2,068

Winona, MS Homes

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  • 304 Tyler Holmes Dr, Winona, MS 38967
    304 Tyler Holmes Dr, Winona, MS 38967
    304 Tyler Holmes Dr, Winona, MS 38967
    /14

    $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.

    Agent Photo

    Wilson Britt

    Smalltown Hunting Properties & Real Estate

    (662) 299-2367

    304 Tyler Holmes Dr, Winona, MS 38967
  • 504 Herod Dr, Winona, MS 38967
    504 Herod Dr, Winona, MS 38967
    /2

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

    504 Herod Dr, Winona, MS 38967

    • 2 Beds
    • 1.5 Baths
    • 1,640 Sq Ft
    • Built 1966

    Last Sold Summary

    • $85/SF
    • 517 Days On Market

    Current Estimated Value $139,521

    Last Listing Agent Kyle Cravens Cravens Properties, LLC

    504 Herod Dr, Winona, MS 38967
    • 1478 U S Highway 51, Winona, MS 38967
      1478 U S Highway 51, Winona, MS 38967
      1478 U S Highway 51, Winona, MS 38967
      /28

      Est $165,000 Not Listed For Sale

      1478 U S Highway 51, Winona, MS 38967

      • 4 Beds
      • 2 Baths
      • 2,200 Sq Ft
      • Built 1975
      1478 U S Highway 51, Winona, MS 38967

      Last Sold Summary

      • $0/SF
      • 39 Days On Market

      Last Listing Agent Chris Reed Coltmor Realty Co.

  • 109 Mission Rd, Winona, MS 38967
    109 Mission Rd, Winona, MS 38967
    109 Mission Rd, Winona, MS 38967
    /11

    $149,000

    • 3 Beds
    • 1 Bath
    • 1,694 Sq Ft

    109 Mission Rd, Winona, MS 38967

    What to love about 109 Mission Road: 2 living spaces—your front porch leads into a spacious living and dining combo with hardwood floors, and your driveway leads to an even larger den with a blonde brick accent wall with cozy raised hearth with ledge seating, wood mantle for family pictures, big screen TV, and seasonal decor, and ceramic tile floor for easy cleanup after entertaining. The laundry

    Agent Photo

    Pam Powers

    Powers Properties

    (662) 443-4319

    109 Mission Rd, Winona, MS 38967
  • 0 New Hope Rd Unit 4093809, Wiggins, MS 39577
    0 New Hope Rd Unit 4093809, Wiggins, MS 39577
    0 New Hope Rd Unit 4093809, Wiggins, MS 39577
    /10

    $299,000 Last List Price Sold Apr 01, 2026

    0 New Hope Rd Unit 4093809, Wiggins, MS 39577

    • Land
    • 74.8 Acres
    • $3,997 per Acre

    Last Sold Summary

    • 478 Days On Market

    Last Listing Agent Christina Fayard Keller Williams

    0 New Hope Rd Unit 4093809, Wiggins, MS 39577
    • 11 Fisher Rd, Winona, MS 38967
      11 Fisher Rd, Winona, MS 38967
      11 Fisher Rd, Winona, MS 38967
      /8

      Not Listed For Sale

      11 Fisher Rd, Winona, MS 38967

      11 Fisher Rd, Winona, MS 38967

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Kyle Cravens Cravens Properties, LLC

  • 621 Middleton Rd, Winona, MS 38967
    621 Middleton Rd, Winona, MS 38967
    621 Middleton Rd, Winona, MS 38967
    /33

    $220,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    621 Middleton Rd, Winona, MS 38967

    Welcome home to comfort and convenience in a prime location! This well-maintained property features an open-concept living room and kitchen with granite countertops, stainless steel appliances, ample cabinet space, and a spacious laundry room. The den offers a cozy fireplace and additional living space, perfect for relaxing or entertaining. The large primary bedroom includes walk-in closets and a

    Agent Photo

    Jim Deweese

    Real Broker

    (662) 674-6753

    621 Middleton Rd, Winona, MS 38967
  • 805 Montgomery St, Winona, MS 38967
    805 Montgomery St, Winona, MS 38967
    805 Montgomery St, Winona, MS 38967
    /27

    $175,000 Last List Price Sold Sep 10, 2025

    805 Montgomery St, Winona, MS 38967

    • 3 Beds
    • 2 Baths
    • 1,561 Sq Ft
    • Built 1964

    Last Sold Summary

    • $112/SF
    • 5 Days On Market

    Current Estimated Value $144,013

    Last Listing Agent Chris Reed Coltmor Realty Co.

