Winona, MS Homes for Sale

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  $1,995,000

  • 2 Beds
  • 2 Baths
  • 3,757 Sq Ft

  2024 Us-51, Winona, MS 38967

  Whether you have been looking for a family property or somewhere to entertain clients, the Montgomery 634 is the place! Providing 365 days of enjoyment, this Montgomery County, MS turn-key property is waiting for you. This 634 acre tract can be accessed from the west off Highway 51 and from the east off Sawmill Road, just north of Winona. A 3,757 square foot lodge offers two bedrooms, two

  Adam ALC

  2024 Us-51, Winona, MS 38967
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  /6

  $30,000

  • Land
  • 1.30 Acres
  • $23,077 per Acre

  0 U S Highway 51, Winona, MS 38967

  This vacant Lot has frontage on Highway 51 between Winona and Vaiden, Mississippi, in Carroll County. This 1.3+/acre tract features a 100' by 50' concrete slab near the highway. Community water and electricity are available, as well as high-speed fiber internet provided by Delta Electric EPA. Please call Tyler Alldread at 662.230.7322 for more information! 5.7 Miles to Winona

  Tyler Alldread SWAPA Land, LLC

  0 U S Highway 51, Winona, MS 38967
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  /49

  $1,995,000

  • 2 Beds
  • 2 Baths
  • 3,757 Sq Ft

  0 Highway 51 Unit 21760851, Winona, MS 38967

  Whether you have been looking for a family property or somewhere to entertain clients, the Montgomery 634 is the place! Providing 365 days of enjoyment, this Montgomery County, MS turn-key property is waiting for you. This 634 acre tract can be accessed from the west off Highway 51 and from the east off Sawmill Road, just north of Winona. A 3,757 square foot lodge offers two bedrooms, two

  Adam ALC Smalltown Hunting Properties & Real Estate

  0 Highway 51 Unit 21760851, Winona, MS 38967
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  /29

  $194,500

  • 4 Beds
  • 2 Baths
  • 1,854 Sq Ft

  700 Westland Dr, Winona, MS 38967

  Recently remodeled and beautifully updated, this home seamlessly blends modern style with functional design. Situated in the highly desired Westland Heights neighborhood, it offers not only an inviting interior but also expansive outdoor space for relaxation and recreation. Boasting four bedrooms, two full bathrooms, a large open living room, and a generous pantry, this home provides the perfect

  BLAKE ESTABROOK OVERSTREET PROPERTIES, LLC

  700 Westland Dr, Winona, MS 38967
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  /30

  $289,000

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  205 Shirley Ave, Winona, MS 38967

  Step into timeless charm and modern comfort with this beautifully updated 4-bedroom, 3-bath brick home in the heart of Winona. Featuring classic Craftsman style, this home welcomes you with rich hardwood floors and a spacious open-concept kitchen that's perfect for gatherings. Enjoy three updated bathrooms with stylish tile work, fresh interior paint throughout, and plenty of natural light.

  Chris Reed Coltmor Realty Co.

  205 Shirley Ave, Winona, MS 38967
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  /18

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  500 Fairground St, Winona, MS 38967

  AGENT OWNED: Completely renovated home with new windows and new siding and roofing. The interior has stylish finishes that are sure to impress.

  Kyle Cravens Cravens Properties, LLC

  500 Fairground St, Winona, MS 38967
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  /11

  $150,000

  • 4 Beds
  • 2 Baths
  • 2,497 Sq Ft

  115 Hampton St, Winona, MS 38967

  Kyle Cravens Cravens Properties, LLC

  115 Hampton St, Winona, MS 38967
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  /27

  $175,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,561 Sq Ft

  805 Montgomery St, Winona, MS 38967

  805 Montgomery Street has been completely renovated and is ready for its new owner! This 3-bedroom, 2-bath home features a bright and open floor plan with new central HVAC, brand new flooring, new updated fixtures, fresh paint inside and out, and beautiful landscaping that gives it great curb appeal. Step inside to an inviting living space that flows easily into the kitchen and dining

  Chris Reed Coltmor Realty Co.

