Refine Search
Map
Sort by
$183,900
11962379 MLS
Welcome to this spacious 4 Bedroom, 3 Bath home offering around 2200 square feet of comfortable living space. Enjoy the large front porch, perfect for relaxing and a great carport with convenient covered parking. located in a nice area just outside Winona, this property offers room to spread out in a peaceful setting. If you are looking for a comfortable home with plenty of space and a convenient location this is the one for you.

807 Applegate, Winona

Listing courtesy of William Daves with Dave's Realty
$389,900
3 Beds ⋅ 2.5 Baths ⋅ 11962296 MLS
Beautifully renovated 3-bedroom, 21/2-bath home ideally located on the third hole of the Winona Country Club. This move-in-ready property offers a fresh, updated feel throughout with modern finishes and thoughtful renovations.This spacious beautiful kitchen has all new stainless steel appliances. There is a game room with plenty of space for entertaining. Enjoy private views of your own yard while being just minutes from everything Winona has to offer. There is also a 20'x 25' Workshop with built in shelves, an exhaust fan and electrical for what ever project you need to complete.Whether you're a golf enthusiast or simply looking for a beautifully updated home in a great location, this one is a must-see!

711 Lynn Dr, Winona

Listing courtesy of Heather Traub with Dave's Realty
$374,500
4 Beds ⋅ 3 Baths ⋅ 11931341 MLS
Welcome to Magnolia Manor, one of Winona's premier Queen Anne Victorian homes, beautifully restored to preserve its 19th-century character while offering thoughtfully updated modern amenities. This exceptional residence features soaring 12-foot ceilings, original woodwork, refinished hardwood floors, period fireplaces, and remarkable architectural details throughout. The main level offers a grand foyer, formal parlor with bay window, guest suite with exposed cedar-plank walls, spacious family room, and a full bath with clawfoot tub. The custom-renovated kitchen features a gas range, cast-iron apron-front sink, large pantry, and an expansive dining area opening to the covered porch and patio. Upstairs, a grand hallway leads to a turret reading nook, guest bedroom with private balcony access, custom built-in bunk room accommodating six, full hall bath, and an impressive primary suite. The primary bath spans approximately 28 feet and includes double sinks, a clawfoot tub, walk-in shower, wall-to-wall built-ins, and dedicated laundry area. Recent improvements include a new roof in 2024, updated electrical and plumbing, dual-zone HVAC systems, tankless water heater, and a beautifully rebuilt wraparound porch. The landscaped grounds are highlighted by mature white and spring-pink magnolia trees, creating a setting worthy of this distinctive historic property. Magnolia Manor offers a rare opportunity to own a beautifully preserved piece of Winona history with the comfort and functionality of modern living.

412 Church St, Winona

Listing courtesy of Kyle Cravens with Cravens Properties, LLC
$319,000
3 Beds ⋅ 3 Baths ⋅ 11925090 MLS
Own a piece of Winona history with this beautifully maintained 1908 home located in the heart of downtown. Offering approximately 3,000 sq. ft., 3 bedrooms and 3 full baths, this home is filled with character while remaining comfortable and move-in ready. Inside you'll find soaring 12-foot ceilings, large rooms, original decorative mantles, hardwood flooring, and beautiful stained and beveled glass that highlight the craftsmanship of the period. Outside is where this property truly stands apart. The private backyard features an in-ground swimming pool, outdoor kitchen, firepit, and a spacious entertainment area perfect for family gatherings or relaxing with friends. A large front porch adds even more Southern character, while the approximately .75-acre lot provides plenty of room to enjoy. The roof was replaced approximately four years ago, and the home has been exceptionally well cared for. If you have been looking for a historic home with plenty of space, original detail, and an outstanding outdoor living area, 104 Church Street deserves a closer look.