    805 Montgomery St, Winona, MS 38967
    • 200 Shirley Ave, Winona, MS 38967
      200 Shirley Ave, Winona, MS 38967
      200 Shirley Ave, Winona, MS 38967
      /15

      Est $152,738 Not Listed For Sale

      200 Shirley Ave, Winona, MS 38967

      • 3 Beds
      • 2 Baths
      • 1,894 Sq Ft
      • Built 1950
      200 Shirley Ave, Winona, MS 38967

      Last Sold Summary

      • $0/SF
      • 449 Days On Market

      Last Listing Agent Kyle Cravens Cravens Properties, LLC

  • 0 New Hope Rd Unit 26104489, Wiggins, MS 39577
    0 New Hope Rd Unit 26104489, Wiggins, MS 39577
    0 New Hope Rd Unit 26104489, Wiggins, MS 39577
    /68

    $256,000 Pending

    • Land
    • 56.7 Acres
    • $4,515 per Acre

    0 New Hope Rd Unit 26104489, Wiggins, MS 39577

    Welcome to the Stone 56.7! Located in Stone County, Mississippi, this 56.7 acre tract fronts New Hope Road and is situated approximately 8 miles north of Wiggins, offering an excellent balance of accessibility, recreation, and investment potential. The property features county road frontage with a gated entrance and an established interior trail system that provides easy access

    Agent Photo

    Dewayne Atkinson

    Smalltown Hunting Properties & Real Estate

    (601) 832-3075

    0 New Hope Rd Unit 26104489, Wiggins, MS 39577
  • 100 S Central Ave, Winona, MS 38967
    100 S Central Ave, Winona, MS 38967
    100 S Central Ave, Winona, MS 38967
    /7

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

    100 S Central Ave, Winona, MS 38967

    • 10,166 Sq Ft
    • Built 1910

    Last Sold Summary

    • $12/SF
    • 22 Days On Market

    Last Listing Agent Kyle Cravens Cravens Properties, LLC

    100 S Central Ave, Winona, MS 38967
    • 514 Speedway Ave, Winona, MS 38967
      514 Speedway Ave, Winona, MS 38967
      514 Speedway Ave, Winona, MS 38967
      /8

      Est $120,702 Not Listed For Sale

      514 Speedway Ave, Winona, MS 38967

      • 3 Beds
      • 2 Baths
      • 1,874 Sq Ft
      • Built 1960
      514 Speedway Ave, Winona, MS 38967

      Last Sold Summary

      • $0/SF
      • 332 Days On Market

      Last Listing Agent Kyle Cravens Cravens Properties, LLC

  • 0 Brister Dr, Winona, MS 38967
    0 Brister Dr, Winona, MS 38967
    0 Brister Dr, Winona, MS 38967
    /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
  • 115 Hampton St, Winona, MS 38967
    115 Hampton St, Winona, MS 38967
    115 Hampton St, Winona, MS 38967
    /11

    $150,000 Last List Price Sold Sep 18, 2025

    115 Hampton St, Winona, MS 38967

    • 4 Beds
    • 2 Baths
    • 2,497 Sq Ft
    • Built 1920

    Last Sold Summary

    • $60/SF
    • 347 Days On Market

    Current Estimated Value $99,658

    Last Listing Agent Kyle Cravens Cravens Properties, LLC

    115 Hampton St, Winona, MS 38967
    • 202 Vista Dr, Winona, MS 38967
      202 Vista Dr, Winona, MS 38967
      202 Vista Dr, Winona, MS 38967
      /36

      Est $175,781 Not Listed For Sale

      202 Vista Dr, Winona, MS 38967

      • 3 Beds
      • 2 Baths
      • 2,060 Sq Ft
      • Built 1965
      202 Vista Dr, Winona, MS 38967

      Last Sold Summary

      • $0/SF
      • 77 Days On Market

      Last Listing Agent Pam Patton Britt Barnes Realty Group

  • 0 SE Frontage Rd, Winona, MS 38967
    0 SE Frontage Rd, Winona, MS 38967
    0 SE Frontage Rd, Winona, MS 38967
    /20

