22

Winona, MS Houses for Sale

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

    $238,000

    • 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
  • 203 Branch St, Winona, MS 38967
    203 Branch St, Winona, MS 38967
    203 Branch St, Winona, MS 38967
    /10

    $65,000

    • 3 Beds
    • 2 Baths
    • 1,709 Sq Ft

    203 Branch St, Winona, MS 38967

    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

    Robin Lea Gold Key Realty LLC

    203 Branch St, Winona, MS 38967
  • 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
  • 599 Highway 51, Winona, MS 38967
    599 Highway 51, Winona, MS 38967
    599 Highway 51, Winona, MS 38967
    /36

    $315,000

    • 4 Beds
    • 3.5 Baths

    599 Highway 51, Winona, MS 38967

    Perched on 5 beautiful acres, this stunning 4-bedroom, 3.5-bath home offers the perfect blend of space, comfort, and timeless charm. With 3,643 square feet of living space, you'll love the expansive living area designed for both entertaining and everyday living. Gorgeous hardwood floors are complemented by large windows that fill the home with natural light and showcase peaceful views of the

    Mary Ann Jackson Landmark Realty

    599 Highway 51, Winona, MS 38967
  • 226 N Quitman St, Winona, MS 38967
    226 N Quitman St, Winona, MS 38967
    /2

    $39,000

    • 3 Beds
    • 1 Bath
    • 1,824 Sq Ft

    226 N Quitman St, Winona, MS 38967

    3-bedroom, 1-bath home offering approximately 1,824 square feet of living space. This property features a functional floor plan with spacious living areas and ample room for a variety of uses. Conveniently located in Winona with access to local amenities, schools, and shopping. Property offers potential for homeowners or investors.

    Arielle Reece EXIT Southern Charm Realty

    226 N Quitman St, Winona, MS 38967
  • 516 Speedway Ave, Winona, MS 38967
    516 Speedway Ave, Winona, MS 38967
    516 Speedway Ave, Winona, MS 38967
    /13

    $40,000

    • 3 Beds
    • 1 Bath
    • 2,498 Sq Ft

    516 Speedway Ave, Winona, MS 38967

    Affordable 3 Bedroom Home with Great Potential!This home offers endless possibilities for the buyer with vision. Conveniently located near schools, medical facilities, and shopping, with easy access to Highways 82, 55, and 51, this property combines value with location.Bring your imagination, Pinterest ideas, fresh paint, and a trusted handyman to transform this home into a cozy retreat

    MADALYN MCBRIDE MCBRIDE & COMPANY REAL ESTATE

    516 Speedway Ave, Winona, MS 38967
  • 115 Pine Dr, Winona, MS 38967
    115 Pine Dr, Winona, MS 38967
    115 Pine Dr, Winona, MS 38967
    /28

    $185,000

    • 4 Beds
    • 3 Baths
    • 1,928 Sq Ft

    115 Pine Dr, Winona, MS 38967

    115 Pine Drive, Winona, MS - This 4-bedroom, 3-bath home is tucked away in a quiet, private, area of Winona offering both space and comfort. The home features: Large whirlpool tub/shower, recessed dimmable lighting, all new electrical wiring, all new plumbing throughout, large electric water heater and additional optional tank-less water heater, New paint inside and out, laminate flooring

    Chris Reed Coltmor Realty Co.

    115 Pine Dr, Winona, MS 38967
  • 1651 U S 82, Winona, MS 38967
    1651 U S 82, Winona, MS 38967
    1651 U S 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
  • 308 Jones St, Winona, MS 38967
    308 Jones St, Winona, MS 38967
    308 Jones St, Winona, MS 38967
    /41

    $225,000

    • 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
  • 123 Branch St, Winona, MS 38967
    123 Branch St, Winona, MS 38967
    123 Branch St, 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
  • 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
  • 624 Summit St, Winona, MS 38967
    624 Summit St, Winona, MS 38967
    624 Summit St, 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
  • 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
  • 810 Michelle Dr, Winona, MS 38967
    810 Michelle Dr, Winona, MS 38967
    /2

    $179,000

    • 3 Beds
    • 1.5 Baths

    810 Michelle Dr, Winona, MS 38967

    Kyle Cravens Cravens Properties, LLC

    810 Michelle Dr, Winona, MS 38967
  • 206 Church St, Winona, MS 38967
    206 Church St, Winona, MS 38967
    206 Church 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
  • 302 Braswell Dr, Winona, MS 38967
    302 Braswell Dr, Winona, MS 38967
    302 Braswell Dr, 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
  • 215 Pearl St, Winona, MS 38967
    215 Pearl St, Winona, MS 38967
    215 Pearl St, Winona, MS 38967
    /12

    $109,000

    • 3 Beds
    • 1 Bath
    • 1,072 Sq Ft

    215 Pearl St, Winona, MS 38967

    Kyle Cravens Cravens Properties, LLC

    215 Pearl St, Winona, MS 38967
  • 1241 U S 51, Winona, MS 38967
    1241 U S 51, Winona, MS 38967
    1241 U S 51, 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
  • 304 Shirley Ave, Winona, MS 38967
    304 Shirley Ave, Winona, MS 38967
    304 Shirley Ave, 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
  • 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
  • 1000 Montgomery St, Winona, MS 38967
    1000 Montgomery 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
Mississippi Montgomery County Winona

Houses for Sale in Winona, MS

Why Live in Winona

Winona, MS, is a small city with a rural, agriculturally-based community that has recently become a local job center due to the opening of Biewer Lumber's $130 million sawmill. This investment has brought jobs and infrastructure improvements to the city of over 4,500 residents. Housing styles in Winona range from Greek Revivals and Tudors to ranch styles and New Traditionals, with a median price of $110,000. Properties are typically on gridded streets with oak and magnolia trees, while homes with more acreage are found on the outskirts. The City of Winona Recreation Park offers baseball diamonds, tennis courts, and a playground, while Old Mountain Outdoor Adventures provides ziplining and hiking trails. The Winona Country Club features a 9-hole golf course and a swimming pool. Cultural attractions include the Montgomery County Performing Arts Center and the Montgomery County Coliseum, which hosts rodeos and concerts. Dining options are plentiful along U.S. Highway 51 and in downtown, with local favorites like The Front Street Bar and Lounge and Greenhouse Coffee Bar. Shopping is limited to downtown boutiques and a Supervalu on U.S. 51, with larger retailers available in Grenada, 22 miles north. Winona faces weather risks such as flooding and tornadoes, but federal grants aid recovery efforts. The city is car-dependent, with Interstate 55 as a main transit route, and the Golden Triangle Regional Airport 73 miles east.

Learn more about living in Winona

Home Trends in Winona, MS

On average, homes in Winona, MS sell after 195 days on the market compared to the national average of 56 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
$104,500
Median Townhouse Sale Price
$100,000
Average Price Per Sq Ft
$57
Number of Homes for Sale
19
Last 12 months Home Sales
14
Months of Supply
16.30
Median List Price
$145,000
Median Change From 1st List Price
19%
Median Home Sale Price YoY Change
-31%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winona, there are currently 22 houses for sale, offering an array of options for potential buyers. With houses priced between $39,000 to $425,000, there's a range to accomodate every budget. As of April, 2026 the median home price in Winona is $145,000, while the average sale price is $124,000, offering insights into the local housing market. On average, houses spend 195 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Winona, MS and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group