Expertly designed. Enjoyable living. Rolling Green

11 Rolling Green Circle, Winona

Listing courtesy of Powers Properties.

$170,000
3 Beds ⋅ 2 Baths ⋅ 11845781 MLS
Welcome home to this beautifully restored 1948 cottage, a cherished family home that has been filled with five generations of love, laughter, and memories. Now, this remarkable property is ready for its next chapter and a new family to make memories of their own. As you arrive, you'll be welcomed by a newly constructed pergola that leads to the front entrance, setting the tone for the thoughtful craftsmanship found throughout this custom remodel. Offering 1,275 square feet of beautifully updated living space, this 3-bedroom, 2-bath home blends timeless charm with modern convenience. Step inside to discover a spacious living room that flows seamlessly into the open-concept dining area and stunning kitchen. The kitchen features custom cabinetry with under-cabinet lighting, custom-designed countertops, and a large walk-in pantry, making it both functional and beautiful. Major improvements include new windows, new electrical wiring, new plumbing, new central heating and air conditioning, updated insulation, and a vapor barrier, providing peace of mind for years to come. The private primary suite is designed as a relaxing retreat, featuring vaulted ceilings and large windows overlooking the backyard. The luxurious primary bath offers a custom-tiled walk-in shower, dedicated makeup area, custom vanity with ample cabinet and drawer storage, and a built-in linen cabinet. Two additional bedrooms share a beautifully updated full bath featuring new tile flooring and custom tile surrounding the tub and shower. Combining modern updates with the warmth and character of a historic cottage, this move-in-ready home is truly one of a kind. Don't miss the opportunity to own a piece of history while enjoying all the comforts of a thoughtfully designed renovation.

400 Fairground street, Winona

Listing courtesy of .

$139,900
3 Beds ⋅ 1 Baths ⋅ 11778756 MLS
Completely remodeled 3 bedroom, 1 bath home located in a very nice area of Winona convenient to everything. This home features brand new paint, flooring, appliances, and fixtures throughout. Step outside and check out the HUGE fenced backyard with a covered concrete patio area that's just right for an outdoor living space, entertaining, or relaxing in the evenings. Whether you're a first-time home-buyer looking to get started or wanting to downsize into something move-in ready, this is definitely one worth checking out. Call today!

107 Webster St, Winona

Listing courtesy of .

$122,000
3 Beds ⋅ 1.5 Baths ⋅ 11742186 MLS
Great opportunity for a new buyer! This 3 bedroom, 1.5 bath home offers 1,193 sq. ft. and lots of potential inside and out. The half bath is already plumbed for a shower, giving you room to add value. Located in Montgomery County, this home is priced with the buyer in mind. Plus, qualified buyers may be eligible for Sumner Grant funds for college. Buyers should verify eligibility requirements. Call today to take a look!

113 Shirley Avenue, Winona

Listing courtesy of .

$143,500
4 Beds ⋅ 2 Baths ⋅ 11740640 MLS
Discover comfort, space, and convenience at 514 Speedway Ave in Winona! This beautifully updated 4 bedroom, 2 Nath home offers approximately 2,057 square feet of spacious living in a great neighborhood conveniently located near the local high school.

514 Speedway Ave, Winona

Listing courtesy of .

$82,152
11740504 MLS
This 39.12-acre rural hunting tract in Montgomery County offers a balanced blend of managed timber investment and diverse wildlife habitat, making it well-suited for both recreational use and long-term value. Approximately 33 acres are established in 13-year-old plantation pine, now entering a prime stage for mid-rotation management. Complementing the pine acreage are roughly 6 acres of natural hardwoods, providing critical diversity across the property. Hardwood stands contribute mast-producing trees-such as oaks-that supply acorns and other forage, while also offering bedding cover and travel corridors for wildlife. This mix of pine and hardwood habitat creates a more complete ecosystem, supporting a wider range of species throughout the year. The combination of managed pine plantation and scattered hardwoods creates an ideal setting for hunting, with opportunities to establish food plots, strategically thin timber, or develop wildlife openings. Overall, this property presents a versatile recreational tract with strong timber potential, diverse habitat structure, and ample opportunity for customization into a productive hunting retreat.

Duck Hill Ranch Road, Winona

Listing courtesy of .

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