    $589,000

    • Land
    • 66 Acres
    • $8,924 per Acre

    0 SE Frontage Rd, Winona, MS 38967

    Welcome to The Montgomery 66, a 66 acre commercial property 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

    Chris Reed Smalltown Hunting Properties & Real Estate

    0 SE Frontage Rd, Winona, MS 38967
  • 422 Speedway Ave, Winona, MS 38967
    422 Speedway Ave, Winona, MS 38967
    422 Speedway Ave, Winona, MS 38967
    /25

    $85,000 Last List Price Sold Oct 02, 2025

    422 Speedway Ave, Winona, MS 38967

    • 3 Beds
    • 2 Baths
    • 1,596 Sq Ft
    • Built 1930

    Last Sold Summary

    • $53/SF
    • 3 Days On Market

    Current Estimated Value $93,932

    Last Listing Agent Chris Reed Coltmor Realty Co.

    422 Speedway Ave, Winona, MS 38967
    • 604 S Applegate St, Winona, MS 38967
      604 S Applegate St, Winona, MS 38967
      604 S Applegate St, Winona, MS 38967
      /14

      Est $121,567 Not Listed For Sale

      604 S Applegate St, Winona, MS 38967

      • 3 Beds
      • 2.5 Baths
      • 1,200 Sq Ft
      • Built 1950
      604 S Applegate St, Winona, MS 38967

      Last Sold Summary

      • $0/SF
      • 40 Days On Market

      Last Listing Agent Marilyn Thomas-Burks EXIT Southern Charm Realty

  • 0 Robinson-Thompson Rd, Winona, MS 38967
    0 Robinson-Thompson Rd, Winona, MS 38967
    0 Robinson-Thompson Rd, Winona, MS 38967
    /61

    $799,900 Pending

    • Land
    • 379 Acres
    • $2,111 per Acre

    0 Robinson-Thompson Rd, Winona, MS 38967

    WELCOME TO THE MONTGOMERY 379, AN EXCELLENT BLEND OF FARMLAND,TIMBER INVESTMENT, AND RECREATIONAL OPPORTUNITIES. Located just 3.6 miles northwest of Kilmichael, Mississippi, in Montgomery County, the 379± acre tract consists of farmland and pine timber that was planted around 2007, making it an appealing optionfor buyers looking for both income and long-term growth. If you have been

    Michael Oswalt SmallTown Hunting Properties & Real Estate

    0 Robinson-Thompson Rd, Winona, MS 38967
  • 101 County Road 54, Winona, MS 38967
    101 County Road 54, Winona, MS 38967
    101 County Road 54, Winona, MS 38967
    /23

    $42,950 Last List Price Sold Nov 06, 2025

    101 County Road 54, Winona, MS 38967

    • 3 Beds
    • 1 Bath
    • 1,240 Sq Ft
    • Built 1965

    Last Sold Summary

    • $35/SF
    • 43 Days On Market

    Current Estimated Value $43,000

    Last Listing Agent Anita Orey Arx Point Realty, LLC

    101 County Road 54, Winona, MS 38967
    • 561 Hwy 51, Winona, MS 38967
      561 Hwy 51, Winona, MS 38967
      561 Hwy 51, Winona, MS 38967
      /39

      Not Listed For Sale

      561 Hwy 51, Winona, MS 38967

      • 3 Beds
      • 2.5 Baths
      • 2,700 Sq Ft
      • Built 1980
      561 Hwy 51, Winona, MS 38967

      Last Sold Summary

      • $0/SF
      • 57 Days On Market

      Last Listing Agent Jessica Butler RE/MAX

  • N Mission Rd, Winona, MS 38967
    N Mission Rd, Winona, MS 38967
    N Mission Rd, Winona, MS 38967
    /49

    $460,000

    • Land
    • 151 Acres
    • $3,046 per Acre

    N Mission Rd, Winona, MS 38967

    Welcome to 151 Montgomery Located on the Carroll-Montgomery County Line, just 3 minutes from Winona, MS and Interstate 55. This beautiful tract offers a rare combination of rolling terrain, diverse timber, established wildlife habitat, and a well-developed trail system creating a turnkey property for the serious outdoorsman or land investor.As you enter the property, you can see the

