Montgomery County Real Estate

Montgomery County Real Estate

Welcome to Montgomery County, Mississippi – a hidden gem nestled in the heart of the Magnolia State. Known for its rich history, charming small towns, and picturesque landscapes, Montgomery County offers a unique blend of Southern hospitality and modern convenience, making it an ideal place to call home.

Montgomery County is steeped in tradition, with a vibrant community that celebrates its heritage through annual events and local festivals. The county seat, Winona, is a delightful town that showcases quaint shops, delectable dining options, and a warm, welcoming atmosphere. Here, you’ll find the perfect balance of rural tranquility and urban amenities, ensuring that residents enjoy a high quality of life.

Nature enthusiasts will revel in the county’s stunning scenery, from rolling hills to serene lakes. Outdoor activities abound, with opportunities for fishing, hiking, and exploring the lush landscapes that define the region. The nearby Yalobusha River provides a beautiful backdrop for picnics and family outings, while the expansive parks and recreational facilities invite residents to engage in an active lifestyle.

Education is a top priority in Montgomery County, with dedicated schools that foster a nurturing environment for students of all ages. Families will appreciate the sense of community and the strong support systems that enhance the educational experience.

Whether you’re looking to buy your first home, retire in peace, or invest in a thriving community, Montgomery County, MS, has something for everyone. Experience the charm, warmth, and opportunity that this beautiful county has to offer – your dream home awaits!

Newest Listings in Montgomery County

$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.

$150,000
4 Beds ⋅ 2 Baths ⋅ 4156148 MLS
This home is absolutely gorgeous and move in ready...won't last long!!!!

291 Henderson Road, French Camp

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.

$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.

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