104 Church Street, Winona

Listing courtesy of Chris Reed with Coltmor Realty Co.
$225,000
4158318 MLS
Discover a truly one-of-a-kind commercial opportunity with this historic cotton gin situated on approximately 4 acres in Winona, Mississippi. Rich in character and history, this unique property features approximately 4,644 square feet on the ground floor and is currently operating as an event venue. Its rustic charm and spacious interior create the perfect setting for weddings, receptions, corporate events, private gatherings, and community functions. The versatile floor plan and expansive acreage open the door to countless possibilities. Continue operating as a successful event space or transform the property into a restaurant, brewery, retail destination, antique mall, entertainment venue, office space, or mixed-use development. The surrounding acreage provides ample room for parking, outdoor events, future expansion, or additional commercial improvements, making it an excellent investment for entrepreneurs with vision. Whether you're looking to preserve a piece of local history or launch your next business venture, this landmark property offers exceptional potential in a convenient Winona location. Opportunities to own a property with this much character, flexibility, and commercial appeal are rare. Schedule your private showing today and imagine the possibilities.

Greensboro Street, Winona

Listing courtesy of Devon Butrick with Southern Oaks RE Properties LLC
$100,000
4158310 MLS
Position your business for success with this outstanding 1.4± acre commercial property in the heart of Winona, Mississippi. Boasting excellent frontage along busy US Highway 51, this highly visible location benefits from consistent daily traffic, making it an ideal site for a wide variety of commercial ventures. Formerly the location of a gas station, the property offers a unique opportunity for redevelopment. The existing foundation slab remains in place, providing a head start for future construction while allowing buyers to reimagine the site to fit their business needs. Whether you're considering retail, office space, automotive services, or another commercial use, this property offers the visibility and accessibility to help your business thrive. With its prime highway frontage, established commercial history, and convenient location, this property is ready for its next chapter. Opportunities like this are becoming increasingly difficult to find. Contact your favorite REALTOR® today to learn more about this excellent commercial investment in Winona.

900 S Applegate Street, Winona

Listing courtesy of Devon Butrick with Southern Oaks RE Properties LLC
$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 Chris Reed with Coltmor Realty Co.
$275,000
3 Beds ⋅ 2 Baths ⋅ 11900009 MLS

106 Hampton St, Winona

Listing courtesy of Kyle Cravens with Cravens Properties, LLC
$379,000
4 Beds ⋅ 3 Baths ⋅ 11878446 MLS

322 Sawyer Road, Winona

Listing courtesy of Kyle Cravens with Cravens Properties, LLC
$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 Tiffany H McCaleb with Powers Properties
$164,000
11848821 MLS
Fully Fenced, Pond, and Just 1 Mile from Hwy 82! Exceptional 41± acre pasture farm with paved road frontage and a convenient location just one mile from Highway 82. This well-maintained property is fully fenced and offers an excellent setup for cattle, horses, or anyone looking for productive pastureland with room to grow. The property features approximately 24± acres of open pasture divided between a 10± acre front field and a 14± acre back field, providing ample grazing space and flexibility for livestock operations. A beautiful 0.50± acre pond serves as a reliable water source while adding scenic appeal to the property. The remaining 16.5± acres consist of natural woods, offering shade, privacy, and a picturesque backdrop to the open pasture. With its combination of productive grassland, water, wooded acreage, and easy access, this property presents an outstanding opportunity for a working farm, horse property, or future homesite. Whether you're expanding your livestock operation or looking for a peaceful piece of land with practical features already in place, this 41± acre tract is ready to meet your needs.

0 Lodi Rd, Winona

Listing courtesy of Taylor Nesbitt with Coltmor Realty Co.
$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 Tiffany H McCaleb with Powers Properties
$165,000
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 Kyle Cravens with Cravens Properties, LLC
$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 Chris Reed with Coltmor Realty Co.
$142,500
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 Pamela Hardiman with Bays Realty & Co.
$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 Jonathan Stevens with America's Land Partners - Mississippi, Kosciusko
$69,920
11686050 MLS
Looking for a fresh start small acreage to call your own? Well this property would be the perfect place! Has Interstate 55 frontage and located between the Duck Hill and Winona exits on the East side of the Interstate. Over 27 acres of fresh cutover and 9 acres of hardwood SMZ's. Property is ready to be replanted and offers someone looking for a longterm timber investment a fresh start. Would also make a nice small hunting tract when the property starts to thicken up in the coming years. Less than 15 minutes from Grenada. Call today for more information!

