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$200,000
3 Beds 2 Baths 4157813 MLS
Welcome to peaceful country living at 2590 Highway 51 in Duck Hill, Mississippi! This charming, move-in ready home offers the perfect blend of comfort and convenience with an updated interior designed for today's lifestyle. This home has a BRAND NEW HVAC UNIT for central heating and cooling capabilities. Propane heaters remain on the walls, as a backup heat source due to our wild winters. Whether you're looking for your first home, a place to downsize, or simply want to enjoy the quiet of rural living, this property is ready for its next owner. Situated on a lot of approximately one acre, you'll enjoy manageable outdoor space with room to relax, garden, or entertain while taking in the surrounding countryside. Inside, the updated finishes create a warm and inviting atmosphere, making it easy to move right in and feel at home. If you've been searching for the simplicity and charm of country living with modern updates already completed, this property is one you won't want to miss. Schedule your private showing today!

2590 Highway 51, Duck Hill

Listing courtesy of Gold Key Realty LLC.

$125,000
5 Beds 2 Baths 4157004 MLS
Step into the timeless charm of this beautifully maintained Southern historic home, where classic architecture meets thoughtful modern updates. From the inviting wraparound porches and intricate trim work to the distinctive roofline, this home offers curb appeal that stands the test of time. Inside, you'll discover spacious rooms with soaring ceilings, abundant natural light, original fireplaces, built-in cabinetry, elegant wall sconces, and new Hunter ceiling fans that enhance both comfort and character. Every detail reflects the craftsmanship of a bygone era while providing the conveniences today's buyers appreciate. Enjoy your morning coffee on the expansive front porch, entertain guests on the side porch, or take advantage of the covered carport for protected parking year-round. Nestled among mature trees on a generous lot, this property offers a peaceful small-town lifestyle in the heart of Duck Hill, Mississippi. Recent improvements provide added peace of mind, including updated electrical and plumbing systems, along with a new roof installed in 2025. If you're looking for a home that blends historic elegance, modern functionality, and Southern hospitality, this exceptional property is one you won't want to miss.

203 S Binford Avenue, Duck Hill

Listing courtesy of EXIT Southern Charm Realty.

$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.

$184,500
4155139 MLS
Whether you're looking for a hunting property or recreational tract to develop over time, The Montgomery 82 offers a great opportunity in a convenient location. Situated on Highway 407 with additional frontage on Ellis Road, this 82± acre property in Montgomery County, MS is just minutes from French Camp and Winona, while still providing the privacy and seclusion that make spending time outdoors enjoyable. The landscape offers a nice blend of approximately 20 acres of bottomland hardwoods along with rolling upland terrain covered primarily in pine timber. This diversity creates the type of habitat that supports both deer and turkey, making the property well suited for year-round recreation. An established food plot is already in place, while the existing habitat leaves plenty of room for additional improvements through trail work, additional food plots, or timber management. Old interior trails can be reclaimed to provide better access throughout the property, and a small pond along with seasonal streams add both character and wildlife value. With power and water nearby, there are potential locations that would make excellent cabin or camp sites (power and water need to be verified prior to purchase). Whether your plans involve improving the hunting, building a weekend getaway, or simply owning a piece of land to enjoy with family and friends, The Montgomery 82 offers a solid foundation with plenty of potential to make it your own.

Highway 407, Kilmichael

Listing courtesy of SmallTown Hunting Properties & Real Estate.

$249,000
4 Beds 3 Baths 4154022 MLS
Get a glimpse of this beautiful 4 bedroom, 2.5 bath residence nestled on a spacious lot in the heart of Duck Hill, Mississippi. Built in 1969, this home blends timeless comfort with a touch of Tuscan charm. The layout provides an inviting, warm, and elegant living space, designed for both everyday life and entertaining! The thoughtfully designed floor plan features generous rooms, including a private primary suite, including its own enclosed side patio, perfect for enjoying your morning coffee or unwinding at sunset. Down the hall, a beautiful step-in shower awaits. The kitchen opens up to the main living area with beautiful beamed ceilings. Throughout the home, you will notice ornate stained glass windows that give the home a custom built feeling. Step through the back door to discover a covered patio as you overlook the expansive yard, creating the ideal setting for outdoor gatherings. This property also includes an attached garage, an additional 2 car carport space for extra parking, as well as two storage sheds that provide abundant space for tools, hobbies, or seasonal equipment! Whether you're looking for peaceful country living or a place to host family and friends, this home offers the perfect combination of space, functionality, and comfort.

123 Devalda Drive, Duck Hill

Listing courtesy of Gold Key Realty LLC.

$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.