  805 Montgomery St, Winona, MS 38967
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  /6

  $135,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,318 Sq Ft

  311 College St, Winona, MS 38967

  Kyle Cravens Cravens Properties, LLC

  311 College St, Winona, MS 38967
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  /28

  $179,000 Last List Price Sold Dec 27, 2024

  • 2,200 Sq Ft
  • $81/SF
  • 39 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1975

  1478 U S Highway 51, Winona, MS 38967

  This spacious 4-bedroom, 2-bathroom home on nearly two acres in Winona, MS is Perfectly situated on the edge of town, this brick home offers the best of both worlds-privacy and convenience. The interior features updated paint and flooring, creating a fresh and inviting atmosphere throughout. The home also boasts a new architectural roof, ensuring long-lasting quality. Outside, you'll find a

  Chris Reed Coltmor Realty Co.

  1478 U S Highway 51, Winona, MS 38967
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  /15

  $135,000 Last List Price Sold Dec 09, 2024

  • 1,894 Sq Ft
  • $71/SF
  • 449 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  200 Shirley Ave, Winona, MS 38967

  Come take a look at this 3 bedroom, 2 bath home. Very clean.

  Kyle Cravens Cravens Properties, LLC

  200 Shirley Ave, Winona, MS 38967
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  /3

  $750,000

  • Land
  • 90 Acres
  • $8,333 per Acre

  0 NE Frontage Rd, Winona, MS 38967

  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.

  Kyle Cravens Cravens Properties, LLC

  0 NE Frontage Rd, Winona, MS 38967
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  /10

  $190,000

  • Land
  • 50 Acres
  • $3,800 per Acre

  000 Highway 82, Winona, MS 38967

  Discover the potential of this rare 50-acre tract located directly on Highway 82 - a major corridor linking Greenwood and Winona, Mississippi. This beautiful property offers a mix of mature timber and open areas, with multiple ideal home sites scattered throughout. Whether you're looking to build your dream home, develop a weekend getaway, or invest in a property with future potential, this land

  William Daves Dave's Realty

  000 Highway 82, Winona, MS 38967
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  /7

  $59,000

  • 3 Beds
  • 2 Baths
  • 2,088 Sq Ft

  624 Summit St, Winona, MS 38967

  Welcome to 624 Summit Street, a charming home located in the heart of Winona, MS! This property features a spacious layout, cozy living areas, and a large yard—offering great potential for first-time buyers, investors, or anyone looking for a project. Conveniently situated near schools, shopping, and dining. Priced to sell and being offered AS-IS, this is a fantastic opportunity to add your

  Marilyn Thomas-Burks Exit Southern Charm Realty

  624 Summit St, Winona, MS 38967
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  /33

  $449,900

  • 4 Beds
  • 2 Baths
  • 2,070 Sq Ft

  400 Oak Dr, Winona, MS 38967

  Designed for those who appreciate fine details and modern living, this stunning 4-bedroom, 2-bath home features an open floor plan that blends comfort and style. The backyard, however, is the true showstopper! Step outside and be captivated by a gorgeous pool with a shallow tanning area and hot tub. The resort-like pool house elevates the experience with two outdoor TVs, a fully equipped outdoor

  Mary Bowering Bowie Realty, Inc.

  400 Oak Dr, Winona, MS 38967
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  /20

  $400,000

  • Land
  • 2.66 Acres
  • $150,376 per Acre

  0 N Mission Rd, Winona, MS 38967

  Prime 2.66± Acre Commercial Lot Near I-55 - Winona, MS Position your business for success with this 2.66± acre commercial lot, ideally situated in a rapidly developing area just off Exit 185 on I-55 in Winona, MS. Located on the outskirts of town, this property offers unmatched commercial potential in a high-traffic corridor, making it an excellent investment for businesses looking to establish a

  Preston Smith Southern Oaks RE Properties LLC

  0 N Mission Rd, Winona, MS 38967
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  /13

  $75,000

  • 3 Beds
  • 1 Bath
  • 1,349 Sq Ft

  56 New Hope Road Extension, Winona, MS 38967

  Enjoy this 3 bedroom, 1 bathroom single family fixer upper home! With a little TLC, this secluded land with plenty of privacy that sits on close to an acre, can be yours! It is has plenty of yard space and will make a wonderful first time home.

