Winona Homes for Sale

Winona Homes for Sale

Welcome to Winona, Mississippi – a hidden gem nestled in the heart of the Magnolia State! Known for its rich history and warm Southern charm, Winona offers a vibrant community that beautifully blends small-town allure with modern conveniences. With a population of just over 5,000 residents, this picturesque city is perfect for those seeking a peaceful lifestyle while still being close to larger urban amenities.

Winona is steeped in history, featuring a delightful downtown area filled with unique shops, local eateries, and cultural attractions. The city's beautiful parks and recreational facilities provide ample opportunities for outdoor activities, whether it’s a leisurely stroll along the scenic trails or a fun-filled day at the local sports complex. The community is also home to several annual events that celebrate its heritage and bring residents together, creating a strong sense of belonging.

For those considering a move to this charming city, you’ll be pleased to discover a variety of homes for sale that cater to diverse tastes and budgets. From cozy cottages to spacious family homes, Winona's real estate market offers something for everyone. Many properties boast beautiful yards and easy access to the city’s amenities, making them ideal for families, retirees, and first-time homebuyers alike.

Experience the warmth and hospitality of Winona, Mississippi. Explore the homes for sale in this enchanting city, and envision your future in a place where community spirit thrives and Southern charm abounds. Your dream home awaits!

Newest Winona Homes for Sale

$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 .

$65,000
3 Beds ⋅ 2 Baths ⋅ 4143907 MLS
Investor Opportunity at 203 Branch Drive in Winona, Mississippi! This property presents a strong opportunity for investors looking to expand their portfolio with a value-add asset in a growing rental market. Located in a quiet residential area, this home offers solid potential for renovation, rental income, or resale. With a functional layout and good bones, 203 Branch Drive is ideal for a fix-and-flip project or a long-term buy-and-hold investment. The property provides the chance to add value through cosmetic updates and improvements, making it a smart choice for those seeking to maximize return on investment. Winona's affordable entry price point and steady rental demand make it an attractive market for investors. Conveniently situated near local schools, shopping, and major travel routes, this location appeals to tenants looking for accessibility and small-town living. Property highlights for investors: • Strong potential for appreciation with updates • Suitable for rental income or resale • Located in an established neighborhood • Affordable investment opportunity with upside potential • Growing demand for quality housing in the Winona area Whether you're a seasoned investor or just getting started, this property offers the kind of flexibility and upside that's hard to find at this price point. Don't miss out on this investment opportunity--schedule your showing today and explore the potential of 203 Branch Drive!

203 Branch Street, Winona

Listing courtesy of Gold Key Realty LLC.

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