    Leland Selby SWAPA Land, LLC

    N Mission Rd, Winona, MS 38967
  • 0 County Road 65, Winona, MS 38967
    0 County Road 65, Winona, MS 38967
    0 County Road 65, Winona, MS 38967
    /63

    $473,600 Last List Price Sold May 13, 2025

    0 County Road 65, Winona, MS 38967

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

    Last Sold Summary

    • 80 Days On Market

    Last Listing Agent JP Clark JP Clark Realty LLC

    0 County Road 65, Winona, MS 38967
    • 561 U S 51, Winona, MS 38967
      561 U S 51, Winona, MS 38967
      561 U S 51, Winona, MS 38967
      /39

      Not Listed For Sale

      561 U S 51, Winona, MS 38967

      • 3 Beds
      • 2.5 Baths
      • 2,700 Sq Ft
      • Built 1980
      561 U S 51, Winona, MS 38967

      Last Sold Summary

      • $0/SF
      • 59 Days On Market

      Last Listing Agent Jessica Butler RE/MAX

  • 2384 Highway 51, Winona, MS 38967
    2384 Highway 51, Winona, MS 38967
    2384 Highway 51, Winona, MS 38967
    /62

    $160,000

    • 3 Beds
    • 2.5 Baths
    • 2,246 Sq Ft

    2384 Highway 51, Winona, MS 38967

    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

    Tiffany McCaleb Powers Properties

    2384 Highway 51, Winona, MS 38967
  • 1401 Mississippi 407, Winona, MS 38967
    1401 Mississippi 407, Winona, MS 38967
    /2

    $59,900 Last List Price Sold Sep 05, 2025

    1401 Mississippi 407, Winona, MS 38967

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • Built 1988

    Last Sold Summary

    • $38/SF
    • 438 Days On Market

    Last Listing Agent Kyle Cravens Cravens Properties, LLC

    1401 Mississippi 407, Winona, MS 38967
    • 407 Sterling Ave, Winona, MS 38967
      407 Sterling Ave, Winona, MS 38967
      407 Sterling Ave, Winona, MS 38967
      /21

      Est $139,994 Not Listed For Sale

      407 Sterling Ave, Winona, MS 38967

      • 4 Beds
      • 1.5 Baths
      • 1,900 Sq Ft
      • Built 1950
      407 Sterling Ave, Winona, MS 38967

      Last Sold Summary

      • $0/SF
      • 16 Days On Market

      Last Listing Agent Terry winter United Real Estate Mid-South

  • 505 Whitehead Dr, Winona, MS 38967
    505 Whitehead Dr, Winona, MS 38967
    505 Whitehead Dr, 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
  • 904 Bar Cove, Winona, MS 38967
    904 Bar Cove, Winona, MS 38967
    904 Bar Cove, Winona, MS 38967
    /15

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

    904 Bar Cove, Winona, MS 38967

    • 3 Beds
    • 1 Bath
    • 1,295 Sq Ft
    • Built 1976

    Last Sold Summary

    • $89/SF
    • 0 Days On Market

    Current Estimated Value $106,405

    Last Listing Agent Elecia Elmore Powers Properties

    904 Bar Cove, Winona, MS 38967
    • 115 Fairground St, Winona, MS 38967
      115 Fairground St, Winona, MS 38967
      115 Fairground St, Winona, MS 38967
      /36

      Est $244,661 Not Listed For Sale

      115 Fairground St, Winona, MS 38967

      • 4 Beds
      • 2 Baths
      • 2,267 Sq Ft
      • Built 1920
      115 Fairground St, Winona, MS 38967

      Last Sold Summary

      • $0/SF
      • 31 Days On Market

      Last Listing Agent Chris Reed Coltmor Realty Co.

