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Winona, MO Homes for Sale | Realty.com

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Before you start looking
The buying timeline

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3 beds New construction

18 listings

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Buy before you sell

Resources

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Homes for Sale in Winona, MO

Homes for Sale in Winona, MO

18 Listings

Homes for Sale in Winona, MO

18 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #2020001504

30Active
$114,900
4 bd · 3 ba · 2,288 sqft
19507 J F Norton Parkway, Winona, MO
MARLA KAY Denton · 37 North Realty - Mountain View
11Active
$72,500
2 bd · 1 ba · 1,280 sqft
5938 Cr-585, Winona, MO
Angela Dawn Needels · Ozark Land Exchange
39Active
$450,000
4 bd · 3 ba · 1,799 sqft
8214 CR 563, Winona, MO
Anthony Rodebush · Red Cedar Land Company LLC

39Active
$350,000
4 bd · 3 ba · 1,799 sqft
8214 CR 563, Winona, MO
Anthony Rodebush · Red Cedar Land Company LLC
36Active
$218,000
3 bd · 2 ba · 1,584 sqft
8028 Weaver Street, Winona, MO
Anthony Rodebush · Red Cedar Land Company LLC
29Active
$289,900
5 bd · 3 ba · 3,584 sqft
9468 State Highway 19, Winona, MO
Natalie Chatman · Missouri Home Realty
32Active
$289,900
5 bd · 3 ba · 3,584 sqft
9468 Mo-19, Winona, MO
Lawanda 'Cricket' Anderson · Missouri Home Realty
20Active
$129,900
4 bd · 2 ba · 2,680 sqft
8286 Lockman Street, Winona, MO
Natalie Chatman · Missouri Home Realty
18Active
$65,000
2 bd · 1 ba · 1,400 sqft
8438 State Highway 19, Winona, MO
Natalie Chatman · Missouri Home Realty
44Active
$194,900
3 bd · 2 ba · 1,629 sqft
8737 Sapper Street, Winona, MO
MARLA KAY Denton · 37 North Realty - Mountain View
32Active
$779,000
4 bd · 3 ba · 1,753 sqft
16428 Mo-19, Winona, MO
Angela Dawn Needels · Ozark Land Exchange
55Active
$140,000
4 bd · 2 ba · 1,920 sqft
5413 County Road 579, Winona, MO
Evan Ball · United Country-Cozort Realty, Inc.
58Active
$170,000
3 bd · 2 ba · 1,768 sqft
17150 3rd Street, Winona, MO
Tom Pringle · Iron Brand Realty LLC
16Active
$63,900
3 bd · 1 ba · 1,440 sqft
17187 Edgewood Road, Winona, MO
Rockie Dailey · United Country Real Estate - Ozark Rivers Realty
24Active
$114,900
4 bd · 1 ba · 1,114 sqft
8643 Sapper Street, Winona, MO
Rockie Dailey · United Country Real Estate - Ozark Rivers Realty
19Active
$59,900
2 bd · 1 ba · 1,260 sqft
18119 Sallee Street, Winona, MO
Darron Combs · Century 21 Combs & Associates
41Active
$149,900
4 bd · 2 ba · 1,237 sqft
8612 Sapper Street, Winona, MO
Rockie Dailey · United Country Real Estate - Ozark Rivers Realty
36Active
$169,900
3 bd · 2 ba · 1,352 sqft
18197 7th Street, Winona, MO
Rockie Dailey · United Country Real Estate - Ozark Rivers Realty

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

MARIS MLS: Based on information submitted to the MLS GRID as of 2026-07-22 20:11:29 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Southern Missouri Regional MLS: The data relating to real estate for sale on this web page comes in part from the Internet Data Exchange (IDX) of Southern Missouri Regional MLS. Real estate listings held by Brokerage firms other than Realty.com are marked with the IDX logo and detailed information about them includes the name of the listing Brokers. The information being provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information being provided is deemed reliable but not guaranteed, and all information should be verified by the consumer. Any representation that a website contains all listings shall only mean that the website contain all listing available to the public through the IDX data feed. There may be other properties offered through a REALTOR® that have not been displayed on this site. Information deemed reliable but not guaranteed. Copyright © 2026 Southern Missouri Regional MLS. All Rights Reserved.

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Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #2020001504

Winona, MO community profile

Population: 989
Median income: $32,813
Housing units: 485
People per sq. mi.: 5.1
Area: 195 sq. mi.

Source: HJN community data

Nearby areas

ZIP codes

65548 (24)
63965 (21)
65466 (18)
65588 (18)
65606 (18)
65438 (16)
65571 (12)
63638 (8)

Cities

Mountain View (23)
Van Buren (20)
Alton (18)
Eminence (17)
Birch Tree (16)
Summersville (12)
Ellington (8)
Doniphan (2)

Winona housing market

August 2026 · This period is still settling

Homes on the market · MLS, as of Aug 31, 2026

Median list price: $159,950
Homes for sale: 14

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,200 sq. ft.