35

Winona, MS Homes for Sale

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  • /17

    $200,000

    • Land
    • 16 Acres
    • $12,500 per Acre

    0 Brister Dr, Winona, MS 38967

    16 acres at the end of Brister Drive in Winona Ms. adjacent to The City of Winona recreation park.Just off I-55 and 1/4 mi from 82 highway. Be a great place for residential homes or commercial property. Winona is a growing community with an outstanding school system. City utilities are available.. Property is hard to find. Take frontage re off 82 at Blue Sky station then left on Brister

    Wayne McPhail McPhail & Associates Inc.

    0 Brister Dr, Winona, MS 38967
  • /16

    $295,000

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

    413 SE Frontage Rd, Winona, MS 38967

    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 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

    Chris Reed Smalltown Hunting Properties & Real Estate

    413 SE Frontage Rd, Winona, MS 38967
  • /16

    $125,000

    • Land
    • 1.8 Acres
    • $69,444 per Acre

    304 Tyler Holmes Dr, Winona, MS 38967

    Have you been searching for that perfect spot for a small business or an additional location for your existing business? This 1.8 acre corner lot in Winona, MS is your answer. Situated at the northwest corner of the intersection of Middleton Road and North Applegate Street (Highway 51), the property consists of 1.8 acres of open, grassy landscape, suitable for a building site and parking lot.

    Wilson Britt Smalltown Hunting Properties & Real Estate

    304 Tyler Holmes Dr, Winona, MS 38967
  • /20

    $54,000

    • Land
    • 18 Acres
    • $3,000 per Acre

    I-55, Winona, MS 38967

    Welcome to the Montgomery 18, located between the Winona and Vaiden exits on the west side of Interstate 55. This 18 acre Montgomery County tract offers prime investment and recreational potential. Stretching over 600 yards along Mississippi’s busiest highway, this high-visibility frontage could be ideal for billboards or other income opportunities. The property consists of a mix of

    Hunter Robison Smalltown Hunting Properties & Real Estate

    I-55, Winona, MS 38967
  • /10

    $300,000

    • Land
    • 74.8 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
  • /19

    $145,000

    • 3 Beds
    • 2 Baths
    • 1,870 Sq Ft

    311 Jones St, Winona, MS 38967

    Kyle Cravens Cravens Properties, LLC

    311 Jones St, Winona, MS 38967
  • /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
  • /15

    $295,000

    • Land
    • 2.7 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
  • /66

    $499,000

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

    57340 County Road 430, Winona, MS 38967

    COUNTRY HOUSE FOR SALE! (Carroll County) Are you searching for a property that gives you PEACE, QUIET, and a PRIVATE way of living?? Well if so then look no further than this house! FEATURES: 3 beds, 2.5 baths, 3100 sq ft, 39 acres, Stocked Pond, Long Driveway, Hardwood floors, Metal Roof, Brand new septic tank, Pantry, New countertops, Remodeled bathroom, Open Kitchen, 2 Car Carport, Walk in

    Perrin Jackson Landmark Realty

    57340 County Road 430, Winona, MS 38967
  • /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
  • /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
  • /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
  • /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
  • /8

    $198,000

    • 5 Beds
    • 3 Baths
    • 2,166 Sq Ft

    505 Whitehead Dr, Winona, MS 38967

    Renovated 3-4 bedroom home with additional guest house. The house is agent owned

    Kyle Cravens Cravens Properties, LLC

    505 Whitehead Dr, Winona, MS 38967
  • /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
  • /20

    $49,900

    • 3 Beds
    • 1 Bath
    • 2,010 Sq Ft

    516 Speedway Ave, Winona, MS 38967

    Kyle Cravens Cravens Properties, LLC

    516 Speedway Ave, Winona, MS 38967
  • /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
  • /22

    $425,000

    • 4 Beds
    • 3 Baths
    • 2,000 Sq Ft

    1651 U S 82, Winona, MS 38967

    This is a beautiful log home with approximately 2000 sq ft of living space and a log building with approximately 800 sq. Feet of versatile space. The additional building could be used as a guest home, an office or meeting space or even converted to a garage/shop. The main home has a rustic but inviting design. It features natural wood, a very large, covered wrap around Porch with views of rolling

    Laura Wood Cravens Properties, LLC

    1651 U S 82, Winona, MS 38967
  • /37

    $395,000

    • Land
    • 27 Acres
    • $14,630 per Acre

    0 Industrial Park Rd, Winona, MS 38967

    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

    John Cartwright Pursuit Properties, LLC

    0 Industrial Park Rd, Winona, MS 38967
  • /18

    $175,000

    • 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
  • /2

    $110,000

    • Land
    • 17.8 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
  • /20

    $54,000

    • Land
    • 18 Acres
    • $3,000 per Acre

    00 Interstate 55, Winona, MS 38967

    Welcome to the Montgomery 18, an 18 acre tract in Montgomery County between the Winona and Vaiden exits on Interstate 55. With over 600 yards of frontage along Mississippi's busiest highway, this property offers excellent visibility and potential income from billboards or future development. The land is a mix of hardwood and pine timber with plenty of deer sign, making it a solid little hunting