  Pamela Hardiman Landmark Realty

  56 New Hope Road Extension, Winona, MS 38967
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  /12

  $320,000

  • Land
  • 16 Acres
  • $20,000 per Acre

  0 S Frontage Rd, Winona, MS 38967

  BUILD YOUR BUSINESS RIGHT ALONG I-55 IN WINONA, MS. The Montgomery 16gives you prime exposure! Currently zoned for highway commercial restricted (C3-R), this16±acre tract is located directly across the interstate from Empire Truck Sales and the Pilot truckstop and next door to the Holiday Inn Express at Winona. The options on this MontgomeryCounty property are numerous!

  Chris Reed SmallTown Hunting Properties & Real Estate

  0 S Frontage Rd, Winona, MS 38967
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  /7

  $318,500

  • Land
  • 50 Acres
  • $6,370 per Acre

  50 SE Frontage Rd, Winona, MS 38967

  LAND FOR SALE ALONG INTERSTATE 55 IN WINONA, MISSISSIPPI! The Montgomery 50 lies outside the city limits of Winona but is close enough to enjoy the nearby amenities. The 50± acre Montgomery County property boasts more than 1,100 feet of frontage along I-55, giving you high visibility from interstate traffic. Located across the interstate from Empire Truck Sales and the Pilot truck stop to the

  Chris Reed SmallTown Hunting Properties & Real Estate

  50 SE Frontage Rd, Winona, MS 38967
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  /15

  $295,000

  • Land
  • 2.70 Acres
  • $109,259 per Acre

  0 S Frontage Rd, Winona, MS 38967

  BRING YOUR BUSINESS PLANS TO LIFE ON THE MONTGOMERY 2.7! Situatedunder the iconic Cross in Winona, MS, this 2.7± acre commercial property provides exceptionalvisibility 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

  Chris Reed SmallTown Hunting Properties & Real Estate

  0 S Frontage Rd, Winona, MS 38967
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  /50

  $1,995,000

  • Land
  • 634 Acres
  • $3,147 per Acre

  0 Highway 51 Unit 4094160, Winona, MS 38967

  Whether you have been looking for a family property or somewhere to entertain clients, the Montgomery 634 is the place! Providing 365 days of enjoyment, this Montgomery County, MS turn-key property is waiting for you. This 634± acre tract can be accessed from the west off Highway 51 and from the east off Sawmill Road, just north of Winona. A 3,757± square foot lodge offers two bedrooms, two

  Adam Hester SmallTown Hunting Properties & Real Estate

  0 Highway 51 Unit 4094160, Winona, MS 38967
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  /10

  $300,000

  • Land
  • 75 Acres
  • $4,011 per Acre

  0 New Hope Rd Unit 4093809, Wiggins, MS 39577

  Discover the beauty of this expansive 74 + acre property, offering a rare combination of natural features. The land boasts a mixture of thriving timber, wild apple and persimmon trees, as well as a rich variety of native flora, including grass grace and Greybeard. A serene pond is nestled within the property, creating a peaceful atmosphere and offering an ideal habitat for wildlife. A flowing

  Christina Fayard Keller Williams

  0 New Hope Rd Unit 4093809, Wiggins, MS 39577
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  /20

  $289,000

  • 5 Beds
  • 3 Baths
  • 3,870 Sq Ft

  414 Summit St, Winona, MS 38967

  Historical Antebellum home with endless possibilities, including Bed & Breakfast or Venue Hall. The dining room is very grand and banquet sized. The other rooms include a Parlor, den, Primary bedroom, and 4 additional bedrooms. From the exterior and interior columns, beautiful millwork, pocket doors and transom windows, this home is sure to impress you with the integrity of craftsmanship. Do not

  Kyle Cravens Cravens Properties, LLC

  414 Summit St, Winona, MS 38967
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  /12

  $79,900

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  1401 Mississippi 407, Winona, MS 38967

  Enjoy this 3 bedroom/2 bath mobile home located on 1.8 acres. Call today for your showing.