$1,297,000
4 Beds 4 Baths 4153482 MLS
A stunning two-story, 4000 sq. ft. brick Colonial Estate gracefully set on approximately 135 acres of rolling Mississippi country side. Offering the charm of small-town life alongside the privacy of rural living,Hamilton Place is a rare opportunity to own a legacy property with open pastures, mature timber, your own private lake and endless possibilities for hunting fishing, camping and outdoor recreation. Montgomery county is one of several that is in the Sumner Grant area. This is a Scholarship/Grant set up by the Sumner family that allows families that have lived in Montgomery co. for a minimum of one year , to send their children who qualify to any university in the state at almost no cost. Owning property in Montgomery co.is definitely a financial advantage if you or family planed to attend a university. In Mississippi. Home Features: * 2-story Brick Colonial * Formal living and dining rooms * Family Den with Fireplace * Office with built in gun cabinet * Breakfast room & Kitchen *Large laundry room * Grand front porch * 2 walk in attics * 2 cedar lined closets * Land and Outdoor Features : * 135 acres total * 11 acre private Lake plus 3 acre pond * Lakeside Picnic area * 35 acre 30 year old Pine Plantation * Property fenced and cross fenced * Barn, shop & tractor shed * Rolling Hills and oak trees * 25 x 40 pool ( needs remodel )

401 S Binford Avenue, Duck Hill

Listing courtesy of Big River Properties.

$609,900
4 Beds 3 Baths 4150321 MLS
Whether you are searching for a private full-time residence, a weekend getaway, or a property with incredible recreational opportunities, this estate delivers! Situated on 16.80 ACRES, this beautifully designed two-story home has it all! Multiple living areas create the ideal setup for both everyday life and hosting guests, including a spacious recreation room with built-ins, formal living and dining spaces, and a separate den featuring a gas fireplace and vaulted ceiling. The kitchen is designed with both function and style in mind, complete with double ovens, a large walk-in pantry, and a comfortable breakfast area. The primary suite offers a private retreat with his and her closets, separate vanities, a Jacuzzi tub, and a separate shower. Step outside and enjoy everything this incredible property has to offer. Outdoor features include a 40x60 shop with endless possibilities—ideal for a guest suite, apartment, entertainment space, or 16+ picturesque acres, this beautifully designed two-story home features over 3,500 square feet of thoughtfully designed living space with room to live, entertain, and unwind. Inside, you'll find 4 bedrooms with the potential for a 5th bedroom, office, hobby area—with a full bath already in place. Relax by the new in-ground pool, unwind on the spacious covered back patio, or enjoy the beauty of two ponds (one stocked), scenic views, and a peaceful creek running through the property. Additional amenities include a private gated entrance, two-car carport, fenced pasture, and barn perfect for animals. With abundant acreage, ponds, a creek, and natural surroundings, it would make an outstanding hunting property, outdoor retreat, or second home escape. Move-in ready and truly a rare opportunity with endless possibilities.

1529 Lower Milligan Springs Road, Kilmichael

Listing courtesy of Southern Homes Real Estate.

$1,053,260
4145621 MLS
LOCATED IN MONTGOMERY COUNTY, MISSISSIPPI, JUST EAST OF VAIDEN, SOUTH OF KILMICHAEL, AND LESS THAN A MILE FROM THE RENOWNED BIG BLACK RIVER, THIS 405.1± ACRE PROPERTY OFFERS AN EXCEPTIONAL OPPORTUNITY FOR THE SERIOUS OUTDOORSMAN. With graveled county road frontage along both Pine Bluff Road and Seymour Road, access is reliable year-round. This turnkey recreational tract has a proven history of producing quality deer and turkey, supported by diverse terrain and ideal habitat conditions. The proximity to the Big Black River enhances wildlife movement and quality, which further establishes this property as a great hunting retreat. The Montgomery 405.1 is divided by Seymour Road, offering two distinct setups. The main cabin sits on the west side of Seymour Road on approximately 130± acres and includes roughly 640 square feet with one bedroom, one bathroom, a kitchen, a living area, and a utility room. On the east side of Seymour Road, the remaining acreage features a secondary 1,100± square foot mobile home with three bedrooms and two bathrooms, providing additional space for family and guests. The landscape offers a mix of hills, rolling terrain, and bottomland areas, creating both scenic appeal and diverse hunting opportunities. An established internal trail system allows for easy access throughout a majority of the property. The timber composition is well-balanced, featuring approximately 60± acres of four-year-old pine regrowth, 70± acres of 11-year-old hardwood regrowth, and 212± acres of 20-year-old pine. The remaining acreage consists of a few food plots, pockets of mature timber, and an old beaver pond bottom that could be converted into a potential duck hole. Water resources include a small pond and a branch off the Big Black River known as Clear Creek, supplying a consistent water source for wildlife and year-round enjoyment for the property owner. Whether you're searching for a quiet recreational retreat or a turnkey hunting property in an area near the Big Black River, the Montgomery 405.1 is ready to deliver.

Seymour Road, Kilmichael

Listing courtesy of SmallTown Hunting Properties & Real Estate.

$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.