    Hunter Robison SmallTown Hunting Properties & Real Estate

    00 Interstate 55, Winona, MS 38967
  • /7

    $8,750

    • Land
    • 0.7 Acre
    • $12,500 per Acre

    106 Pine Dr, Winona, MS 38967

    ** 0.70-Acre Lot for Sale - Winona, MS** Build your dream home or grow your investment portfolio with this **beautiful 0.70-acre lot** located in the heart of **Winona, Mississippi**! **Prime Location:** Just minutes from **I-55** and **Highway 51**, offering convenient access to nearby towns, shopping, and dining. **Ideal for Building:** Perfect site for your new home, mobile home, or potential

    Devon Butrick Southern Oaks RE Properties LLC

    106 Pine Dr, Winona, MS 38967
  • /7

    $250,000

    • 2 Beds
    • 2 Baths
    • 1,648 Sq Ft

    5 Sawmill Rd, Winona, MS 38967

    Kyle Cravens Cravens Properties, LLC

    5 Sawmill Rd, Winona, MS 38967
  • /41

    $249,000

    • 3 Beds
    • 2 Baths
    • 2,734 Sq Ft

    308 Jones St, Winona, MS 38967

    Wonderful opportunity to own a historic home located in the city limits of Winona with an adjacent lot with rental property.

    Kyle Cravens Cravens Properties, LLC

    308 Jones St, Winona, MS 38967
  • /2

    $155,000

    • 3 Beds
    • 3 Baths
    • 2,355 Sq Ft

    1000 Montgomery St, Winona, MS 38967

    Kyle Cravens Cravens Properties, LLC

    1000 Montgomery St, Winona, MS 38967
  • /21

    $249,000

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

    206 Church St, Winona, MS 38967

    Kyle Cravens Cravens Properties, LLC

    206 Church St, Winona, MS 38967
  • /2

    $80,000

    • 3 Beds
    • 1 Bath
    • 1,227 Sq Ft

    805 Obryan Cir, Winona, MS 38967

    This cozy, 1227 square foot home has 3 bedrooms and 1 bath. Its sits in a calm, quiet community near seniors. With a little bit of work, this home has endless potential. If your looking for a great neighborhood this is perfect for you!

    Pamela Hardiman Landmark Realty

    805 Obryan Cir, Winona, MS 38967
  • /10

    $239,900

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

    907 Westland Dr, Winona, MS 38967

    Completely remodeled home with hardwood flooring in most rooms. Kitchen was completely renovated wit new cabinets, appliances, and marble countertops. The home features 2 full baths that have been completely updated. The home is agent owned.

    John Cravens

    907 Westland Dr, Winona, MS 38967
  • /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
  • /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
  • /9

    $175,000

    • 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
  • /57

    $210,000

    • 5 Beds
    • 3 Baths
    • 2,941 Sq Ft

    343 Highway 82, Winona, MS 38967

    WINONA, MS HOUSE FOR SALE!! FEATURES: 5 Beds, 3 Full Baths, 2941 Sq Ft, 2.50 Acres, 2 Car Carport, Huge Open Kitchen, 2 Front Doors, Upstairs (for bedroom, gameroom, or storage) Office desk, 2 Fireplaces, and so much more....Looking for a house that just needs a little love with great potential??? Well if so then heres YOUR HOUSE!! Call/text today to get a FREE copy of the property information

    Perrin Jackson Landmark Realty

    343 Highway 82, Winona, MS 38967
  • /8

    $119,000

    • 3 Beds
    • 2 Baths
    • 1,315 Sq Ft

    302 Braswell Dr, Winona, MS 38967

    Kyle Cravens Cravens Properties, LLC

    302 Braswell Dr, Winona, MS 38967
  • /11

    $95,000

    • 3 Beds
    • 1.5 Baths
    • 1,661 Sq Ft

    123 Branch St, Winona, MS 38967

    Enjoy this cozy 3 bedroom, 1 and half bath home in Winona. This home would be a perfect place to start making your own!

    Pamela Hardiman Landmark Realty

    123 Branch St, Winona, MS 38967

Why Live in Winona

The city of Wenona is primarily a rural, agriculturally-based community, but recent investments have made the Montgomery County seat a center for local lumber production. In 2021, Biewer Lumber opened a $130 million sawmill on the northern edge of ...

Frequently Asked Questions

What is the average home price in Winona, MS?
Homes for sale in Winona, MS have an average home price of $167,882.
Are home prices dropping in Winona?
Yes, home prices in Winona are down 17% in the last 12 months.
How many homes have sold over the last 12 months in Winona, MS?
13 homes have sold in Winona, MS over the last 12 months.
What are the most popular zip codes in Winona, MS?
The most popular zip codes in Winona, MS include 38967, 39747, 38943, 38925 and 39176.
How much do you need to make to afford a house in Winona?
The median home price in Winona is $155,000. If you put a 20% down payment of $31,000 and had a 30-year fixed mortgage with an interest rate of 6.22%, your estimated principal and interest payment would be $760 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $33K a year to afford the median home price in Winona. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Winona, MS?
Winona, MS has highly rated public and private schools. Some of the best schools in Winona based on Niche Grades are Winona Christian School, Winona Elementary School and Winona Secondary School. Browse all the schools in Winona, MS to learn more.

Home Trends in Winona, MS

Housing Trends

Median Sale Price
$107,000
Median Single Family Sale Price
$115,000
Median Townhouse Sale Price
$100,000
Average Price Per Sq Ft
$57
Number of Homes for Sale
17
Last 12 months Home Sales
13
Months of Supply
15.70
Median List Price
$155,000
Median Change From 1st List Price
20%
Median Home Sale Price YoY Change
-29%
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