  • 205 Shirley Ave, Winona, MS 38967
    205 Shirley Ave, Winona, MS 38967
    205 Shirley Ave, Winona, MS 38967
    /31

    $279,000

    • 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
  • 1549 U S 51, Winona, MS 38967
    1549 U S 51, Winona, MS 38967
    1549 U S 51, Winona, MS 38967
    /20

    $140,000 Last List Price Sold Dec 26, 2025

    1549 U S 51, Winona, MS 38967

    • 3 Beds
    • 2 Baths
    • 1,833 Sq Ft
    • Built 1951

    Last Sold Summary

    • $76/SF
    • 82 Days On Market

    Current Estimated Value $152,390

    Last Listing Agent Robin Lea Gold Key Realty LLC

    1549 U S 51, Winona, MS 38967
    • 373 Spring Hill Rd, Winona, MS 38967
      373 Spring Hill Rd, Winona, MS 38967
      373 Spring Hill Rd, Winona, MS 38967
      /49

      Not Listed For Sale

      373 Spring Hill Rd, Winona, MS 38967

      373 Spring Hill Rd, Winona, MS 38967

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Houston Primos Primos Land & Homes

  • 1509 Highway 407, Winona, MS 38967
    1509 Highway 407, Winona, MS 38967
    /2

    $160,000

    • 3 Beds
    • 2 Baths
    • 1,269 Sq Ft

    1509 Highway 407, Winona, MS 38967

    Kyle Cravens Cravens Properties, LLC

    1509 Highway 407, Winona, MS 38967
  • 400 Oak Dr, Winona, MS 38967
    400 Oak Dr, Winona, MS 38967
    400 Oak Dr, Winona, MS 38967
    /33

    $375,000 Last List Price Sold Oct 08, 2025

    400 Oak Dr, Winona, MS 38967

    • 4 Beds
    • 2 Baths
    • 2,070 Sq Ft
    • Built 1956

    Last Sold Summary

    • $181/SF
    • 205 Days On Market

    Current Estimated Value $322,000

    Last Listing Agent Mary Bowering Bowie Realty, Inc.

    400 Oak Dr, Winona, MS 38967
    • 0 Scotland Rd Unit 1320006, Winona, MS 38967
      0 Scotland Rd Unit 1320006, Winona, MS 38967
      0 Scotland Rd Unit 1320006, Winona, MS 38967
      /4

      Not Listed For Sale

      0 Scotland Rd Unit 1320006, Winona, MS 38967

      0 Scotland Rd Unit 1320006, Winona, MS 38967

      Last Sold Summary

      • 323 Days On Market

      Last Listing Agent Barry Holt Tom Smith Land & Homes

  • 500 Fairground St, Winona, MS 38967
    500 Fairground St, Winona, MS 38967
    500 Fairground St, 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
  • 135 Fox Rd Unit A, Winona, MS 38967
    135 Fox Rd Unit A, Winona, MS 38967
    135 Fox Rd Unit A, Winona, MS 38967
    /13

    $59,000 Last List Price Sold Dec 09, 2025

    135 Fox Rd Unit A, Winona, MS 38967

    • 4 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1999

    Last Sold Summary

    • $51/SF
    • 59 Days On Market

    Current Estimated Value $73,452

    Last Listing Agent Robin Lea Gold Key Realty LLC

    135 Fox Rd Unit A, Winona, MS 38967
    • 0 Graysport Crossing, Winona, MS 38967
      0 Graysport Crossing, Winona, MS 38967
      0 Graysport Crossing, Winona, MS 38967
      /19

      Not Listed For Sale

      0 Graysport Crossing, Winona, MS 38967

      0 Graysport Crossing, Winona, MS 38967

      Last Sold Summary

      • 463 Days On Market

      Last Listing Agent Adam Hester Tom Smith Land & Homes

  • 59 Redell Dr, Winona, MS 38967
    59 Redell Dr, Winona, MS 38967
    59 Redell Dr, Winona, MS 38967
    /14

    $250,000

    • 3 Beds
    • 2.5 Baths

    59 Redell Dr, Winona, MS 38967

    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

    Mary Spell Cravens Properties, LLC

    59 Redell Dr, Winona, MS 38967

Showing Results 1 - 40, Page 1 of 18

Mississippi Montgomery County Winona

Real Estate & Homes

Home Trends in Winona, MS

On average, homes in Winona, MS sell after 188 days on the market compared to the national average of 55 days. The median sale price for homes in Winona, MS over the last 12 months is $103,500, down 31% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$103,500
Median Single Family Sale Price
$112,000
Median Townhouse Sale Price
$100,000
Average Price Per Sq Ft
$67
Number of Homes for Sale
23
Last 12 months Home Sales
14
Months of Supply
19.70
Median List Price
$155,000
Median Change From 1st List Price
19%
Median Home Sale Price YoY Change
-31%
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