Winona, MS Homes for Sale

Q: What are the most popular zip codes in Winona, MS?

The most popular zip codes in Winona, MS include 38967 , 38925 , 38943 , 39176 and 38917 .

/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

Pam Powers

Powers Properties

(662) 443-4319

109 Mission 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

Jim Deweese

Real Broker

(662) 674-6753

621 Middleton Rd, 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.

Wilson Britt

Smalltown Hunting Properties & Real Estate

(662) 299-2367

304 Tyler Holmes 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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/15
$175,000
- 5 Beds
- 2 Baths
- 1,783 Sq Ft
579 U S 51, Winona, MS 38967

This is it! Call today to see this 3 bedroom, 2 bath home.

Kyle Cravens Cravens Properties, LLC

579 U S 51, 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
/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
/15
$275,000
- Land
- 2.7 Acres
- $101,852 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
/2
$400,000
- Land
- 1.5 Acres
- $266,667 per Acre
0 NE Frontage Rd, Winona, MS 38967

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

Prestley Vaughan Southern Oaks RE Properties LLC

0 NE Frontage Rd, 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
/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
/66
$499,000
- 3 Beds
- 3 Baths
- 3,100 Sq Ft
57340 Cr 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 Cr 430, Winona, MS 38967
/11
$589,000
- Land
- 66 Acres
- $8,924 per Acre
01 S Frontage Rd, Winona, MS 38967

This 66± acre tract is 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 directly across I-55 from Empire Truck Sales and

Chris Reed SmallTown Hunting Properties & Real Estate

01 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
/13
$59,500
- 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
/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
/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
/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
/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
/20
$400,000
- Land
- 2.66 Acres
- $150,376 per Acre
0 N Mission Rd, Winona, MS 38967

Don't miss this excellent opportunity to own 2.66± acres in Montgomery County, conveniently located just off Highway 82 near the I-55 exit. With easy access to major highways, this property offers great visibility and accessibility, making it an ideal location for a future homesite or potential commercial use. Whether you're looking to build your dream home with room to spread out or invest in a

Prestley Vaughan Southern Oaks RE Properties LLC

0 N Mission Rd, Winona, MS 38967
/2
$750,000
- Land
- 11 Acres
- $68,182 per Acre
0 NE Frontage Rd, Winona, MS 38967

Position your business where it will be seen! This 11+/- acre property is strategically located at the intersection of Interstate 55 and Highway 82 in Montgomery County, offering outstanding visibility and easy access for travelers and local traffic alike. With its high-traffic location and excellent exposure, this property presents the perfect opportunity for a wide range of commercial ventures.

Prestley Vaughan Southern Oaks RE Properties LLC

0 NE Frontage Rd, Winona, MS 38967
/48
$460,000
- Land
- 151 Acres
- $3,046 per Acre
0 N Mission Rd, Winona, MS 38967

Welcome to 151± acres in Montgomery County located on the Carroll-Montgomery County line just 3 minutes from Winona and Interstate 55. This tract features rolling hills with a mix of pine and hardwood timber creating excellent wildlife habitat and scenic terrain. The property is well set up for hunting with seven established food plots and a well-maintained internal trail system providing easy

LELAND SELBY SWAPA LAND, LLC

0 N Mission Rd, 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
/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

Mississippi Montgomery County Winona

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

Frequently Asked Questions

What is the average home price in Winona, MS?

Homes for sale in Winona, MS have an average home price of $170,522.

Are home prices dropping in Winona?

Yes, home prices in Winona are down 21% in the last 12 months.

How many homes have sold over the last 12 months in Winona, MS?

14 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, 38925, 38943, 39176 and 38917.

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 6.38%, your estimated principal and interest payment would be $770 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

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

Last 12 months Home Sales

Months of Supply

19.70

Median List Price

$155,000

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

Winona Types of Homes for Sale

Winona Land for Sale

Winona Homes by Price

Winona Homes for Sale under $200K

More About Living in Winona

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