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$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 .

$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 .

$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 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 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 Southern Oaks RE Properties LLC.

$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.

$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 .

$179,000
3 Beds ⋅ 1.5 Baths ⋅ 11679832 MLS

810 Michelle Drive, Winona

Listing courtesy of .

$120,000
3 Beds ⋅ 3 Baths ⋅ 4141682 MLS
Family farm including 2.2 acres +/- with 3 bedroom 2 1/2 bath home and 2 bay tractor shed with pond access perfect for homesteading. With open-concept living, dining, and kitchen, this home has a spacious feel. Winter-weather-ready with Kozy Heat wood-burning fireplace. Covered back patio overlooking a beautiful country landscape. Wide-open spaces with pear blossoms, magnolias, azaleas, and pond view.

2384 Highway 51, Winona

Listing courtesy of Powers Properties.

$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 SmallTown Hunting Properties & Real Estate.

$185,000
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 .

$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 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 .

$225,000
3 Beds ⋅ 3.5 Baths ⋅ 11578743 MLS

206 Church Street, Winona

Listing courtesy of .

$119,000
3 Beds ⋅ 2 Baths ⋅ 11474871 MLS

302 Braswell Drive, Winona

Listing courtesy of .

$155,000
3 Beds ⋅ 3 Baths ⋅ 11553393 MLS

1000 Montgomery, Winona

Listing courtesy of .

$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 .

$275,000
4100454 MLS
BRING YOUR BUSINESS PLANS TO LIFE ON THE MONTGOMERY 2.7! Situated under the iconic Cross in Winona, MS, this 2.7± acre commercial property provides exceptional visibility from Interstate 55 and is conveniently located close to hotels, restaurants, and businesses, ensuring steady traffic and a built-in customer base. With its Commercial Highway Restricted (C3-R) zoning, mostly level terrain, and available utilities, this Montgomery County property is ready for development. Easy access from Highway 82 and I-55 adds to its appeal, making it an ideal spot for retail, hospitality, or other commercial ventures. Don't miss the chance to establish your business in a prime, high-visibility location and capitalize on the growth taking place both north and south along the Interstate 55 corridor.

S. Frontage Road, Winona

Listing courtesy of SmallTown Hunting Properties & Real Estate.

$549,999
11348570 MLS
28+/- acres of prime commercial/agricultural land, located on Hwy 82 less than 4 Miles from Interstate 55. Excellent location with Water, electricity and natural gas readily available. Multi-use zoning with unlimited possibilities

0000 Highway 82, Winona

Listing courtesy of .