  Kyle Cravens Cravens Properties, LLC

  1401 Mississippi 407, Winona, MS 38967
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  /2

  $75,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  526 N Central Ave, Winona, MS 38967

  AGENT OWNED

  Kyle Cravens Cravens Properties, LLC

  526 N Central Ave, Winona, MS 38967
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  /2

  $110,000

  • Land
  • 18 Acres
  • $6,180 per Acre

  0 New Hope Rd Unit 4060063, Wiggins, MS 39577

  17.8 acre +/- site with a roughed in road in place and engineered plats on file. Great location for development. Located just west of the city limits of Wiggins in Stone County on New Hope Road. The property is located approximately .90 mile West of Highway 49. Community water is available from New Zion Water System and sewer is available from Stone County Utility Authority.

  Paul Hardy Paul Hardy Properties

  0 New Hope Rd Unit 4060063, Wiggins, MS 39577
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  /6

  $100,000

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  1241 U S 51, Winona, MS 38967

  Kyle Cravens Cravens Properties, LLC

  1241 U S 51, Winona, MS 38967
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  /9

  $179,000

  • 3 Beds
  • 2 Baths
  • 1,581 Sq Ft

  304 Shirley Ave, Winona, MS 38967

  Kyle Cravens Cravens Properties, LLC

  304 Shirley Ave, Winona, MS 38967
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  /10

  $147,500

  • 3 Beds
  • 1.5 Baths
  • 1,193 Sq Ft

  113 Shirley Ave, Winona, MS 38967

  Kyle Cravens Cravens Properties, LLC

  113 Shirley Ave, Winona, MS 38967
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  /6

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,542 Sq Ft

  117 Shirley Ave, Winona, MS 38967

  Kyle Cravens Cravens Properties, LLC

  117 Shirley Ave, Winona, MS 38967
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  /3

  $32,500

  • Land
  • 2.62 Acres
  • $12,405 per Acre

  731 Middleton Rd, Winona, MS 38967

  Kyle Cravens Cravens Properties, LLC

  731 Middleton Rd, Winona, MS 38967
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  /25

  $85,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  422 Speedway Ave, Winona, MS 38967

  This 3-bedroom, 2-bath home in Winona, Mississippi, offers classic Southern style with a beautiful yard, mature trees,and colorful flowers that create a peaceful setting. A wide, welcoming front porch stretches across the front of the home - perfect for rocking chairs, sweet tea, and visiting with neighbors. The property has been well cared for, inside and out, and offers the kind of character

  Chris Reed Coltmor Realty Co.

  422 Speedway Ave, Winona, MS 38967
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  /23

  $42,950 Pending

  • 3 Beds
  • 1 Bath
  • 1,240 Sq Ft

  101 County Road 54, Winona, MS 38967

  This 3-bedroom, 1-bath, 1,240 sq. ft. single-family home, built in 1965, sits on a 1-acre lot in a quiet setting, offering plenty of space for outdoor activities. The home features a kitchen, living room, and a deck, providing a comfortable and inviting living space. With its peaceful surroundings, this property is perfect for those seeking a cozy home with room to enjoy nature.