Interstate 55, Winona

Listing courtesy of Jonathan Stevens with America's Land Partners - Mississippi, Kosciusko
$400,000
4144508 MLS
Prime commercial opportunity! This is one of two available lots located at the high-visibility intersection of I-55 and Highway 82. With approximately 1.5+/- acres, this property offers the perfect location to build your business and capture maximum exposure from interstate and highway traffic. The excellent access and prominent positioning make it ideal for retail, service, or investment development. Don't miss the chance to secure a spot in one of the most strategic and highly traveled areas in Montgomery County.

NE Frontage Road, Winona

Listing courtesy of Prestley Vaughan with Southern Oaks RE Properties LLC
$400,000
4144505 MLS
Prime commercial opportunity! This is one of two available lots located at the high-visibility intersection of I-55 and Highway 82. With approximately 1.5+/- acres, this property offers the perfect location to build your business and capture maximum exposure from interstate and highway traffic. The excellent access and prominent positioning make it ideal for retail, service, or investment development. Don't miss the chance to secure a spot in one of the most strategic and highly traveled areas in Montgomery County.

NE Frontage Road, Winona

Listing courtesy of Prestley Vaughan with Southern Oaks RE Properties LLC
$750,000
4144497 MLS
Position your business where it will be seen! This 11+/- acre property is strategically located at the intersection of Interstate 55 and Highway 82 in Montgomery County, offering outstanding visibility and easy access for travelers and local traffic alike. With its high-traffic location and excellent exposure, this property presents the perfect opportunity for a wide range of commercial ventures. Whether you're planning a retail space, travel center, restaurant, or other business development, this prime location provides the accessibility and visibility needed for success. Large enough to accommodate multiple development possibilities, this tract offers both convenience and potential in one of the most traveled corridors in the area. Don't miss the chance to secure a highly visible, high-potential location for your next business venture.

NE Frontage Road, Winona

Listing courtesy of Prestley Vaughan with Southern Oaks RE Properties LLC
$228,000
3 Beds ⋅ 2.5 Baths ⋅ 11680349 MLS
Prime location on the outskirts of Winona, MS in a wonderful, established neighborhood! This charming single-story brick home offers 3 bedrooms and 2.5 bathrooms with plenty of comfortable living space and classic curb appeal. Highlights include: a large flat yard perfect for family gatherings, a covered carport for convenient parking and protection from the elements, an additional storage shed for tools, lawn equipment or hobbies, a welcoming front porch with room for rocking chairs, and a solid brick construction with a durable roof and functional layout. Priced to sell - Don't miss this opportunity!

59 Redell Drive, Winona

Listing courtesy of Mary Spell with Cravens Properties, LLC
$179,000
3 Beds ⋅ 1.5 Baths ⋅ 11679832 MLS

810 Michelle Drive, Winona

Listing courtesy of Kyle Cravens with Cravens Properties, LLC
$589,000
4136582 MLS
This 66± acre tract is located just outside the city limits of Winona, Mississippi, delivering exceptional visibility and access along Interstate 55. With over 1,100 feet of I-55 frontage, this Montgomery County property is positioned in a highly trafficked commercial corridor ideal for a wide range of development opportunities. The property sits directly across I-55 from Empire Truck Sales and the Pilot Truck Stop, adjacent to the Winona Baseball Complex, and next door to the Holiday Inn Express, placing it among established commercial and recreational anchors. Sixteen (16±) acres of the tract are zoned Highway Commercial Restricted (C3-R), providing immediate commercial potential, while the remaining acreage offers flexibility for expansion, investment, or future development. The land is primarily composed of natural mixed hardwood regeneration with some mature timber, with approximately 30 acres having been cut 15-17 years ago. This tract's size, zoning, and strategic location make it well-suited for commercial, mixed-use, or long-term investment purposes.