$1,077,000
4138045 MLS
Welcome to White Oak Plantation, an exceptional 359 +/- acre hunting tract offering a truly turnkey experience - just show up and hunt! This property has a great road system and is fully equipped with 7 box stands strategically placed throughout, several ladder stands and well-established food plots that have been meticulously managed. Annual soil testing, lime applications as needed, and targeted fertilizers based on soil samples and planting goals have built high-quality habitat and consistent deer and turkey activity over the years. The property consists of mixed pine and hardwoods there is a roughly 36Ac clear cut that is approximately 3 years old that was cut for the sole purpose of creating more habitat in the center of the property. Big Black River genetics - producing exceptional whitetail deer with superior antler size and body potential - without the flooding risks associated with bottomland areas directly on the river. Located less than 5 miles from the Big Black River, the property captures those legendary genetics while remaining high and dry for reliable access, year-round use, and peace of mind during wet seasons. The tract also supports a strong turkey population, creating outstanding opportunities for spring turkey hunting. The land currently is under a forestry management plan consisting of controlled burns and timber management. The property was previously enrolled in a 5-year Conservation Stewardship Program (CSP) contract via USDA/NRCS, which expired around 2022-2023. The contract generated over $130,000 in total income (based on the enrolled 255 acres), potential re-enrollment or similar programs to could generating income if a new farm bill is approved. There is a proposed power line right-of-way crossing the property that, if approved, could provide up to $60,000 in potential revenue for the new owner. Improvements & Infrastructure • Spacious 16x48 cabin with front porch and a large back covered deck over looking the hill side (~7 years old) equipped for comfortable hunting stays: • 3 brand-new Mitsubishi mini-split ductless HVAC units (installed last year) • Full kitchen with gas stove/oven • Washer/dryer combo • All appliances remain with the property • On-site rented propane tank (from local gas company) • Large 48x35 barn/shop with water connected • Septic system serving the improvements Everything is approximately 7 years old (except the new mini-splits) and in excellent, ready-to-use condition. White Oak Plantation combines substantial acreage, elite genetics, proven wildlife management, solid infrastructure, and meaningful income opportunities from conservation history and potential easements - all in a low-maintenance recreational package. This is a rare opportunity for the serious hunter, family group, or investor seeking immediate, high-quality hunts with added financial upside in a sought-after location!

Bagasha Road, Vaiden

Listing courtesy of Buck Commander.

$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.

$675,000
4135983 MLS
WELCOME TO THE MONTGOMERY 243.3, LOCATED JUST SOUTHEAST OF DUCK HILL, MISSISSIPPI. This 243.3± acre hill region farm features a buffet for the outdoorsman—a barn, small pasture area, farmland, live creek, pond, timber, wildlife plots, and great hunting opportunities. If you're looking for a diverse property in the Mississippi Hill Region, we need to put the Montgomery 243.3 on the list! As you arrive at the property, you will notice the horse barn with horses currently enjoying the pasture area. The three-stall barn features concrete floors, a storage room, and one ½ bath. The pasture area encompasses a little over 2.5 acres with a three-rail wood fence. As you leave the barn area to the east, you will cross about 42 acres of the tillage ground before you arrive at Eskridge Creek, a beautiful live creek meandering through the property from north to south. It's hard to beat a live creek in the summer months, not to mention the added value it brings for the wildlife. The farmland has previously been leased by a local producer on a year-to year basis for $4,500 annually. After crossing the low water at the creek, you will access the timbered area, which is the eastern portion of the property. The timber make-up is mostly a mature mixed pine/hardwood stand offering the perfect diversity for a deer and turkey tract. You will find an excellent road system allowing you to reach most areas of the property. Wildlife plots are scattered about with opportunities to hunt every wind direction. From a turkey hunting standpoint, they can't not be in there—big timber, big ridges, big bottoms, and open ground...it's the recipe you want! There is also a small pond within the timber area that is full of bass. Lastly, an 18± acre farmland area is on the east side of the creek that you could leave in production or convert to a monster wildlife plot. If you're looking to build, this area is serviced by Entergy Mississippi Inc. and Eskridge-Rose Hill Water Association. The barn already has community water and a septic sewer in place. The location is convenient, with the property being located along the east side of Highway 51, just 14 miles southeast of Grenada and 82 miles northeast of Madison. If you have been looking for a truly diverse Mississippi Hill Tract, come take a look at this.

U.S. Highway 51, Duck Hill

Listing courtesy of SmallTown Hunting Properties & Real Estate.

$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.

$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.

$395,750
4050368 MLS
Have you been searching for a great recreational spot your family can enjoy? Welcome to your new 174± acre recreational tract in Montgomery County, MS, located roughly 30 minutes south of Winona, MS, 45 minutes south of Grenada, MS, and a little over an hour from Madison, MS. The property offers 140.6± acres of 7-year-old pines that will make an excellent future timber investment with proper management. The remaining acreage is a mixture of mature hardwoods and pines of various ages. A well-established internal trail system makes for easy navigation around the property. Entergy provides power, while water is through Poplar Creek. If you've been looking for a place that offers hunting and investment potential, this is it!

Tom Mans Road, Vaiden

Listing courtesy of Tom Smith Land & Homes.