  Anita Orey Arx Point Realty, LLC

  101 County Road 54, Winona, MS 38967
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  /15

  $115,000 Last List Price Sold Jul 23, 2025

  • 1,295 Sq Ft
  • $89/SF
  • 0 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1976

  904 Bar Cove, Winona, MS 38967

  Nice, Move-in Ready! This brick, ranch style home is tuck away in a quiet cul-de-sac in Winona, Ms. Features include laminate wood and ceramic tile flooring, breakfast bar, central heat and air, large laundry room, attached and detached carports, exterior storage with deck, concrete driveway and a patio. Its location and design lends itself to entertaining but is also suitable for quiet

  Elecia Elmore Powers Properties

  904 Bar Cove, Winona, MS 38967
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  /7

  $125,000 Last List Price Sold Jul 15, 2025

  • 10,166 Sq Ft
  • $12/SF
  • 22 Days On Market

  • Built 1910

  100 S Central Ave, Winona, MS 38967

  The Historic "Wisteria" Hotel located in Winona, Mississippi. The building was a true masterpiece of its era and is waiting for someone to bring it back to its former glory. The building features 3 levels and most of the original hotel rooms have been combined into small apartments. The structure is of solid wood and has many historical features still in-tact.

  Kyle Cravens Cravens Properties, LLC

  100 S Central Ave, Winona, MS 38967
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  /18

  $59,900 Last List Price Sold Jun 26, 2025

  • 1,568 Sq Ft
  • $38/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  68 Stafford Wells Loop, Winona, MS 38967

  Nice property at a fantastic price! This 3 bedroom 2 bathroom mobile home is situated on 1 acre in Winona, MS. Enjoy the open floor plan, gas fireplace, and beautiful views from the front porch and back deck. Features include central HVAC, 2 car detached carport, carpet and vinyl flooring.

  Elecia Elmore Powers Properties

  68 Stafford Wells Loop, Winona, MS 38967
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  /22

  $129,000 Last List Price Sold Jun 26, 2025

  • 1,360 Sq Ft
  • $95/SF
  • 271 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1965

  723 Enterprise Dr, Winona, MS 38967

  723 Enterprise Dr. 3 bedroom, 1 bath home located in Winona sits on 1 acre just off Highway 407 only a short drive to town. This has a wonderful deck for entertaining which overlooks the large backyard perfect for gatherings, children or pets. The 1 vehicle carport has a storage room and breezeway leading to the deck. Roof is approximately 1 year old.

  Robin Lea Gold Key Realty LLC

  723 Enterprise Dr, Winona, MS 38967
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  /17

  $98,000 Last List Price Sold Jun 25, 2025

  • 1,310 Sq Ft
  • $75/SF
  • 32 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1954

  502 Montgomery St, Winona, MS 38967

  ✨ Renovated Classic with Space, Style & Charm - 502 Montgomery St, Winona, MS | 1,300 Sq FtThis beautifully updated 3-bedroom, 1.5-bath home blends classic charm with modern comfort—perfect for first-time buyers, investors, or anyone looking for a fresh start in a move-in-ready home.Inside, enjoy the warmth of original hardwood flooring in the main living areas and bedrooms.

  Arielle Reece Exit Southern Charm Realty

  502 Montgomery St, Winona, MS 38967
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  $473,600 Last List Price Sold May 13, 2025

  • Land
  • 128 Acres
  • $3,700 per Acre

  • 80 Days On Market

  0 County Road 65, Winona, MS 38967

  Choctaw Farms: 128+- acres with a 13+- acre lake, located in Carroll County, MS. This one of the most well rounded recreational tracts I have ever seen. New owners can do it all on this place... Hunt trophy deer & turkeys, & also catch a cooler full fish in the off season. Potentially build your weekend cabin on any of the multiple cabin sites located along the well established road system,

  JP Clark JP Clark Realty LLC

  0 County Road 65, Winona, MS 38967
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  /2

  $139,000 Last List Price Sold May 01, 2025

  • 1,640 Sq Ft
  • $85/SF
  • 517 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1966

  504 Herod Dr, Winona, MS 38967

  Just maybe this is the starter home you are looking for. Call today.

  Kyle Cravens Cravens Properties, LLC

  504 Herod Dr, Winona, MS 38967

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