01 South Frontage Road, Winona

Listing courtesy of Chris Reed with SmallTown Hunting Properties & Real Estate
$179,950
4 Beds ⋅ 3 Baths ⋅ 11618184 MLS
115 Pine Drive, Winona, MS - This 4-bedroom, 3-bath home is tucked away in a quiet, private, area of Winona offering both space and comfort. The home features: Large whirlpool tub/shower, recessed dimmable lighting, all new electrical wiring, all new plumbing throughout, large electric water heater and additional optional tank-less water heater, New paint inside and out, laminate flooring throughout, updated kitchen and bathrooms with modern finishes. A privacy fence surrounds one side of the yard, complemented by beautiful, well-maintained landscaping. There is abundant extra storage, including a large storage room/workshop located on the side of the home - perfect for hobbies, tools, or additional workspace. Call today for a private Showing!!!

115 Pine Dr, Winona

Listing courtesy of Chris Reed with Coltmor Realty Co.
$395,000
4131438 MLS
Montgomery • 27± Acres • Prime Commercial & Industrial Opportunity Discover the ideal property to launch a new family business or expand your company's footprint in a fast-growing region. This 27± acre tract offers outstanding infrastructure, multiple improvements, and excellent access—making it a rare, turnkey opportunity with room to grow. Situated near active rail lines, the property offers an option for direct railroad access, with the option to add a new spur if desired. A wide creek bottom borders the back of the land, adding natural beauty and recreational appeal. A small food plot is already in place—perfect for early-morning hunting before the workday begins. The owner is open to dividing the property with an acceptable offer. Property Highlights Land Features 27± acres with excellent commercial or industrial potential Railroad access; option to install a new rail spur Creek bottom along the rear boundary Existing food plot Space for expansion, storage, or additional development Structures & Improvements 1. 60' x 120' Red-Iron I-Beam Pole Barn - Concrete slab - Partially enclosed - Water and power available 2. 50' x 150' Red-Iron I-Beam Pole Barn - Open pole-barn design - No slab 3. Multi-Purpose Commercial Building (65' x 50' covered area + 50' x 35' enclosed structure) - Water and power available - Two bathrooms - Two office rooms - Two roll-up doors - Up stair office space/storage Ideal for shop space, storage, office use, or light manufacturing Key Advantages Turnkey facilities suitable for a wide range of business operations Ample acreage for expansion, parking, or additional buildings Rare combination of commercial utility and recreational appeal Owner willing to subdivide with the right offer

Industrial Park Road, Winona

Listing courtesy of John Cartwright with Pursuit Properties, LLC
$225,000
3 Beds ⋅ 2 Baths ⋅ 11600326 MLS
Wonderful opportunity to own a historic home located in the city limits of Winona with an adjacent lot with rental property.

308 Jones, Winona

Listing courtesy of Kyle Cravens with Cravens Properties, LLC
$225,000
3 Beds ⋅ 3.5 Baths ⋅ 11578743 MLS

206 Church Street, Winona

Listing courtesy of Kyle Cravens with Cravens Properties, LLC
$109,000
3 Beds ⋅ 1 Baths ⋅ 11548555 MLS

215 Pearl Street, Winona

Listing courtesy of Kyle Cravens with Cravens Properties, LLC
$750,000
11542441 MLS
Approximately 90 acres of undeveloped commercial property that borders the east side of the northbound lane of interstate 55 at the Winona exit and also has frontage on the NE Frontage road easy access. This property is ready for development and could be used from commercial or industrial uses.

0 NE Frontage Road, Winona

Listing courtesy of Kyle Cravens with Cravens Properties, LLC
$160,000
3 Beds ⋅ 2 Baths ⋅ 11436619 MLS
AGENT OWNED: Completely renovated home with new windows and new siding and roofing. The interior has stylish finishes that are sure to impress.

500 Fairground Street, Winona

Listing courtesy of Kyle Cravens with Cravens Properties, LLC